Build

Ready for more myth busting around startup funding? Let’s get to it then!

Last week I shared a number of reasons you should share care fundraising whether you’re a founder or startup employee. Here they are again, and in the Build episode we talked about why it’s a bad idea to reach out to investors when you have an idea.

This week we’re going to continue our theme and focus on what compels us to think we need to raise capital like competition heating up, the belief that the business will stop growing, or that the idea we’re pursuing isn’t really BIG enough. We’ll also be diving into the mechanics of investment talking about the nuances of an angel versus a venture capitalist, and why it’s important to look for investors that have knowledge of your marketing or industry.

Erica Brescia is back to help us out with this episode. Erica the COO and co-founder of Bitnami. Erica has also recently joined XFactor Ventures as an investment partner. XFactor is an early-stage investment firm that's looking to fund female founders as well as mix-gendered teams.

Erica is a founder and investor, and having sat on both sides of the table, she knows how to dispel fact from fiction!

As you listen to today’s episode you’ll learn:

• Why Erica and her partners at XFactor are putting their money where their mouth is and starting a fund to invest in female founders and mix-gendered teams
• What the XFactor investment partners and other angels look for versus venture capitalists, and how much they are willing to invest
• Why competitors will come and go, and you cannot let their actions intimidate you or direct your business goals
• Why only you as a founder, can decide when is the right time to raise for your business

In the next two episodes we’ll explore handling all the rejections you receive from investors, how to motivate yourself to keep going, and what it’s going to take to get that first check!

-- 

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

 

## Startup Funding: When It Does And Doesn’t Make Sense To Fundraise For Your Startup Transcript

 

Poornima Vijayashanker:         Last time, we talked about how as a first-time founder, you don't necessarily need to immediately rush out and get investment to get your tech product off the ground. We discovered some alternate ways of funding your product development and company growth. If you missed that episode, I've included it in the link below this video.

 

In today's episode, we're going to dive in a little bit deeper, and talk about when it makes sense to go out for that angel investment, and then how do you transition from getting capital from angels to eventually getting it from venture capitalists, and what you need to do in the interim to make sure you're growing your company. So stick around.

 

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. In each episode, I invite innovators, and together we debunk a number of myths and misconceptions related to building products, companies, and your career in tech.

 

What Compels Startup Founders To Fundraise

 

One myth a lot of founders fall prey to is the need to constantly fundraise. They're worried that if they don't, their competition is going to swoop right in and outpace them. Or their business is just going to stop growing, and even worse than that, people might not think that they are actually onto a big idea.

 

To debunk these myths and more, I've invited Erica Brescia, who is the COO and co-founder of Bitnami. Erica has also recently joined XFactor as an investment partner. For those of you who aren't familiar, XFactor is an early-stage investment firm that's looking to invest in female founders and mixed-gender teams. Thanks again for joining us.

 

Erica Brescia:      Thanks for having me!

 

Poornima Vijayashanker:         Yeah! I know we talked a little bit in the last segment, but let's just quickly do a refresher, tell us a little bit about your background and what you do at Bitnami.

 

Erica Brescia:      Sure. Bitnami automates the packaging and maintenance process for server software for containerized, cloud, and behind-the-firewall deployments. We're most known right now for the Bitnami Application Catalog, which contains over 150 different pieces of server software, ranging from business schools, like content management systems, more project management systems, to development tools like GitLab and Jenkins for building out your development processes and pipeline, to stacks of things for building applications, like Node, or Rails, or Django. We work with all of the major cloud providers, and have over a million deployments a month of the apps we package across all the platforms that we support.

 

Poornima Vijayashanker:         Awesome. In addition to Bitnami, you recently joined XFactor as an investment partner.

 

Erica Brescia:      I did, yes.

 

The Difference Between Angel Investors And Venture Capitalists

 

Poornima Vijayashanker:         Yeah! We talked a little bit about that last time, and I want to pick up the conversation from our last time and dive a little bit more into not only what does XFactor do, but this whole position between angels and venture capitalists. How do you guys think of XFactor? Are you considering yourselves as angels or VCs? Would it help to start with defining angels and VCs?

 

Erica Brescia:      Sure. I mean, I tend to think of angels as primarily investing their own capital, and VCs are investing other people's capital. We all actually have our own funds in the fund as well, so we're LPs in addition to being the investment partners.

 

Poornima Vijayashanker:         What does that mean?

 

Erica Brescia:      That means that we're the people who put money into the fund, as the limited partners, who just put money in the fund, and then they step away, and they entrust, basically, the team of investment partners to invest that capital in companies that will produce ventures that yield returns.

 

Poornima Vijayashanker:         Where is that money coming from? Is that your own hard-earned money, or is that from somewhere else?

 

Erica Brescia:      In the case of the LPs for the XFactor fund, it's from a range of different people. Some of them have just been very successful in business. Some may be managing endowments or trusts, or other investment vehicles, and they invest both in the stock market and in VC and angel funds as part of their diversification strategy.

 

Poornima Vijayashanker:         Got it. I think some of you have also contributed personal funds, right?

 

Erica Brescia:      Yes. We have put our own funds into the plan as well.

 

Poornima Vijayashanker:         That's important to note. Yeah.

 

Erica Brescia:      You've got to put your money where your mouth is, right?

 

Poornima Vijayashanker:         Great! No, I certainly appreciate you guys doing that.

 

Erica Brescia:      Plus, honestly, I think we're going to make money off of it! So why would you not do that?

 

Poornima Vijayashanker:         Exactly!

 

Erica Brescia:      That is the whole point.

 

Poornima Vijayashanker:         Yeah. You guys are operating a little bit like angels, but a little bit like VCs as well, but let's dive into more of a traditional VC model. What does that look like?

 

What Seed Stage Investors Are Really Looking For And The Size Of Check They Write

 

Erica Brescia:      Sure. The distinction there is interesting, because I would say there's seed-stage financing, which a lot of people think of as coming from angels a lot, but VC funds do as well. Those are typically much smaller rounds and much earlier stage. The company probably has something built, probably has some users, probably can show some traction, but they're usually not raising huge amounts of money, at least not by Silicon Valley standards, which are different than the rest of the world.

 

Poornima Vijayashanker:         Yeah. Let's get some ranges. Because I know some seeds can get crazy.

 

Erica Brescia:      Huge. Yes.

 

Poornima Vijayashanker:         So let's do a more middle-of-the-road seed. What would that look like?

 

Erica Brescia:      These days, I would say they're usually between $500K and $2 million. I know that's a wide range, sometimes it's smaller, sometimes it's bigger, but the fundraisings that we're participating in are usually somewhere around there. We have had some companies raise significantly more than that, and we've almost gone in more at like a Series A stage. But typically you're raising $1 million or $2million to get your idea off the ground and show a little bit more traction, before you go and raise at a Series A. Those used to be maybe $2 or $3 million. Now, most of the time, you're looking at maybe $6, $7, even $10 or $15 million as a Series A, which we certainly see in the cloud and container space in particular, which is where I'm focused with Bitnami.

 

Poornima Vijayashanker:         OK. That makes sense. Now, I'm not going to dive into microfunds and syndicates, and all that stuff. We're going to do that in a later episode. But let's go back to you, and let's talk a little bit about how you initially funded Bitnami.

 

How To Initially Fund Your Startup When You Cannot Attract Investment

 

Erica Brescia:      Customers.

 

Poornima Vijayashanker:        Customers!

 

Erica Brescia:     We sold stuff. Yeah.

 

Poornima Vijayashanker:         Yeah. When was this, by the way?

 

Erica Brescia:      We started with a company called BitRock over 10 years ago, and BitRock built some really interesting technology around application packaging and deployment, which has become the foundation of Bitnami. We're very unique, I would say, for a Silicon Valley company. We developed a package software product. We sold it to customers, and we generated money that way.

                   

Then we started providing a subscription service to a lot of software companies that needed us to build, we called them "stacks" of software, so their products could be installed and distributed very easily, and we worked with a lot of the biggest names in open source, in those days. So we had that money coming in—

 

Poornima Vijayashanker:         If you don't mind sharing, how big were some of those contracts?

 

Erica Brescia:      They were in the tens of thousands of dollars a year. So reasonably sized, but we now, in retrospect, we charged far too little. But that's one of the lessons that you learn as a founder, you're always underpricing yourself in the early days.

 

So we did that, and built up the company that way. Then we decided to evolve into Bitnami. We went through Y Combinator in 2013—

 

Poornima Vijayashanker:         So before you did that, you actually had revenue coming in?

 

Erica Brescia:      Yes.

 

Poornima Vijayashanker:         Give us a range of how big you were at that size?

 

Erica Brescia:      We had 12 people, and seven figures in revenue, when we—

 

Poornima Vijayashanker:         Oh! That's fabulous!

 

Erica Brescia:      —went through Y Combinator.

 

Poornima Vijayashanker:         Yeah. OK. So why even bother going to—

 

Erica Brescia:      That's a great question! It was a subject of much debate, but again, interesting story, I suppose. My co-founder's wife had gone through Y Combinator with her own company, and had a great experience with it. And we knew that we wanted to send the company on a different trajectory—

 

Poornima Vijayashanker:         Which was?

 

Erica Brescia:      Growth.

 

Poornima Vijayashanker:         OK. OK!

 

Erica Brescia:      We wanted to build a huge business, and the model that we'd had previously was really what we talked in the last episode about, more of a lifestyle business. Right? We built a solid business, but that's not what we were there to do. We wanted to build a huge and very meaningful company. And we felt like Y Combinator was the right way to do that.

                

It gave us a lot of focus, and helped us make some interesting and difficult decisions. It also helped us a lot with hiring in the early days, and bringing more folks to the team. We've been on a pretty healthy  trajectory since then. Over 75 people. I don't give out revenue numbers, but we're profitable and growing, and doing well.

                   

All of that money, except for a million dollars, which we still have sitting in the bank, has come in through customers. And that million dollars we raised after going through Y Combinator. We brought in some angel investors whom we really liked, for different reasons. Some of them have a lot of experience in building companies, specifically in our space, and we felt like they could help us a lot with that.

                   

A couple of them are VCs who invested personally in us, because we didn't want to raise a VC fund, and a few were overseas venture investors, but they make seed stage investments. One from Japan, and one from China. And that was purely because we plan on going into those markets, and we thought it would make sense to have some people over there with a vested interest in our success.

                   

Y Combinator served as a good catalyst to bring that round together-

 

Poornima Vijayashanker:         How big was that round?

 

Erica Brescia:      It was just a million dollars?

 

Poornima Vijayashanker:         Oh! OK. But you were already in the seven-figure revenue at that point, when you raised that million.

 

Erica Brescia:      Exactly.

 

Poornima Vijayashanker:         OK.

 

Erica Brescia:      And that money is still sitting in the bank, and we've added a healthy amount to it, and—

 

Poornima Vijayashanker:         That was what year?

 

Erica Brescia:      2013.

 

Poornima Vijayashanker:         Oh! It's been a while. It's been four years.

 

Erica Brescia:      Yep.

 

Poornima Vijayashanker:         Now, interestingly enough, you have that million, you're raising revenue, and you had grown without a lot of outside capital. I mean, you were already growing, so in that span of time, weren't you afraid that some competitor was just going to swoop right in and go out and raise $10 million or $100 million dollars, and put you out of business?

 

Don’t Let Competitors Intimidate You Into Fundraising For Your Startup

 

Erica Brescia:      What's actually funny about that question is we had a bunch of competitors do that, and they all went out of business..

 

Poornima Vijayashanker:         Oh, OK! Yeah!

 

Erica Brescia:      OK! Some spectacularly so. One raised $40 million, had huge names. One of the people on their board tried to come and intimidate me, and say I could never compete with—it was actually a woman running that company, too. But I won't name her, because that's not good for anyone.

                   

Yeah. We had a lot of companies come and raise money, but the model wasn't there yet. And that's why we didn't raise, either, right? There's a time, and we talked about this in the last episode. It's my belief that in most cases, you're better off raising when you have product-market fit. We had that at small scale, but we hadn't found what was really going to fuel exceptional growth of the company. It took us a while to get there, and a bunch of other companies tried to come in and do that, and they all went bust.

                   

I mean, there is a time and place when I think it does make sense, and when you do have to worry about competitors, because the truth is, once a big name competitor raises a big round, it's really hard to get anyone else to invest in you. I think Docker's a pretty good example of that in my space, right? They have tons of money. Nobody's going to invest in another container startup. Why would you do that? It doesn't make sense for investors.

                   

It is something to consider, but I think a lot of people spend way too much time worrying about their competitors, and not enough time worrying about their own business.

 

Poornima Vijayashanker:         Yeah. Or their customers.

 

Erica Brescia:      Yeah! Or their customers. Exactly. So, yeah, that matters, but you need to do what's right for you, and what's right for what you want out of your life and your business. You should ask yourself those questions. Taking on VC is taking on a lot of additional responsibility, too—

 

What Kind Of Return Venture Capitalists Look For

 

Poornima Vijayashanker:         Like what?

 

Erica Brescia:      Well, they're expecting a certain level of return, right? A $100 million exit is not something a VS wants, where it might be completely life changing for you, if you don't have venture capital in the company. If you're taking venture capital, you're committing to running the company for at least 5–10 years, providing they don't push you out, which happens sometimes, too, if you're not doing things the way they want.

                   

You're committing to managing a board, with outside parties who are going to have sometimes divergent interests from you. It could even be the case that the fund cycles are usually 10 years, and they have to return the capital to their limited partners, which we talked about earlier. They might need to get out, and want to push you to sell when you don't want to. They might want you to sell to somebody you don't want to.

                   

There are a lot of great things that come from venture capital, if you partner with the right people. Obviously, you get the capital you need to fuel the growth of your business, and that can be incredibly important, especially to support go-to-market activities, or SaaS business models, where customer acquisition costs might be high, but the LTV is huge. There are reasons to take money.

                  

I'm not against that. But you also need to understand what you're signing up for, and what it really means, and that there may be an alternative path for you if that's not the path that makes the sense for you. If you don't want to run this company for 5–10 years, and you don't expect to sell it for hundreds of millions, if not billions, of dollars, don't take venture capital.

Startups That Focused On Growing Their Business First

 

Poornima Vijayashanker:         Yeah. Some folks in our audience might be thinking, "Erica, that's fabulous for you and Bitnami, and all of the success, but I could never do that. I couldn't just sit and wait for my business to grow organically." Are there other examples of companies here in the Valley, that you're familiar with, who have done a similar approach? I know I can think of a couple, but I'm curious—

 

Erica Brescia:      Absolutely! Well, Atlassian, they're in the Valley now, but they came from Australia, and that's a spectacular story. They really couldn't raise, because they were in Australia, and especially back then, the VC climate in Australia was almost nonexistent. They raised very late, and a lot of it was secondary to the employees, and they've done spectacularly well. GitHub's another example. They raised very, very late in the process, in a very big round, and that gave them a lot of flexibility to do other things.

                   

We've seen that happen a lot. It really depends. Again, I think, going back to what I said before about product-market fit. It's my view that the best time to raise is when you just need fuel for the engine. You already know how the engine works, and it's already built, and the machine is there, and you know, "If I put X in, I'm going to get Y out." Right? That's when you can really take advantage of venture capital, and that's when it can really make a difference.

                  

I'm not saying take a long time to build your company like I did. I would certainly do a lot of things differently this time around, but a lot of it just has to do with where the business is, and what the capital's going to be used for.

 

Poornima Vijayashanker:         It's been a four-year period, right? Where you haven't taken outside investment. You took the initial million. But in that period of time, how has not taking capital, or not thinking about fundraising, how has that helped you and Bitnami?

 

Erica Brescia:      Well, several ways. I think the most important thing is focus. Not having $10 or $20 or $50 million in the bank makes you focus on what's really going to move the business forward. It's really easy, and I have seen this countless times with companies that I will not name. They raise a ton of money, and they go out and hire a ton of people, and everything falls apart.

                   

Because humans are humans, right? These are not just cogs in the machine, especially when you're trying to build a breakthrough or game-changing product. You need incredibly smart people. They're going to have strong personalities. They're going to have past experiences from other companies. And you need to be able to get those people to work well together. So many startups have failed in doing that, and it's led to their own demise, or at least slowed them down a lot, and really burned a lot of bridges with fantastic employees.

 

I'd say it's allowed us to build out the infrastructure to responsibly scale the team, and it's helped us to focus, again, on making the right investments in terms of where we're spending our time. It's also great for negotiating business deals, I will tell you. That doesn't come up a lot—

 

How To Compel Customers To Do Business With Your Startup

 

Poornima Vijayashanker:         How so?

 

Erica Brescia:      I was in meetings, even earlier this week, and these are quite big, multimillion-dollar-a-year deals, and they were asking some questions about what the business model looked like, and I could look at these people with a straight face and say like, "Look, we're not VC backed. My company needs to make money. You want me to be around. This needs to make sense for us, financially."

                   

That drives a lot of my decision making. I'm very, very involved in the corporate and business development stuff that we do. I need to do deals that make sense for my business. For some reason, it's a lot easier for people to get their heads around that when you don't have venture capital, which is kind of a funny thing, right?

 

Poornima Vijayashanker:         Well, people understand where you're coming from, and what resources you have at that level.

 

Erica Brescia:      Yeah! I'm not BSing them. "I have to pay people, and you're going to get a lot of value out of this, and you need to pay me, and I'm not going to do it on a bet that the relationship itself is going to benefit me enough, because that wouldn't be responsible business." That's what I go to all the time. It's not responsible business, you're not doing it. I think being bootstrapped and funding through customers really helps you think through that and make very good business decisions. We say no to all kinds of things, too. And I think that's easier, as a result of that.

                  

The one other aspect I'd say is, we don't have to manage investors. It takes a lot of time to build investor relationships, which I do do that anyway, because we may raise in the future. But also just to raise funding, to go through the diligence process, and then to manage a board of directors that involves VCs, again, who might have competing priorities, or other things going on.

                  

Again, we don't get some of the pixie dust you might get if you're VC funded, and sometimes we have to have interesting conversations with procurement departments, and show them our financials, to prove that we've got a great business, and that they can feel comfortable working with us, but it saves a lot of time and overhead.

 

Poornima Vijayashanker:         Yeah, that's interesting. So you feel, because you're in the B2B space, the enterprise space, some companies may feel like, "Oh, you're not VC backed, so you might go out of business sooner." But what you're saying is, "Actually, we've got customers. We're going to stick around because we've got real revenues coming in, so no need to worry about this."

 

Erica Brescia:      Yeah. And I can point to, we do business with Microsoft, Amazon, Oracle, Google. All these big companies. It's gotten a lot easier, now.

 

Poornima Vijayashanker:         Right. You've got the credibility.

 

Erica Brescia:      Exactly. And we've got a track record. We've not just been around for a year, and we have an established team of senior people, and we've proven that we can execute, and we can deliver. And what often happens is we'll start with a smaller relationship, and it grows over time. After you get your foot in the door, what they care about is do you deliver on your commitments, not whether or not you have a VC in the company.

 

Keeping Your Options Open When It Comes To Investment

 

Poornima Vijayashanker:         Awesome. Now, I know you said, "Never say never." So you are thinking about capital, and then your future. How are you thinking about attracting that VC capital?

 

Erica Brescia:      Let me be clear: we haven't decided to raise capital, but it's a discussion that we're having currently between my CFO, my co-founder, me, and some of the other people on the executive team, because we're launching this new enterprise business. We're incredibly lean as a company right now.

                   

I told you we have in the mid-70s in terms of employees. Over 50 of those are in engineering and product. So the business team is quite lean, and we have very, very little sales on the sales side. Building on an enterprise business means I need a whole new go-to-market plan that involves field people, inside sales, solutions architects, and support people, and a bunch of other folks. Account executives, all these things.

                  

That's very capital intensive to build. We can do it off of cash flow, actually. We're in that fortunate position, but at the same time, we might grow a little bit more slowly, and especially hire more slowly, than we would if we had, say, $15 or $20 million in the bank. So we're starting to think through the tradeoffs, and what might make sense there.

                   

I've been in the Valley now long enough, I know a lot of VCs. There's several whom I like and respect quite a bit, and I still develop relationships with them, and we talk about the industry in general, and Bitnami, and where we're going. I think it's a little bit different than a company that's just coming out of nowhere. We have people who know us, who know the business, who have said that they're interested. So when the time comes, it's more of a matter of sitting down with people who are already friendly and interested in the company, and talking through what makes the most sense.

 

Poornima Vijayashanker:         It's a partnership.

 

Erica Brescia:      Mm-hmm, absolutely.

 

Poornima Vijayashanker:         Yeah. Wonderful. Well, thank you for sharing your experience with us today, Erica. I know our audience is going to get a lot out of this episode.

 

Erica Brescia:      Thank you so much!

 

Poornima Vijayashanker:         That's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive the next episode, where we'll dive in deeper with some of Erica's co-investors and explore more topics around funding your startup. Ciao for now!

 

Voiceover:          This episode of *Build*is brought to you by our sponsor, Pivotal Tracker.

 

It’s the start of a new year, which is an exciting time all around. You’re probably excited about new opportunities, starting a company, or building product in 2018!

 

While I’m all for optimism, I’ve also gotta stay true to them theme of Build: debunking myths and misconceptions when it comes to building tech product, companies and your career in tech ;)

 

So we’re going to spend the next four episodes of Build debunking themes around fundraising for startups.

 

I know what you’re thinking: “Poornima, is this really necessary?! Can’t we just focus on product and engineering? How about some Build Tips with those friendly product managers, designers, and engineers from Pivotal Labs?”

 

Don’t worry we’ve got plenty of those in store for you! Before we dive back into the fun and friendly banter of Ronan and his team, I thought it was necessary to start 2018 debunking myths around fundraising.

 

Here are my reasons for doing this:

 

Reason #1: If you want to be a founder and start a startup in 2018, you need to know how to control your own destiny.

 

Gone are the days of a quick and easy seed deal. If you don’t believe me, then here are two posts from very active investors Fred Wilson and Jason Calacanis with compelling data spanning the past 5 years. They show you that investment in early-stage companies is indeed slowing down, and why the trend is going to continue. #byebyebubble

 

Reason #2: If you want to be a founder and fundraise, you need to know what it’s really going to take to get the first check that gives you the freedom to quit your day job.

 

I know I previously explored what it takes to raise capital from investors and how investors add value beyond the check. But times are changin’! As I went back and reviewed the episodes I realized that while much of the advice still applies, there are new challenges founders, especially first-time founders face.

 

If you’re going to be one of them, then you need to be aware of them as you build your startup. There are also going to be a lot of sacrifices that you will need to consider making. As you’re faced with them, you might feel like you’re doing things wrong, when others have had an easier time. But you cannot compare when the market is in flux.

 

Reason #3: Don’t want to be a founder? Even if being a founder is the furthest thing from your mind, you might be thinking about joining a startup as an employee at any stage — garage to growth.

 

Well you need to be able to tell fact from fiction. You don’t want to get lured into visions of billion-dollar exits, only to discover that they are going to be cutting health care benefits, won’t be able to make payroll next month, or all that equity won’t help you buy my 2005 Honda Civic!

 

You need to be able to ask tough questions to understand the real health of the company, and market opportunity, so that you can decide if it’s worth taking the risk.

 

Reason #4: As an employee at a startup, every quarter you are going to be tasked with challenging milestones.

 

Metrics matter more and more these days, and every department has a funnel.

 

For engineering, it’s making sure the team is continuing to build and ship a quality product, balancing out features with infrastructure and keeping an eye out for that pesky tech debt to avoid slowdowns.

 

For product, it’s making sure there is a good balance of attracting new customers, while engaging and monetizing existing ones. And holding the engineering team accountable to spending time on paying down product debt.

 

While marketing has to keep growing traffic no matter what!

 

Teams are also staying lean longer, and founders are looking for employees with generalist backgrounds who can #GSD.

 

Everyone’s contribution matters to achieving metrics, which makes you feel wanted as an employee. But it also means that you need to be good at prioritizing, understanding tradeoffs, and a fast learner!

 

At the end of the day, you need to know and understand that what you are doing is actually moving the needle and going to help attract investment and customers.

 

There is no point in building product or marketing just for the sake of it.

 

Hopefully my reasons have convinced you why learning about fundraising is integral to your own success at a startup, and we can move on to the first episode of the year! In it, we’re going to tackle the first misconception a lot of first-time founders fall prey: thinking they need to reach out to investors the moment they have an idea.

 

It turns out you actually don't need to reach out to investors and you can get started by funding your idea on your own. You’ve probably heard this a lot already…

 

Quite frankly, investors won’t even take meetings if you do reach out. I can count on two hands the number of investors who I had successfully raised from in previous years that wouldn’t even return my emails recently! Why? Because it’s getting really competitive out there and they want to make sure startups have substantial progress before they are willing to take time to meet.

 

To help us out, I've invited Erica Brescia, who is the COO and co-founder of Bitnami. Erica has also recently joined XFactor as an investment partner. XFactor is an early-stage investment firm that's looking to fund female founders as well as mix-gendered teams.

 

I choose Erica and her peers to come on the show because they are ALL founders first and investors second. Meaning they have sat on both sides of the table.

 

As you watch today’s episode you’ll learn:

 

• Why investment may not be applicable to the type of business you are building and alternate approaches to funding your startup
• The questions investors ask themselves before they will respond to a meeting request or write a startup a check
• When startups are “too early” to fundraise and why the definition of “too early” is inconsistent — who really gets funded early and why
• The work that startup founders and teams must do, if they are keen on attracting investment

In future episodes we’ll dive into topics like why raising capital won’t help you outdo competition, how to get over the constant rejection, and what it’s going to take to get that first check.

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

Episode Transcript

Poornima Vijayashanker:           Got an idea for a tech product that you want to scale into a big business? You probably think that you need to go out and raise capital from an investor, right? Well, it turns out that you may not need to. In today's *Build* episode, we're going to explore when it makes sense to reach out to investors.

                   

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. In each *Build* episode, I invite innovators and together we debunk myths and misconceptions related to building products, companies, and your career in tech. One misconception a lot of first-time founders fall prey to is thinking they need to reach out to investors the moment they have an idea. It turns out you actually don't need to reach out to investors and you can get started by funding your idea on your own. In today's episode, we're going to dive in deep to understand some of the mistakes that first-time founders make when it comes to funding their idea. We'll also talk about what investors are looking for and when it makes sense to reach out to them. To help us out, I've invited Erica Brescia, who is the COO and co-founder of Bitnami. Erica has also recently joined XFactor as an investment partner. XFactor is an early-stage investment firm that's looking to fund female founders as well as mix-gendered teens. Thanks for joining us today, Erica.

 

Erica Brescia:              Thanks for having me. It's great to be here.

 

Poornima Vijayashanker:           This is the first time that you and I are meeting. Thanks for being here. I want to know a little bit more about you. Let's start with your background. What got you interested in tech?

 

Erica Brescia:              I've always been very interested in gadgets. It started out actually with mobile phones way back in the day, but I've always been curious about learning more about technology and gadgets and how things work. I really wanted to understand how mobile phone networks worked back in the day. Don't ask me why. I went on to study investment finance. A different path than a lot of people in Silicon Valley take. My father is an entrepreneur and I always had it in the back of my mind I wanted to start my own company. I got introduced to my co-founder and decided I was just going to help him work out a few kinks in the business and get it off the ground. Here I am now running a software company. It's really a case of being open to new opportunities, but also just having this lifelong interest in understanding how things work and learning new things.

 

Poornima Vijayashanker:           Let's talk about Bitnami, your current company. What exactly does Bitnami do and what inspired you to start it?

 

Erica Brescia:              Bitnami is a catalog of open-source applications that you can deploy on servers. It's primarily like B2B software. Things like maybe Moodle or Druple or WordPress, if you're familiar with that. We also package up a lot of development environments and development tools, things like Jenkins and Get Lab or Anode or Rails or Django Development environment. We have over a million deployments a month of the applications that we package. We publish them both through Bitnami.com as well as on all of the major cloud bender platforms. Users choose Bitnami because they know everything is going to work right out of the box every time, and they get a consistent experience wherever they deploy the software. If I can just add one more thing to that, one thing I'm particularly excited about is up until now we've been bootstrapping through our relationships with cloud vendors, but we're about to launch a new product for the enterprise. We're essentially taking the next step in the company's evolution by productizing all of the automation that we've built to deliver this catalog of applications so that others can take advantage of it, too.

 

Poornima Vijayashanker:           It sounds like Bitnami has been going strong for a long time. How long have you guys been around?

 

Erica Brescia:              We've been working on the Bitnami part of the business since 2013, but the technology dates back about ten years to when we started Bitrock, which is the predecessor. We do have several years in now.

 

A Day In The Life of a Startup COO

 

Poornima Vijayashanker:           That's great. As a COO, what's your day to day like?

 

Erica Brescia:              It was funny, when I thought through that question, there's no day to day. I spent Monday and Tuesday in some really key BD meetings. In Seattle yesterday, I was in LA for an open-source conference. I'm obviously here today. The way that we have our leadership roles between my co-founder and I might be different than a lot of other companies. I run everything except for product and engineering. That means that marketing, sales, BD, legal, finance, everything rolls up to me. That basically keeps things running and make sure that the company is growing and bringing on the right people and has revenue coming in and all those good things. Obviously as a quickly growing startup that's very, very tech heavy, I'm still involved in everything including product and engineering, too. There's never a typical day. It varies a lot and the days are long, but a lot of fun.

 

Poornima Vijayashanker:           Very good. Now you have actually taken on another role. If Bitnami isn't enough, you decided to join XFactor as an investment partner. Tell us a little bit about XFactor and why the decision to go into investment.

 

Erica Brescia:              Absolutely. I'll start with XFactor and tell you about the fund. Then I'll talk about why I joined. XFactor is a $3 million seed fund. We're making $100K investments in 30 companies. Pretty easy math. The genesis was really a woman named Anna and a guy named Chip. Chip is a partner with Fly Bridge. They got together and wanted to find a way to fund more women in technology because they had read some of the statistics about how difficult it can be for women to raise funding. The truth is, it's really an untapped opportunity. There's a ton of brilliant women building some very interesting companies. They were having problems in some cases getting through the traditional VC process because of some of the biases that we've all read about. We probably don't need to go through that. The idea was that they were going to get together a group of operating female founders. I think that's really the key is we're all women who have built and scaled our own businesses across a variety of sectors. I have a lot of experience in B2B and closing very big BD deals.

                   

I've acquired companies and things like that. Some of the other women are very heavy on the consumer side and they're great at branding and rolling out new products. We got a really diverse team of women, but who are actually still on the ground running businesses, very in touch with the problems that founders have in getting new companies off the ground. We think we have a pretty unique perspective and also an edge in terms of what we can offer founders because we're so close to the challenges that they're experiencing. We're very focused obviously with that check size on pretty early-stage companies and helping set those founders up for success. We do expect most of them will go on to raise for their venture capital. We're there to support them in doing that. I actually haven't raised VC for my company, but all the other women have. We have a good diversity of experiences and opinions around that too.

 

Being A Startup Founder And Angel Investor

 

Poornima Vijayashanker:           Why'd you join?

 

Erica Brescia:              It took a lot of thought. They came to me. At first, I thought they just wanted to run the idea by me back in February. Then I get an email a few days later saying, “We'd love to have you join us.” I really did spend some time thinking about it and talking to my co-founder and my husband about whether or not I'd be able to balance everything, because it is a big commitment. If I make a commitment, I want to come through on it and make sure that I'm not letting the founders and my fellow investment partners down. It really came down to the opportunity both for personal growth for me and to give back. There's a financial opportunity, too, which is fantastic. I really saw that we have a pretty unique angle into both deal flow. Several of us are YC founders as well. We have access to the YC network and obviously just good networks in Silicon Valley and outside as well. I felt like we could do something really interesting. I could meet a lot more women in technology. Also, I really do think there's a huge untapped opportunity there. I think we'll be able to produce above-average returns. It really came down to me asking the question, “Do I have time for this?” I'm going to get less sleep for sure. That's definitely been the case.

 

Poornima Vijayashanker:           Sure. You can make time.

 

Erica Brescia:              It was just too good to pass up. This is one of those things that I just couldn't say “no” to because the opportunity is so big and it's something that I'm enjoying doing so much.

 

Poornima Vijayashanker:           Wonderful. As soon as I saw the news, I wanted to reach out to you guys because I thought it was fabulous and needed to be spread to everyone else. Let's talk about your investments then. I know everyone has probably got different things that they want to invest in. We're going to talk to some of your partners later on. Let's talk about what you like to invest in.

 

Why Angel Investors Focus On Making Investments In Markets and Business Models They Are Familiar With

 

Erica Brescia:              Sure. I right now am very focused on things that I am passionate about. I think about whether or not the company keeps me up at night thinking about it later. I am usually receiving on the deal flow that it's on B2B and enterprise sales in particular because that's where my expertise and experience is. I found myself drawn to some other things, too. One of the investments that'll be announced soon, I wish I could name some of them.

 

Poornima Vijayashanker:           That's OK.

 

Erica Brescia:              I think we're about to announce that we've made eight investments in the first two months.

 

Poornima Vijayashanker:           Oh, awesome.

 

Erica Brescia:              We've been very busy and we've met some amazing women. One of the investments that I've led so far is very much a technology, cloud-focused company, which is absolutely my bailiwick. The other one is a fin-tech company. I was really drawn. I loved the founder. Was very impressed by her and the team that she's put together. Also, it was just the problem that they were solving, I could see it so clearly. It was palpable and I was staying up at night and I was talking to my husband about what they were doing and why I thought it was exciting. When I start thinking about how they can make the business successful and what they should be thinking about, that's a very good sign to me. I know it's not direct answer. I invest in this list of companies, but that's really not the way that it's worked out so far. I've looked at a variety of med-tech companies, fin-tech companies, more women in technology and sourcing and recruiting companies. Some people doing interesting stuff with NLP. It's really been a very diverse range of companies.

 

Why Women Founded Tech Companies Are Broader Than Gets Portrayed

                   

One of the things that I think you'll see us talking about more, which is very cool, is a lot of these companies are not what you would typically think of as the women-in-tech companies. A lot of people think all we want to work on is beauty. I like makeup and clothes and everything as much as the next person, but I don't know anything about those businesses. A lot of the deal flow that we've had, it's coming from all kinds of very hardcore tech, a lot of VR stuff, too, and AR. We've seen a broad range. Right now we're looking for the next billion-dollar businesses really. Any other VC it's, “Is this something I'm passionate about and can it be huge and can I add value in helping them make it so?”

 

Poornima Vijayashanker:           Actually, that's a good segue into talking about I think one of the things that confuses some folks in our audience and even first-time founders is, what qualifies as a tech product and then what—let's start there and then we can talk about maybe what a big idea is.

 

Understanding If Your Startup Is A Tech Enabled Business Or A Tech Product

 

Erica Brescia:              Sure. Almost anything these days is tech enabled. If it's not, you might have a scalability problem. I don't think we have very strict definitions as to what is tech or not. If excelling in technology and in the technical underpinnings of the product is going to give people an advantage, that's probably a tech company or something that we would think of as such. Some of the subscription businesses or there's a food device I can't talk too much about, but that we're looking at. A really novel subscription business around it. Another two companies have come through that are working on breast pumps for women. They're hardware companies but there's a lot of technology obviously that goes into the hardware. Obviously a lot of tech powering how they're approaching the businesses. It's really a pretty loose definition of what a tech company is. Even some of them are physical spaces now that we're looking at. It's a pretty broad range. It's not like we're only investing in software or we're only investing in sass or something like that.

 

Poornima Vijayashanker:           That's good to know. Tech enabled but there's probably some conversation that needs to be had around, “Are you really just selling water online or is there a distribution model that is tech enabled and it's cool if you sell water online.”

 

Erica Brescia:              Exactly.

 

Why Finding An Investor Isn’t Good Enough — You Need To Find THE Investor Who Understand Your Market and Business Model

 

Poornima Vijayashanker:           Got it. Then let's talk about I think another area, though, which is—you've already started talking about you enjoy the deals that are B2B, more enterprise, and maybe a little bit more saas heavy. I think one of the concerns that a lot of first-time founders have is, “I just need to find an investor.” I just need to find one investor, but they may not necessarily find that right investor. It's interesting because it's not just limited to tech. I was reading Barbara Lynch's memoir, who's a restaurateur, and she talked about going and finding the investors who invested in restaurants for her nine restaurants. Talk to me a little bit about what it means to be vertical focused as an investor.

 

Erica Brescia:              You want investors who understand your business or at least have the capacity and time to learn about it and who are upfront if they don't understand things, too. There's several things that make people good investors. One is, don't be an asshole, if I can say that on your show.

 

Poornima Vijayashanker:           Sure. Of course.

 

Erica Brescia:              I just don't want to work with people who are not good people. To me, some people don't care about...I've actually had people come to me and say, “It doesn't matter. All VCs are going to be assholes, you just need to accept that and move on.” I'm like, “Uh, uh. No. No, I don't. There's a lot of great VCs out there.”

 

Poornima Vijayashanker:           That's the normal assumption.

 

Erica Brescia:              There are a lot of good people out there, men and women in venture capital. I do think it's important that you understand somebody who understands your business and the cycles. Before, example, we've had a lot of very hardware-centric businesses come through. Those are difficult to invest in. In particular, if you don't have experience in hardware because you don't have a really good understanding of how long it's going to take and what the development cycle should look like and how capital intensive that you're going to be. It's harder to make good investment decisions. It's harder to be helpful for the founder, because if you have unrealistic expectations for the type of business they're building, nobody wins. It's the same, we've seen a lot of robotics companies doing super cool stuff, but I've told them, “Look, I'm not an expert in robotics. I'm going to have to go out.” We do have an associate who does some work for us, but we have to go out and be willing to invest our time to get up to speed in those industries in order to feel comfortable making an investment.

                   

It's good advice. I think what you're alluding to is, find an investor that actually knows what they're talking about in your space because otherwise they could really do damage by slowing you down, refusing to fund a second round or something like that. A follow on or just inundating you with questions all the time. The last thing you want to be doing is just educating your investors on the market when you have a company to build.

 

The Sacrifices Founders Have To Make To Get Their Startup Off The Ground

 

Poornima Vijayashanker:           Exactly. No, that's a good point. Let's talk about the other side of this, which is also, it's very tempting, as a first-time founder or somebody who’s green, to have an idea, whether it's hardware or anything that we feel is capital intensive or sometimes we just don't even have the capital as a founder. We haven't quite got to the financial point of our life. It's tempting to immediately say, “Oh my gosh, to get this thing off the ground I need to go and get investment. That might not be the right time.” Let's talk about what time horizon makes sense. I know it's going to be product specific, but I think it would be helpful to just—

 

Erica Brescia:              It really depends on so many different variables. One of them I think is important is to be realistic about where you are in your life and what kind of sacrifices you're willing to make. The reality is, if you have a family and a mortgage, it's a heck of a lot harder to stop taking a salary—particularly if you were to work in Silicon Valley because the salaries are quite high here right now—and go and start something from scratch. If you're 22 and right out of college and have none of those financial responsibilities, you might have more flexibility. My vote is do as much as you can before raising funding. Build as much as you can. First of all, there's so many good investment opportunities right now that I think most investors, they want to see...first they want to see that you're committed. If you just go out with a pitch deck—like I took two weeks of holiday for my job to put together a pitch deck and if you fund me, I'll go do this—you're never going to get funded because we want to see conviction.

 

We want to see that you quit your job, you're committed, you've been working on this with somebody else preferably for six months. You have the personality and the skills and the charm or whatever it may be, the conviction to actually get other people to join you. That's important, too. Unless you absolutely can not do it without raising money up front, I would say get at least to a prototype or as far as you can to be able to go show people and prove to people that you're there for the long haul and that you're willing to make sacrifices to make something happen. I will also plug incubators, like Y Combinator. Obviously I'm biased because we went through the program. That was a great experience for us in terms of helping us just build some momentum and we did rebranding of the company and accomplished a lot during that period. It's not about the funding necessarily, but it can give people who are cash wrapped a bit of cash to fund those first few months. It really helps you to accelerate that initial process and sets you up very well to raise from VCs after the fact.

                   

We've certainly sourced a lot of our deal flow from YC. We try at XFactor to be very broad and we've had people from all over the world, in fact, contacting us. Of course, we're going to look to YC because they've already been through that filter. They've achieved something during the period that they're in Y Combinator. It's a three-month sprint. We've found that looking at people that have at least gotten to the point where you would be if you've gone through a Y Combinator or similar. They've got something to show. That's when it makes sense. I will say, this is really the approach that we've taken with Bitnami is try to find money from customers. Let's not undervalue the fact that people will pay you for what you're building. Hopefully if you're building something valuable, and you're much better off going through that experience, learning what it takes to sell to people and collect their money—there's a lot of details there—and try to build your business that way. You don't need to go for VC right away. There are great examples of companies that have been hugely successful doing that like GitHub and Atlassian.

 

Why It’s OK To Build A Lifestyle Business

 

Poornima Vijayashanker:           I'm going to have you hold that thought because we are going to talk about that in a little bit. Now, the other thing I want to point out because you said customers, but I think also bootstrapping with a pay check to get off the ground. A lot of times people are worried about quitting their job and having a source of income, so using that especially for businesses that a little bit more capital intensive early on. Want to throw that out there. I want to dive a little bit deeper into this whole idea of, “I do want to get investment eventually.” Let's say I have gotten to a point, maybe I've gone to an incubator or I've gotten it off the ground, I have some customers. Then there comes that period where you're talking to an investor and they may not really understand how big your idea is. It's oftentimes that thing that people nitpick over and over again that, is this a big idea? Is this a big market? Or sadly people like to say, it's a lifestyle business. There's a stigma here in Silicon Valley against that. Let's talk about what exactly defines a big idea—if we can even define it because I know it's a little amorphous—versus a lifestyle businesses and maybe even break that stigma of that lifestyle business.

 

Erica Brescia:              Sure. First I'll say I don't think there's anything wrong with a “lifestyle” business. There have been a lot of deals that we looked at. There was this one amazing woman, I won't name the company, but she came through my network actually. She developed some really interesting technology. It was my belief after talking to a lot of people that she's going to sell the company for somewhere between $30–50 million within two years. Awesome for her. Not a great VC investment?

 

Why Venture Capitalist Don’t Invest In Lifestyle Businesses

 

Poornima Vijayashanker:           Why?

 

Erica Brescia:              Because we can't produce the kind of returns that we're looking for. We have LPs just like any other VC fund. We have a responsibility to them to generate returns. I told this woman I want to help her in any way I can. She's incredibly bright. I just couldn't see a path to them building a billion-dollar business. That's really what it needs to be. There needs to be a path that you can understand for how this can be huge. It's going to be very risky. I should say we always know that businesses are going to change and evolve and you're very much betting on the founders. That's absolutely true, but at the same time, if they have conviction around a specific idea and we don't see how it can get to be a huge business, and some of the great hardware companies we're looking at are like that. I think they will have fantastic businesses and fantastic exits. I certainly wouldn't call them lifestyle businesses because they're life changing in terms of the returns that they'll create for the founders. They may not be appropriate for a VC fund. I don't think there's anything wrong with that.

                   

You need to take a dispassionate look about what you're building, how big the market really is, how much of it you have an opportunity to grab, and be realistic about that. Then think about the kind of funding that makes sense. You might be able to find a family office or something or angel investors who are not looking for the same VC-style risk and returns. They'll be totally happy with the company selling for $10, $20, $30 million. In a couple years, they'll double their money and everybody's fine.

 

Where Do Venture Capitalist And Angel Investors Get Money To Fund Startups

 

Poornima Vijayashanker:           On that note, let's actually define what an LP is and why VC versus angels that people understand if they're not familiar.

 

Erica Brescia:              Sure. An LP is limited partner and they're the people that put money into the funds. They're often wealthy. They always have some money coming from somewhere. Often wealthy individuals, but depending on the fund, they might also be pension funds or endowments and things like that from universities or different trusts and things like that. Basically the people who put money into the hands of the venture capitalists who are the people who actually invest that money. In the case of angels, angels I think have evolved a lot. Now we have the super angels.

 

Poornima Vijayashanker:           We'll get into that in a future episode. I keep saying this, but it's gonna happen. It's gonna happen guys.

 

Erica Brescia:              I won't take us to off course then. There are a lot of different kinds of angels. I was an angel investor before joining XFactor. I mean, not at a huge scale, but I'd made a few investments myself.

 

Poornima Vijayashanker:           What's the scale?

 

Erica Brescia:              I was writing like $10,000 checks.

 

Poornima Vijayashanker:           Perfect.

 

Erica Brescia:              Smaller checks. Then there are people like—I'll take my father, who's one of my closest friends and heroes and has inspired me to do all of this. He built a brick and mortar contracting business that did quite well. He's been making tons of angel investments and all kinds of different things. Some tech, some very, very nontech. You have people like that. Then you have people like Eric Han for example. My company did raise a bit of angel funding primarily to get some really great folks involved with the company. Some of these people were like Eli Gillin, Eric Han. Eric Han was the CTO of Netscape. He went on to be a very early investor in Red Hat. Since then, has been one of the first checks into a ton of companies that have IPO'd. He was on the board of Red Hat after they IPO'd. Eli Gillin is running his own company now, but he started and sold a company to Twitter and ran a bunch of stuff there. These are people who have done well in their career, typically understand tech. They make a lot more investments than somebody like maybe me or my father who might've written a couple of checks a year. These people are doing several key deals a year, usually only investing their own funds. That's one of the big differences. They don't have LPs. It's their own money. They might be doing it more at scale. We call them usually professional angels or super angels.

 

Poornima Vijayashanker:           Business angels.

 

Erica Brescia:              Exactly. Who are making a lot of investments, but they don't have LPs to answer to.

 

When Does It Make Sense To Approach An Investor With Your Startup Idea — First Know What You Are Going To Do With It!

 

Poornima Vijayashanker:           Great. Let's end with this question. When does it make sense then when you think you have this big idea, to approach an investor? I know you guys said early, but what is maybe too early and what's a reasonable early to get a meeting?

 

Erica Brescia:              It depends on what you need. Let's start with why do you need the money? That's the first question you should be asking yourself. Where is this money going to get you? You better have a good answer before you go talk to VCs. What milestone are you going to hit with this? Then the second question you should ask is, could I get it from anywhere other than VCs? Do I have friends and family who might want to just give me some money? Could I even take out a loan? Sometimes these other things make sense. There are a bunch of diverse opinions on this, but my view is you don't take VC unless you absolutely need it. Until it's holding you back from scaling. In the particular case of Bitnami, for example, we've primarily bootstrapped. We've only taken a million dollars in outside funding in total. I have over 70 employees in 12 countries. We're cash-flow positive. We've built quite a stable and steady business. We are starting to talk about potentially raising venture capital because we're launching this enterprise product that I mentioned before.

                   

That involves building out an entirely new part of the business. I can do that off of cash flow, but I'll probably go a lot slower and we see that there's a limited window of opportunity here. I think it really depends on your specific case and whether you can do it any other way. Or if there's an investor that you can feel or that you feel can add a lot of value. There are certain investors who might have a ton of experience in your space. Maybe they started an earlier company and exited it and are just itching for the chance to do it better now that the technology is evolved or what have you. If you find people like that, I think they can be really helpful to building the business. Otherwise, it's like, you should raise when you need to raise. If you feel like you could run out of money in the near future and not be able to actually execute on your plan.

 

Yes There Is Such A Thing As Being Too Early To Fundraise For Your Startup And Yes It’s Inconsistent!

 

Poornima Vijayashanker:           Let's admit. There is a time that's too early.

 

Erica Brescia:              Oh yeah. There always is. It's funny. We funded a company that was quite early and quite a high evaluation. That's one of the deals I led actually. I knew the founder and he'd already built a successful company.

 

Poornima Vijayashanker:           There you go.

 

Erica Brescia:              You're much more willing then, almost eager, to get in because this is a male, female team. I happen to know the male better than the female. I told him I wanted into that deal because I think this guy has a ton of potential. Even though it was early, I would write him a check, but he's proven. That matters.

 

Poornima Vijayashanker:           Exactly. I think that's a big stigma, or rather a big misconception around who's getting a deal, who hasn't built a product yet, or it's not on the market. It's great that you mentioned that. I think for most other folks, they need to see something. They need to see product. They need to see at least a concierge-style minimal bible product or service, some cash flow, some customers. They really want to...those who don't have a track record need to step up their game and show a little bit more credibility.

 

Questions Investors Ask Before They Take A Meeting Or Write A Check To A Startup Founder

 

Erica Brescia:              Yeah. The things I look at is, are they committed is the number one thing. Starting a company is hard and a lot of people underestimate how hard and how many sacrifices you make. You can do a whole episode on what's involved in that. Are they committed? Can they build a team? I look at that a lot. That's one thing where people who want to move to Silicon Valley who have no connections there, that's one of my questions. How are you going to find people and convince them in a highly competitive job market to join your team? If you can do that, it also speaks pretty highly of you and your ability to convince people and help them see the vision. Then can they build the product? Is it something that people will pay for? Those are the checklist items that I have. The more that you can demonstrate, the easier the time you're going to have with fundraising.

                 

If you can't prove that people will pay for your product, if you can't prove that people will use it, especially if you can't prove that you can build it, that's when we're going to have a lot of challenges getting to the next step. That's when I try to give people a clean “yes” or “no.” Sometimes it's like, “You're just not there yet. If you do these things, then I might be interested. I'm sorry. I need to see more before I can make the call.”

 

Poornima Vijayashanker:           Yeah. I think that's fair. Thank you so much Erica for sharing all this information with us today.

 

Erica Brescia:              Thank you for having me.

 

Poornima Vijayashanker:           That's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive the next episode where we'll continue the conversation and talk about when it makes sense to transition from angel investment to seeking investment from venture capitalists and what you need to do in that interim period. Ciao for now.

 

This episode of *Build* is brought to you by our sponsor Pivotal Tracker.

 

Blog Post 2

Subject: When It Does And Doesn’t Make Sense To Fundraise For Your Startup

Title: Startup Funding: When It Does And Doesn’t Make Sense To Fundraise For Your Startup

Subtitle: Interview with Erica Brescia COO and Co-Founder of Bitnami and Investment Partner at XFactor Ventures

 

Ready for more myth busting around startup funding? Let’s get to it then!

 

Last week I shared a number of reasons you should share care fundraising whether you’re a founder or startup employee. Here’s they are again, and in the Build episode we talked about why it’s a bad idea to reach out to investors when you have an idea.

 

This week we’re going to continue our theme and focus on what compels us to think we need to raise capital like competition heating up, the belief that the business will stop growing, or that the idea we’re pursuing isn’t really BIG enough. We’ll also be diving into the mechanics of investment talking about the nuances of an angel versus a venture capitalist, and why it’s important to look for investors that have knowledge of your marketing or industry.

 

Erica Brescia is back to help us out with this episode. Erica the COO and co-founder of Bitnami. Erica has also recently joined XFactor Ventures as an investment partner. XFactor is an early-stage investment firm that's looking to fund female founders as well as mix-gendered teams.

 

Erica is a founder and investor, and having sat on both sides of the table, she knows how to dispel fact from fiction!

 

As you watch today’s episode you’ll learn:

 

• Why Erica and her partners at XFactor are putting their money where their mouth is and starting a fund to invest in female founders and mix-gendered teams
• What the XFactor investment partners and other angels look for versus venture capitalists, and how much they are willing to invest
• Why competitors will come and go, and you cannot let their actions intimidate you or direct your business goals
• Why only you as a founder, can decide when is the right time to raise for your business

 

 

In the next two episodes we’ll explore handling all the rejections you receive from investors, how to motivate yourself to keep going, and what it’s going to take to get that first check!

 

Listen to the episode on iTunes!

You can listen to this episode of Build on iTunes.

 

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

 

## Startup Funding: When It Does And Doesn’t Make Sense To Fundraise For Your Startup Transcript

 

Poornima Vijayashanker:         Last time, we talked about how as a first-time founder, you don't necessarily need to immediately rush out and get investment to get your tech product off the ground. We discovered some alternate ways of funding your product development and company growth. If you missed that episode, I've included it in the link below this video.

 

In today's episode, we're going to dive in a little bit deeper, and talk about when it makes sense to go out for that angel investment, and then how do you transition from getting capital from angels to eventually getting it from venture capitalists, and what you need to do in the interim to make sure you're growing your company. So stick around.

 

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. In each episode, I invite innovators, and together we debunk a number of myths and misconceptions related to building products, companies, and your career in tech.

 

What Compels Startup Founders To Fundraise

 

One myth a lot of founders fall prey to is the need to constantly fundraise. They're worried that if they don't, their competition is going to swoop right in and outpace them. Or their business is just going to stop growing, and even worse than that, people might not think that they are actually onto a big idea.

 

To debunk these myths and more, I've invited Erica Brescia, who is the COO and co-founder of Bitnami. Erica has also recently joined XFactor as an investment partner. For those of you who aren't familiar, XFactor is an early-stage investment firm that's looking to invest in female founders and mixed-gender teams. Thanks again for joining us.

 

Erica Brescia:      Thanks for having me!

 

Poornima Vijayashanker:         Yeah! I know we talked a little bit in the last segment, but let's just quickly do a refresher, tell us a little bit about your background and what you do at Bitnami.

 

Erica Brescia:      Sure. Bitnami automates the packaging and maintenance process for server software for containerized, cloud, and behind-the-firewall deployments. We're most known right now for the Bitnami Application Catalog, which contains over 150 different pieces of server software, ranging from business schools, like content management systems, more project management systems, to development tools like GitLab and Jenkins for building out your development processes and pipeline, to stacks of things for building applications, like Node, or Rails, or Django. We work with all of the major cloud providers, and have over a million deployments a month of the apps we package across all the platforms that we support.

 

Poornima Vijayashanker:         Awesome. In addition to Bitnami, you recently joined XFactor as an investment partner.

 

Erica Brescia:      I did, yes.

 

The Difference Between Angel Investors And Venture Capitalists

 

Poornima Vijayashanker:         Yeah! We talked a little bit about that last time, and I want to pick up the conversation from our last time and dive a little bit more into not only what does XFactor do, but this whole position between angels and venture capitalists. How do you guys think of XFactor? Are you considering yourselves as angels or VCs? Would it help to start with defining angels and VCs?

 

Erica Brescia:      Sure. I mean, I tend to think of angels as primarily investing their own capital, and VCs are investing other people's capital. We all actually have our own funds in the fund as well, so we're LPs in addition to being the investment partners.

 

Poornima Vijayashanker:         What does that mean?

 

Erica Brescia:      That means that we're the people who put money into the fund, as the limited partners, who just put money in the fund, and then they step away, and they entrust, basically, the team of investment partners to invest that capital in companies that will produce ventures that yield returns.

 

Poornima Vijayashanker:         Where is that money coming from? Is that your own hard-earned money, or is that from somewhere else?

 

Erica Brescia:      In the case of the LPs for the XFactor fund, it's from a range of different people. Some of them have just been very successful in business. Some may be managing endowments or trusts, or other investment vehicles, and they invest both in the stock market and in VC and angel funds as part of their diversification strategy.

 

Poornima Vijayashanker:         Got it. I think some of you have also contributed personal funds, right?

 

Erica Brescia:      Yes. We have put our own funds into the plan as well.

 

Poornima Vijayashanker:         That's important to note. Yeah.

 

Erica Brescia:      You've got to put your money where your mouth is, right?

 

Poornima Vijayashanker:         Great! No, I certainly appreciate you guys doing that.

 

Erica Brescia:      Plus, honestly, I think we're going to make money off of it! So why would you not do that?

 

Poornima Vijayashanker:         Exactly!

 

Erica Brescia:      That is the whole point.

 

Poornima Vijayashanker:         Yeah. You guys are operating a little bit like angels, but a little bit like VCs as well, but let's dive into more of a traditional VC model. What does that look like?

 

What Seed Stage Investors Are Really Looking For And The Size Of Check They Write

 

Erica Brescia:      Sure. The distinction there is interesting, because I would say there's seed-stage financing, which a lot of people think of as coming from angels a lot, but VC funds do as well. Those are typically much smaller rounds and much earlier stage. The company probably has something built, probably has some users, probably can show some traction, but they're usually not raising huge amounts of money, at least not by Silicon Valley standards, which are different than the rest of the world.

 

Poornima Vijayashanker:         Yeah. Let's get some ranges. Because I know some seeds can get crazy.

 

Erica Brescia:      Huge. Yes.

 

Poornima Vijayashanker:         So let's do a more middle-of-the-road seed. What would that look like?

 

Erica Brescia:      These days, I would say they're usually between $500K and $2 million. I know that's a wide range, sometimes it's smaller, sometimes it's bigger, but the fundraisings that we're participating in are usually somewhere around there. We have had some companies raise significantly more than that, and we've almost gone in more at like a Series A stage. But typically you're raising $1 million or $2million to get your idea off the ground and show a little bit more traction, before you go and raise at a Series A. Those used to be maybe $2 or $3 million. Now, most of the time, you're looking at maybe $6, $7, even $10 or $15 million as a Series A, which we certainly see in the cloud and container space in particular, which is where I'm focused with Bitnami.

 

Poornima Vijayashanker:         OK. That makes sense. Now, I'm not going to dive into microfunds and syndicates, and all that stuff. We're going to do that in a later episode. But let's go back to you, and let's talk a little bit about how you initially funded Bitnami.

 

How To Initially Fund Your Startup When You Cannot Attract Investment

 

Erica Brescia:      Customers.

 

Poornima Vijayashanker:        Customers!

 

Erica Brescia:     We sold stuff. Yeah.

 

Poornima Vijayashanker:         Yeah. When was this, by the way?

 

Erica Brescia:      We started with a company called BitRock over 10 years ago, and BitRock built some really interesting technology around application packaging and deployment, which has become the foundation of Bitnami. We're very unique, I would say, for a Silicon Valley company. We developed a package software product. We sold it to customers, and we generated money that way.

                   

Then we started providing a subscription service to a lot of software companies that needed us to build, we called them "stacks" of software, so their products could be installed and distributed very easily, and we worked with a lot of the biggest names in open source, in those days. So we had that money coming in—

 

Poornima Vijayashanker:         If you don't mind sharing, how big were some of those contracts?

 

Erica Brescia:      They were in the tens of thousands of dollars a year. So reasonably sized, but we now, in retrospect, we charged far too little. But that's one of the lessons that you learn as a founder, you're always underpricing yourself in the early days.

 

So we did that, and built up the company that way. Then we decided to evolve into Bitnami. We went through Y Combinator in 2013—

 

Poornima Vijayashanker:         So before you did that, you actually had revenue coming in?

 

Erica Brescia:      Yes.

 

Poornima Vijayashanker:         Give us a range of how big you were at that size?

 

Erica Brescia:      We had 12 people, and seven figures in revenue, when we—

 

Poornima Vijayashanker:         Oh! That's fabulous!

 

Erica Brescia:      —went through Y Combinator.

 

Poornima Vijayashanker:         Yeah. OK. So why even bother going to—

 

Erica Brescia:      That's a great question! It was a subject of much debate, but again, interesting story, I suppose. My co-founder's wife had gone through Y Combinator with her own company, and had a great experience with it. And we knew that we wanted to send the company on a different trajectory—

 

Poornima Vijayashanker:         Which was?

 

Erica Brescia:      Growth.

 

Poornima Vijayashanker:         OK. OK!

 

Erica Brescia:      We wanted to build a huge business, and the model that we'd had previously was really what we talked in the last episode about, more of a lifestyle business. Right? We built a solid business, but that's not what we were there to do. We wanted to build a huge and very meaningful company. And we felt like Y Combinator was the right way to do that.

                

It gave us a lot of focus, and helped us make some interesting and difficult decisions. It also helped us a lot with hiring in the early days, and bringing more folks to the team. We've been on a pretty healthy  trajectory since then. Over 75 people. I don't give out revenue numbers, but we're profitable and growing, and doing well.

                   

All of that money, except for a million dollars, which we still have sitting in the bank, has come in through customers. And that million dollars we raised after going through Y Combinator. We brought in some angel investors whom we really liked, for different reasons. Some of them have a lot of experience in building companies, specifically in our space, and we felt like they could help us a lot with that.

                   

A couple of them are VCs who invested personally in us, because we didn't want to raise a VC fund, and a few were overseas venture investors, but they make seed stage investments. One from Japan, and one from China. And that was purely because we plan on going into those markets, and we thought it would make sense to have some people over there with a vested interest in our success.

                   

Y Combinator served as a good catalyst to bring that round together-

 

Poornima Vijayashanker:         How big was that round?

 

Erica Brescia:      It was just a million dollars?

 

Poornima Vijayashanker:         Oh! OK. But you were already in the seven-figure revenue at that point, when you raised that million.

 

Erica Brescia:      Exactly.

 

Poornima Vijayashanker:         OK.

 

Erica Brescia:      And that money is still sitting in the bank, and we've added a healthy amount to it, and—

 

Poornima Vijayashanker:         That was what year?

 

Erica Brescia:      2013.

 

Poornima Vijayashanker:         Oh! It's been a while. It's been four years.

 

Erica Brescia:      Yep.

 

Poornima Vijayashanker:         Now, interestingly enough, you have that million, you're raising revenue, and you had grown without a lot of outside capital. I mean, you were already growing, so in that span of time, weren't you afraid that some competitor was just going to swoop right in and go out and raise $10 million or $100 million dollars, and put you out of business?

 

Don’t Let Competitors Intimidate You Into Fundraising For Your Startup

 

Erica Brescia:      What's actually funny about that question is we had a bunch of competitors do that, and they all went out of business..

 

Poornima Vijayashanker:         Oh, OK! Yeah!

 

Erica Brescia:      OK! Some spectacularly so. One raised $40 million, had huge names. One of the people on their board tried to come and intimidate me, and say I could never compete with—it was actually a woman running that company, too. But I won't name her, because that's not good for anyone.

                   

Yeah. We had a lot of companies come and raise money, but the model wasn't there yet. And that's why we didn't raise, either, right? There's a time, and we talked about this in the last episode. It's my belief that in most cases, you're better off raising when you have product-market fit. We had that at small scale, but we hadn't found what was really going to fuel exceptional growth of the company. It took us a while to get there, and a bunch of other companies tried to come in and do that, and they all went bust.

                   

I mean, there is a time and place when I think it does make sense, and when you do have to worry about competitors, because the truth is, once a big name competitor raises a big round, it's really hard to get anyone else to invest in you. I think Docker's a pretty good example of that in my space, right? They have tons of money. Nobody's going to invest in another container startup. Why would you do that? It doesn't make sense for investors.

                   

It is something to consider, but I think a lot of people spend way too much time worrying about their competitors, and not enough time worrying about their own business.

 

Poornima Vijayashanker:         Yeah. Or their customers.

 

Erica Brescia:      Yeah! Or their customers. Exactly. So, yeah, that matters, but you need to do what's right for you, and what's right for what you want out of your life and your business. You should ask yourself those questions. Taking on VC is taking on a lot of additional responsibility, too—

 

What Kind Of Return Venture Capitalists Look For

 

Poornima Vijayashanker:         Like what?

 

Erica Brescia:      Well, they're expecting a certain level of return, right? A $100 million exit is not something a VS wants, where it might be completely life changing for you, if you don't have venture capital in the company. If you're taking venture capital, you're committing to running the company for at least 5–10 years, providing they don't push you out, which happens sometimes, too, if you're not doing things the way they want.

                   

You're committing to managing a board, with outside parties who are going to have sometimes divergent interests from you. It could even be the case that the fund cycles are usually 10 years, and they have to return the capital to their limited partners, which we talked about earlier. They might need to get out, and want to push you to sell when you don't want to. They might want you to sell to somebody you don't want to.

                   

There are a lot of great things that come from venture capital, if you partner with the right people. Obviously, you get the capital you need to fuel the growth of your business, and that can be incredibly important, especially to support go-to-market activities, or SaaS business models, where customer acquisition costs might be high, but the LTV is huge. There are reasons to take money.

                  

I'm not against that. But you also need to understand what you're signing up for, and what it really means, and that there may be an alternative path for you if that's not the path that makes the sense for you. If you don't want to run this company for 5–10 years, and you don't expect to sell it for hundreds of millions, if not billions, of dollars, don't take venture capital.

Startups That Focused On Growing Their Business First

 

Poornima Vijayashanker:         Yeah. Some folks in our audience might be thinking, "Erica, that's fabulous for you and Bitnami, and all of the success, but I could never do that. I couldn't just sit and wait for my business to grow organically." Are there other examples of companies here in the Valley, that you're familiar with, who have done a similar approach? I know I can think of a couple, but I'm curious—

 

Erica Brescia:      Absolutely! Well, Atlassian, they're in the Valley now, but they came from Australia, and that's a spectacular story. They really couldn't raise, because they were in Australia, and especially back then, the VC climate in Australia was almost nonexistent. They raised very late, and a lot of it was secondary to the employees, and they've done spectacularly well. GitHub's another example. They raised very, very late in the process, in a very big round, and that gave them a lot of flexibility to do other things.

                   

We've seen that happen a lot. It really depends. Again, I think, going back to what I said before about product-market fit. It's my view that the best time to raise is when you just need fuel for the engine. You already know how the engine works, and it's already built, and the machine is there, and you know, "If I put X in, I'm going to get Y out." Right? That's when you can really take advantage of venture capital, and that's when it can really make a difference.

                  

I'm not saying take a long time to build your company like I did. I would certainly do a lot of things differently this time around, but a lot of it just has to do with where the business is, and what the capital's going to be used for.

 

Poornima Vijayashanker:         It's been a four-year period, right? Where you haven't taken outside investment. You took the initial million. But in that period of time, how has not taking capital, or not thinking about fundraising, how has that helped you and Bitnami?

 

Erica Brescia:      Well, several ways. I think the most important thing is focus. Not having $10 or $20 or $50 million in the bank makes you focus on what's really going to move the business forward. It's really easy, and I have seen this countless times with companies that I will not name. They raise a ton of money, and they go out and hire a ton of people, and everything falls apart.

                   

Because humans are humans, right? These are not just cogs in the machine, especially when you're trying to build a breakthrough or game-changing product. You need incredibly smart people. They're going to have strong personalities. They're going to have past experiences from other companies. And you need to be able to get those people to work well together. So many startups have failed in doing that, and it's led to their own demise, or at least slowed them down a lot, and really burned a lot of bridges with fantastic employees.

 

I'd say it's allowed us to build out the infrastructure to responsibly scale the team, and it's helped us to focus, again, on making the right investments in terms of where we're spending our time. It's also great for negotiating business deals, I will tell you. That doesn't come up a lot—

 

How To Compel Customers To Do Business With Your Startup

 

Poornima Vijayashanker:         How so?

 

Erica Brescia:      I was in meetings, even earlier this week, and these are quite big, multimillion-dollar-a-year deals, and they were asking some questions about what the business model looked like, and I could look at these people with a straight face and say like, "Look, we're not VC backed. My company needs to make money. You want me to be around. This needs to make sense for us, financially."

                   

That drives a lot of my decision making. I'm very, very involved in the corporate and business development stuff that we do. I need to do deals that make sense for my business. For some reason, it's a lot easier for people to get their heads around that when you don't have venture capital, which is kind of a funny thing, right?

 

Poornima Vijayashanker:         Well, people understand where you're coming from, and what resources you have at that level.

 

Erica Brescia:      Yeah! I'm not BSing them. "I have to pay people, and you're going to get a lot of value out of this, and you need to pay me, and I'm not going to do it on a bet that the relationship itself is going to benefit me enough, because that wouldn't be responsible business." That's what I go to all the time. It's not responsible business, you're not doing it. I think being bootstrapped and funding through customers really helps you think through that and make very good business decisions. We say no to all kinds of things, too. And I think that's easier, as a result of that.

                  

The one other aspect I'd say is, we don't have to manage investors. It takes a lot of time to build investor relationships, which I do do that anyway, because we may raise in the future. But also just to raise funding, to go through the diligence process, and then to manage a board of directors that involves VCs, again, who might have competing priorities, or other things going on.

                  

Again, we don't get some of the pixie dust you might get if you're VC funded, and sometimes we have to have interesting conversations with procurement departments, and show them our financials, to prove that we've got a great business, and that they can feel comfortable working with us, but it saves a lot of time and overhead.

 

Poornima Vijayashanker:         Yeah, that's interesting. So you feel, because you're in the B2B space, the enterprise space, some companies may feel like, "Oh, you're not VC backed, so you might go out of business sooner." But what you're saying is, "Actually, we've got customers. We're going to stick around because we've got real revenues coming in, so no need to worry about this."

 

Erica Brescia:      Yeah. And I can point to, we do business with Microsoft, Amazon, Oracle, Google. All these big companies. It's gotten a lot easier, now.

 

Poornima Vijayashanker:         Right. You've got the credibility.

 

Erica Brescia:      Exactly. And we've got a track record. We've not just been around for a year, and we have an established team of senior people, and we've proven that we can execute, and we can deliver. And what often happens is we'll start with a smaller relationship, and it grows over time. After you get your foot in the door, what they care about is do you deliver on your commitments, not whether or not you have a VC in the company.

 

Keeping Your Options Open When It Comes To Investment

 

Poornima Vijayashanker:         Awesome. Now, I know you said, "Never say never." So you are thinking about capital, and then your future. How are you thinking about attracting that VC capital?

 

Erica Brescia:      Let me be clear: we haven't decided to raise capital, but it's a discussion that we're having currently between my CFO, my co-founder, me, and some of the other people on the executive team, because we're launching this new enterprise business. We're incredibly lean as a company right now.

                   

I told you we have in the mid-70s in terms of employees. Over 50 of those are in engineering and product. So the business team is quite lean, and we have very, very little sales on the sales side. Building on an enterprise business means I need a whole new go-to-market plan that involves field people, inside sales, solutions architects, and support people, and a bunch of other folks. Account executives, all these things.

                  

That's very capital intensive to build. We can do it off of cash flow, actually. We're in that fortunate position, but at the same time, we might grow a little bit more slowly, and especially hire more slowly, than we would if we had, say, $15 or $20 million in the bank. So we're starting to think through the tradeoffs, and what might make sense there.

                   

I've been in the Valley now long enough, I know a lot of VCs. There's several whom I like and respect quite a bit, and I still develop relationships with them, and we talk about the industry in general, and Bitnami, and where we're going. I think it's a little bit different than a company that's just coming out of nowhere. We have people who know us, who know the business, who have said that they're interested. So when the time comes, it's more of a matter of sitting down with people who are already friendly and interested in the company, and talking through what makes the most sense.

 

Poornima Vijayashanker:         It's a partnership.

 

Erica Brescia:      Mm-hmm, absolutely.

 

Poornima Vijayashanker:         Yeah. Wonderful. Well, thank you for sharing your experience with us today, Erica. I know our audience is going to get a lot out of this episode.

 

Erica Brescia:      Thank you so much!

 

Poornima Vijayashanker:         That's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive the next episode, where we'll dive in deeper with some of Erica's co-investors and explore more topics around funding your startup. Ciao for now!

 

Voiceover:          This episode of *Build*is brought to you by our sponsor, Pivotal Tracker.

 

 

I don’t know about you, but I cringe at the thought of having to commute. The traffic, road rage, not to mention having to find parking… it was enough to make me throw in the towel 7 years ago!

 

Since then I have been managing remote teams around the world, and as I continue to scale my team I learn best practices from companies who have been doing it for longer than I have like Olark.

 

But, I know there are a lot of people out there who just don’t know if they can do it.

 

Maybe you’re one of them. You worry if you’ll be productive, able to communicate effectively and fit into the company culture.

 

One of my employees, Meghan Burgain felt the same way about a year ago. She had a number of reservations having never worked remotely before.

 

In today’s Build episode, Meghan and I are going to dive into some of these reservations, how you can get over them, and of course the wonderful benefits aside from working in your jammies ;)

 

You’ll learn:

 

• The tools and processes to use to stay productive and on top of your projects and tasks
• How to handle working across multiple time zones
• How to communicate more effectively with your teammates across a number of channels
• How to train new hires when you can’t sit right next to them
• How you can cultivate a great company culture across continents

 

Here’s another great source to check out on managing your day-to-day when remote working, from our friends at Skillcrush.

 

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

 

Transcript for Remote Working: How To Succeed In Your First Remote Working Position 

 

Poornima Vijayashanker:        Hey, guys. I'm hanging out here in beautiful Bordeaux, France, and taking you behind the scenes this week to show you what remote working is like at Femgineer. If you've been on the fence about taking a remote position, stay tuned for a number of tips in today's *Build* episode.

                   

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. For the past seven years, I have been managing remote teams around the world for my startup as well as other companies. Today, I'm joined by Meghan Burgain, who is the mother of twins and expat who lives here in Bordeaux, France, and is Femgineer's community manager. For the last year, Meghan has been working remotely and she's going to share some of her favorite tips to help you get over any reservations that you might have when it comes to taking on a remote position. Thanks for joining us, Meghan.

 

Meghan Burgain: Thanks for being in France, Poornima.

 

Remote Working Reservations

 

Poornima Vijayashanker:        I know a year ago when I approached you about remote working, you were on the fence. Let's talk about what some of your reservations were.

 

Meghan Burgain:     Yeah. My education and a lot of my experiences are in education. I was actually a teacher before I moved here. I was a little concerned about getting up to speed, getting trained at Femgineer. That was one of my concerns was getting trained.

                   

The other one of course was that Bordeaux is nine hours ahead of San Francisco. I knew that there was going to be some difficulty there. Would I have to stay awake at night to get all of the work done or not? Those are my two concerns.

 

How To Handle Time Zones When Remote Working

 

Poornima Vijayashanker:        While you got over the hurdle and joined the team, I know there was that first hiccup that you had where you missed a meeting due to the time zone. What did you learn from that experience?

 

Meghan Burgain:     Time zones are really tricky. I learned that basically communication is paramount, especially when you're working remotely. You need to be explicit, very clear, search for the clarification, ask the questions that you need and really just be polite when you're dealing with people through email. With chat, it can be difficult to maybe misread something so just to be polite and that avoids 90% of the issues.

 

Poornima Vijayashanker:        Then you eventually got over that and learned a number of things over the last year. Let's start with the first thing that you learned.

 

Recommended Tools And Processes To Stay Productive As A Remote Worker

 

Meghan Burgain:     Right. The first thing I learned basically was the importance of the tools that we use. Being that we're not in proximity, we use the tools like Trello and Slack. Trello is great because obviously for communication you can see who's doing what, if it's done or not, but also allows for transparency. You can see the bigger picture: what we're focusing on at Femgineer, what the priorities are, and how that should affect how I prioritize my own tasks as well.

 

Poornima Vijayashanker:        Now, I know another thing you've learned that is even though we're a remote team we still do weekly check-ins where we sync up. Walk us through how weekly check-ins have benefited you.

 

Meghan Burgain:     Weekly check-ins are really important. In startup plans, especially, products change, priorities change, and the weekly check-ins really help me, us both I feel, to stay focused and to stay in the same page working towards the same goal.

 

Training New Remote Hires

 

Poornima Vijayashanker:        Now, I know the third thing is that you were concerned about training, getting trained, training other people. I know as we've scaled the team, you had to train others. How have you gotten over that hurdle?

 

Meghan Burgain:     It's funny that that was one of my reservations and that's actually something that I've been doing at Femgineer. Well, I've realized that training someone via Zoom or Slack, it's not that much different than training someone in person and, in some cases, can actually be better because we can record the training and use it in the future which is what we've done a lot. I've also been relying a lot on our handbook.

 

Poornima Vijayashanker:        What's our handbook?

 

Meghan Burgain:     Our handbook is basically a recipe book for anything that's recurring at Femgineer so whether it's daily or just a certain time of the year, if it happens more than once, it's in the handbook. It's outlined. There's helpful tips and there are links to any outside resources that we might need.

 

Remote Working Benefits

 

Poornima Vijayashanker:        Great. Walk us through what a typical day is like for you.

 

Meghan Burgain:     A typical day I wake up. We get the girls ready. Send them off to daycare. Then I have the majority my day to do the daily tasks that I need to get done, answer emails that came through to do all of my tasks. Towards the end of the day, when the States wakes up, I'm able to schedule phone calls, have meetings and that sort of thing. It's where I base the first part of my day, I didn't have any of those interruptions. I was able to just do whatever I wanted at my own pace. At the end of the day, I have all the things that I need to interact with people. Then I do my to-do list for the next day and it's off to get the kids.

 

Poornima Vijayashanker:        Nice. It sounds like you have a lot of flexible hours.

 

Meghan Burgain:     Oh, yeah. Well, for sure. I have deadlines just like anyone else, but I do have a lot more flexibility with how I get those things done.

 

Poornima Vijayashanker:        What do you think are the key benefits that you've experienced by remote working?

 

Meghan Burgain:     You mean besides being able to work anywhere in the world and in my own kitchen and in my own sweatpants?

 

Poornima Vijayashanker:        Yes. Those are great benefits, by the way.

 

Meghan Burgain:     I would say that the biggest benefit of working remotely is that I've really been able to find a work-life balance that works well for me. I'm able to not only be there for my kids and my family but to provide for them as well. I think that that's just an invaluable thing. It's a win-win.

 

Remote Company Culture

 

Poornima Vijayashanker:        I know for some folks out there they might be on the fence about remote working because of the culture. They might feel like, oh, it's isolated or distant. How have you managed to manage that?

 

Meghan Burgain:     I could see how it could be lonely. You don't have someone just next to you to talk to or whatever but I haven't felt that way and I think to go back to the weekly check-ins, that that's really one of the reasons is that we do get that face time. Also we have Slack which we can talk to all of our team members. I would say when it comes to the culture and the team feeling, you get what you give. It can be tempting in any working relationships, especially in remote working, whenever you find someone that's available within your timezone to just ping them with the 20 questions that you have or to ask a hundred things of them. But, I would suggest to all of you that the first thing that you do to someone should really be to ask them how they're doing, to find out what their interests are. It goes a long way towards creating the spirit and creating a team.

 

Poornima Vijayashanker:        Building a rapport maybe through a water cooler channel on Slack.

 

Meghan Burgain:     Yes. Yes. That's what we have.

 

Poornima Vijayashanker:        Wonderful. Well, thank you, Meghan. This has been really helpful. I know our audience out there is going to benefit from these tips.

 

Meghan Burgain:     It's been my pleasure.

 

Poornima Vijayashanker:        Wonderful. Well, that's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive the next episode where you'll get more helpful tips like this.

 

Meghan Burgain:     Ciao for now.

 

Poornima Vijayashanker:        Ciao for now.

                   

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.

                   

Hey, guys. I'm hanging out here in beautiful Bordeaux and I'll just start again. All right.

                  

In today's Build episode, we're going to talk to you about ...

 

Meghan Burgain:     Remote working.

 

Poornima Vijayashanker:        Yeah, I know. I forgot what I should introduce you before I ... I think I do need to. OK. Take two.

Did you share last week’s Build episode on product design sprints with your teammates?

 

Wait! Give me two chances to guess what the outcome was...

 

… you did and you faced some pushback? Well, kudos to you for putting it out there!

 

… or maybe you didn’t because you were afraid of the pushback you’d get? That is OK too!

 

Charbel Semaan and I are back this week and prepared to help you get over the pushback you received or will receive once you bring up the idea of product design sprints to your teammates.

 

You’ll recall Charbel Semaan has been a product designer for the last 20 years and recently launched his brand, Made in Public.

 

Charbel and I have built a lot of products, and we know that even if our teammates hate the current process and the outcomes it produces, they will still find comfort in it and resist adopting a new one because there’s a lot of fear when it comes to change.

 

But no one is going to willingly admit to being scared, so they’re going to couch their fear in remarks that are skeptical, just say no, or create excuses like: “Now is not a good time.” “We just don’t have the money to run extra experiments.”

 

Then there’s my personal favorite: “Prove to me that this is going to work!” But the whole point of an experiment is to test assumptions by following a process, and then seeing if they were right or wrong. You can’t prove anything until you do the experiment! #chickenegg

 

Because we want you to be really prepared for all the excuses and pushback around a design sprint, here are a few more excuses that you’ll hear when it comes to product design sprints from our friends at Invision. There are also some guidelines and prerequisites that we recommend you consider mentioned in this post to make sure a product design sprint is right for your team.

 

By the time you finish watching today’s episode you will have learned how-to:

 

• Get people to adopt design sprints
• Convey the number # 1 benefit of a product design sprint
• What to do if all else fails and you just can’t get over the pushback
• Make product design sprints work for larger teams
• Convey who does and doesn’t need to be involved in a product design sprint

• Highlight how a product design sprint is different from lean startup methodologies and Agile

 

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

 

Transcript: Product Design Sprints: How To Get People To Adopt Product Design Sprints

 

Poornima Vijayashanker: In the previous episode of *Build*, we shared how you can use design sprints to help you test ideas out faster and get that much-needed feedback. If you miss the episode, I've included a link to it below this video. And of course, anytime you want to institute a new process in your organization, there's going to be some pushback, so in today's *Build* episode, we're going to tackle how you can evangelize design sprints within your organization. So stay tuned.

                               

Welcome to *Build*, brought to you by PivotalTracker. I'm your host Poornima Vijayashanker. In each episode, innovators and I debunk a number of myths and misconceptions related to building products, companies, and your career in tech. Today we're continuing our conversation with Charbel Semaan, who has been a product designer for over 20 years, and most recently launched Made in Public.

 

How To Handle The Pushback When It Comes To Trying Out Product Design Sprints

                               

OK, Charbel, you and I have built a lot of products, and we know that even if our teams hate our current process, and we give them a new one, they're still going to be reluctant to adopt that new one because there's that fear of change.

 

Charbel Semaan: Sure.

 

Poornima Vijayashanker: And we're going to get pushback. So how do we handle that pushback?

 

Product Design Sprints Aren’t Meant To Replace Existing Product Development Process

 

Charbel Semaan: I think one of the ways I found to handle it successfully is to emphasize it's not a replacement to your existing process. It's a way to supplement, complement, or augment. And if you can run a design sprint in parallel and you're really doing it as a side branch to what you're already doing, and it gives you an opportunity to learn quickly in five days, and then be able to integrate that back into your existing processes. It's super helpful.

 

Poornima Vijayashanker: OK. So that's great in theory. But I know having to run a parallel process oftentimes for either a small team or even in a large organization can be a lot of setup. It can mean trying to carve out that time, so one of the key things to consider is what are going to be the benefits. Someone's going to come and say why should we do this, how is it going to help?

 

The #1 Benefit of Product Design Sprints: Speed of Execution

 

Charbel Semaan: Great questions. Why should we do it, how is it going to help. I think there are two key areas. One is speed of execution.

 

Poornima Vijayashanker: OK.

 

Charbel Semaan: And what comes along with that, with the sprint, is constraints. And through those constraints you get clarity. So you're moving quickly, you're going from thinking to action in a quick way, and you're also constraining yourself so you don't have an infinite amount of time to decide what features, what angle, should we try it this way or that way, so you get to move quickly and you constrain yourself, so you get to clarity faster.

 

Poornima Vijayashanker: OK. So I'm sure for our audiences out there, there's probably going to be some pushback around, ah that's great on like a nimble team of maybe five, six people—but I've got 10, 20, 30 decision makers or stakeholders. I'm not going to be able to mobilize my team fast enough. So how do we get to handle those folks?

 

Can product design sprints work for larger teams?

 

Charbel Semaan: Yes. I think you can work with those 10 to 20, or even 30 people to understand what are some big problems that you're facing, that you'd want to solve, that are top priority, or they're really affecting and impacting your productivity and your flow, your ability to ship.

 

Poornima Vijayashanker: Even if they're conflicting?

 

Charbel Semaan: Even if they're conflicting. I think you first start by gaining an understanding. So with a team that large, I've got 20 to 30 product managers and squads of teams of PMs and developers and designers, etc. You gain an understanding, if you're that org leader, gain an understanding of what are some of the top big, immediate problems that are affecting the team and affecting shipping and product and affecting the business. And prioritize those. And then think about if I can run a sprint, if I could run something within five days and gain clarity and be able to unlock some blocker that's going on across those 10 to 20, then who of that large group, who would make most sense to bring into this sprint.

                               

We're not going to stop the presses on everyone's workflow. But we can at least prioritize, run a sprint with some key players, see how that goes. In some ways it's a look at like an 80-20 perspective of 80% of the orgs, when you continue going as-is, there's going to be this 20% or even 90-10, there's going to be this small experiment we're going to run. And if that's successful, then we can see if we can apply it to other areas or aspects of the org, no matter how large.

 

Poornima Vijayashanker: Of course there's fragile egos. So some people are going to want to be in that special pool.

 

Charbel Semaan: Sure.

 

Poornima Vijayashanker: Why wasn't I picked?

 

Charbel Semaan: Sure.

 

Poornima Vijayashanker: So how do you message that?

 

How To Convey Who Does And Doesn’t Needs To Be Involved In A Product Design Sprint

 

Charbel Semaan: Not easily. Not easily. It's not always easy. I think one thing I've found a bit helpful is to communicate openly that we understand we have X-Y-Z challenges. We're all clear on that. And there's...hopefully you have consensus, you have agreement. And from there it's...we can't tackle them all at once. We all agree to that. And so I think you're gaining that consensus and that understanding. That mutual understanding. And then communicating, we want to try something that might help us start to chip away at the stack of challenges that we have. We're going to run small experiments. As those turn out to be successful and we learn from them, we want to continue embracing and permeating through more teams and more people in the org.

                               

So it's coming and if it's going to work, they know it's coming, if you have a deep interest and you have a really...you're raising your hand and you really want to be a part of this, please come to tell me. If you're the org leader or the business leader, whoever you are. I think that kind of openness and communication starts to also be a signal for you to understand who are the people who, as you mentioned before, who are the people who can become those evangelists and those change agents in your organization as influencers to adopt something new like design sprints, and then be able to take it to their parts of the org as well.

 

Poornima Vijayashanker: I think it also serves as a signal to see how open your organization is, right?

 

Charbel Semaan: Absolutely, absolutely.

 

Poornima Vijayashanker: So I think maybe some people may get disheartened as they do this exercise and find out that they're not getting a lot of interest, so how should they take that? It's not a reason to send in your resignation letter.

 

Charbel Semaan: No, no, not at all. Don't do that yet. I think one thing though, is just discussing with a CO of a global manufacturing business, is people need to feel involved. In my experience, in org development and innovation with an organization, especially large ones that no one really wants to have something just told at them, and that this is the way we're doing things now. So introducing something like a design sprint into your organization, that can foster and cultivate innovation throughout all your people. Doing so by involving them.

                               

So first it just starts with communicating that. We're thinking of doing something new. Who has some initial interest? They're like you said, you'll start to see if there is or isn't. That might be an indicator that are you really getting that kind of engagement from your folks, and as you test and as you do small experiments and you see who continues to raise their hand and want to be more and more involved. And when you're not seeing that engagement, it may actually be an opportunity to run a design sprint on internal communications.

 

Poornima Vijayashanker: OK, yeah.

 

Charbel Semaan: So that's the beauty of it for me is, I think you can sprint on any kind of challenge you have.

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: It may not always be a business challenge in the product sense, or in the service sense. Sometimes it may be about your internal organization.

 

Poornima Vijayashanker: And what happens if you get too much interest? Everyone's like, “Oh yes, I want to participate,” and all of a sudden you've got your 5,000-person organization and it's like, “I've got things to say. I see things that are broken.” Yeah, I get this a lot when I go into places.

 

Charbel Semaan: Sure, sure. I think for starters, I think that's a great problem to have. I think you want that level of engagement, that employee engagement, and your people care about solving challenges in your business. It's far better than the opposite. Two, there is such a thing called mega sprints, and Jake Knapp actually runs mega sprints, which were pretty interesting, where there's simultaneous sprints happening in one large room.

                               

Short of that, the—to your point about the question is to get to a place where there's an opportunity for people to raise their hand, have a voice, to be able to add to the mix and add say, “Here's the challenge I'm facing,” and then it's really, I think, an opportunity to create a culture of that mindset. So I go back to design sprints not just being this rigid five-day process, and the irony is it's...it can be viewed as some rigid five-day process even though it's a sprint, it's meant to move quickly. The reality for me is that when you embrace it as a mindset, and that people in your organization, no matter if you have 5,000 people with 1,000 problems each, it's an opportunity to think, “How could I solve this problem or test a new idea quickly, and can I use the framework of the sprint, can I use the elements of the sprint to take action faster?”

                               

And I think anybody who's leading an organization, no matter how small or large, would love for their people to have that type of empowerment and to be able to feel enabled and equipped to take action.

 

How Product Design Sprints Different From The Lean Startup Methodologies And Agile

 

Poornima Vijayashanker: Now there's also a lot of skeptics out there who might say, “Yeah, you know, I hear what Charbel's saying but I've tried something like this a year ago, or like five years ago we tried lean or agile—how do I know that this is the new thing?” So a lot of times the concern is how is this going to be any different from what we tried in the past that failed miserably, and in the wake of it, caused a lot of destruction.

 

Charbel Semaan: Yes. Great question. This has actually been coming up recently for me and I've been doing more and more review and research on this. I think for starters it's valid. It's absolutely valid to be wondering, “Great, this is just the methodology du jour. This is now the new thing, and everyone's going to jump on this bandwagon.” I completely understand that.

 

Product Design Sprints Are All About Constraints And Speed Of Execution

                               

What I come back to though is the corner about the mindset. Lean can be thought of as a mindset. Agile can be thought of as a mindset. It's a way to knock down blockers that otherwise impede you from trying something, learning from it, and iterating on it. So whether it's this model, that model, or this or the other. I think the nice thing about sprints is that for me as a designer, because it's rooted in design thinking, and it provides this construct to float through five days—and again I mentioned clarity through constraints and that speed of execution—it gives you an opportunity to go from empathy all the way to testing the idea. And prototyping is of course in there, inside of that.

                               

Whereas lean is focused on build, measure, learn. So you just start out by building and you're going to put it out and then learn from the reactions. As a designer I am a big believer in that initial upfront step of empathizing and understanding. When you understand what that problem is and who you're solving it for, and it carries you through that initial slice of the prototype that's just enough to get in front of users, and I have a hard time imagining folks who wouldn't want to move faster and learn more, and be able to then iterate.

                               

And this is one way of doing it. It's a methodology that I've embraced that I...it gets me out of my own decision deadlock as well.

 

Poornima Vijayashanker: Yeah. So in the wake of that kind of feedback around, “Hey, how is this going to be any different, you're saying treat it as a mindset,” hopefully people are willing to adopt a new mindset or at least test it out. But there are also those who start to get kind of nitty gritty, right? They might say something like, “Oh, I don't even know where to get customers to test this prototype,” or, “I don't want to bother our existing customers.” How do you get over some of those more practical hurdles?

 

Charbel Semaan: Sure. That's a great question. On the customer front, I think, on one hand, you hopefully have a pocket of customers who have a major interest in everything you're doing. They want to be those early adopters. They want to test new features. They're your biggest fans. And so on one front you can always start with them and then treat them right, treat them in a way where you have this open communication that we appreciate coming to you because you're such a fan of ours and we're a fan of you, and we want to come bring you our latest and greatest to see are we doing right by you. Are we solving the problems that you need solved, are we getting the jobs done that you need done through our software or through our product or service?

                               

So I think on that front you build those ongoing and sustainable relationships with them.

 

Poornima Vijayashanker: And if it's a new customer base?

 

Charbel Semaan: If it's a new customer base, I think going back to that understanding the problem and understanding who. When you understand those two things, it's surprisingly simple to find where they are. If you understand their habits, you understand their desires and their pains and their struggles, you understand where they seek the solution to this problem elsewhere, you can go to those places.

 

Poornima Vijayashanker: So do you have an example of a situation where a lot of these practicalities started to add up and people just completely lost sight of making a decision on design sprints?

 

Case Study of A Product Design Sprint

 

Charbel Semaan: Yeah. Great question. There's an example where...come back to the internal learning development team at Medallia. We had big needs, we had problems to solve in terms of scaling, training, especially for the growing sales team, the growing engineering team, which are very common teams that start to spark and grow quickly. And especially globally. So how do we scale the training? And practicalities like, well, video's going to be expensive. Getting all the equipment. Having the studio. Do we even have time to shoot video and do that. People don't watch online learnings. A lot of the common...what might be common sense or these truths that we think we have in our businesses, and the reality was when we ran a sprint, it was actually a colleague of mine and we ran a sprint.

 

Poornima Vijayashanker: So how did you get over that hurdle to actually get them to run the sprint given these practicalities?

 

Charbel Semaan: That's a good question. There were a couple of people who were advocates. They wanted to embrace it.

 

Poornima Vijayashanker: OK.

 

Charbel Semaan: And the challenge was showing that running the sprint and the output of the sprint...the output of the sprint was actually more important than the sprint itself in a way. So because the output...and first they wanted to embrace the approach. They embraced the approach. They wanted to try it. And they wanted to get to that output. So we shared that video with the entire HR organization, and the output, the video itself, was what people focused on. Then when they wondered, “Well wait a minute, when did you do this and how did you do it so quickly?” That's when we were able to say, “Well, we ran a sprint on it.”

 

Poornima Vijayashanker: Interesting.

 

Charbel Semaan: And we just shortcut a lot of the decision deadlock, a lot of the concerns and a lot...we did it with an iPhone on a makeshift tripod in this corner office that we blacked out the windows and we were able to just run with it. And it's not the greatest-looking video but it's a prototype. Then people realized, “Wow, we can go this quickly and this nimbly, why don't we embrace this and actually try to do more?”

                               

And the greatest part about that—I love the outcome here—is that, the head of the team said, “Great. Here's a budget to go get the equipment you need, on a reasonable amount of money, and why don't we use this corner room more frequently for these videos and let's run with this.”

 

If All Else Fails: Show People The Output of The Product Design Sprint

 

Poornima Vijayashanker: So that's pretty cool. You basically turned design thinking on its head. Instead of trying to get people to adopt the methodology, just show them the output, tell them about the outcomes, and then when there's a curiosity for how did this all come about, then you can say, “We used design thinking.”

 

Charbel Semaan: That's right.

 

Poornima Vijayashanker: Cool. And I think then people are going to start to embrace it in more sections of the organization, or on more projects.

 

Charbel Semaan: That's right.

 

Poornima Vijayashanker: Well, that is an awesome insight, Charbel. So for those of you out there who are stuck, feeling a lot of pushback, maybe instead of trying to get people to adopt the methodology, present them with the output and the outcomes and use that to strike the conversation.

                               

Thank you for joining us, Charbel, and for our audience out there, how can they get in touch with you?

 

Charbel Semaan: Great. Thanks for having me on. This has been blast. You can reach me at [email protected], and visit madeinpublic.com, and see the projects that I'm working on, the sprints that I run publicly to help teach and empower to run sprints themselves. And sign up for the newsletter as well.

 

Poornima Vijayashanker: That's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive more great episodes and short build tips. Ciao for now.                                

                                                 

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.

How many times have you and your team spent countless hours building, bug fixing, finally releasing a new feature only to hear feedback from a customer that it’s not what they wanted?

 

Or worse, they don’t say anything…

 

Why?

 

Because they aren’t even using the new feature!

 

Back to the drawing board…

 

Yet again it again takes weeks or months to build and tweak and nothing changes. You just keep missing the target, asking for more time, money, and resources.

 

But it doesn’t help, and people just end up burning out building the wrong thing.

 

What if I told you that the problem in your product development process is that you are spending too much time, money, and resources and need to cut back?

 

OK, I’ll give you a minute to shake your head at me...

 

Sometimes when we have too much it causes us to go in a lot of different directions. Or worse no direction at all because we’re stuck in a decision deadlock!

 

We lose sight of our customers and end up building just for the sake of building, thinking that we know what problem we are solving, but we don’t.

 

As a result, our product debt keeps growing and a redesigns don’t help.

 

So how can we stop building the wrong thing and solving the wrong problem?

 

We can start by constraining the amount of time we have to help us focus on uncovering and solving one problem at a time.

 

And in today’s episode, we’re going to dive into the framework behind this new approach called product design sprints.

 

To help us out, I've invited Charbel Semaan, who has been a product designer for the last 20 years and recently launched his brand, Made in Public.

 

If you’re eager to get an idea out, worried about how long it’s going to take your team to execute, and concerned about wasting time, money and other resources, then you owe it to yourself to watch today’s episode!

 

Here’s what  you’ll learn:

 

• What is a design sprint
• When does it make sense to a product design sprint
• What do each of the days look like
• How constraining the time, energy and money you spend on a problem leads to clarity
• How a product design sprint can benefit your overall product development process

 

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

 

## Product Design Sprint: How a Product Design Sprint Fast Tracks Testing Your Ideas Transcript

 

Poornima Vijayashanker: Eager to get an idea out there but worried about how long it's going to take you and your team to execute? Well, in today's *Build* episode, we're going to show you how you can embrace design sprints as a way to test your ideas and get your prototype out there faster. Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. In each episode, innovators and I debunk a number of myths and misconceptions related to building products, companies, and your career in tech.

 

One misconception a lot of us fall prey to is this need to do a massive build out before we launch a product. The results, unfortunately, are that we end up spending a lot of time, money, and energy possibly building the wrong thing. As a result, customers don't want it, teams burn out, and companies lose sight of their business goals. In today's episode, we're going to tackle this misconception, share with you how you can embrace design sprints to help you iterate faster and get your prototypes out there, and in future episodes, we'll talk about how you can evangelize design sprints within your organization and handle any pushback that you might get from your teammates or stakeholders. To help us out, I've invited Charbel Semaan, who has been a product designer for the last 20 years and recently launched his brand, Made in Public. Thanks for joining us today, Charbel.

 

Charbel Semaan: Thanks for having me.

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: I'm excited to be here.

 

Poornima Vijayashanker: Yeah. For our audiences out there, let's start by digging into your background a little. I know you've been a designer for the last 20 years and recently started Made in Public, but walk us through that evolution.

 

Charbel Semaan: Sure. I started out as a designer, self-taught, when I was 15 and fell in love with it. I continued to design through college, would dabble with side projects, and never formally studied it and was formally trained, but continued to develop my skills as much as I could. I've had this interesting blend of design specialties throughout my career. I've done product design, brand design. I've done curriculum design for training programs. Bringing all of that together, I've realized I've broadened my career or widened my career. What I enjoy most is using design as a way to solve problems as a methodology, and I also enjoy teaching it. I enjoy teaching designs so people can embrace it in whatever area of work they do.

 

Poornima Vijayashanker: Yeah, that's great. Now, what does Made in Public do?

 

Charbel Semaan: Made in Public now combines all of that and I get to run my own side-project design sprints. I run sprints publicly so people can see what it's like to go through the process of going from idea to action in a very short amount of time.

 

And then in that way, as well, I use it as a way to teach. I really like to teach design through live experiments.

 

Poornima Vijayashanker: Let's dive into today's topic of design sprints. Before we talk about what design sprints are, let's maybe start with that product design background that you have and showcase what you saw was broken and why the need, maybe, for a new process.

 

Why Do We Need A New Process For Designing Products

 

Charbel Semaan: Sure. I think part of it is...there may not always be something that's broken, per se. I think design thinking has influenced my career heavily, and I've learned a lot through what IDEO has put out into the world and other great design firms out there. I think design sprints, in some ways, is a derivative of design thinking. It's another way of thinking about the design process.

 

What it can help guard against or help avoid are things like decision deadlock. Or it helps guard against overthinking what the big thing should be and helps you pair down because of constraints. You have five steps, and according to the Google Ventures-inspired design sprint and Jake Knapp and the author, the co-authors, the five-day approach constrains you so you're not trying to build something that could take you five months.

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: Really, you're trying to create something in five days.

 

What Does A Product Design Sprint Look Like

 

Poornima Vijayashanker: Let's talk about what that looks like. What is that design sprint over those five days?

 

Charbel Semaan: Sure. The first step of the five steps, or five days depending on if you want to compress it even further, the first step is to understand. Map and understand and unpack the problem you're trying to solve and for whom you're solving it.

 

I think for anybody who's creating any kind of product, it's always essential to get down to: what problem am I solving, and who has the problem?

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: And do I understand that person and their journey and how they first might interact with my product all the way through to the interaction and to the end result, or what I like to call the desired outcome? What's the desired outcome that they want after using your product? What is it solving?

 

Poornima Vijayashanker: It's one person. A lot of times, we have multiple users or multiple personas, but in this design sprint, we're going to limit ourselves to one persona.

 

Charbel Semaan: You can. It's important in that unpacking and understanding to understand: who might the other people be?

 

Poornima Vijayashanker: OK.

 

One Key To A Successful Product Design Sprint Is To Pare Down The Problem And Who You Are Solving It For

 

Charbel Semaan: If there are multiple people, acknowledging that and having an understanding and awareness of that is great. Then you might, through the rest of the course of the sprint, you might say, "We're only going to focus on this one particular person or particular user of the product, because that's basically the breadth that we have." We can't really do much more. We know we've got other folks, but we're at least going to focus this sprint on this person.

 

Poornima Vijayashanker: Got it.

 

Charbel Semaan: And then that leads to, when you understand the problem, and you understand that person and how they're facing that problem, then the second step is to sketch. This is a fun part where...this is where most people want to get into brainstorming and get a lot of ideas on the table. One of the things I like to say—and I borrow this from what I've learned through IDEO—is to think with your hands.

 

Now you get to actually get pen to paper, pen to Post-its, and you get to sketch a variety of solutions. If you've got about six or so people in this room with you, even if you're running it with a co-founder or you're running it solo, this is where you get a chance to get a number, a variety of sketches out on the table or out on paper.

 

Poornima Vijayashanker: OK.

 

Charbel Semaan: The third step is to decide. You go through all the sketches that you've laid out, and through a number of exercises, like noting and voting and dot voting. There are a number of different ways to approach it...you actually decide: what will the blueprint be for your prototype?

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: And then the prototype is the fourth step.

 

Poornima Vijayashanker: Yep.

 

Charbel Semaan: That's where you actually get to create a realistic version of what you want this product to be, or the service, for that matter, and you get it out to real users by the fifth step or the fifth day. That's where folks get to interact with what you've created, the prototype, and then you can learn and observe and understand what you can improve, or did you—and this is a key part—did you validate your hypothesis? Did you validate or invalidate what you had sought out to figure out?

 

How Dot Voting Works In A Product Design Sprint Gets Rid Of Decision Deadlock

 

Poornima Vijayashanker: There's a few things going on. Let's kind of unpack them in more detail. The first is, you mentioned this concept of voting and dot voting, which I like the concept a lot. I've started implementing it. But maybe for our audience out there who's not familiar, we can shed some like into what that is.

 

Charbel Semaan: Sure. One of the exercises after you've gone through sketching...let's say you're in a room with about six people. You're running the sprint with six people.

 

All six people have generated really interesting ideas and really interesting concepts or mock-ups of what the product might be. Dot voting and noting and voting, especially if you've decided ahead of time—and hopefully you have—who the decider is. There will be one person who's going to be the decider, and they get the majority vote, or they get extra votes.

 

Poornima Vijayashanker: Right. Two votes.

 

Charbel Semaan: Or extra dates. Exactly.

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: One of the things that's fun is doing what's called a museum gallery, where everyone's mock-ups on their 8-1/2 x 11 sheets of paper and Post-its go up on the wall. Everyone has a chance to review everyone else's mock-ups. You can vote with dots, like a marker and dots, on the elements or aspects that you find compelling or you find interesting. When it comes to decision time after the voting and whatnot, you actually get to distill the best ideas from the entire group. That's one of my favorite aspects of the sprint, is that...some people say, "Oh, I'm not very creative."

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: Or, "I'm not the designer." Or, "I'm not the engineer. I'm a technical person."

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: What I have found is when you bring a collective creative together like that, then sometimes the best ideas come from someone you might not expect to come from.

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: Then the voting allows for decision making, because you can't do all the features. The voting helps you distill it down to some of the key elements that you want to focus on for the prototype.

 

Who Needs To Participate In A Product Design Sprint

 

Poornima Vijayashanker: Let's talk about who needs to be involved in this process. We've already kind of mentioned that designers, engineers are great, people who are going to be building out that final prototype, but who, aside from them, needs to be involved?

 

Charbel Semaan: Great question. I found what's very important is to have someone who is part of the overall decision-making process. That can either be one of the founders or any of the founders or all of the founders, someone who's at a VP level or a C-suite level, depending on the structure of your organization and how large your organization is.

 

Poornima Vijayashanker: So maybe whoever understands the business goals?

 

Charbel Semaan: The business goals, for sure, and anyone who is even involved in sort of the direction and vision of the overall business.

 

Poornima Vijayashanker: OK.

 

Charbel Semaan: Certainly the people who would be doing the building itself and the designing itself, and definitely folks who are involved in the business side of things.

 

Poornima Vijayashanker: Why? I mean, doesn't that feel like they're micromanaging? Shouldn't they just trust their designers and engineers and let them run free?

 

Charbel Semaan: Yeah. It's a great question. One of the key principles of design that I've embodied and believe in so much is this two-part or two-fold aspect of inclusivity and collaboration.

 

You want to be inclusive and collaborative, and that avoids this waterfall effect where...if just the engineers and the devs and the designers are in the room, and the so-called business folks are out of the room, then it becomes this, "Now let's go back and take it to them and show them this, get approval, and then..." But when folks are in the room together, that's when those ideas can come out. More often than not, an idea gets sparked from one person, and especially if you embrace this yes/and approach.

 

It's like, "Oh, that's a great idea. You know, what if we also did this." Or, "Could we also try this?" "I didn't think of that. That's great. OK." And then you get back to that voting and say, "Great. We can't do it all, but let's distill them." You actually have a richer conversation and a richer collaborative experience when you include more aspects of the business.

 

Poornima Vijayashanker: Yeah. I think that's great that you're bringing all these people to the table, involving them in the process. Now, that's obviously a lot of overhead, right, for a founder or for a VP or some of these people to come in and sit in on a five-day design sprint. I'm sure there's going to be some pushback around it, which we're going to get to in the next episode. But for the purpose of this episode, how do we kind of constrain the time so that they don't feel like they're sitting in on a whole-day session?

 

Charbel Semaan: Right. I think there are a couple of ways of approaching it. One is to think about design sprints more as a mindset, or an approach. The pushback I hear a lot is this five-day—"We don't have five full days to have six critical members of our team..." I completely understand that. It makes a lot of sense. The response I often share to that is, "Would you rather invest up front in those five days, where all five or six of you or seven of you can come in, and you're investing that time, which is money. I understand. Would you rather invest that and have the opportunity to come out with something that yields you a real opportunity to engage with a real prototype with real people in five days instead of five months?"

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Instead of five months of a bloated product that you're not even sure is actually something that the people want or are going to use or pay for.

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: You haven't validated. You may have those silos that you mentioned earlier. There tends to be tension. I mean, we've experienced it where there's tension between engineering and design and product and marketing and sales, etc. And you mentioned earlier about the business folks. It can be the founders. It can be the head of sales. It can be anyone who's involved in key elements of the business. When you bring them together for those five days, you tend to circumvent a lot of wasted money, wasted time, and I come back to decision deadlock. That's a key thing I've noticed, is the inability to get through that decision, that blocker, that keeps them from—

 

Poornima Vijayashanker: Yeah. Let's talk about that. Yeah.

 

Charbel Semaan: Sure. The key thing about the sprint...and whether it's five days...sometimes it can be compressed to three if done well. I've tried one. It's very hard.

 

Poornima Vijayashanker: Yeah.

 

How Having Constraints In A Product Design Sprint Leads to Clarity

 

Charbel Semaan: It's extremely challenging to do it in one day. I don't always recommend that. But the key part about the decision deadlock in the sprint—when you're using the sprint as a methodology, as an approach and a mindset, as opposed to fixating on the number of days and time—is it's going so fast, and there are so many constraints, that constraints lead to clarity.

 

You don't have a whole lot of time to spend on, should it be this way, or should it be that way? You're simply saying, "Here are the ways. Let's pick one, and let's try it. We're going to find out if it's validated or not—”

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: “—and then we can run another one again."

 

Poornima Vijayashanker: I see. That's great. Yeah, because I think that's actually...I was going to ask the question around scope creep, but it sounds like if you're whittling things down, it becomes very obvious what that particular thing is that you're building, whether it's a feature or whatnot, and what the problem is that you're solving versus all these other problems that might be tangential.

 

Charbel Semaan: Right.

 

Poornima Vijayashanker: Yeah, you get that real level of focus, but I'm sure unifying people around what that one thing is is a challenge.

 

The Role Of The Facilitator In A Product Design Sprint

 

Charbel Semaan: It is. That's why it's important at the start of the sprint for me, as a facilitator, to first get permission and to get that commitment from everyone that I'm here to facilitate. I'm here to guide the process and really help extract or be able to foster and cultivate their ability to create and to go validate what it is they're trying to find out. The second part is having that decider in the room. When everyone agrees and commits to who the decider is...and for that decider to be convicted in their decisions and to truly commit to, "Lot of these things are great things we can do. We could save them for another sprint. We're really going to hone in on and focus on this particular aspect."

 

Poornima Vijayashanker: I could imagine that whoever the decider is needs to have done their homework and be really wedded to the customers, the problem. Are there ever times where they're not sure? They may need to say, "Oh, you know what? It's two problems here. Not really sure which one. I need another day to go back and do research, or a week," in which case, now you're holding up the sprint.

 

Charbel Semaan: Yes. Great point. Again, the beauty here is, because you're aiming for that fifth step or that fifth day to get the prototype in front of users, to take another day, which will turn into a week, as you said, is not helping anyone.

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Instead, note that you've got this second thing that you might want to do, or you think you have a hunch that maybe that's also a problem. It very well could be, and that's perfectly fine. Just let it be there.

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Pick one and go with it, and get to that fifth day or get to that fifth step. Get the feedback. Learn from it. And observe how folks are interacting with it, whether it's a feature, like you said, or it's the entire mock-up of a product, and then iterate and do it again.

 

Poornima Vijayashanker: OK. Yeah, so then there's not a lot of leeway for ambiguity, and you have to get comfortable making those firm decisions to keep the sprint moving forward.

 

Charbel Semaan: Absolutely. I think that's the key part, is to be convicted in your decisions and to keep moving forward, because this is a sprint.

 

Poornima Vijayashanker: Yeah, yeah.

 

Charbel Semaan: You're just getting to that finish line.

 

Poornima Vijayashanker: We've talked about these five days. Day one is sort of this brainstorming session.

 

Charbel Semaan: Day one's actually unpacking and understanding.

 

Poornima Vijayashanker: OK.

 

Charbel Semaan: You want to have a good understanding of the problem and who has the problem. Then you go into sketching a variety of solutions. The third day, you decide what you're going to prototype. The fourth day is the actual prototyping. And the fifth day is getting that prototype in front of real people.

 

How To Measure Success For A Product Design Sprint

 

Poornima Vijayashanker: OK. How do you know, once you've done these five days and put something out there, whether or not the sprint was successful?

 

Charbel Semaan: That can vary sometimes from team to team and people to people, and depending on the product and service. What I like to anchor to, though, is, did you get some level of a lightbulb moment or an a-ha moment?

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Did you learn something? If you didn't learn anything by the end of the sprint, then you may not have understood the problem as deeply as you thought you did, and you may not have understood the person for who you're solving it for.

 

Poornima Vijayashanker: Nice.

 

Charbel Semaan: I like to measure it in terms of, on one hand, there's the analytical side.

 

Poornima Vijayashanker: Sure.

 

Charbel Semaan: Like, do we get buy-in, or do we get people who are turning into customers saying, "If you're going to launch that and that actual product in the next two weeks or month, OK, here's my preorder"? Great. On the other side of it, have you learned something from it?

 

Poornima Vijayashanker: Mm-hmm. Even if it's an epic fail here, nobody likes it, they thought the feature was just crap, there's insight there where it's like, "Hey, we're not going to be building that."

 

Charbel Semaan: Right.

 

Poornima Vijayashanker: Or, "We're not going to flesh that out in greater detail."

 

How Product Design Sprints Help You Fail Faster And Cheaper!

 

Charbel Semaan: Like the majority of my products and ideas. I've learned something, though, or the team has learned something. If it's an epic fail, great. And this goes back to what I mentioned earlier. Would you rather have the epic fail and realize that in five days, or five months later after you spent tens of thousands of dollars or more? If you're outsourcing it, tens of thousands or more. If you've got an internal team, and you've got all your engineering and design and development time and dollars, that a-ha moment can go on the positive. Let's keep moving forward with this. We're onto something...or it's the, "OK, start over. But at least we only spent five days doing it."

 

Poornima Vijayashanker: Right. Yeah. I think that time investment is great. I think even in those epic failures, a couple things develop. You now have a process with your team. There's some comradery and some communication barriers that have been broken down. Then there's still some interesting customer insights. A customer telling you, "Hey, I didn't like this feature. What I was really looking for was X, Y, Z," that's a valuable conversation to have.

 

Just kind of developing, like you said, that confidence around, "OK, I'm going to practice active listening for what it is they're looking for."

 

Charbel Semaan: Great point. There are two things that...

 

Poornima Vijayashanker: Yeah.

 

How Product Design Sprints Bring Teams Together And Improve Communication

 

Charbel Semaan: You just triggered a couple of thoughts for me. One is on the team communication and bonding front. What I've noticed is the team ends up developing a common language and a common baseline or foundation to work with. The next time, I'll hear something like, "Well, why don't we go sketch this? Let's go sketch some...we're talking about a lot of ideas or a lot of ways that we could do this feature. Let's just sketch them out, and let's vote on them." Right? "And let's make sure one of us is the decider," or whatever it might be. The other part that you mentioned around the lessons that you'll learn from the actual people who are interacting with is, more often than not in my experience, folks don't simply say, "I don't like that feature."

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Or, "That didn't solve my problem. Thanks. Bye."

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: They're usually walking through. And if you're facilitating that empathy interview and that observation time, you're asking questions like, "Could you walk through, think out loud, while you're engaging with this?" More often than not, they're going to say something like, "Well, this confuses me. I'm not sure what this does. I kind of wish it would do this."

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Or you could ask, "Well, what do you wish it would do for you?" You're going to learn so much more. It's not a binary: they didn't like it and you're going to walk away.

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: You're still going to learn so much, like you said.

 

Poornima Vijayashanker: OK. We've run a sprint. We got some feedback. Maybe it was successful. Maybe it was not successful. But what's the next step?

 

Charbel Semaan: The next step, I think, is to understand: what did you get out of this? What was the yield? Did you learn something about what's working, and you want to double down on that?

 

You can double down on that in your existing product development methodology, whatever you have. Maybe it's agile, or whatever it might be.

 

If it's something that turned out to not work out so well, it was a failure—if you want to call it that—then you could think about, "Well, could we run a sprint on one of those other ideas that we sketched out?" Or taking what we learned from the people who interacted with it, it turns out, we had that in some of the sketches. Why don't we incorporate that next?

 

Poornima Vijayashanker: Oh, nice. Yeah.

 

How Product Design Sprints Help With Your Existing Product Development Process

 

Charbel Semaan: You may not run another five-day sprint the following week, but you now are so much more informed about your existing product development cycle that you could start to pull in some stories, if you run agile, or whatever your approach is.

 

Poornima Vijayashanker: OK. The idea is to use design sprints for moments where you've got a lot of ideas, you're not sure which one to execute on, and really for that quicker design feedback, but not as a standalone methodology for every week, we're doing a design sprint.

 

Charbel Semaan: I don't think so.

 

Poornima Vijayashanker: Yeah.

 

Charbel Semaan: Yeah. I think it works out better in the way you described it. I think, particularly, sprints are great when you start to notice a little bit of that clog.

 

Poornima Vijayashanker: OK.

 

Charbel Semaan: You're getting to that decision deadlock, or you've got a problem you want to solve, but you're just grinding on it.

 

Poornima Vijayashanker: Right.

 

Charbel Semaan: The sprint allows you to just get moving. It allows you to go from thinking to action.

 

Same when you have a new idea. You've got lots of new ways that you think...well, we think we might be able to roll out a feature that could generate another hundred grand in revenue. Or we think we could branch off the product. There's this whole other market, and that could be a million-dollar product on its own or more. Well, run a sprint on it instead of thinking about it or figuring out, “could it be? Should it be? What do we do with it?”

 

Poornima Vijayashanker: I'm sure other teams—maybe marketing, sales, customer support, all these other teams out there—are probably going to start embracing design and using it. Have you seen the design sprints used for other things?

 

Charbel Semaan: Yeah. Actually, this is my favorite part.

 

Poornima Vijayashanker: Yeah.

 

Why Product Design Sprints Aren’t Just For Product Teams

 

Charbel Semaan: It's not just for product teams, at least anymore. Two favorite examples of mine, where teams that you might not expect have used design sprints and they've used them successfully: learning and development team at Medallia used a design sprint. We ran a design sprint to think about: how could we start scaling training across the entire company through video and through online learning? We ran a sprint where we had a scrappy video set up in one of the small corner offices, and we got out an example, a prototype, of a training video on a completely low, tight budget. It showed a proof of concept to the team and the entire organization what's possible.

 

My other favorite example is my friend Brian Bautista at SoundHound. He's the customer support person and customer success for SoundHound, and he's been transitioning, actually, and has officially transitioned to the product marketing team because of a prototype and a sprint that we ran.

 

Poornima Vijayashanker: Cool.

 

Charbel Semaan: Not necessarily on the product itself, but he was helping educate on the product and wanted to ensure that people were using SoundHound and Hound in the best possible way. What he wanted to do was test a new type of video. It was more personable. Could showcase a little bit more of the humanity of the brand and the personality of the brand. In eight hours, believe it or not—

 

Poornima Vijayashanker: Oh, cool.

 

Charbel Semaan: —ran a prototype on what that video could be, takes it to his VP of marketing, and she loved it and greenlit more videos.

 

Poornima Vijayashanker: Well, thank you so much, Charbel, for teaching us about design sprints today.

 

Charbel Semaan: My pleasure.

 

Poornima Vijayashanker: Yeah. For all of you out there who are watching and listening, Charbel and I want to know, is there something that you've been stuck on? Maybe a decision deadlock when it comes to a product or a service, or even something in your personal life. Let us know what it is in the comments below this video. That's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive the next episode, where we'll dive into how you can evangelize design sprints at your organization. Ciao for now.

                                                 

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.

Transcript for What Is Product Debt And Why You Need To Prioritize Paying It Down

 

Poornima Vijayashanker: Did you recently show your designs to an engineer and hear this?

 

Ronan Dunlop:       It is going to be challenging to implement in time for the next release.

 

Poornima Vijayashanker: Why?

 

Ronan Dunlop:       They're pretty complex.

 

Poornima Vijayashanker: Why are they complex?

 

Ronan Dunlop:       This slider alone is new functionality that is going to take at least two days’ worth of time to implement on the front end, maybe more.

 

Poornima Vijayashanker: OK, what else?

 

Ronan Dunlop:       To do these visualizations we're going to need to pull in a lot of data, and that's going to slow down the performance of the app. Some of these new workflows require changes to our current APIs, which have already accrued a significant amount of tech debt.

 

Poornima Vijayashanker: OK.

 

Ronan Dunlop:       It doesn't seem doable for the upcoming release. I'd recommend changing the designs.

 

Poornima Vijayashanker: I think we should go talk to Leslie about the importance of paying down product debt in every release.

            

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker, and I've got a new *Build* tip for you. Remember we talked about tech debt with Jay Hum from Pivotal? If you missed that *Build*, tip I've included a link to it below this video. Today we're going to explore product debt. To help us out, I've invited Leslie Yang, who's a Senior Product Designer at Pivotal Labs. Thanks for joining us, Leslie.

 

Leslie Yang:    Thanks for having me.

 

Poornima Vijayashanker: So Leslie, tell me what's product debt?

 

Leslie Yang:    Great question. Product debt is the debt that a product incurs when the UX is really starting to change and cease to be as successful and helpful as it used to be.

 

Poornima Vijayashanker: Can you give some examples?

 

Leslie Yang:    For example, you'll hear someone say, "Hey, I want to test this new feature. Where should I put it? Let's put it in the tabs." You're like, "Should we put in the tabs? Let's go figure this out."

 

Poornima Vijayashanker: What else?

 

Leslie Yang:    Let's see, so you can say that our workflow is complicated because our users have gotten so used to it, so we just end up annoying them or losing them if we change anything.

 

Poornima Vijayashanker: Anything else?

 

Leslie Yang:    Another one is we just added a new feature and we want to promote it, so can we just add a button next to everyone's name and just highlight the hell out of it? No.

 

Poornima Vijayashanker: These are all great examples I think of product debt that we have experienced both as consumers of a product, but also folks who are designing products?

 

Leslie Yang:    Absolutely.

 

Poornima Vijayashanker: I'll have to admit, as an engineer I have been guilty of ganging up on those designers responsible for deprioritizing product debt, and no, it's not a good practice. How can we help people in our audience who are designers avoid being ganged up on and making sure that product debt remains a priority?

 

Leslie Yang:    Absolutely. As a designer it's great to be able to focus on the research, to focus on the user experience, but you should also focus on being a really good facilitator. Control the dialogue around feedback. Focus on the product vision and the product strategy and the business strategy and then connect that design feedback to it.

 

Poornima Vijayashanker: What does that look like in practice, as an example?

 

Leslie Yang:    Let's say, for example, a business strategy is to improve the number of active daily users for monetization reasons. You want to make sure that the user experience is focused on building up to that and meeting that metric. One more thing. You can totally work with PMs on this as well.

 

Poornima Vijayashanker: OK, so as a designer approach a PM? How would that help?

 

Leslie Yang:    You can work with product on this by pulling the data and looking at it together and then figuring out where the areas you want to improve on.

 

Poornima Vijayashanker: Great, so it actually provides some evidence for why you need to

pay down that product debt?

 

Leslie Yang:    Exactly.

 

Poornima Vijayashanker: What about engineers? I'm sure they want to contribute and make sure that the conversations are useful.

 

Leslie Yang:    Absolutely and I love that when engineers are in those conversations on product with us. What someone like Ronan could do if he was concerned about data visualization, he could come up to one of us as designers and say, "Hey, how does this idea of introducing data vis tools really fit in with the product vision? What do you think?” Just coming from a place of curiosity is really helpful. That creates this really positive dialogue.

 

Poornima Vijayashanker: He's probably going to learn more and not jump to, “Oh my gosh, this is going to cause a performance issue and a bottleneck” and all this stuff.

 

Leslie Yang:    Exactly, and I think riffing with, I love the riffing that happens between designers and developers because you can come up with some really creative solutions you otherwise would not have come up with separately.

 

Poornima Vijayashanker: What can teams do to continue to prioritize and pay down product debt?

 

Leslie Yang:    What my belief is is that developers should be brought into work early and often. They should be in the feature ideation process. I will have devs sketch with us on UIs.

 

Poornima Vijayashanker: Oh, great. How does that help?

 

Leslie Yang:    It makes a huge difference because by being involved early and in frequent times they're able to contribute ideas and also understand and have user empathy. The work that we create together is not going to be overly complex. It will be well thought out and by the time that the work comes to them it's not a surprise. They know what to expect.

 

Poornima Vijayashanker: These are fantastic tips, Leslie. Thank you so much for sharing them with us today.

 

Leslie Yang:    You're so welcome.

 

Poornima Vijayashanker: Leslie and I want to know, how do you handle product debt at your company? Let us know in the comments below this video. That's it for today's *Build* tip. Be sure to subscribe to our YouTube channel to receive more episodes of *Build* and great *Build* tips like today's. Special thanks to our sponsor, Pivotal Tracker, for their help in producing this episode. Ciao for now.

            

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.   

Transcript for Should You Worry About Your Skills Getting Rusty?

 

Poornima Vijayashanker: In the last episode, we talked about what it's like to transition from being an individual contributor into a leader, and explored some tradeoffs. If you missed the episode, be sure to check it out in the link below this video. In today's episode, we're gonna talk about one of the major concerns people have that holds them back from doing the transition, which is the concern that their skills are gonna get rusty. So, stay tuned.

            

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. In each episode, innovators and I debunk a number of myths and misconceptions related to building products, companies, and your career in tech. One myth that often holds us back from transitioning from being that individual contributor into a leader is the fear that we're gonna get rusty when it comes to the skills that we've worked painstakingly hard to craft. If you're an engineer, you're gonna lose the ability to code. If you're a designer, you lose the ability to design. And if you're a salesperson or a marketer, you lose your ability to close. Well, in today's episode, we're gonna debunk that myth and more. And to help us out, Jean Hsu is back, who is an engineering leadership coach. She's gonna help us dive into this myth.

            

Thanks again for joining us, Jean.

 

Jean Hsu:   Thanks for having me again.

 

Poornima Vijayashanker: Yeah. Last time we talked about the benefits of going from being an individual contributor to a leader, especially in engineering. And not to shy away from it if we feel worried that we're not capable of doing it. But I know another concern that people have is not about their capabilities of doing the future work or being a leader, but, "Oh my gosh. I'm no longer going to be capable of doing my current job," whether that's coding, designing, marketing, or so on. Why do you think people have this fear?

 

Jean Hsu:   I think it's something we touched on last time, which is they don't see the path of the leadership role. So of course you're going to hold onto what you know, which is the technical skills, the coding, all that stuff. A lot of the times when I have this conversation with people, what I say is, "As a coach what I'm gonna do is I'm gonna illuminate that other path, the leadership path." And for most of the people I'm talking to, it's not as much of a technical leadership path. It's more of a people management path, which are both leadership paths. But part of my role is to illuminate that, so that they then...then the question is, implies that you don't want those technical skills to get rusty, right?

 

Poornima Vijayashanker: Right.

 

Jean Hsu:   Which I often feel like it's a symptom of they're not getting enough investment in seeing the rewards of stepping into a leadership role and having a more broader impact.

 

Poornima Vijayashanker: Yeah, or learning new skills.

 

Jean Hsu:   Right, or learning new skills.

 

Poornima Vijayashanker: Yeah. Is this a legitimate fear, though? Do our skills become rusty as we go into a new leadership position or any new role?

 

Jean Hsu:   I mean, for my technical skills, yeah for sure, they're rusty. They're definitely rusty because I'm not practicing them. I think you do have to get to a point where you feel comfortable with that. I definitely was at a point when I wasn't comfortable with that, when I was in transition. I remember one morning, I woke up and my calendar was back-to-back, 9:00 to 5:30 filled with meetings. I pulled out my laptop and I opened up three pull requests, just delete code that I had found that was unused. It was like 15 minutes. I was like, "OK. Good. I've done something today."

 

Poornima Vijayashanker: Well, sometimes throwing out trash is helpful.

 

Jean Hsu:   Yeah. And when I told my manager this, he was like, "Is that the best use of your time?" He asked me this. Like, OK clearly you know the answer to that. It's a rhetorical question. It's not the best use of my time, and it's actually indicative of something else, which is that I haven't really transitioned my mindset to the actual work that I'm doing in this new role, is work. And seeing the impact of it. That wasn't clear to me yet. So that's why I was holding onto this thing that made me feel good in my past role.

 

Poornima Vijayashanker: Yeah. How can you figure out what the new work is? I think that's a big problem for people, is they're thrust into this role, or it's a nice promotion, or maybe they genuinely want it, but then in that first week, month, even year, they're not really sure what to do on a day-to-day basis.

 

Jean Hsu:   Yeah. I mean, I think adding to that is that a lot of companies have founders or managers who also haven't done it before. They're not getting that model of, oh this is who I want to be as a manager. As an engineer, you see all sorts. Oh, this person went to Android or front end, they're more of a tech lead. This person's more of a Ten-X engineer type. And you don't really get to see that as much if you're talking purely about the people side of leadership, the people management.

            

One of the ways that you can do that is, I mean it's a little bit self-promotional, but working with a coach like me, who can help you see that path or help the people on your team see that path. There's books. There's definitely resources. There's a lot of Slack teams, that I think just being in the Slack teams is lurking. You kind of absorb what are the topics people talk about. And what are the things that come up. When you're not managing people, you don't see the things, like performance reviews, performance improvement plans, how to reward people, how to give them positive feedback and incentivize them and motivate them. You don't see that as a post lead.

 

Poornima Vijayashanker: Yeah. I think you're onto something, the concept of shadowing. Actually it can be really valuable. For me personally, I got to do a lot of that, having been at a very early stage startup and not as the founder, but rather as a founding engineer. Seeing how marketing and sales and engineering and product all operated and the leaders in those was valuable because when you're on the ground floor, you see how people develop, but not everybody has access to that. And not every manager enjoys being shadowed. What are some other ways you could simulate that kind of behavior?

 

Jean Hsu:   You know, I think if you have a close peer group at your company, that can be a good place to start to have these conversations. Someplace that's trusted and confidential. If you're a tech lead or you're a first-time people manager, to have someone you can say, "Hey, I have this situation," and you don't have to be alone in figuring out a strategy to deal with it, but you can go to your peer and have this peer mentoring or coaching relationship. I found that that's useful just in seeing what other people are doing and their perspectives.

 

Poornima Vijayashanker: Yeah. What about setting expectations? I think some managers are good at setting expectations and some are more carefree and want you to discover it yourself. What have you seen in your experience?

 

Jean Hsu:   What do you mean by the expectation?

 

Poornima Vijayashanker: So the expectation of, hey if you're a hiring manager, for example, you're gonna hire 30 direct reports.

 

Jean Hsu:   Oh, I see.

 

Poornima Vijayashanker: Or if you are the team manager, you're gonna push this product. Whatever the goals are of the organization. Some people are better at delineating and having a clear set of expectations, along with standards. And others are like, "Well, here's the company motto. Do no evil and ship." So you're like, "Within the confines of that, what do I do on a day-to-day?"

 

Jean Hsu:   Yeah. I think having some quarterly or monthly alignment and expectation setting is useful. It's the same as the first time you become a manager or a tech lead, it feels really awkward to not have...most people start off with like no stand-ps. Then they're like, "Well, I don't know what this person's working on. I haven't heard from them in three days." It's like, well maybe you should have standups, or maybe you should have some sort of weekly or bi-weekly, every other, twice a week meeting where people say if they're on track or not. I think that's generally a good strategy, is to set the high level expectations and then report back on those. Am I on track to hit those goals? Because then it feels like it's set up beforehand, so it's not, "Hey I noticed things aren't going well, so that's why I'm checking in on you."

 

Poornima Vijayashanker: Sure. Then it feels like am I getting reprimanded or am I getting guided.

 

Jean Hsu:   Right.

 

Poornima Vijayashanker: So, coming back to this concept again of the skills. And as somebody who is either technical or has a craft, and moving away from that into this more amorphous, squishy leadership role, are there actual skills that you acquire as a leader?

 

Jean Hsu:   Oh yeah, for sure.

 

Poornima Vijayashanker: Yeah, what are those?

 

Jean Hsu:   One of the ways that I was told to think about it, for me, I was sort of like, "I don't understand. I have these technical skills and now I'm being asked to do this thing where I feel like it's a completely different skill set. I'm talking to people one-on-one all day and dealing with the things that are coming up there." The way I was told, or asked to think about it, was that it's still problem solving, it's just that the interfaces and the APIs are people and teams, rather than code and services and the systems. They're still systems, but it's people and teams, and you have to think about how do these teams, what's the API between them and it's more like that.

 

Poornima Vijayashanker: What are some skills that you can point to now on your resume or LinkedIn?

 

Jean Hsu:   How to give difficult feedback.

 

Poornima Vijayashanker: That's important.

 

Jean Hsu:   How to debug teams that are not working efficiently. There's the low-level tweaks, like, oh, email once a day. The low-level things. But then taking a team that's not working very effectively and making a bunch of high-level changes in staffing, and then have them actually be able to execute because of the changes you made. That's something you don't get to see. Rather than the little refactors, you're doing more of a full rewrite or something.

 

Poornima Vijayashanker: Yeah, a re-org, right?

 

Jean Hsu:   Re-org, yeah.

 

Poornima Vijayashanker: Yeah. Anything else?

 

Jean Hsu:   Yeah. There's a ton. As many technical skills there are, there are as many in leadership and people management.

 

Poornima Vijayashanker: Yeah. I think it's important for people to understand that. What about writing? Do you feel like that's a valuable skill?

 

Jean Hsu:   Yeah. I mean, Medium was very much a writing culture. Everything was written internally, the internal version of Medium. I feel like that's something that—I consider myself also still in a leadership role, even though I just work for myself, but I work with a lot of people and I feel like all the time I spend in writing has come back. It's a huge investment for me. Yeah, it pays off.

 

Poornima Vijayashanker: Yeah. So in being a leader, investing in writing is good, whether or not you're actually comfortable doing it or you feel like you're particularly good at it.

 

Jean Hsu:   Yeah. I think it's something that's really valuable to get better at. Even if you're not publishing. Whether it's writing emails. I'm sure you've all had this experience where you get this massive email and you don't even read it. And then whoever sent it is like, "But I sent you all the information." It's sort of this brain dump, over-communication strategy. I think writing is just a part of communication and figuring out what's the right level of communication because you can under-communicate, and most people in engineering teams tend to under-communicate. And then there's this tendency to over-communicate, to try to correct for it. And then people just tune you out. Figuring out what do people want to hear. What do they care about. That's all part of the writing, too.

 

Poornima Vijayashanker: Nice. Now what prompted you to transition to being an engineering leadership coach?

 

Jean Hsu:   In reflecting in my time at Medium, I realize that I had a lot of peer support. A lot of peer support and my manager's support in making that transition. And even then it was hard. So I started talking to people at different companies and realizing that that transition, most people don't have any support. They have their direct reports and they have to keep it together, so they seem like things aren't falling apart. And a lot of times, they have the absent, whoever, CEO or CTO, who's not really helping them and they don't have that peer. And so I really wanted to...I saw how the benefits of having a really people-centric and caring engineering manager, because that's really the type of team we built at Medium, and thinking about how to expand my own impact. It was like, "Oh, what if I worked with a bunch of different companies and tried to help them level up their engineering management game?"

            

That's kind of how I landed on that. I also really enjoyed the one-on-one work that I was doing at Medium for the team.

 

Poornima Vijayashanker: Nice. So that's what you're doing now? You are a leadership coach for engineering teams.

 

Jean Hsu:   That's right, yeah.

 

Poornima Vijayashanker: What's your sweet spot in terms of a team size?

 

Jean Hsu:   See, it depends. I work with some companies that are like six people. I work with some companies that are like 3,000 people, but the teams themselves are smaller. I really enjoy the 10 to 50 people engineering teams, because I feel like there's still a lot of malleability in what they're doing and how they're building out their management structure. I like to work with first-time managers, because I feel like there's no bad habits to break. You can just be the one who is like, "This is what management is." They're like, "OK. Yes.” That's where I initially started when I created my business, but now I'm working with anyone from trying to figure out whether they want to go in the people management direction or stay in the technical side of things, or all the way through directors and VPNs.

 

Poornima Vijayashanker: That's awesome. What are some questions or problems that you help them with?

 

Jean Hsu:   A lot of it is honestly the mindset. A lot of it is as people move into leadership roles, or they don't have leadership roles, but they are expected to step up so they can get the explicit role. A lot of it is seeing that they don't really need the permission or they don't need someone to be like, "I bestow on you this role. Now you may do these things." So just getting people to see that. As a coach, I'll push them like, "Hey, what do you need to try? What are some things you can try out this week or next week?" Then they report back and I'm like, "OK, cool." It's really cool when you have a whole team of people just all experimenting with their behavior and you just see everyone just stepping up a bit more and taking initiative.

 

Poornima Vijayashanker: Awesome. Well, thank you, Jean. For our audience out there who may want to get in touch with you because they have an engineering team or an organization that could use some of your coaching, how can they do that?

 

Jean Hsu:   They can go to my website at [jeanhsu.com](jeanhsu.com) and I also have a link to my writing, too, there as well.

 

Poornima Vijayashanker: Great. Well we'll be sure to include the link right below this video.

 

Jean Hsu:   OK, thank you.

            

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.

Have you been in your current role for a while, and are eager to try something new?

 

Perhaps you’ve thought about transitioning from being an individual contributor into a leadership role, but you’re not sure if it’s the right move for you?

 

You worry about being qualified enough, leading people, being an authority figure, and what your day-to-day will be like.

 

While it sounds exciting and maybe a great opportunity to grow, you worry about your existing skills getting rusty.

 

Well, all this month on Build we’re going to be exploring the tradeoffs that aren’t talked about when we choose to transition from being an individual contributor to a leader. In today’s episode, I’ve invited Jean Hsu who was formerly an Engineering Manager at Medium and is now an Engineering Leadership Coach.

 

Here’s what you’ll learn in this episode:

 

• Why our perception of who or what we think it takes to be in a role is often wrong, and why we are more capable of learning and growing in a new role than we realize
• When it comes to leadership, it’s OK to take time to discover your own style
• Why the comfort and well-defined nature of our current role makes a transition harder and make us feel less accomplished in the beginning

In the episode Jean mentions the book: The Manager's Path, check it out here. 

--

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

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Transcript for What Stops Us From Transitioning Into A Leadership Role

 

Poornima Vijayashanker: Have you been in your current role for a while and maybe you're considering a transition from being an individual contributor to a leader, and you're not sure if it's right for you? Well, in today's *Build* episode, we're going to explore some of the tradeoffs that aren't talked about, so stay tuned.

            

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker. In each episode, innovators and I debunk a number of myths and misconceptions related to building products, companies, and your career in tech. Now one myth that I came across early in my career was the transition from being an individual contributor to a team leader. I struggled with this transition because I worried about my skills getting rusty and whether or not I had the skill set to actually lead people. So if you're grappling with this, we're going to cover it in today's episode. To help us out, I've invited Jean Hsu, who is an engineering leadership coach. Thanks for joining us today, Jean.

 

Jean Hsu: Thanks for having me.

 

Poornima Vijayashanker: Yeah. You and I met a couple months ago at a event. I'm really curious to know a little bit more about your background. If you can walk us through what drew you into tech and ultimately led to what you're doing today.

 

Jean Hsu: Sure. I went to school for computer science. I actually went to a liberal arts school. A few years in, I started trying to figure out what I wanted to do and what I really enjoyed was the coding and the projects and the—I didn't really know anything about applications, what the applications were going to be, or what software engineering was as a job, but I really loved the classes. I think that when people talk about how to attract women to tech, a lot of the conversations are actually, they don't seem as relevant to me because I really loved the actual coding itself, and I didn't know anything about what I would do after I graduate.

 

Poornima Vijayashanker: So where did you land after college?

 

Jean Hsu: I had interned at Google the summer before I graduated, and then I ended up taking a full-time offer at Google that started right after I graduated. I moved up to Mountain View and I was there for about a year and a half. Then I quit and wanted to see what else was out there, and kind of had the sense that Mountain View and the Google campus is a little bit of a bubble, and so I started to dabble in Android development. I ended up at Pulse and did some of the Android development there. Then after that—I was there for about a year and then I ended up at the Obvious Corporation, which later became Medium. I worked on their first prototype. Then I was there for about five and a half years.

 

Poornima Vijayashanker: Oh, wow.

 

Jean Hsu:   And then I left about six months ago.

 

Transition from engineer To engineering manager

 

Poornima Vijayashanker: So what catapulted you to strike out on your own?

 

Jean Hsu:   It was kind of the right time to make a big change. I don't know if it's like, I have two kids. I have an almost two-year-old and a four-and-a-half-year-old and that's very, it's not stable, but there's sort of a monotony in taking care of them. I had been at Medium for five and a half years, so I think there was a part of me that just really wanted a really big change and I was ready to kind of jump in the deep end again and figure something out that was completely new to me.

 

Poornima Vijayashanker: Now when you're at Medium, that's when you did your transition, right, from being an engineer to an engineering manager.

 

Jean Hsu:   That's right, yeah.

 

Our perception of who or what we think it takes to be in a role

 

Poornima Vijayashanker: What kind of prompted you to even consider this transition? Because a lot of people just think, “I'm happy kind of coding away. Why rock the boat?”

 

Jean Hsu:   Yeah, I mean for me I was pretty happy coding away, but I think I wanted to see where I could be more impactful. I don't know that I really chose it for myself. I was sort of, I wanted to have more impact and influence. Sometimes I was stepping into tech lead or project lead roles. I think at some point it was like everyone kind of knew that this was kind of the path I was headed and I was almost the last person to know. It was interesting because when I made that switch and started to take on a few direct reports, I think everyone was like, “Oh, it should have happened like a long time ago.”

 

Poornima Vijayashanker: What do you think they saw in you that maybe took you a while to see in yourself?

 

Jean Hsu:   I don't know. I guess I didn't really know what a manager did. Even at the time at Medium it wasn't called manager. I think they still call it a group lead, so it was very much this mentor, advocate, coach role, which is sort of, what I'm doing now is very similar to that. I think it was that people saw that in me, that they felt like they could talk to me about things and that I would help them solve their problems. I was never very much of a command and control, top-down type manager, which is maybe what I thought managers did.

 

Poornima Vijayashanker: Yeah, so maybe it was your perception or, “My misperception of this is what a manager is, so clearly I'm not a manager because that's not what I want to do,” when really you've naturally been doing a lot of great tasks or I guess things that managers would do.

 

Jean Hsu:   Right, yeah, like when you, if you ask me like, “Oh, do I want to help people and support them and help them solve their problems,” like, “Yeah.”

 

Poornima Vijayashanker: Right, but not maybe the “I want to enforce strict process or—”

 

Jean Hsu:   Right, like I'm just going to tell you what to do every day.

 

Why we think we aren’t capable of leading

 

Poornima Vijayashanker: Got it. Tell us some of your concerns, then, going in, aside from this “I don't know if I'm capable of being a manager or what a manager role entails.” What were some concerns with that?

 

Jean Hsu:   I mean my transition was pretty gradual. But as I got more and more in it, I definitely had this concern that it was too early to go 100% in that direction.

 

Poornima Vijayashanker: Why?

 

Jean Hsu:   I mean I think a lot of it is the tech industry. I sort of have this sense that people who don't look like me, specifically white males, if they are, they look young and they're in a management position, people tend to give them more the benefit of the doubt and think, “Oh, that's someone who is like so talented that he got promoted into management.” I sort of worried the opposite would happen to me where people would look at me and say, “Oh, she doesn't even have that much technical experience,” or like, “She looks really young. She came out of a boot camp,” or something, whereas I really had like a decade full of experience. I definitely had that anxiety of how will I be perceived once I leave this company.

 

Poornima Vijayashanker: And how did you handle that perception, kind of get over it?

 

Jean Hsu:   That’s a good question. I think that a lot of it was sort of—I mean I also had the sort of struggle of do I then count as someone who's like nontechnical anymore. You see these statistics of like, “Oh, 70% of women leave their technical roles.” I’m like, “Am I contributing to that?”

            

But I think what I landed on is sort of like the whole point is that you should be able to do what you feel, like is your calling, and that you want to do and not that I'm contributing to the statistic that we want to go down, not up. I think that's part of how I kind of came to terms with it. Then when I was thinking about how to, like if I was leaving the IC work too early, what my manager helped me focus on was what would I get out of doing more of it.

            

He's like, “Well, if you want to do VP eng or a head of engineering type role, I feel like you've already demonstrated that you can do that. Even if it's areas that you're not familiar with, you can work with engineers to figure it out, you've done that before, and so what would you get out of it.” I was like, “Oh, I guess I just…” It's sort of this feeling of like I should do it, I should do more technical work, not that I really wanted to or that I was drawn to do more of it.

 

Poornima Vijayashanker: It's interesting that he led you down that path of what would it look like in your current role if you were to do more of maybe the same, or where would that kind of take you longer term, and is that the kind of work that you want to do.

 

Jean Hsu:   Right, and he was very open with me and saying like, “OK, well, you know what? I understand that you may want to go, kind of like shift back a little bit, but for this quarter we really need you here and let's reassess.” It felt very like a temporary, not temporary, but it was like an ongoing conversation. It wasn't like if I wanted to go back into IC work, I'd have to leave the company. I always had that advocate in him.

 

How long it really takes to transition into a leadership role

 

Poornima Vijayashanker: So you ultimately decided to take the choice and go from being an individual contributor, an IC, into a leadership. What were the first few months like in that transition?

 

Jean Hsu:   It was kind of a long transition. I'd say it was like over maybe two years. The first few months I mean I definitely had this sense of like, I don't have time to get my work done because when you're responsible for both the coding work and being responsible for teams or people, it's really hard to have that, like make your time.

 

Poornima Vijayashanker: Right, contact switching.

 

Jean Hsu:   So I definitely felt like it was easy to just say, “Oh, I had a day full of meetings. I didn't get any work done.” That’s a very, very common mindset to have when you make that transition.

 

When we don’t have something tangible to point to we feel unaccomplished

 

Poornima Vijayashanker: I think for me when I went from being an engineer to a founder, the hardest thing was I'm no longer going to have something to point to at the end of the day because before I could build something and deploy it and be like, “Look, what I built,” and at the end of the day I was like, “Yeah, I talked to five people.”

 

Jean Hsu:   Yeah, I started keeping, in the times where I felt like the transition was the roughest I started keeping a log of what is the one thing that I felt was most impactful that I did that day, and sometimes I kind of had to make it up. I was, “Oh, I had a one-on-one with this engineer, and maybe she thinks about herself fundamentally differently now and is now going to interact with people in a slightly different way.” You kind of have to take those where you can get them.

 

Poornima Vijayashanker: It's squishy and you don't see the results immediately and it’s developing a level of comfort with that. I think that's one of the harder pieces and where people get demotivated when they're not seeing their results fast enough versus with code it can be very instantaneous.

 

Jean Hsu:   Yeah, and I think management success or being a leader is a little bit more subjective and the feedback loop is a lot longer.

 

Poornima Vijayashanker: Yeah, let's talk about that. Yeah.

 

Jean Hsu:   I mean it could be, I mean if you're just talking about actual feedback that you get, that's, I don't know, at companies that kind of have—can I curse on here?

 

Poornima Vijayashanker: Of course.

 

Jean Hsu:   —have their shit together, it’s like six months. Every six months you get some feedback on how you're doing, the official formal feedback loop. But beyond that you have the one-on-one. That's a very individual relationship. I think for a lot of people they don't really see the impact of their work. One of the things I've been thinking about is for engineering work for the most part your impact is somewhat proportional to the work you put in. If you spend two months building a system with a team, that's two months that you put in. Hopefully it's an important thing that you've done. Then the management work sometimes you can do some tweaking or some restocking up front that can have really big impact that people might not trace back to you, and so you sort of have to see that loop, that feedback loop for yourself.

 

Managing and leading your peers

 

Poornima Vijayashanker: Were you ever in a situation where you also went from being an engineer with a bunch of teammates to then being their manager and having them as direct reports?

 

Jean Hsu:   Mmm-hmm. Most of my early direct reports were new grads. In some ways that was sort of easier. I had just been there eight years ago and so I had a very good sense of like, “Oh, this is kind of where you are now, and here's the type of support you need.” I'd say as a tech lead it was sometimes a little bit more difficult, especially when I was suddenly responsible for managing the work of people who were more senior than me, that I feel like I kind of took a very hands-off approach, which sometimes was like, there’s just miscommunication. But it is something I feel like especially as a manager you have to navigate, like how, it's OK to be friendly with people. I mean obviously you want to be friendly with people in the workplace, but how much you can be like good friends outside of work.

 

Poornima Vijayashanker: And how to be authoritative.

 

Jean Hsu:   Right, and navigating that was a little bit tricky to me. Figuring out if someone invited me to something, “Should I go?” I’m like, “What? If I did something, who should I invite?” In some ways I just didn't hang out with people at work who were on the engineering team because it was like, I felt like I had to invite 30 people. I don't want to invite 30 people.

 

Poornima Vijayashanker: Right, so you want to be careful about playing favorites and stuff like that.

 

Jean Hsu:   Right. I think I was especially sensitive to that, because I had seen it, I'd seen it happen. People who are friends go to Vegas together and then you're just like, “Whoa, I understand you’re friends, but it's hard to say that that's completely separate from your work.”

 

Poornima Vijayashanker: What about the boss factor? I know for myself as an older sister bossiness is just totally normal for me. But did you have a sense of like, “How do I go and be more of an authoritative figure or disciplinarian” sometimes?

 

Jean Hsu:   Yeah, most of my—that kind of stuff was in one-on-ones. I feel like one of the areas that I kind of grew into was to bring that to a more group setting and a lot of my feedback would be around like, “Jean has,” like, “We want to hear more from her, like we want…” People wanted to hear more from me. They knew that I was, kind of like, I had an opinion but I wasn't like—

 

Poornima Vijayashanker: Voicing it.

 

Jean Hsu:   Voicing it. Actually after I had to figure out that I was going to leave and do my own thing, I kind of became more unintimidated. I was sort of just saying whatever I wanted to say in meetings, which probably actually made me better at my job.

 

Poornima Vijayashanker: What do you think kind of got you to that level aside from putting in your notice? Did you have a mentor that kind of helped you see these were hurdles or things that were holding you back as you were doing the transition into a leadership role?

 

Jean Hsu:   Yeah, I mean I had a lot of peer support and my own manager was very helpful and kind of providing that feedback in an ongoing basis. I think for me it was also seeing that when I spoke up in meetings, because one of my pet peeves is like inefficient meetings and—

 

Poornima Vijayashanker: I agree.

 

Jean Hsu:   One of the things I would start to do a few years in was like, “OK, I'm just going to get up and start to facilitate the meeting and get people on track and kind of cut people off,” and that came out of a facilitation role that we had at Medium, but sometimes there’s unstructured meetings so I kind of just take that role. The first few times it was like, “I don't know if this is OK. Do people think I'm being overbearing?” But once I started getting feedback of like, “Oh like, thank God you were there to do that,” or people would start electing me to be the facilitator—

 

Poornima Vijayashanker: You're doing the things they’re thinking of doing, yeah.

 

Jean Hsu:   Right. I was like, “Why do I just sit here with this sinking feeling of like, ‘Ugh, this meeting, why don't I do something about it.’’”

 

Poornima Vijayashanker: Oh, that's great, so you were, yeah, naturally gravitating towards taking the reins and steering people in the direction. It wasn't as if you were having one-on-ones with your boss, your manager every week and saying, “I have this problem. How do I deal with it?” You naturally saw opportunities and thought, “I'm going to dip my toe in and see what happens.”

 

Jean Hsu:   Yeah, I think there was probably a long way I could have gone before. One of my goals—actually I never achieved this—was for people to tell, for my manager to get feedback about me that I was over the top because I knew there was a long way to go.

 

Poornima Vijayashanker: Oh god, yeah. I always push people for that. It’s like yeah, push to a level of aggressiveness and then they’ll know.

 

Jean Hsu:   Yeah, because I could tell that it was really myself holding me back and there was so far from where I was and where that was really going to be a problem, and so I kind of wanted to see what was the range there.

 

Poornima Vijayashanker: Did you ever hit the—

 

Jean Hsu:   No I did not, I left before.

 

Poornima Vijayashanker: Something new to aspire to then.

 

Jean Hsu:   Yeah, maybe.

 

The choice to stay with the known path

 

Poornima Vijayashanker: What do you think you've gotten out of the—now, what is it, a year, two years since you've been a leader—what do you think you've gotten out of that experience that maybe you wouldn't have gotten had you stuck to your individual contributor role?

 

Jean Hsu:   I think there's equal—I was going to say impact and influence, but I feel like even in the IC track there's ways to achieve that and to lead also.

 

Poornima Vijayashanker: Yeah, we’ll get to that. Let’s talk about the leadership.

 

Jean Hsu:   As a manager, I felt like it's definitely pretty exhausting to be the person sort of taking care of people and supporting them, but there's a lot of rewards there too, which is like you know that these people have someone who they feel safe coming to and there's issues. I don’t know. It's just like a level of influence that, what I had from my manager, just being able to extend that to everyone else, that was really, that really meant a lot to me.

 

Poornima Vijayashanker: Any impact on the product or the company that you can speak of?

 

Jean Hsu:   In terms of the company a lot of my role was also doing engineering operations work, so kind of like team-wide processes, taking what was working on my team or other teams and kind of expanding them to be part of, more of the whole engineering team’s processes. Then something I also saw at Medium was engineering was the largest team. A lot of times engineering would pilot something and then it would work really well and so we’d expand it to the rest of the company. That was kind of cool too, to see that level of like, “Hey, like what's going on over there? They seem to be like pretty well supported.”

 

Poornima Vijayashanker: Then coming back to the question that you proposed. If you had stayed in your individual contributor role, how do you think it would have manifested itself?

 

Jean Hsu:   I don't think that was ever really for me, but I think that once I could see that I was capable of doing it, that also made me much more comfortable to switch to the management track, because I really felt like for a while that I wasn't cut out to do the hardcore infrastructure platform work, and they're kind of going that way as my career route. Then I did spend like a quarter or two, really diving deep into platform work, and I could see the path there. Once I could see the path and I was like, “OK, I can see this, if I don't do people management and some of the other things I'm doing and I just focus on this, I could see how I could get to where this person is in five years or 10 years.” It was interesting because just seeing that helped me kind of be comfortable with moving to the management track more fully.

 

Poornima Vijayashanker: You mentioned there being opportunities for leadership for individual contributors. So for folks who might in our audience choose to stay as individual contributors for the long haul of their career, what do those opportunities look like?

 

Jean Hsu:   I mean there's a lot of different, even in the individual contributor, I mean some people include tech lead as part of that track. I think in the more purely individual contributor track you can still expand your influence and you can be the architect of larger, larger and larger things or just be able to coordinate. I mean it becomes less individual even though you're still doing the work.

 

Poornima Vijayashanker: Sure, you’re just divvying it up or directing people, but maybe not responsible for their career.

 

Understanding the path of a new role

 

Jean Hsu:   That's right, or you're thinking more about the high-level technical strategy of the company or—I mean, that I think eventually leads to architect or CTO type roles, whereas once I had kind of figured out the paths, I didn't really have a sort of canonical like VP eng, like, “Oh, this is what a VP eng does, and this is what a CTO does.” Had worked at Google where you have no visibility, to those people, Pulse, which we were just all kind of figuring things out, and then Medium where my manager was the head of engineering and it was very much like a hybrid VP eng/CTO role. But once I had figured out what that actually meant, it was pretty clear to me that the path that appealed to me most was sort of the VP eng route.

 

Poornima Vijayashanker: Yeah, it's nice when you have a little bit more transparency.

 

Jean Hsu:   Yeah, because otherwise it's just like, “I don't, I don’t know,” like, “I don't know where I'm going because I don't even know what the options are.”

 

Poornima Vijayashanker: That's a good final set of words for our audience, is getting a sense of what the various tracks look like before you pre-select or make the decision to not participate, just kind of get your facts straight, get a sense of what each role is like.

 

Jean Hsu:   Yeah, the book *The Manager’s Path* was really good for that because she, Camille, the author, she lays out a lot of the—I like how she lays it out because at the end she talks about all the core things that a company needs and then the different combinations of roles that they use to achieve them, because VP, eng, and CTO can actually mean very different things depending on the company you’re at.

 

Poornima Vijayashanker: Nice. We'll put a link to it in the show notes. Thank you so much Jean for sharing all this awesome information. I know our audience out there is going to get a lot out of this. For those of you now in the audience, Jean and I would like to know: have you recently done a transition maybe from being an individual contributor to a manager or a leader? What were some of the concerns you had, and how did you go about handling that transition? Let us know in the comments below this video.

            

That's it for today's episode of *Build*. Be sure to subscribe to our YouTube channel to receive the next episode, where we'll dive in a little bit deeper and talk about how you want to manage your concerns around your skills, getting rusty when you go from being that individual contributor to a leader. Ciao for now.

 

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.

A redesign is a great way to reinvent your brand, get a leg up on the competition, and revisit those clunky and outdated workflows.

 

While we may be eager to jump right in, we have to be careful about what is actually going to help us accomplish our business goals.

 

In today’s Build Tip, I’m joined by Leslie Yang who is a Senior Product Designer at Pivotal Labs. Leslie and I are going to talk about how much to include in a redesign and what you need to do before you start a redesign.

 

You’ll learn:

 

• The hidden risks of jumping into a redesign and how to avoid them
• What happens when we redesign too many pieces of the product
• The type of metrics you need to be tracking for each piece of the product you redesign

 

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

--

Transcript for Product Re-design: What To Do Before You Redesign Your Product

 

Ronan: I'm not sure about this, Poornima.

 

Poornima: What? What? What's going on?

 

Ronan: We've redesigned the entire landing page, the onboarding workflow, and the customer checkout experience. From the analytics, I can't tell which of these redesigns actually moved the needle.

 

Poornima: Did you redo them all at once?

 

Ronan: That's what I thought I was asked to do.

 

Poornima: I think we're going to need to talk about how much to redesign in today's *Build* tip.

                                                 

Welcome to *Build*, brought to you by Pivotal Tracker. I'm your host, Poornima Vijayashanker, and I've got a new *Build* tip for you. Today, I'm joined by Leslie Yang, who is Senior Product Designer at Pivotal Labs. Leslie and I are going to dig into how much to include in a redesign and what you need to do before you start a redesign. Thanks for joining us, Leslie.

 

Leslie Yang: Thanks for having me.

 

Poornima: Let's first talk about why teams even want to do a redesign.

 

Leslie Yang: Totally. The ones that I can think of are three. One is you have your company and you really want to have brand refresh. You want to be out there in the market and you want people to get excited. The second thing, as a company, you want to get a leg up on the competition so you really feel like if I defined myself in the market against our competitors, we will have a winning advantage. The third thing is maybe you put your product out for a few years and you're feeling like all these workflows are pretty clunky, so we want to make sure we simplify it and take a step back and look at that, too.

 

Poornima: I know companies are really eager to do a redesign. What happens if they jump in too fast?

 

Leslie Yang: Totally. There is a lot of hidden risks involved. The number one thing is that companies can invest a lot of money and time into the visual design and improving that at the detriment of the user experience and that's always a bad call.

 

Poornima: Got it. How can they avoid doing that?

 

Leslie Yang: Sure. One of the things they can do is take a look at your workflows. If they're already doing really well for your company, don't change them. Don't fix what's already working really well. Definitely do user research to test to make sure that a redesign is something that people actually would find value in. Then you want to make sure that your design patterns are consistent across web, and mobile, and everywhere else, people are able to use the app.

 

Poornima: What does it mean, like design patterns are consistent?

 

Leslie Yang: Design patterns are the interactions are going to be the same ones you would experience similar in mobile versus web.

 

Poornima: What's an example of that?

 

Leslie Yang: For example if you're using Yelp. My experience on Yelp for mobile, if I'm going to see a list of search results, I'm on web, I should see something very similar to that.

 

Poornima: Got it. Consistent user experience.

 

Leslie Yang: Absolutely.

 

Poornima: What else?

 

Leslie Yang: Let me think. You should definitely work on developing a style guide that will work across all parts of your app.

 

Poornima: Great. If you have those four things nailed down, then it makes sense to start the redesign?

 

Leslie Yang: Yeah. It's definitely worth looking at it from that point.

 

Poornima: You mentioned a lot of times you want to revisit those clunky workflows. How can you do that in a way that's not going to end up causing you to go down a rabbit hole?

 

Leslie Yang: Oh, definitely. What you really want to do is work with product to look at your metrics. Find those areas where there's some hidden pains and work on improving those areas first.

 

Poornima: You look at the drop-off points and then go from there.

 

Leslie Yang: Absolutely. Yeah.

 

Poornima: One new insight that I learned in this conversation is a lot of people spend time doing visual design versus actually investing in the workflows. How can you make sure that that's not what's happening?

 

Leslie Yang: Well, a big thing is you need to look at your data. You look at your qualitative data and your quantitative data. From looking at that, you can figure out where in the user experience you want to improve that experience. Then you work on the visual design last.

 

Poornima: It's definitely the priority of workflow first, visual design second.

 

Leslie Yang: Yes.

 

Poornima: Now, let's go back to our initial example where Ronan had, bless his heart, changed a lot of things all at once. He redesigned the landing site. He redesigned the onboarding and finally the checkout and sometimes it makes sense to do them all at once if you've got the resources. But, in his case, things just weren't working out.

 

Leslie Yang: Yeah, totally. I think what would really help Ronan in those moments is if he had permanent metrics for each of those different experiences that he was looking to test and understand.

 

Poornima: For example, like the landing site, the metric for the landing is—

 

Leslie Yang: It's just checking to see how many people have had signed up for the site.

 

Poornima: Then for the onboarding—

 

Leslie Yang: It's improving the user experience from signup to becoming an active user.

 

Poornima: Right. Then the final checkout is monetize.

 

Leslie Yang: Monetize.

 

Poornima: For Ronan's case, I think where he probably did a lot of redesign within each, like changing a number of elements in the landing site, changing a number of elements within onboarding, and finally checkout. He doesn't know within each what's working. But then overall, not having those metrics siloed also made it confusing.

 

Leslie Yang: Exactly. In a specific workflow, if you're going to change something, change one thing at a time and then have some good metrics to test to see if it's successful or not.

 

Poornima: Well, thank you so much, Leslie, for sharing these tips with us today. I know our audience out there is going to get a lot of benefit when they consider doing a redesign next.

 

Leslie Yang: Thanks so much for having me.

 

Poornima: Yeah. Now, Leslie and I would like to know if you've done a redesign recently, what did you consider redesigning and how did it turn out? Let us know in the comments below this video. OK. That's it for today's *Build* tip. Be sure to subscribe to our YouTube channel to receive more episodes of *Build* and *Build* tips like this one, and special thanks to our sponsor, Pivotal Tracker, for their help and support in producing this episode. Ciao for now.

                                                 

This episode of *Build* is brought to you by our sponsor, Pivotal Tracker.

All this month on Build, we’ve been talking about project management. First, we shared two ground rules you need to set for yourself to get through a software project successfully, and in the last episode, we shared strategies for handling new ideas and unexpected challenges that may derail your project.

 

But you’re probably left wondering, what do you do to get through the last 20% of a project? Especially when the deadline changes, and it’s clear that teammates are starting to burn out and become demotivated? Is it even possible to get through it and successfully ship?

 

And if you are able to get through those hurdles and successfully ship, what next?

 

In today’s Build episode, Jen Leech who is the VP of Engineering at Truss, and I are going to share proven strategies to get you through that last 20% and successfully ship!

 

You’ll learn:

 

- Why the last 20% of a project is really a lie!

- How to avoid the complacency that comes with a deadline that are very far away in the future.

- What to do when the deadline gets pushed up or back.

--

Build is produced as a partnership between Femgineer and Pivotal Tracker. San Francisco video production by StartMotionMEDIA.

 

##Project Management: How To Keep Your Team Motivated And Successfully Ship transcript

 

Poornima: We've been talking about how to manage your first high-stakes project. We started by alleviating some of your anxieties, and then we talked about how to manage situations where people want to change course or bring up new ideas. In today's final episode on this topic, we're going to talk about how to keep your team motivated to help you ship your product. So stay tuned.

                                                 

Welcome to *Build*, brought to you by PivotalTracker. I'm your host, Poornima Vijayashanker. In each episode, innovators and I debunk a number of myths and misconceptions when it comes to building products, companies, and your career in tech.

So finishing that 20% of any project can be challenging. People get burnt out and demotivated. In today's episode, we're going to talk about how you can keep them motivated and get them to successfully ship. And to help us out, Jen Leech is back. You'll remember Jen is a VP of engineering at Truss, a software consultant. Thanks for joining us, Jen.

 

Jen Leech: Absolutely. Thank you for having me.

 

Why people get demotivated and burn out during the last 20% of a project

 

Poornima: So you've done a lot of projects throughout your career, and you know as well as anybody out there that that last 20% is the hardest. People get demotivated, they burn out. So let's talk about why this happens to begin with.

 

Jen Leech: Yeah. So really the fundamental reason that this happens is that the last 20% is never actually 20%. It's the 20% that you imagined when you thought about the project. But in terms of the amount of work involved, it's usually the most tedious and painstaking tasks that are reserved towards the end. When you get towards the end of the project, that's when new stakeholders start showing up and having ideas about things that need to happen on the project that weren't already there. So the final 20% ends up being like another 80%. So four times as big as you thought it was going to be. So that can be demotivating for people. And people who thought—if they really thought they were towards the last 20%, then it's especially demotivating because they suddenly see the work explode in front of their eyes when they hadn't really thought that it was going to be that much more.

 

How to handle project scope creep

 

Poornima: So there's a number of things that are causing the project to get bigger towards the end. One of them you mentioned, scope creep. How do we handle the situation?

 

Jen Leech: Yeah. So this is the point in the project at which you need to get really aggressive about defining exactly what you're trying to deliver and why, and for whom, and digging into every request that comes in and understanding how that impacts the final project. So the process of digging into that involves really having a good sense of who the users are, who the stakeholders are, and talking with those people as much as you possibly can. If a person comes in and wants to see a particular feature, you need to really understand why they want that feature, whether it's something that they dreamed of as part of the project from the beginning. That's something that they thought would be really wonderful for users, or whether it was something they determined through recent user's testing is going to actually dramatically impact the target market for this product.

                                                 

Understanding where those ideas come from, the business impact of those ideas, how well vetted the idea is in terms of hard data, and then from there you can parametrize whether, "OK. This has been vetted. It's really clear how it connects to our business interests. It's a great path towards our goal. We need to get this particular thing in. Do we need to cut any other features? Are the other features irrelevant now?" You know, how does that change the whole scope of the project? So that's one angle.

                                                 

Another angle is, "This idea is something that sounds pretty great. I love the idea. We haven't tested it. What's the quickest path to create a test to try to validate this hypothesis. Can we create a little feature? Can we create a mini version of this thing? Do we need to have a fully fledged version of this thing. How do we gather information to inform our direction so that we can make sure that we're going on the right course?"

 

Poornima: I really like what you said about being aggressive with pushing back, especially when it's going to expand the scope and it's not something that has a clear business goal versus the thing that has a very clear direction. The challenge though for many of us, is if that is an important stakeholder coming in then we worry about what will happen if we push back. So how do you navigate that conversation?

 

Jen Leech: Yeah. So I feel as though many of the tactics that we described in the last episode apply here. So when someone comes in and they have their idea, how they want to see something go, they're not going to be happy if they feel like you're shooting them down without having thoroughly considered the idea. And if you begin to really investigate that idea with them by asking questions to reveal assumptions about the idea, following the idea through to its ultimate conclusion. That can clarify both for you and also the other stakeholder at the same time, the aspects of that idea that are things that you should run with that are going to improve the product and that are maybe relatively low cost. And maybe there are aspects of that that you can leave on the table for now, and you can tease those things apart.

                                                 

And if you go through that process collaboratively with the person who brings the idea in, then at the end of the conversation they're going to both feel like they've been heard, that you have really fully considered their idea, and very likely they will be glad at the things that you pulled out and left on the table. And you have facilitated the process of helping them see what the most valuable nuggets of that idea are and that's a huge value to bring to a project.

What to do when you’re burnt out working on a project

 

Poornima: But here's the deal. I am so exhausted. It's been three weeks on this project. I don't even have the energy to facilitate that conversation because I'm borderline burnt out and this is maybe the second or third request that this stakeholder has done. What do I do?

 

Jen Leech: Well to be honest, you should probably walk out of the room.

 

Poornima: Yeah, OK. Politely maybe?

 

Jen Leech: Politely. Politely walk out of the room. When you truly are burnt out, and you truly exhausted your emotional reserves, that's when it's time for somebody else to step in and take that role. And you should expect that that may happen some point in time and prepare for it. And so the preparing-for-it process is all about sharing your load with other people on the team, teaching other people on the team to do what you do. So on this particular project I have been referring to from last year, one of the things that I did on that team is I asked individuals from the team to rotate through the team facilitator role.

                                                 

So I would ask everyone from the team, whoever they were, to run sprint plannings, to run retrospectives. We would have design discussions where we would have design exploration, and then design critique. We would pair discussions where we...they weren't exactly brainstorming. Not like the “everyone puts sticky notes up” kind of brainstorming thing. It's not like that. But the exploration and exploding of an idea to gather as much as you can. Then somebody would go and write those ideas up, and then we would get back together to make a decision.

                                                 

All those processes have some kind of facilitation involved. And we would have everyone from the team facilitate those processes. Then when it came time, such that somebody was out sick, somebody needed to take a break, or was on vacation, those processes continued to occur without interruption and they vary a little bit and that's fine. And each person who has taken that role then is also much more invested in the team, and a much better contributor to the process. So essentially you need to produce your best factor. I'm sorry. Improve your best factor by increasing the number of people who have that skillset.

 

Poornima: Now the challenge with doing this though is there's a lot of handoffs. Which means a lot of setup and tear down, right? Like if I'm handing something over to you, I might say, "Here are the things we talked about before." I mean, like you said it's great for the bus factor, but it is not so great when it comes to that added investment of, "OK. Now I need to talk to Jen, and then Jen needs to talk to so and so." And each time they're doing that, that's an additional time cost.

 

Jen Leech: So you're referring to handing off responsibilities. So one thing that I discovered is that...so part of the handoff process involves creating a set of really simple, well-defined processes that are easy for anyone to follow. And each time a new person stepped into the role, they would refer to those processes and say, "Hm. I don't fully understand X." And then we would augment the process to cover, "OK, so somebody didn't understand and need an explanation for ..." And we use these process documents to hand off the roles. So eventually it didn't really require a conversation.

 

Poornima: OK. But what about people who might game the system? Like, say somebody is a stakeholder, right? They know, "OK, Poornima. She's kind of a pushover. So when she's the facilitator next time, I'm going to make sure I get my ideas in because Jen, she's really good and aggressive. I'm never going to get my ideas passed through her." How do you handle those kind of—

 

Jen Leech: Well you know, what ends up happening is that although one person is designated to make sure the processes are happening, everyone in the room eventually becomes a facilitator. And the facilitator role is really just about setting the stage. And if everyone in the room has rotated through that role, everyone in the room is trying to make it happen. And you no longer have a single point of failure. Let's say that facilitator doesn't show up that day, or they're not feeling very well. Someone else just does it because everyone's done it.

 

Poornima: OK. So do you feel like there's a level of accountability then where people wouldn't necessarily be able to come in and game the system?

 

Jen Leech: Yeah. Because the more people who...every time someone steps up and begins running the system, that really clarifies why there's value with facilitating a collaboration in a way that includes everyone's opinion, for example. The more people facilitate it, the more they understand the value in it, and then the more they reinforce it whenever they're in a discussion.

 

How to handle changing deadlines for a software project

 

Poornima: So there's that dreaded deadline. And sometimes it gets moved up or it gets pushed back. In the event that it gets moved up, we're kind of scrambling. In the event that it gets pushed back, we start procrastinating. So how do we hold ourselves to that deadline?

 

Jen Leech: I actually think that the case where it's moved up is the easier case. Yeah. So when a deadline gets moved up, assuming that you're working with humans, you have resource constraints. So the first thing that I look at is the project scope. And if you have defined what your deliverables are, the things that you absolutely have in your project, then you can look at those and think, "Well are there ways that I could deliver that in a way that is slightly simpler, or in a way that maybe doesn't handle quite the data throughput that we're going to need to handle?" Because maybe in the first week maybe we don't really need to handle that data throughput.

                                                 

So having the deadline moved up can actually reduce you to be more aggressive in pairing down what you're delivering in a way that can actually really help. And if the pairing down process is something you bring to stakeholders and they say, "Oh, but we really need all these features." Then you have hard data that you can point to and say ... Especially if you're using a project tracker system like PivotalTracker, which is what we use, then you get estimates for the amount of work that the team can do in a sustainable basis, and projections for how much they'll be able to complete by a certain amount of time.

                                                 

And those are real data-based estimates. So, didn't intend to pitch Pivotal here, but I actually, I love their company. They do some great things. So then you can bring that to the table and then have a really clear, honest discussion about, "Here's the what the team can do. Here's the features we can deliver. What do you think? How do we solve this problem?" Again, trying to solve it together. When the deadline gets moved out, that's when it gets more difficult.

 

Poornima: Right. People start procrastinating.

 

Jen Leech: Exactly, exactly. You already have people who are thinking of the last 20% as 20% when it's actually 80%. And then all of sudden when you move the deadline out, then it's so easy to—

 

Poornima: Check out.

 

How to manage a software project when the deadline is far away

Jen Leech: Relax a little bit. To think, "Oh, well. That feature isn't so big," and not realizing that you're misestimating the amount of work that's involved. So one of the things that I try to do, especially...so this works for both when deadlines are moved out, and when a deadline is being set for you that's actually really far in the future.

                                                 

So as an example, we had a deadline last year that was nine months in the future. So we...what I did is I created an internal milestones document. So I created a bunch of internal deadlines for the team that we should be aiming to hit, and if we weren't hitting those things then we should be reconsidering what we're doing. That helped a lot to focus the team and to keep us on track. And then when you build out intermediate milestones then you can set an internal deadline for completion that's even months ahead of when you think it's going to be. And create that paired-down, really lean version of the product that is going to maybe validate the hypothesis you have about what you're building and why you're trying to build it, and add extra business value to the project for the company by saying, "OK, so you asked us to build this. You want it by December. How do you know that's the right thing to build?"

                                                 

So you get to then have a version that lets people play with it enough so that if you're building the wrong thing, you can change it before the real deadline, and even though the business has told you they want X by date Z, if you give them a smaller version earlier and discover they were wrong, they will be singing your praises to high heaven. That's what they really want. What they really want is the answer that's going to serve their customers. And if that's what you're keeping in mind, then you're going to have a really successful project.

 

What to do after you’ve successfully shipped your software project

 

Poornima: Awesome. So you've done these kind of shorter shipping dates with the milestones. So you're kind of doing it iteratively, you're shipping periodically. What do you do though, right after maybe that first or second time that you've shipped? Because I think a lot people forget. They're like, "Ship. Time to go on vacation." It's like, "Hold up here." Right? Because you've broken it into milestones, there is another one coming up. There's another sprint, release, whatever you like to call it.

 

Jen Leech: Right. Right. Well it depends on what you've shipped. I mean if you really shipped your true milestone, you should probably go and have a party. Like celebrating your results has real value to it. Aside from that, you're getting ready to collect data about what you've built. And this is part of the process that I think is sometimes...although we talk in our industry a lot about gathering research and being product driven, and making sure that we're building for the actual users, however I think that...I've seen fairly often that people feel as though they've built a great product. "Great, let's move on." And they can sometimes forget who all the users are. Can sometimes forget what it means to be successful.

                                                 

And as an example...and then maybe not gather enough data. And that's a huge failure mode that I'm constantly trying to correct for. The one example is, I talked about a validation system that somebody might build in one of your earlier episodes and we came up with an idea for this validation system which was based on real user experience from the previous system the company built. We built this new design, we rolled it out, and it was basically working. It was basically...it was allowing us to quickly and easily specify checks on data that we had generated. It was doing it in a way that didn't cause us to repeat ourselves too frequently in the code. It was doing it in such a way that people who were not engineers could author the validations and look at the results. We were able to say with a higher degree of certainty that the data was correct.

                                                 

However, at the end of the day, because it was serving these fundamental use cases that we knew we had, that maybe the previous system had not solved these use cases well. So it was already better. We knew that. But we could have dug in a bit more. And we could have dug in a bit more by going back to the users and saying, "OK, do you want to use this? When you use it, what are the things that really irritate you?" And dig into those and get a good sense of why your baby's ugly. It sometimes is painful to do that.

 

Poornima: Yeah. Because you just shipped and you just had that party, and nobody wants to have a downer after that.

 

Jen Leech: Yeah. Exactly. That's exactly right. Yeah and you want to celebrate. But then after that, kind of pull your boots back on. Get back out there and be like, "OK. We were wrong. How were we wrong?" And that's the thing is that every time I ship a product, my first question is, "OK. Let's assume we're wrong. Let's find out how."

 

Poornima: Make it a game a little bit.

 

Jen Leech: Yeah. Well, you know, and if you come from the assumption that you're always going to have it wrong, then that's how you get it right. If you ever come from the assumption that you were right, it's guaranteed that you're going to miss how you're wrong.

 

Poornima: Or maybe that situation, but there's a new situation you can't apply that same assumption.

 

Jen Leech: It's new. Situations change. There's going to be data left on the table if you don't go back.

 

Poornima: Right. Yeah that's fantastic. Well thank you so much, Jen. I know I can talk to you about project management forever. But I think this is a great place to stop and I know you've given our audience a lot of awesome strategies. So thank you.

 

Jen Leech: Absolutely. Thank you for having me.

 

Poornima: So any final words for our audience out there?

 

Jen Leech: Yes. So I...Poornima mentioned that we run a consultancy, Truss. And we do consulting so we build all sort of different kinds of software, we do infrastructure, we work with big data, we work with highly sensitive data for the government including healthcare data, things that are highly regulated. We solve a lot of different kinds of problems and we would absolutely love to help you solve yours. So if you have a hard problem to solve, please come hit us up. You can find us online at Truss.works, and we have a form that you can fill out there to request a quote. Thank you.