In this episode, Rick helps Tyler think through how to roll out a major product redesign for his 20,000 users. Tyler has a plan, but he’s concerned about losing customers through the transition. His biggest roadblock is figuring out how to roll this out without causing his customers to get angry and leave.

After going back and forth, the following framework emerged for communicating major product changes to existing users:

• Why you are making the product changes in the first place?
• How will you measure success (i.e. the desired outcome)? 
• What are the key messages you need users to understand?
• What proof points (e.g. screenshots, quotes, stats, etc.) can you provide that your key messages are true?
• How can you segment users and prioritize them?
• What mediums should you use to communicate?
• How often and over what time period can you communicate these key messages and proof points to each segment?

Takeaways include: 

• Start with why. Identify why you are doing this. Is it for customer acquisition, customer retention, or something else?
• Recognize that some users will go through change cycles, and help them through it. This starts with clear messaging.
• Don’t surprise your users. Give them plenty of notice and time to get through the change cycle.
• Treat this like a marketing funnel or sales pipeline. It’s a conversion.
• Segment customers by risk and value so you can prioritize outreach. This might be based on revenue, net promoter score (NPS), product usage or a new survey.
• Choose mediums and frequencies that support your annual contract value (ACV). If you are a low-ACV product, you probably can’t afford 1:1 phone calls for every customer. 

The change cycle concept

Source: changecycle.com

What’s the product change?

Tyler: The topic for this week is how to communicate major product changes to your users. This could go any number of directions, but the reason I'm bringing this up is, I've referenced the last few episodes where we're working on this big redesign of Less Annoying CRM. It's both a redesign and two major new features. It’s the biggest update we've had in at least five plus years, if not ever.

Rick: Did you say two new features?

Tyler: Two new features. Yeah, outlook, calendar sync. And we're completely redoing custom fields. Pretty big features, but the thing people will notice most is the redesign. And so I've been kind of thinking, "how do we communicate this to people?" The traditional way to think of this is, "how do you build hype and use it as a marketing event?", which we can talk about. But the theme of the podcast is "how do you build a business to last?" And I think a lot of companies change and eventually it leads to their downfall if they do this wrong. They forget their core audience and all that. They get too excited about the upside. Our audience is not one that loves change. And so most of the communication side that I'm thinking of is not, "how do we market this?", but instead, "how do we reveal this to people in a way that will minimize their likelihood of flipping out and leaving." Basically.

Rick: In other words, a lot of companies might see this as an opportunity to wow users. You don't see that. You see this as a threat to users.

Why you are making the product changes in the first place?

Tyler: I think it's good for them, but if I'm being totally honest, the reason we have to do this, is to keep getting new users. The two new features will be helpful to our existing users. The redesign won't. They already know how it works. It'll look nicer, but that doesn't provide any value to them and they're not going to be excited about the fact that we redesigned.

Rick: Is this true in most cases? When companies do redesigns, is it always usually for new users?

Tyler: Yeah, I think so. I was just kind of thinking of this case, but if your audience is really into design or something like that, maybe they get excited about it. But for the most part, if you think of software as a tool, which CRM software certainly is. I think most B2B software is a tool. Once you know how the tool works, I can't imagine much benefit to saying, "okay, now you have to learn a new way for it to work."

Rick: If it works currently?

Tyler: Yeah. Yeah, true.

Rick: Got it. Yeah. Okay. Man, I guess, if the redesign is valuable to new users, there's got to be some benefit to switching to the new design for old users.

Tyler: Yes. And so a couple things on that. First of all, this is one reason why we're bundling it with two new features. We've done this throughout our history. You know how anytime Facebook changes anything? Everyone on Facebook's like, "oh, I hate it, I'm quitting." And then they forget about it a couple of weeks later. One way we try to minimize that reaction is saying, "there's an actual new feature for you here that you care about." And probably it doesn't have to come with the redesign, but to a user, it seems like they're a package deal.

Rick: Yeah. I'm also realizing that your users are probably highly sensitive to this because this is a CRM product. They use it every minute of every hour of every workday.

Tyler: And there's also a history here, which is a lot of our users are older, 40 plus years old and they've been through multiple cycles of CRM companies screwing them over. And so part of this is a lot of them, their natural reaction is, "oh, you're getting ready for an acquisition. You're getting ready to raise prices." They see the writing on the wall anytime anything changes. So I have to kind of reassure them like, "no, no, no. We hadn't redesigned the software in seven years. We need a new design here."

Rick: I think we should dive into why you're doing this. Just because you need to do it for seven years doesn't resonate with me. It probably won't resonate with your users. So why do a redesign? Let's actually exclude the two new features from this conversation.

Tyler: Yeah, I agree.

Rick: Why are you prioritizing a redesign and what does it mean for the company?

Tyler: Okay. Let's break this into two categorie...