The Heartbeat

As the Founder of Copy Hackers and Airstory, Joanna gets real about her biggest struggles as a leader. Joanna Wiebe is the founder of Copy Hackers – an acclaimed site + service that helps businesses write better. She also most recently co-founded Airstory. I’m a big fan of her work. In this interview, she opens up about what she…

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As the Founder of Copy Hackers and Airstory, Joanna gets real about her biggest struggles as a leader. Joanna Wiebe is the founder of Copy Hackers – an acclaimed site + service that helps businesses write better. She also most recently co-founded Airstory. I’m a big fan of her work. In this interview, she opens up about what she… Read the full article

As an acclaimed nonprofit leader and public speaker, Halleemah Nash reveals what “authentic leadership” really means… Claire Lew: Hi everyone! I’m Claire Lew, and I’m the CEO of Canopy (formerly Know Your Team/Know Your Company). Today, I am incredibly excited because I have a very special guest and dear friend with me today. I have Halleemah Nash, who…

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As an acclaimed nonprofit leader and public speaker, Halleemah Nash reveals what “authentic leadership” really means… Claire Lew: Hi everyone! I’m Claire Lew, and I’m the CEO of Know Your Company. Today, I am incredibly excited because I have a very special guest and dear friend with me today. I have Halleemah Nash, who is the Executive Director… Read the full article

As the founder of a 300+ software company, Des talks about the silence cost to being nice, the pitfalls of transparency as a leader, and the power of consistency. Claire Lew: Hi everyone, I’m Claire and I’m the CEO of Canopy (formerly Know Your Team/Know Your Company). I’m really excited today to have a special guest with me, Des…

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As the founder of a 300+ software company, Des talks about the silence cost to being nice, the pitfalls of transparency as a leader, and the power of consistency.

Claire Lew: Hi everyone, I’m Claire and I’m the CEO of Know Your Company. I’m really excited today to have a special guest with me, Des Traynor, the founder of Intercom.

Des is someone who I’ve gotten to know over the past few years. We’ve spoken at a few of the same conferences and I’ve always been blown away, to be frank Des, by some of the insights that you’ve shared around product, around growing teams. It’s always so interesting to learn from you.

So, really grateful to have you here today and to ask you one question around leadership.

Des Traynor: Wow, it’s cool to be here. Been a fan of you and your talks and your company for quite a while so it’s great to be here.

Claire: Thanks so much Des, appreciate that. So here’s the thing, here’s the one question I’m going to ask you, which is…

What’s something you wish you would have learned earlier as a leader?

Des: There are so many, do I have to pick one?

Claire : You can pick as many as you want. You can get started going through the list and I’ll cut you off when I feel like it’s too much.

Des: Okay. All right. I’ll go though the list and you can just mute me if it gets to be too much….

Des: I guess something that I try to talk to people a lot about is the importance of being clear and honest in communication. I think that often goes directly at odds with the social skill of being likable. I think as a leader, you have to understand that your job isn’t to leave a room whatever thinking you’re a swell person who they really want to hang and go to beers with. If someone has done great work, they should feel great about after talk to you about it. Similarly, if someone hasn’t done great work they shouldn’t feel great about it.

You shouldn’t optimize for your own perspective when you’re sharing feedback. You should optimize for the clearer I feel about it, it helps the person advance in their career. I think there’s a real silent cost to being nice.

I think it is part of the “radical candor” concept. I think there’s a danger that people adopt: They apply the same skills they use in social dynamics when they’re at a cocktail party to management.

I think I learned very early on in my career that my job isn’t to be really popular. My job is to be really honest and fair and treat people with respect they deserve and give them the feedback that they need to improve in their career. I think that, for me, is something that most people who find themselves in leadership position early…

By the way, this is very true in startups when they grow so quickly, before you know it you have a team of six or more reporting to you and you never asked for this, but now it’s happened or whatever.

Claire: Right.

Des: I think there’s a silent cost to optimizing for being nice. I think you really need to think about that as a leader. That’s probably my first one, I think. It’s the one that maybe bites you early in your career.

Claire: Right. Is it something that you remember? Was there anything that happened where you were like, “Oh my god, I never imagined myself optimizing for nice.” I mean, you’re a nice guy, let’s be real right? You’re a good person, right? Most people, I would like to say, are. But was there a moment where you’re just like, “Wow, I think I’m actually sort of wanting to be liked by my team more than I am trying to make the right decisions here.”

Des: I think the moment for me came when I remember going into a meeting and we’re having to share feedback with somebody. It wasn’t even particularly bad, it was just like hey here’s a few things that can be better… At the time, it was customer support, it was a couple conversations that just could have gone better. I just wanted to let the person kn

As the CEO and co-founder of Stripe, a payments company processing billions of dollars each year, Patrick Collison shares with me what he wishes he learned earlier as a 28-year-old leader of an almost 900-person company. You cannot be all things to all people. This is true of building products, socializing with others — and true of leading a company. Patrick Collison,…

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As the CEO and co-founder of Stripe, a payments company processing billions of dollars each year, Patrick Collison shares with me what he wishes he learned earlier as a 28-year-old leader of an almost 900-person company.

You cannot be all things to all people. This is true of building products, socializing with others — and true of leading a company. Patrick Collison, the CEO and co-founder of Stripe, shared this insight with me and how it’s shaped the way he’s thought about running and growing an organization.

“It’s reframing the question, not as, ‘How do you keep people happy,’ but, ‘How do you keep the right kind of people for your organization happy?’”

Watch or listen the full interview above.

As a world-renowned designer, thinker and executive, John Maeda shares with me what he wishes he learned earlier as leader.

“Just execute.”

In a world where there is no shortage of self-help literature, management books, and conferences for leaders, John Maeda reminds us that no book, article, or talk can replace simply doing the thing, messing up, and moving forward.

I first met John Maeda back in 2014.

He’d stumbled across my website for my consulting business, ClarityBox, which helped CEOs uncover their blindspots, and sent me a nice note saying how much he appreciated the premise. When I became the CEO of Know Your Company and happened to be out in San Francisco, we grabbed sushi.

I’ll never forget how insightful, curious, and hilarious he was to talk to.

So as part of this interview series, The Heartbeat, John was one of the first people I wanted chat with. I was interested to get to the heart of what he saw as leadership.

For those you unfamiliar with John’s work, he currently serves at the Global Head of Computational Design & Inclusion at Automattic. Previously, he was the Design Partner at Kleiner Perkins Caufield Byers, and the 16th President of the Rhode Island School of Design.

I was honored to steal some time with him for this interview. Hope you enjoy watching it.

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Every few weeks as part of The Heartbeat, I asks one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. In the inaugural interview, I spoke with Jason Fried. As CEO and co-founder of Basecamp and a NYTimes best-selling author, Jason shares three things he wish he learned earlier in running Basecamp for the past 18 years. Watch or listen to the full…

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