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