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Episode 4: Interview with Des Traynor, Co-founder of Intercom

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 know there is standard and these couple of occasions you didn’t hit it. I want to talk about it.

But I wrote down my honest thoughts before I went into the meeting. I went in and I had the meeting, then I came back and my notepad was still open on my screen. When I sat down and replayed the conversation in my head of the words I had said, I looked at the difference at the words I had written down.

What I had written down was: “Not acceptable standards, understand why it might have happened, let’s talk about this scenario which all this played out.” But I need to be clear from my end that we can’t treat our customers like this. It’s needs to be higher quality, we need to be more compassionate, more empathetic with the customer, etc.

But then I thought about the meeting and I was like, “Hey look you’re doing awesome, there is a couple little things that” … And how quickly I had degraded the message in order to make it a nice, easy conversation for me.

Claire: Yes.

Des: Because I wasn’t thinking about them, I was thinking how do I make this an easy Tuesday afternoon? When that realization hit home as I re-read my notes I was like, “I’m fucking this up.” Wait, can I curse?

Claire: Haha, you’re good. I can so relate. I think sometimes we unintentionally dilute a message without, almost subconsciously, right? Almost subconsciously, just because I think a lot of, it’s human instinct, we fear the reaction. We’re trying to control for the reaction so we bend the words a little bit. We do the shit sandwich, so to speak, where you’re giving the compliments right around the shit because you’re like, “Oh I just got to say the good stuff just so that person feels good.” You’re so right, it’s dangerous because what did that teammate walk away with? They probably thought, “Oh, I’m doing okay.”

Des: How could they walk away thinking that? I slipped up a couple of times, the teams like, that’s fine. Because that’s the message I gave, nearly a 180 to what was on my screen.

Claire: Right.

Des: I guess another thing that comes up a lot is, that I think about a lot, is transparency, right? How it’s such a double edge sword.

Claire: Yes.

Des: Specifically there’s been a lot movement towards the transparent company. Let’s share everything with everyone on the team. There’s a lot of good quotes and good arguments that support this, which is like, if you want your team to behave the way that you would behave they need access to the same information that you have.

Claire: Right

Des: I think that’s generally true. I 100% agree with that. The key thing people forget in transparency is it’s not about opening up the Google Drive and making sure that everyone can read everything. It’s about transparency of context as well. As in, I find myself constantly saying, “Here’s a piece of information. Then here’s a shit load of context you need to understand, that’s what makes this interesting.”

Claire: Yes.

Des: It’s so messed up, where the cost of, the size of the context, it could be anything. It could be like, “Well, in order to understand this you first of all need to understand the theory of disruptive innovation so let me start there.”

Claire: Right.

Des: Genuinely, I’m not saying transparency is bad. But I think transparency where it causes more confusion than it resolves is risky. Where it make it people want to ask more questions rather than answering questions, you need to think about this. That’s why I think the sharing nuggets of information, whether it’s a spreadsheet or whatever, if you have people either misinterpreting or just frankly lost for interpretation, you need to think about whether or not that was fully transparent thing to do.

Like in some sense, no company is 100% transparent because for that to happen every time you go for a walk with somebody you have to write the conversation down and share it with the entire team.

Transparency is some sort of spectrum. I think one thing that people over-engineer for is let’s let everyone have access to absolutely everything and somehow magically assume that you’re going to understand it all on how we think about everything all the time. That’s just not how it works unfortunately.

Claire: Yep.

Des: So I think that’s understanding that transparency’s a spectrum. Some areas where it’s really ROI positive: So all of our product ideas, all of our product’s strategies etc, you want everybody in company to understand that so the can make the smartest local decisions. Random stuff like how we think about a new market force. Or hey, once we pay our PR agency or something like that. It’s just, in order to understand you have to provide all this other stuff such that the message becomes really just a waste of time.

Claire: Sure.

Des: I think it’s worth having a critical threshold to decide what’s actually good for everyone to know, what’s not a secret but needs context, and what actually genuinely might be a secret and you don’t want everyone panicking about something or whatever. Understanding that transparency is a spectrum is something that, as a leader, I think you need to get your head around pretty quickly.

Claire: I also could not agree more with that. I think it runs, honestly like you were saying, counter to a very popular idea these days, which is just open up everything. Which again, in theory, I mean, hey I run Know Your Company, right? It’s like of course, transparency is good, but I could not agree more that transparency is only useful with meaning assigned to it, right? Like you were saying, in context. So it’s a lot for a leader, I think also, to be very conscious about how they invest in training folks and giving that context. Like you said, where is it appropriate and honestly in what cases is it distracting? I personally, can only handle so much information in a day. I don’t want to know the details of every single little thing that’s happening on support. I don’t want to know the details on every single thing that’s running on product. I would go insane.

It’s the same way. To what extent, as a leader, and this is what you have to decide, is that information useful, do we invest in proving that context? What point is it actually distracting? So, I think that’s very, very spot on.

Des: Do I have time for one more?

Claire: Go for it Des. I was just about to say, I’m not going to cut you off yet, these are all so good. What’s your last one?

Des: This is my last one because I got a meeting after. I think something that wasn’t obvious to me until maybe about year two or year three was the importance of consistency in who you are, who you meet, and your behavior in general. I think I always thought, you have this attitude of, oh consistency means boring. It means repetitive. It also genuinely means calmness and predictability. It means you’re easy to interpret and easy to predict by your team, which means if you consistency behave in a certain way, people can preempt and predict what you’re likely to do. As a result they know how to act as if you weren’t there, which is a really vital thing.

There’s this quote that people fall in love with, which is something like, “If foolish consistency is the hobgoblin of a simple mind” is the quote I often hear back at me when I talk about consistency. I think the key there is foolish consistency, it’s consistency where you’ve gotten the information you should be acting differently but you’re still doing the same thing. But in general, one example I see of this all the time is people who apply what I call central standard. So that is, some projects they jump into and some projects they stay out of. Some people they go hard on and some people they go easy on.

Claire: Yes.

Des: Some things they’re crazy about, some things they’re quiet about. It becomes quite chaotic because people never know where they stand in relation to anything. So I think having a set of principles that have a setup, here are the things that I really care about when you share work with me and I love to give you feedback along these lines. Here are the things that I frankly don’t care about unless it crosses some crazy threshold.

Claire: Mm-hmm.

Des: I think doing that, but it’s so important to do it consistently. It takes a lot of discipline to be like, I will always, whatever, point out a typo in a blog and have headliners. I’ll never be like, “That’s okay.”

Claire: Right.

Des: It’s that consistency always being a thing, people learn and they learn how to work with the set standards you set.

Claire: Yes

Des: There’s a quote by some off brain military person like, “The standards you walk past is the standard you tolerate.” I think that’s why it has to be consistent. Not opportunistically say, “oh we have to do a really good job here, but this thing over here can be shit.” I really felt that, again, it’s forced a greater discipline and basic leadership hygiene on me to know that I don’t actually get to pick and choose. You’re doing the job all the time, not just the times you show up and you’re excited. You’re doing your job all the time.

When your job is leading, you’re basically setting a precedent for acceptable and expected behavior. Which means, every single negative thing you do, every bad behavior you have, you’re basically admitting that you think that’s acceptable.

Claire: Yes.

Des: So you really need to get your shit together, you know?

Claire: Oh my gosh, that’s an amazing nugget there, Des. Because I think what you’re also talking is that is how a leader sets the culture, right? Because at the end of the day, culture is just the byproduct of consistent actions, behaviors, and beliefs right? So, without that consistency then your culture becomes, yeah, it becomes a morphosis, it becomes this thing that gets shaped by external factors or just by a whim of what happens to be going on in the moment. A lot of people, they’ll approach me and talk about, “Yeah Claire, how do you shift culture? How do actually get a culture to be open and honest?” My answer is always, well, it’s always the consistent behavior first and foremost from the leader. It starts there.

Like you were saying, if she or he is setting the standard for, “Oh when someone has a desenting opinion I don’t yell at them in front of my team. I actually thank them and I tell them ‘You know what? I disagree with you but I love that you brought that up.’” Right? That sets the expectation then for that next person to come up to you and bring that view point. Without that consistency, just as you were saying, then that culture doesn’t exist, it doesn’t grow. So that’s, yeah, I love that. Thank you so much for sharing that.

Des: That’s it. I’m done at three. I could keep going.

Claire: Oh my gosh, you know what? I was about to say, I’m going to have to come back to you for more because wow, I’m blown away. I think so many of the folks who follow along with this will really appreciate you sharing all that. Thanks so much for your time. Really enjoyed having you here, Des.

Des: Thank you so much for the opportunity.

Claire: Of course, okay, talk soon. See you.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.