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Episode 19: Interview with David Cancel, CEO of Drift

David Cancel is the CEO of Drift, a conversational sales platform that has over 100,000 customers. Having started five companies previously, David shares lessons learned as a leader – including the importance of people, one-on-ones, and “no consensus” in teams.

Claire: Hi, everyone. I’m Claire Lew and I’m the CEO of Know Your Company. Today we have a super special guest with us. We have David Cancel who is the CEO of Drift, this incredible sales conversational marketing platform that I believe has over 100,000 customers. Just has seen a ton of success. David is just a really amazing entrepreneur having started I believe I was reading five companies before he was formally the chief product officer at Hubspot. When it comes to talking about leadership we are so excited to have you. Thanks for being here.

David: Thanks for having me, Claire. I’m a big fan of the newsletter. Everyone here should be subscribing if they’re not.

Claire: Thank you.

David: It’s amazing. Thank you.

Claire: All right. Well, you heard it from David. I did not pay him to say that. Do it if you were not subscribed.

David: I’m also a subscriber to your app as well. I check The Watercooler every day.

Claire: Awesome. Yes. Love it. Thanks. Thanks for the plug there too. We have an online community for leaders called The Watercooler. David, that’s awesome that you’re a part of it. Well, you know the drill. You know what the question is coming up but I’m going to pose it your way. The question I’ve been asking all these leaders lately is: “What’s something that you wish you would have learned earlier as a leader?”

David: So many things. I think the thing I think about the most … There’s so many. The list is long. I should do a long blog post or something about this but the biggest one I think now is that it’s 99% people and 1% everything else.

What I mean by that is having spent my first half of my career focused on everything else, which is like building the software, building marketing, sales, this, that. All the stuff that we actually spend all our time reading and doing all day that was the 1% of it. The real thing is it’s 99% people. Those people being inside your company and those people being your customers and it’s all that.

Once you look at it from that lens then you think, “Well, those problems are pretty well-known” and it leads you to a whole different discovery in terms of reading, in terms of understanding about just how to communicate and how to talk to people.

Claire: Absolutely. Was there anything across your career like a moment you can nail down or look back to where that shift happened? Or was it a gradual process?

David: Yeah. I think it was gradual in that it took a long time.

I think what happened was you fail or you feel the pain, I should say, you feel pain enough times that you finally wisen up. Mother Nature is going to teach you the hard way or the easy way and I was choosing the hard way.

Where I would hit this is at a certain scaling point there’s always these magical scaling moments in companies that make no sense when you get beyond 10 and 50 and 100 then everything starts to break. I just kept going back to focusing in on the stuff that I thought was important but all the real problems and all the things stopping the company were all of these people issues inside, outside the building.

They weren’t the technical things. They weren’t go-to-market. They weren’t the technology. They weren’t the stack. They weren’t any of that stuff. It was really the people.

Claire: Absolutely. What would you say is the biggest people issue, if you had to choose? What do you feel like is one of the most challenging? I know, take your pick, right?

David: Yeah. I think basically it’s the communication. It’s the aspect of communication is we don’t really understand that everyone is slightly different or wildly different and that they need to be communicated to in different ways and absorb information and communication in different ways.

I think we all know that on the surface. Everyone would say, “Yeah. Yeah. That’s obvious. Yeah, I know that. I know that.” Then when we go and turn around and try to communicate to someone we communicate to them in the way that we want to be communicated to. It took me I’d say back in 2007, 2006, I had a company called Compete and we were just getting acquired. That was in 2007. I remember the dates.

Someone on the team, our VP of marketing at the time, wanted everyone to take a Myers-Briggs test. I was the CTO, I was engineer background, I thought it was the dumbest thing ever. I hated it. We were probably 150 or so people and I think I was number 150th to take it because I was just silent protest.

I took it and now it’s all I talk about is personalities and this and that. It was a discovery for me because not really in what it told me about myself because most of us kind of know a lot of that but the fact that everyone was so different and just looking at them and just trying to understand them just logically of like, “Oh, this is why when I say X, Y, Z in a certain way they’re not really getting it.” It was just this big light bulb moment from a very simple test that anyone can take online. Simple personality kind of assessment.

Claire: Yes. What are you, by the way, for the Myers-Briggs?

David: I am INTJ.

Claire: Ah, amazing. You know what’s crazy?

David: Yeah. I am INTJ.

Claire: Yeah. As am I, by the way. We are like 1% or 2% of the population, right?

David: Oh, really?

Claire: Yes. I know. I was about to say that’s super rare. No, but I find … First of all, I think that’s absolutely hilarious because I think there’s a healthy, natural skepticism around personality tests. I think we all like to think that we’re special or we all like to think that everyone is kind of like us. It’s usually one of the two or sometimes even a mix.

Right now I guess with your team how do you, as you lead Drift … Remind me how many employees that you are at today?

David: We’re 130 some odd. 130-ish. Yeah.

Claire: Excellent. 130 some people. How do you think about very, perhaps a little bit more tactically with 130 people, communicating in a way where you’ve got 130 people who are all over that Myers-Briggs test results, right? You’ve got INTJs, you’ve got ENFPs. How do you think about in your role as the CEO 130 people? Everyone needs a different communication style. What do you do in that situation?

David: I think one thing that I discovered over the time was that the most scalable thing in terms of keeping all of this working as teams were scaling here and then previous companies was actually the one on one. The one on one, which inherently seems like the least scalable thing possible and is the first thing that everyone pushes aside because they don’t have time for that was actually the key to actually scaling teams and helping make them effective.

In that context, the one on ones, we use a different set of personality tests but we talk a lot about Myers-Briggs and everyone knows that in a joking and posts their stuff and everybody wants to know what they are. Then we use something called Predictive Index, which is another flavor in this world. We use that in the hiring profile but as well as post-hiring to bring up these areas.

People are using this all the time internally even in their one on ones, kind of ongoing, and reminding themselves about it, “Well, this is how we communicate to Emily and Claire likes to be communicated this way so I need to tailor my approach.” It’s an active thing.

I kind of think about most of this stuff as English gardening. If you want an English garden most of the work is actually the pruning and the taking care of. It’s not the planting, it’s not the plant selection. It’s this constant pruning. The day that you stop pruning is the day that the garden is full of weeds and overrun.

Claire: Yes. I love that analogy. I also love that analogy just in the sense that it’s this idea of almost micro choices and actions that actually build a successful team. I think what a lot of people think about leadership, at least in how our society has thought of it, is it’s bold action. It’s big steps. It’s crazy decisions in moments of crisis and that’s what defines us as leaders.

Your take and what I’m inferring here is it’s actually the pruning. It’s the small day to day actions. It’s things you don’t say and do say in those one on one conversations. I think that’s incredibly valuable for the people listening. I guess … Go for it.

David: I think just to pull on that thread there I think that I take it to the extreme. I think it’s never the case that it’s these big bold actions. That’s a Hollywood myth. Now I’ve been doing this long enough that I’ve known tens of thousands of entrepreneurs and leaders. That has never been the case. That is a make-believe story that we tell ourselves and then we feel anxiety when leadership doesn’t look like that.

It’s not like that. It’s really a game of inches. It’s just like these micro little things and if you do them over time and long enough then you wake up one day and it’s magically this great result. It’s so weird to me that for whatever reason in leadership, especially in this time, we think it’s these big bold actions because it’s never been the case.

If you look at anything else in life it’s never worked that way. There is no this big bang thing and then I’m an Olympian athlete because I discovered some magic secret. It was starting at five years old and training for 10 years and then finding this overnight success.

Claire: Absolutely. Yeah, it’s that athlete that stays 30 minutes after practice but they do that every day for 12 years. That’s what separates those super athletes from the rest of us.

What would you say, David, are some of the other micro actions? Aside from communication and one on ones but other small nuances that you feel like most leaders don’t take the time to make time for or they overlook. What are some things that we should be considering?

David: Yeah. To me, it all comes back to the people stuff. It’s those one on ones. It’s the spending time in the hiring practice. We’re 130 right now and we are going to be around 200, add about 100 people this year, by the end of this year, to the team so we’ll be about 220, 230. I’m still involved in every one of those interviews.

Claire: Really?

David: Yeah. I’m at the end of the chain so it’s been very well-filtered by then so I’m not taking the bulk of that but still it’s 100 people that I’m going to talk to. I find the way to make time, even if it’s a 10 minute call, with those people because it’s a super important part of the process. I think that’s one of the first things that we’re like, “Oh, we’re 50 people now. I shouldn’t be in the interview process.”

Like, no. You should be in the interview process for as long as possible. I’m going to try and push that as far as possible and I think that’s important. My co-founder is the same. He’s involved in the process. If I’m not there he’s there or someone else on the team jumps in as well. It’s a super important thing. I would not give that up for anything because a lot of it is that and then a lot of it is the one on one and then the other stuff takes care of itself.

Claire: Definitely. I think some CEOs that are probably running smaller companies are thinking, “Oh, shoot. Oh my gosh. Maybe I got to involve myself in that.” David, what else would you say then … You said you had a big list of stuff so other than the people or the communication issues, anything else that … Here’s the thing. You’ve sat on numerous boards. You’ve mentored so many entrepreneurs over the years. Any parting words or advice for any aspiring leader or current leader who feels like they’re just struggling right now?

David: Yeah. I’d say we’ve all been there. One thing I would say is basically I think about this triangle and I think there’s three things that matter when it comes to your business. One is the market that you’re in. Two is people. Three is your product or solution or your service or what have you.

I’m most comfortable when I come from the product side of things. That’s where I come from. I kind of organize them first as market and then there’s a big gap, and then it’s like team — people — and then there’s product is third.

I always think about it in that order now but for the first half of my career I thought about it like most entrepreneurs do, which is the other way around, which is like it’s all about the product, it’s all around the service. No one ever thinks about the market. Like the market will will that to happen somehow.

Claire: Yeah, exactly.

David: Then they kind of think about the people a little bit. It’s kind of the opposite. It’s like big markets that are changing that allow you to relook at them or allow you to create a niche within them. Think a lot about that. Think a lot about the team. Those are the two big levers.

Then the product, we’ve all seen many examples. Not to say that we should aim for a mediocre product but great markets with great teams they can be mediocre products or not as good of a product that you can create that can own that market because those two things are true.

For us, engineers or geeks or what have you, we like to think about all the product, really the people, and that market that you’re in. That’s my advice. Really take a look at those two things.

Claire: I love that. I think what that speaks to is I think our desire as entrepreneurs, as leaders, to control. The product we can control it. Absolutely. We can build it. We can write about it. We can design it. It’s within our control. People, oh my God, no. There’s no way we can control in terms of people. Market? Forget about it. That is out of our control so we don’t spend the time.

David: I think you nailed it.

Claire: Yeah. As humans, that’s our natural tendency is we love to create any sort of semblance of control. That’s why we like to plan. I’m a big planner. I’ve noticed this even in myself as a leader. It’s like, Claire, you’re trying to create this plan because you’re trying to control for something that honestly you cannot control for.

David: Can’t control.

Claire: Right. It’s great to come up with those contingency … I think I love that share of focus and realizing that just because you can’t control it doesn’t mean you shouldn’t be spending the time and energy to think about it. Thanks for that, David.

One other thing that actually just came to mind. I was reading something on The Drift blog post recently. You had written a little bit about Peter Drucker, who is a seminal author of management. Love Peter Drucker. Who doesn’t, right?

David: Yes.

Claire: One of the things that you talked about that he talks about and I absolutely loved was this idea of no consensus in leadership. I thought it was really counterintuitive. Yeah, I would love to actually talk a little bit about that with some of our viewers here. Tell us a little bit about what no consensus is and what you mean by that and why you were so passionate about this idea in leadership.

David: One, I love Peter Drucker and we read a lot of Peter Drucker here. I’m about going back to the greats. You can skip most business books and go to Peter Drucker because they’re all derivative of him.

Claire: Yup. I agree.

David: That you read out there today. That’s where I would start. For us, no consensus, that idea really started with me with probably a decade ago, or maybe a little more, probably 15 years ago. Seth Godin who is another great writer, one of the marketing staff, had really wrote about picking an edge. What he would say is you’ve got to pick an extreme.

You’ve got to pick an edge. You can’t be in the middle. Then what I learned on my own after having that in my mind was that in creating a company the worst thing that you wanted was indifference. That’s what entrepreneurs battle in terms of creating a product is indifference.

It’s okay to have people love your product. That’s awesome. It’s also okay for people to hate your product because you can take someone who hates your product, who has an emotional connection to it, and move them closer to … You can move them to be fans. You can almost never move someone who is indifferent about something to be a fan.

Anyway, I had been thinking about that for a long time. One of our values here, we have eight, is no consensus. Consensus is the norm. We all regress to this idea of consensus within the company of, “Let’s all vote for something. Let’s hold hands. Let’s not be offensive. Let’s not take an edge.” I was all about picking an edge because that’s where I think the great things are created and consensus by definition is averaging down to the least offensive, least controversial thing, which is just going to lead you into the center of indifference. You’re just going to create something that nobody cares about, even the people that are creating it.

For us, it’s about picking an edge, going out there, getting a reaction from that even if it’s sometimes not the reaction that you wanted. Like people don’t love it but at least you can work from that because you’ve actually hit on something that they are connected to.

Claire: Absolutely. I find this concept so fascinating because I think a lot of entrepreneurs would agree and for folks who are starting successful businesses they reflect on their own product and they go, “Oh, we are doing well because we’ve picked an edge.” I think the tension in this concept of no consensus happens when we think internally with our teams about collaborating and moving forward.

In so many teams and CEOs that we’ve worked with there’s always this fascinating dynamic and conflict between how do you pick that edge but at the same time get people on your team not to kill each other and be bitter about the fact that it’s not their idea, it’s not maybe their edge?

David: You know how I do that?

Claire: Yeah. How do you negotiate that? For folks who are like, “But David, you can’t collaborate. How do you make decisions if you’re always picking the edge? Aren’t people going to get pissed off and leave?” Yeah. I’d love to hear your thoughts on that.

David: I stumbled on the answer back at Performable, which is like two companies ago, by accident. The answer that we’ve been using since then is this idea to create this customer-centric approach to building anything. We’ve taken it so far adrift that everyone and this is a kind of daily mantra here is that we tell everyone, including ourselves, that your idea and my idea is wrong. 100%.

The only thing we know for sure is that whatever idea we have is wrong. What we need to figure out now is we need to get out and work with our customers to figure out how wrong. It might be 5% off. It always is. It’s never you just create something and divine inspiration and then that’s the thing and it never changes. There’s always going to be a tweak to it.

Or it could be 100% off. It’s usually somewhere in between those two extremes. Why not get out there? Work with our customers from the very beginning to figure out how off we are. What we’re trying to do by doing that is to break down our collective egos, our personal and collective egos, and get out there and get over this part of, “Well, we can’t collaborate. We can’t do this stuff because we all are defaulted to say …”

Back to what Peter Drucker would say, the only goal of business is to serve a customer, right? We’re only here to serve. It doesn’t matter what Claire’s idea is or my idea or this person’s idea. What matters is what does the customer need? How do we best serve that?

Claire: Absolutely.

David: The only one who can tell us that is that customer. Not us.

Claire: Absolutely.

David: We’re never the customer.

Claire: I love that approach in, like you were saying, taking the ego, the personal or collective ego, out of it because I think that is …

David: It’s hard.

Claire: It’s so hard. I think it’s a huge reason for why a lot of decisions or a lot of progress isn’t made. I think helping to depersonalize any sort of potential source of conflict is huge. Then something interesting that I’d love to get your thoughts on is one approach as well when you think about consensus and collaboration or how do you build consensus when there’s conflict, is this idea that, yes, we’re all trying to serve the customer but also we can agree to move forward but not even have to agree on the same things.

I might move forward because I feel like I want to give this idea a shot and another person might move forward because, “No, this is actually going to be the thing that really helps us win as a company”. Whatever it is. We can move forward for different reasons and everyone actually doesn’t even have to move forward for the same reason as long as we can move forward.

Just accepting that there’s some plurality in that decision making process when you’re trying to find that edge. I could not agree more with you and I think it is such a hard and messy thing in practice. It really is. At least from what I’ve observed. Yeah.

David: This is why it’s all about people. Back to the beginning. It’s 99% people. It’s this. It’s like the ego stuff is a daily battle. In terms of pruning that’s mostly pruning all day. Including myself. Including everyone in the company. No one is immune from this.

I’d say at the beginning of this year I sent out a letter to the team that I wrote up, like a shareholder’s style of a letter, and I looked back at all the great stuff. It was an amazing year. I look back and I say, “Okay, let’s talk about the top five mistakes that I think we made as a team.”

I traced back and I said, “I think every single one of these mistakes” and I highlighted how, “Were due to ego.” Every single time we made a mistake it was due to our collective ego.

I traced back and I said, “I think every single one of these mistakes” and I highlighted how, “Were due to ego.” Every single time we made a mistake it was due to our collective ego.

What I’m trying to point out there is we made these mistakes. We don’t need to make these mistakes and we didn’t need to make any of the mistakes we did if we didn’t let our egos get in the way. How do we get better so that we don’t let our ego get in the way in 2018?

Claire: Absolutely. I think on that note that is a beautiful reflection that I’m going to be taking away from this interview. That’s for sure. I think for everyone watching there’s so much wisdom that you shared, David. Thank you so much for your time. This has been a blast.

David: Thank you so much for having me, Claire. I’m a big fan. Everyone sign up for The Watercooler.

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.