Pushing Past Pushing: How to Create a Pull Culture of Leadership with David Cancel

Andy Cook
March 30, 2018
Interview with David Cancel

Read almost any job description and “driven” is likely to figure in it as a desirable characteristic. So why do most leaders (perhaps yourself included) end up having to push their teams towards goals with either deadlines or numbers? Where does that inner drive go? It’s still there; problem is most leaders leave it untapped.

David Cancel has discovered how to tap into that drive so he never has to push his teams towards shipping deadlines or targets. And he’s got the resume to prove that his method works.

David has so far founded five different successful tech companies, several of which have been acquired.  His previous company, Performable, was acquired by marketing tech giant HubSpot. With the acquisition, Cancel became Hubspot’s Chief Product Officer and helped position the company (which is now worth over $4 billion) to go public. His current company, Drift, is the world’s leading conversational marketing and sales platform.

So what’s his secret sauce for not pushing teams? Harnessing employees’ inner drive through autonomy.

I’ve taken away the burden of dates and I’m giving you the autonomy to decide when something is ready to go out. I’m giving you the autonomy to prioritize what you work on.

Autonomy to prioritize, David explains, doesn’t mean team members aren’t held accountable for results. In fact, they’re more accountable since they’re the ones who decide on the work. And setting the expectation of accountability up from the beginning is important—or you may run into trouble.

Autonomy comes with the responsibility of accountability for your actions. Autonomy with no accountability isn’t autonomy—that’s anarchy.

So how can you build a team that functions on this autonomy-cum-accountability model? David has a two-step process. When you apply both steps, as David does, (and as he’s trained his managers to do,) you’ll be able to harness your team’s inner drive and pull each team member forward by their own volition, rather than push them on with the traditional stick and carrot method.

  • Step 1: Check for inner drive. True inner drive to succeed translates to a desire to learn and grow—a desire not to remain stagnant. Not everyone is going to have this trait, though David finds the current generation of workers is much more interested in personal progression than people of his generation. That’s the easy step.
  • Step 2: Understand what propels that drive. Understand what truly propels an individual’s drive to learn and grow. The process is harder than it sounds, David warns, because often people don’t understand this themselves. But it’s your responsibility as a good leader to tease it out of them. When you do, you’ll be able to understand if you have a fit between their motivations and your goals. You need alignment between what you’re building and challenges that pull them towards achieving their own goals (without having to push them once).

When these two things overlap, then this pull model begins, and magic happens. All of a sudden this individual is all in and consumed with whatever the task at hand is. Not because they’re necessarily trying to hit a number for the company or get something shipped, but because the challenge is moving them forward on their own personal progression, and that’s when that passion kicks in.

In our podcast conversation, David shares with us the exact steps he’s developed for building teams on the pull model of inner drive. He walks us through his process with candidates and the types of questions he asks them. He also explains what he’s looking for and how he approaches goals that are tough to quantify (which is not a bad thing!) We talk about abandoning derivative processes that don’t work and going back to first principles for building a successful team.

If you’ve disliked being pushed by others or pushing your team to perform (like David has), then this is the episode for you. Click play to get David’s best tips, and don’t forget to subscribe to Org Uncharted on your favorite podcast player for more insightful conversations with innovative business leaders.



David Cancel 00:00

Yeah, it’s I flipped it, and basically went back to first principles, AKA, grandmother’s wisdom. If we care about the customers being happier, why don’t we just measure that? Or we care about like X result, let’s start there. If we start from there, all of a sudden it just changes that first principle approach just changes everything. It’s like, and you start to look at most of the processes and approaches that we have whether it’s in developing products, marketing and sales, and whatever, and we see that because we’ve become so derivative, they’re insane. They actually make no sense.

Jay Acunzo 00:34

You’re listening to this show for people who empower other people to do their best work. I’m Jay Acunzo, and this is Org Uncharted.

Jay Acunzo 00:56

Hello once again, and welcome to the show that believes, I think, what you believe. We believe in putting the customer first, and making decisions from the bottom up and in fighting against top down leadership. This is the official podcast from Tettra, which makes knowledge management and sharing software for modern, fast-growing teams. Tettra has also collected all kinds of great company culture decks for our show website. So you can go to OrgUncharted.com and check out the behind the scenes of how companies like Buffer, Google, GitHub, Lululemon and a lot more are building thriving cultures. That’s OrgUncharted.com.

Jay Acunzo 01:42

My friend, people are just so much more than little shapes on an org chart, so much more. So it’s time we actually treated them like that, and ventured beyond the org chart to explore today’s theme, pushing beyond pushing. Here’s the deal, we hear these phrases a lot when it comes to team management and motivation. Carrots and sticks. I’m sure you’ve heard those words applied to leadership before. The carrot of course is a reward and the stick obviously a punishment. Carrots and sticks.

Jay Acunzo 02:12

This idea of these two divergent approaches to team motivation has been in use for decades with some citations dating back to the 1940s. This idea seems harmless enough at first, sometimes people need the promise of rewards, sometimes the threat of punishment in order to motivate in their work. But put aside the fact that lots of psychological studies and authors have largely discredited this idea, and instead let’s focus for a moment on the origin of the phrase itself, and how that changes our beliefs as leaders. Think about the phrase carrots and sticks.

Jay Acunzo 02:46

Gee, what comes to mind when you hear those phrases? I mean, what’s become lost in the jargon? How about the fact that the original story is about a boy trying to motivate a donkey? Is that what influences our thinking as leaders today, viewing people like donkeys? I mean, even if that thought never enters somebody’s mind at work, I’d argue that the very fact that this is the originating notion has echoes throughout time that still shapes our leadership behavior in terrible ways in the corporate world.

Jay Acunzo 03:14

Okay, maybe the carrot doesn’t sound so bad, a little hummus on the side would be kind of nice, some sliced peppers and celery, and you have the makings of a nice little appetizer. But then there’s that damn stick in the mix. I mean, what the actual hell? I mean, in this metaphor the stick is used to smack somebody forcibly to drive them forward. It’s that idea of constantly pushing people to motivate. But did you ever notice that when you’re pushed too hard, it’s just not all that motivating, unless you actually believe in where you’re going, unless you feel a pull towards the destination.

Jay Acunzo 03:46

I mean, we all want to see our companies succeed, I get that, but a lot of times the mile markers on the journey toward success feel a little arbitrary. You know, every day we get pushed to hit deadlines, and reach benchmarks to ship this project or that one. Yet, the rational around that work isn’t always clear. Whether due to outdated thinking or lots of pressure put on ourselves as leaders, whatever the case might be, sometimes when those screws tighten, we turn to the stick instead. So that brings us back to today’s theme, pushing beyond pushing. There must be a better way to lead.

David Cancel 04:27

I don’t like being told what to do, I don’t like being pushed myself.

Jay Acunzo 04:30

That’s David Cancel, co-founder and CEO of Drift. The former Queens native and current Bostonian has founded five different tech companies in his career, several of which were acquired. The last one, Performable, was acquired by the marketing tech giant HubSpot, which installed Cancel as their Chief Product Officer. There, he helped turn around a product that was hemorrhaging customers and position that business to go public. HubSpot is now worth over $4 billion. Today, he’s building Drift, which makes in their words conversational marketing software, including a flagship product, a chat bot for marketing, sales and support teams to speak directly to website visitors.

Jay Acunzo 05:08

David comes from an engineering background, and when he first made the transition from engineer to leader, he says pushing was the only way he knew how to lead.

David Cancel 05:17

There was a time where we didn’t have access to the world’s information, where you couldn’t just watch a YouTube video from a famous leader or a speaker, like where information was actually hard to get, and so I grew up in that world. In that world, trying to become a leader and learning how to manage teams, the only role models and playbooks that we had was to read books that at the time were mostly written by Jack Welch, and lots of other Fortune 100 or Fortune 50 CEOs who were famous at the time. They almost can never be applied to a startup for sure. But even a smaller, non-global company that they were leading, but these were the only lessons that existed. There were no other lessons. In that world, I ended up learning the only way I could, which was through trial and failure, and through reading some of those books and trying to apply whether it was Jack Welch, or Andy Grove in How Output Management, some of that stuff.

David Cancel 06:13

I found that it led to me creating environments that were very prototypical, they were a top down command and control kind of like, “Here’s a plan, and here’s how we’re going to roll out the plan.” It ended up being, and I think most companies still operate this, being a push. So you’re always trying to push people within your company to achieve some goal for the company. It’s always revenue. But some revenue goal that you have for the company, but you’re always figuring out ways to push, push, push people.

Jay Acunzo 06:46

For David, this whole push culture thing didn’t really jibed with who he was or how he wanted to lead, so he decided to create a whole new culture himself, one that he called a pull culture. But what does that really mean? More importantly, what does it entail to create it? David says that he begins by figuring out what motivates his people. He discovers what they each want to learn, what big challenges they want to tackle, or what they want to achieve in their careers, and once he figures that out, he gears their work around it. David has found that when people are motivated by personal goals, instead of business ones, they become super powered. They begin to pull the business forward. They have this own momentum as an individual in their career that does indeed pull the rest of the team or the company and the results along with them.

Jay Acunzo 07:31

So what if we also wanted to create a culture based on the motivational principles that David Cancel expouses. What if we wanted to build a company full of super charged individuals all of whom feel empowered, all of whom pull the business along. We’ll learn about that after the break.

Jay Acunzo 07:52

So, speaking of push versus pull. I think when somebody pushes their team as a leader, it’s because they believe they have all the answers, the information to do the job well. Now they’re asking the team to carry out their mandate or their ideas. But I think the modern way of doing leadership, the best way to get the best work from your team is to share all the information, all the context that you have in making decisions. That way, teams can decide for themselves what’s right and what’s wrong, because you’re trusting them to do that work. They’re on the front line speaking to customers. They’re the talented people that you brought into the organization. We should all have access to the right information that we need to do our jobs well. And doing so we might create a pull culture.

Jay Acunzo 08:32

That’s exactly why Tettra has created their product a knowledge management software for fast-growing teams. Tettra is a place where you can make better decisions faster as a team, because it’s a place to put and share your information, your knowledge for doing your work. So if you believe what we believe on this show, and if you’re interested in checking out more about their product, visit Tettra’s website at Tettra.co. That’s Tettra with two Ts, .co. Now, back to the show.

Jay Acunzo 08:59

We’re in uncharted territory now, so let’s dive even deeper, let’s push on further into this idea of a pull culture and try to take with us a few treasures, a few gems that have floated to the bottom here that we’ve distilled from David Cancel. So now we can go back to our work and execute better. If you want to assemble an all-star team of highly motivated, super charged people, where do you even start? David says that he begins the moment he meets a potential new employee during the interview process. He’s got a really unusual but refreshing take on interviews.

David Cancel 09:43

It all starts with recruiting. What we’re looking for when we’re recruiting people are people that are one, eager to learn, which is our core principle, it’s the thing that’s the same about all of us. Luckily, most people in the world now, especially the younger they are, they more they are obsessed with personal progression. So this one is an easy one. It’s actually harder with some of us older folks, because you get stuck in your ways. So you want to progress, you want to learn, and what we’re trying to figure out is one, that they have that trait or that desire. Two, that do we have the opportunity, the right context here, the right challenge that will put them in a role where they can achieve that?

David Cancel 10:24

Sometimes, it’s hard because the more introverted, you know, my engineers, it’s harder for that personality type to express maybe what they want to learn, or how they want to progress. So it’s actually harder than it sounds, so it takes work trying to tease that out in the recruitment process. But once we know it, or we have a vague idea of it, we try to align their mission within the company with that thing that will overlap with that personal progression, because what I found, and I found that by accident, was when those two things overlap, then this pull model begins and this magic happened, because all of a sudden this individual is all in, is consumed with whatever the task is at hand, not because they’re trying to just necessarily hit a number for the company, or get something shipped or not, but because this is moving them forward on their own personal progression. That’s when that passion kicks in.

Jay Acunzo 11:16

Okay, so I think as an individual, I would fit really well into this mold, because I now have the ability and the self-awareness to articulate what I’m trying to do in my work. I’ve gone through enough ups and downs where I know what I believe in and you could really easily get me to talk about it, but for everybody else, for other people who that information isn’t coming as freely, maybe they’re introverted, or they don’t have that self-awareness yet in their careers, are there any specific questions or exercises that you use that you can share with us now where you can pull that information out of them? Because it seems to me like without getting that information, the pull approach to leadership won’t actually work.

David Cancel 11:51

Super hard, right? It’s hard to pull it out of people in theory, but it’s actually pretty simple. I go back to grandma’s advice and that is to pay attention to how people are reacting, and what are they getting excited about. So let’s talk about the interview process. In the interview process, a lot of times what I’m viewing is, I’m asking people and I’ve trained other people to do this, we’re asking people about random things that are related to both on a personal side, and on a professional side. What we’re trying to do is we are trying to figure out and calibrate when that person is excited, or not.

David Cancel 12:31

And how do you know when someone is excited? It’s pretty darn simple. You look at them, their eyes light up, they get engaged, they lean in, especially if they’re quiet, they start to talk a lot about that subject area, and it’s almost like our laboratory tests. I’m going through lots of different things and the person on the other end doesn’t know until they listen to this, that I’m necessarily doing this, but I’m just randomly having a conversation. They’re waiting for me to ask them interview type questions, but I never do. I’m just asking them lots of random questions and I’m seeing, “Okay, now Jay is nodding off. Okay, now he’s disinterested. Now he’s not leaning in. Okay, I’d mentioned podcasting, he just woke up, his eyes lit up, he can’t stop talking about it. Okay, I’m going to go on to something else, now we’re going to talk about process and blah blah blah. Okay, he’s asleep again.”

David Cancel 13:22

It’s more that I’m less listening for the answer that they have, and I’m more watching them and observing them. When I tell people this, they’re like, “Oh, this is crazy. How do you do that?” It’s like, “No, this is the most basic thing that all of us have, right?” Jay is married, if Jay’s wife is angry at him, he does not need to have a survey filled up by her, he could probably see her from four city blocks, Manhattan city blocks away, and you could be like, “Okay, she’s mad.” It’s that simple. But people overcomplicate things. They over like … “How am I going to know? How do I quantify it?” It’s actually very simple.

David Cancel 14:02

If you start doing this in an interview process, you’ll start to notice. If you stop getting wrapped up in the necessarily the words that they’re saying and you start actually feeling and looking at how they’re reacting and just listening for the signs you can see excited, not excited, interested, not interested. And by that, that’s how I tease out what they might be passionate about, even if they can’t express it yet.

Jay Acunzo 14:26

This is helping me explain to myself what are my favorite questions that I ever asked when I hired writers. Which was, and I think this could apply to a lot of makers in a different flavor, but I would ask two different questions that would reveal this stuff, I never knew that’s what I was doing, but I knew that I got good information. One questions was, if I handed you two years worth, or I would promising you two years worth of salary, and you would have to earn this by doing one thing, which is write a blog, a side project, about anything at all in the world, what would you write about? If they said, they’re working at a marketing team, they’d say, “Well, I’d really write about the evolution of SEO.” “No you wouldn’t, you’re pandering to me.”

David Cancel 15:02

Yeah, yeah. It’s nonsense.

Jay Acunzo 15:04

What I wanted to see wasn’t what they said to your point, it was how they reacted. Did they light up and have a visceral reaction and start to just almost like I’m doing now, rant about something in an excited way?

David Cancel 15:16

Or give you some generic nonsense answer, right?

Jay Acunzo 15:19

Exactly. That reveals something about the person.

David Cancel 15:21

Yeah, that’s why it’s super important to almost step back from the words that people are saying, especially the smarter the candidate is, or the closer they are to sales, the more they’re going to be, and even outside of sales, I’ll take that away. The smarter they are, more polished they are, the more they’re going to want to take you on a specific track, some talk track that they have, and the more they’re going to want to keep coming back to whatever polished set of answers that they have. Because it’s an interview process, they are in interview mode. They’re selling themselves, whether they think so or not. Everyone wants to be liked. You have to separate yourself from that. One of my other things that I always do in that process is that I won’t let people go off on their little, their speeches. Whatever prepared thing. As soon as I feel like they’re going down a talk track that they want to get into, like that seems well rehearsed, even if they haven’t done it specifically or not, I will break it and I will distract them and go off somewhere else. I just need to break them from the nonsense and those generic answers like, “I would write a blog post about SEO.” And actually get to the truth about who is this person.

Jay Acunzo 16:31

All right. Quick aside, here’s what I’m learning about this pull model. You have to get to the truth about the person, about your team. You have to figure out what really motivates each individual and then you drive their work around their goals. What a refreshing take. It’s a hard truth to swallow for many corporations that want cogs in a wheel. It’s not historically how we’ve built businesses. But I think it is indeed how you get the best work from people. You customize the work around their goals not the company goals. In doing so, the company goals get met better. But how do you do that in a way that benefits the business and actually in the corporate world? That’s what I asked David.

Jay Acunzo 17:09

I want to move to this idea, the way you encapsulate this pull model, which you call servant leadership, and the two pillars that you talk off and about as signs that servant leadership is perpetuating around your company autonomous teams and accountable individuals, and autonomous individuals of that. Autonomy and accountability. Let’s get super tactical, can you point to anything at Drift where you’d say, “Look, this is how our people are both autonomous and accountable, you can see it clearly compared to other people or teams.” What would you point to at Drift specifically?

David Cancel 17:43

I always point to the hardest one for most companies, which is engineering, software engineering. One thing that I try to do there is we try to push autonomy and decision making about, for instance, at HubSpot, the last company I was part of, and in this company, I had this belief where we don’t have roadmaps. We don’t have dates for when we’re going to release something from a product and engineering standpoint, and that always drove people crazy to think about that. What I replaced that with, and that was the give, that was the autonomy. Now team, engineering team, product team, I’ve taken away roadmaps, I’ve taken away the burden of dates.

David Cancel 18:22

I’m giving you the autonomy for you to decide when something is ready to go out. I’m giving you the autonomy for you to decide how you prioritize what you work on this month versus last month, versus next week. Whatever. You make all those decisions, no one is going to make those decisions for you. But the flip side of that is you have to have the equal amount of accountability. Now I’m going to start to measure you in customer terms. You’ll no longer get credit for, “I shipped this on X date. We worked on it this long. We have these many points from agile methodology standpoint associated to something.” Those no longer mean anything.

David Cancel 18:55

What means something is this product has generated this much revenue. These customers broken down by cohort are happy because of this thing that we did this month. Our internal customer sales, support, marketing and customer success are happier because we are addressing X, Y, Z month over month and making the product better. So now you have that accountability. I find that when everyone wants autonomy, but usually everyone’s definition of autonomy is anarchy. They want autonomy, but they want no accountability. That doesn’t exist. That’s anarchy. That’s not autonomy. Autonomy comes with the responsibility to have that accountability for your actions.

Jay Acunzo 19:34

I think this reasoning from, first, principles where a lot of metrics in the business world, in any department for any role, they’re built on the assumption that, “Look, this is out proxy for the next thing, the next thing, the next thing all the way down until you get to the customer.” And what you’re saying is, “No, no, no. Start at the customer, build back up your metrics from around that.” So points in some echoed way somehow get back to, “Well, points lead to these many things shipping, and this much productivity, and this type of product, and on and on and on.” Until you’re like, “And happy customers, who buy and refer people. So you’re like, “Why don’t we just start at that and reverse engineer it from there instead of starting so distantly from the customer?”

David Cancel 20:19

Yeah, I flipped it and basically went back to first principles, AKA, grandmother’s wisdom. If we care about the customers being happier, why don’t we just measure that? Or we care about X result, let’s start there. If we start from there, all of a sudden, it just changes that first principle approach just changes everything, and you start to look at most of the processes and approaches that we have, whether it’s in developing products, marketing and sales and whatever, and you see that because we’ve become so derivative, they’re insane, they actually make no sense.

David Cancel 20:49

They shouldn’t work, and then we’re surprised when they don’t work. But they shouldn’t work. Because they’re like so removed, they’re like 10 steps away from the actual thing that you’re trying to affect.

Jay Acunzo 20:59

Right. It’s like the customer is super mad. The VP is kind of disappointed in the progress, the sales team is angling for some kind of update or, if you’re in marketing, some piece of collateral. They’re like, “People are pissed.” But you’re like, “Yeah, but look at this metric that I have, I’m doing well. Aren’t I?” It’s like, “You lost sight of the stuff.”

David Cancel 21:17

It’s crazy. We’ve reached peak insanity in letting everyone just choose whatever metric that they want to use, which was always one of my rants, which is people were like, “Oh, we’re data driven.” It’s like, “Yeah, but if I can pick metric that I want, I can tell you any make-believe story.” That’s not data-driven that I can just pick whatever metric, and show you whatever chart I want.

Jay Acunzo 21:37

It’s the old, what is it? What’s that show? Portlandia, put a bird on it. No, just put a number on it. No, that’s not data-driven, just because you put a number against what you’re talking about to justify it, it doesn’t make you actually driven by the data.

David Cancel 21:52

Exactly. It’s crazy, but everyone does it. You’re like, “Is everyone insane? Are we insane? What’s happening?”

Jay Acunzo 21:59

Grandma’s wisdom. So putting grandma aside, are there people at Drift or in your career that you can mention, maybe even by name, give them a nice little shout out, that you think have really thrived with this pull model? How have you seen their careers unfold? What have they done better and how have they been unleashed, so to speak, because of this approach?

David Cancel 22:18

Yeah, I think lots of them. Lots of people that we’ve worked with, the two of us, in the past. Whether it’s like Meghan Keaney Anderson, who’s VP of Marketing over at HubSpot now, we worked together at Performable before we were acquired and went in there. I think she’s a perfect example of it. Elias, my co-founder is a perfect example. Dave Gerhardt, who runs Marketing here is a perfect example of it. I’m surrounded by an endless number of these people that are by their own motivation been able to progress, leaps and bounds, and it’s been because they’ve been able to one, put their pride to the side and show some humility and be coachable.

David Cancel 22:56

And two, because they brought their own motivation, their own hunger to want to improve something and do something. They’ve all been able to achieve amazing things. But I have a long list, and I’m proud to have worked with all of those people in different points in history and see their progression.

Jay Acunzo 23:16

All right. We’ve ventured away from the org chart on this episode, away from the typical push culture, and we dove deep into creating a pull approach to leadership where everybody is motivated in all the right ways. But we can’t empower others like that in our careers without others first empowering us. So, let’s now hear from David Cancel about the person or people that he would like to thank. The intrepid explorer who empowered him to do his best work.

David Cancel 23:43

I had many mentors in my life, virtual and real. I have three, three of my earliest mentors that I’d like to thank. They’re all named Sam. Right? The first one is named Sam Lee, and I worked for him. I worked in a warehouse when I was in high school and college. He was my first mentors. He taught me, he was a businessman in New York City, owned a bunch of B2B businesses, but more in the warehousing and retail side of things. So I worked for him, and he taught me a lot and I owe a lot to him. I look back and think about many of the lessons I learned, I actually learned through him.

David Cancel 24:21

My second mentor, Sam Walton, virtual mentor. Founder of Walmart, and by his book, Made in America, which I’ve read about six times, he’s my next mentor. He’s taught me a lot, and I continue to reference back to him and what he’s learned. Then, the last Sam, is named Sam Zales, and he’s the COO of a company called CarGurus, just went public here in Boston. I worked with him, I started working with him 18 years ago, and Sam has taught me the importance of people. This whole podcast is about people, many of these lessons that I’ve learned around how to properly lead came from Sam. I was the prototypical engineer, and he was the people oriented leader, and he taught me a lot around most of what we talk about today.

Jay Acunzo 25:18

Big thanks to David Cancel. Uncle DC, with all that wisdom today. If you liked what he said as much as I did, say hi on Twitter @DCancel. I got to shout out Tettra one last time, because this is their show. They’re not sponsoring it, is their show, they’re making it with me. It’s just awesome to see a company that gives a damn about great leadership. Again, Tettra helps you make better decisions in less time as a team by sharing knowledge more freely and openly together. So you can check them out at Tettra.co, Tettra with two Ts, .co, or visit the show side that we built together. It’s OrgUncharted.com. That contains all kinds of company culture decks, employee handbooks, more podcast episodes, interviews with leaders in text format, you name it. OrgUncharted.com. This show is a production of Unthinkable Media, makers of refreshingly entertaining shows about work. It’s hosted by me, Jay Acunzo and produced by Annie Sinsabaugh. Thank you, Annie, for your help today. On behalf of Tettra, thank you so, so much for listening to this show. I will talk to you next time in two weeks on another episode of Org Uncharted.