Guest

01

Our version of servant leadership is the idea that if you're a manager or a leader your job is to serve those above you. The people above you are the individual contributors... the people closest to the customer.

In this episode

In episode #1, David Cancel (CEO of Drift) shares his insights and practical advice to implement servant leadership, skip-level meetings, and learning loops in your organization.

David is a five-time founder, two-time CEO, and best-selling author of “Conversational Marketing”. He was named the top-ranked CEO by USA Today and is currently an Entrepreneur in Residence at Harvard.

Tune in to hear all about David’s leadership philosophy!

. . .

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


03:40

David Cancel’s first mentor (Sam Lee) and his experience working at a warehouse.

05:11

David’s “Spock-like” leadership style and the importance of self-awareness as a leader.

07:45

Acknowledging your weaknesses and asking your direct reports to call you out on them.

09:10

David Cancel’s definition of Servant Leadership and how Drift is putting this leadership model into practice.

13:54

How to let your team know that it’s ok to fail and make mistakes.

15:07

Drift’s processes to encourage learning: Root Cause Analysis, 5 Whys Analysis, and Engines.

17:26

Drift’s monthly senior leadership team meetings and quarterly off-sites.

19:05

Why you should think about meetings as rituals.

19:40

David Cancel’s system for skip-level meetings.

22:10

David Cancel’s “Zoom-in, Zoom-out” management style / over-the-shoulder management.

23:22

The power of observation and social psychology.

26:14

How David Cancel designs skip-level meetings to ensure there are different personality types.

27:37

David Cancel’s advice for someone who hasn’t been doing skip-level meetings.

29:50

Lessons from interviewing thousands of engineers and naturally introverted people.

32:05

The importance of knowing what motivates and excites your direct reports.

33:45

David Cancel’s advice for new managers.


Resources


Episode Transcript

Aydin Mirzaee 1:47

David, welcome to the show. This is very awesome. You know, we were just having a chat and realized that we both grew up in Forest Hills, Queens, like in the same neighbourhood. That’s pretty random.

David Cancel  2:00  

A few blocks away. Yeah, I’ve never run into someone like that.

Aydin Mirzaee  2:02  

I know. It’s amazing. And you know, for the audience like, obviously, we’re recording this in Ottawa, Canada. So to have this coincidence is pretty remarkable. You know, Dave, super excited to have you on the show. I feel like even though we haven’t met until today, I feel like I kind of know you because, you know, I almost want to call you like DC and like the nicknames and so on and so forth. And, you know, you’ve obviously, you’ve been an entrepreneur, you’ve been a CTO, you’ve been a CEO, you’ve played like, all these different roles. And it almost seems like for someone on the outside that you’ve just been this natural-born leader that has been doing this from the get-go. So have you ever had a real job where you reported to a traditional manager?

David Cancel  2:48  

I have, plenty of times, but I will say that I spent my entire life trying to avoid a real job. So I had many you know, growing up in Queens. I worked in lots of places, warehouses, and they were all very formative. My first mentor experience, first real mentor was working at a warehouse in Woodside, Queens, the owner of that warehouse, his name is Sam Lee was my first mentor. So I worked for him. I had lots of those jobs before I started my own company. I worked for three others where I was CTO, head of technology, whatever. So I did have bosses there. But they were highly entrepreneurial, you know, small company, so never really felt like I had a boss I would say in a typical sense.

Aydin Mirzaee  3:29  

Yeah. So you must have had like a favorite or like, who is your favorite person to report to or a leader that you looked up to?

David Cancel  3:38  

It was Sam Lee, my first mentor. So I worked in this warehouse for a number of years. Woodside Queens is cash and carry warehouse and was the only I would say, you know, I was the only person from not from Taiwan or Mainland China who worked in this warehouse and I only got a job there because my friend who was from Mainland China, his mom convinced him to let me work there. So I worked there, was a super hard job. I did it while going to college, I worked full time went to school full time. And it was the most impactful because Sam was basically the typical, almost stereotypical kind of like, stoic leader, you know, who’s super hard, super tough. No compliments, you know. But I loved it. And because he actually cared. So there’s like, you know, there’s like this emotional way of caring that some people have, but like, they might not necessarily look out for your best interest. He was always looking out for my best interest, putting me pushing me and then putting me in roles that were kind of above what I thought I could do, and really causing me to stretch. And so he kept doing that repeatedly and kept pushing me to grow even outside of work. So he actually even though he looked cold, he actually cared very much. And I would say the highest compliment I’ve ever gotten in my career was from Sam because he told me when I left that, that I worked like a Chinese person. If you knew Sam, it was the highest, highest form of compliment.

Aydin Mirzaee  5:06  

That’s super cool. So, this concept of not giving compliments and so on and so forth? Is this something that you have adopted in your leadership style? Or how do you play that?

David Cancel  5:18  

My personality is naturally that way. So in Myers Briggs, I’m an INTJ and disc I’m a DC so I’m very direct. Spock like personality – that’s a Star Trek reference, so very logical kind of, and so empathy and compliments are hard for me. You know, I take a lot of energy to think about them and most in the situation in when I’m in the middle of something I almost never think about that side. And so it’s been hard for me I have over time as I’ve become a people manager, have learned how to be better at that and actually spend more time doing that. I would probably say like, I’m still pretty low but I spend a lot of time working on it.

Aydin Mirzaee  6:04  

So is it the sort of thing, I mean, you’re very self-aware. And you know this about yourself. Is it like when someone joins your team, do you have a conversation with them to say like, just so you know, like, this is how I communicate?

David Cancel  6:21  

Yeah, I have that. I have a guide which I stole from the idea from… I can’t remember her name… She’s the COO of Stripe. So she wrote an article on this at some point, but basically create a guide to working with me, it includes my personality types, things that I like, how I respond best in emails, how I don’t respond best in emails, and I use a lot of different… the email based one is called crystal nose. So I use that. I use Myer Briggs, I use this I use predictive index, I use all these different personality kind of tests and the results of those things to share with people like how best to communicate with me. And we do that not only for myself, but we do that kind of internally at Drift with other managers, leaders and individual contributors, it’s an important part of how we work is really understanding and being transparent about what works for me versus what works for you. Which is, I always say it’s, you know, we on the surface think we assume that we know how to communicate to other people, but all of us don’t really know how to communicate and how to give feedback to people.

Aydin Mirzaee  7:24  

But I guess, you know, I mean, it’s obviously the sort of thing you figured out over time. You’re just short-circuiting it, making it happen faster. You guys are obviously fast-growing company. It’s important for people to gel right away. That’s a great hack. And I think something that everybody should do.

David Cancel  7:43  

Oh, yeah, it’s pretty clear. Like you have I’m sure you have your ways that you like to work or your personality, plusses and minuses we all have those. So we shouldn’t hide from those. We should be clear about those and in some cases, you know, with some of my people directly that report to me, my deficiencies or the things that I’m naturally bad at, I ask them to help me. I tell them that I want to work on them and I try to get them to help me with some of those things and call me out. And when I’m doing that, I was talking to Mike Zanny, who’s a couple weeks ago who’s a leader at predictive index. He’s the CEO of Predictive Index. And I was giving a talk at his conference and he said, we were talking about the subject, he said that he has a code word, which is a word that you would never stumble upon in natural conversation that he gives all his team to basically use it if he’s going down.

Aydin Mirzaee  8:36  

Oh, really?

David Cancel  8:37  

Yeah. Cuz otherwise, yeah. He has a similar personality to me because like, once I get like, on a bone, like, right off of it, you know, I’m like, tunnel vision on it.

Aydin Mirzaee  8:47  

Obviously, like a word that you don’t use all the time. That’d be like, yeah, SHOCK. That’s interesting.

So, David, you have this notion of, you know, of Servant Leadership, and I feel like you have a super creative twist to it. And I’d love for you to just explain to everyone like how you think about servant leadership and how it works at Drift.

David Cancel  9:10  

So Servant Leadership is like, it’s a very old concept, but it actually came from again from my first mentor Sam Lee. He had recommended a book on bazillion years ago, which is a book I give out to everyone now, which is called Made in America. It’s the story of Sam Walker, the founder of Walmart. So I recommend that book all the time. It’s a $5 payment back. It’s been around forever. He basically recommended that book to me. I read it a million years ago. I reread it like five times since and basically in that book, whatever you think about Walmart, there, it’s an incredible story. And one of the things in it is this idea of servant leadership. He talked about it there.

But it took me years to really kind of lean into it, and our version of servant leadership is basically the idea that if you’re a manager, if you’re a leader, your job is to serve those above you and those people above you are the individual contributors, the managers, basically like the people closest to the customer.

And it just clicked and made sense to me because I thought from a math standpoint, like whatever size of your company, most people, the most amount of people that you’re going to have ar the people that are those individual contributors who are close, and those are the closest to the customers. They have first-order feedback, versus, you know, the CEO, the manager, whatever that’s gonna have, you know, basically the telephone version of feedback. That’s where the truth is in our world.

And so, we took that model, and we added to it and said, like, at the very top of our pyramid, right, inverted pyramid is the customers then individual contributors, then the managers then the directors and VPS. And then finally, the lowest is me. And so like, what that means is my job is really to support everyone above me. And that’s how we think about things.

Aydin Mirzaee  10:46  

Yeah. Do you think that, like this model of leadership, obviously, you know, one of the greatest companies ever built, you know, being Walmart. Do you think that, this is a model that should be practiced everywhere? Like should it be practiced at, you know, traditional, corporate America?

David Cancel  11:03  

I’m not a corporate person. So I probably don’t have the right context. But I don’t see the downside of doing it. I will say that it is. I’ll take that back. There’s one downside to doing it. It is way harder and takes way longer to get anything done than the opposite command and control method of just like doing don’t ask any questions.

But in the end, if you want the best type of people with the best performance on your team, you’re going to have to adapt this model and it’s it’s very, it’s almost like the model in Jocko Willink who’s an ex Navy SEAL, talks about in the navy seals and special ops. They in the military. They have a very servant leadership approach. Because it’s the only way that you’re going to get people in high-risk situations to do things right.

Aydin Mirzaee  11:50  

Yeah, like push things, push down decisions to the highest level of information. That’s pretty cool. So okay, so a lot of people they might hear that and say, okay, that’s really cool to hear. And it’s Yeah. And it sounds fantastic. But to the cynical out there, like, what are the things like what’s a practical implication of this, like in real life that you practice it and say like, this is why, this is an example of us practicing servant leadership at Drift.

I’d say, for the first comment, I think a lot of people bristle on the idea of servant leadership because they believe that servant leadership means that I’m going to be subservient to people, which doesn’t mean. In some cases, like serving people just like if you have family, your friends, sometimes the best way to serve someone is to be very firm with them. Right and have very clear boundaries.

It is not you know, like, I’m just gonna pat you on the back and say, everything’s great, right? Servant leadership is the most direct form of feedback to someone. So it doesn’t mean you’re gonna be subservient.

In terms of how we implement it an example would be that we try to have the most autonomy in the individual contributor level of the company. And we do that so because again, they have the most information the closest customer, what it ends up doing is that we’re able to move faster than other people than our competitors, other people, similar-sized company, because we have individual decision making happening on the field, let’s say, versus happening in the boardroom or in the conference room. So the impact is, these people are on, you know, on average, happier because they make decisions, they have ownership, but more importantly, to the business, you know, we move faster, right, because of this decision-making.

Aydin Mirzaee  13:38  

Yeah, and I guess like, I mean, as part of that, you know, sometimes people will make decisions that you may disagree with. So when that happens, I mean, you know, and if there are mistakes, like are there ways where you make it known that it’s okay?

David Cancel  13:54  

Yes, there’s many ways that we make it known that it’s okay to fail. You know, For us, failure is not an issue. The issue is like if we don’t learn from it. So we get really spun up or wound up if we feel that we’re not one, we didn’t pull a lesson out of the failure, or two, we keep repeating that mode of failure over and over. So therefore we haven’t learned as an organization or as individual or team.

And so that’s where we really get stuck on. But in terms of failure, it’s part of the feedback loop. And we want to have those happen as quickly as possible with the least impact to the customer, obviously, but like, we want to learn from them. And so our currency is learning, right? So that’s, that’s all we care about. We think about Drift as like a learning machine, what we’re trying to build is not software, not a, you know, a software company, a technology company, we’re just trying to build a learning machine that is, has a certain proximity to the customer, in our case, very close. And if we think we can basically have this very tight feedback loop that continues to learn, then we will figure things out that help our customers and therefore help the company.

Aydin Mirzaee  14:56  

Right. That’s really cool. So in feeding this learning machine is there a process that you use you know, some people you know that there’s the five why’s…

David Cancel  15:07  

We use five why’s as one of our processes, we have root cause analysis on our failures, we have one of the methods that we use in it is so we have an RCA process which is the root cause analysis. Then we one of the things that we do and there’s the five why analysis so we do that, but we start with this idea that we call it internally engines and so someday we’ll write about it but basically engines are very similar to something that Bridgewater capital, Ray Dalio and Amazon have.

You know, Bridgewater calls it machines and mechanisms and then I believe Amazon calls them machines. And basically the idea is like, they are a learning loop version of a process. So if you were to take a process and flowchart it out, basically, it’s static from A to B with a decision tree, basically the engines or one of these Other ways that you call it basically has a whole bunch of things in there like, you know, what is the process? How do you measure it? How do you learn from it? How do you improve? How does it not have dependencies and individual people and so that it basically becomes a flywheel that can move on its own and that can be monitored independently of it.

And so we have this, we have it from everything from how do we throw a small event to how do we do a certain type of marketing to how we do a sales process. So we have these engines within an engine dashboard within the company. So we understand all of these different pieces and what’s happening. So that’s our flywheel. That’s our learning method. And that’s how we ensure that we have learning happening non-stop. And when we have kind of our monthly management kind of meetings where all the teams come in and present. We talk in those terms of the engines, how are they going? What have they learned? What is the learning at the, at the end? What is the observation, what’s the learning? And then what is the call to action that’s going to happen on that? And then we measured that again, so we’re constantly just measuring these loops over and over again.

Aydin Mirzaee  16:58  

I mean, that’s awesome. Like, it’s obviously framing it in the form of a loop. It’s antifragile, it keeps getting better. What is the so you talk about, you know, you mentioned the word management meeting? How does that structure work at Drift? Like, is there a, you know, is there like a monthly thing that your leaders come in and present on each one of the engines? Like, what is your workflow around? How do you keep abreast of like, what’s going on in the different parts?

David Cancel  17:26  

At this point, you know, we have a… it evolves all the time… so these are not static things. But we’ve had this for a long time now, which is we have a monthly where we call management, we call it senior leadership team meeting, SLT. And in that meeting, it’s an all-day meeting, all of the different business units we’re broken into business units, right? Segment based, like enterprise team, mid-market team, and then there’s also skews different products that we have all of those different teams. And by teams, I mean like the marketer assigned to the sales lead, the product lead, you know, basically all the functional leads for that product or that area come in present, they have a very short time to present. There’s a format that we use. And it basically starts with an engine dashboard of like all the different engines that they have in there. And those engines represent the goal that they’re going for, for that team. So there’s a goal, the team, and then there’s a bunch of sub-processes you can think of right into those sub-processes has a way to measure them. And so we can measure that that machine is working, is getting better, getting worse staying the same. So it starts that way. Then it goes into, you know, observations and learnings, customer anecdotes, or feedback or measurements, and then you know, a call to action or an ask at the end.

Every team does that. We do it all day. Then we have a quarterly off-site for the whole SLT thing where we go deeper into more strategy stuff. We have a whole bunch of meetings I can talk about. I’m the most anti meeting person but I could talk about meetings all day.

Aydin Mirzaee  18:51  

That’s awesome. That’s, it’s actually super, super interesting because I think you know, I mean, one thing is calling the meetings but you’re actually getting work done.

David Cancel  19:03  

They’re called meetings. But yeah, we think about them as rituals. Yeah, important rituals in our system. We have weekly rituals that we do, we have monthly rituals, we have quarterly and we have annual rituals. Some of them are all company. Some of them are very small. But these are rituals. And there’s a purpose behind all of them, not only from a reporting standpoint, but from a gathering and interpersonal standpoint. There are reasons for it.

Aydin Mirzaee  19:27  

I like that framing, I like rituals. Yeah, it sounds so much nicer. Yeah, it makes me want to actually participate. Yeah, it’s good. So speaking of rituals, you also have this ritual, obviously, you guys you know, Drift, you do your one-on-ones. But you also do skip-level meetings. And so I’m very curious about you know, the process of skip-levels. Obviously a lot of people work at Drift. So who do you have skip-levels with?

David Cancel  19:56  

I have a series, a whole system around skip-levels, there are skip levels that I do that are just random skips of the people who report to me. So let’s say the CRO reports to me, I might go to their VPS or their directors, their direct reports randomly and I do them randomly. And I kind of do that on a monthly, you know, maybe twice a month basis. I’m going through those across all the teams. So that’s one that’s a one on one skip.

And then I do group skips. So I used to do this idea of a random lunch every Friday. So I do a random lunch of, I don’t know, six or seven different people from all different levels at the company. I used to do this at the last company, HubSpot as well. And the reason I did it was like, I would always do it around a meal. Like we’d go to lunch or we go somewhere and I’d just be quiet. And I wouldn’t try to really direct the meeting the lunch. It was just like a social ritual. But in it I am learning and I’m hearing and I’m seeing the way people are communicating with each other. So I learned so much from that meeting.

And then I have one more skip level type thing, which is, I do a monthly dinner drinks kind of thing, which is like 12 to 15 people. And it’s called the Drift swizzle. And in those people are random as well, all different levels. But there’s a lot of skip level in there. And in that I’m forcing people to interact with one another across teams. But I’m also learning across teams, and so super important to do it. It keeps me close to the company. That’s how I can observe things beyond metrics. Yeah, but otherwise, outside of those kind of one on ones and those groups, and then the metrics at the very high level. I spend all my time now trying to stay out of the middle of the company. Because I naturally tend to want to like, put my hands in. And so it takes all of my energy not to like, get in there and build dependencies around me. And so I’m spending all my time trying to pull myself out of it.

Aydin Mirzaee  21:58  

Yeah. So you’re almost like you go and this will inform something but if you find a problem, you’re not going to dig in, you’ll go to whoever is in charge and just get them.

David Cancel  22:10  

Yeah, I’ve always thought about like, the way that I like to manage is like zoom in, zoom out. So I work at zoom out level, which is like this high level and you know, thinking about the themes for next year and all that kind of stuff. And then I work really zoom in at the very lowest level with an individual and I am not naturally suited and great at all those different process-based things in the middle of the company. And so we have great leaders that do that and so like I don’t spend a lot of time trying to get really good in the middle.

I get good at like the top and the bottom and just zoom in and zoom out.

Sam Walton in the book, he would call this style over the shoulder management which is like give you know, tons of autonomy but always look over the shoulder once in a while to make sure things are going okay.

Aydin Mirzaee  22:52  

Yeah, and he would I guess like fly on this plane. Go to all the stores.

David Cancel  23:00  

Boom, boom, boom, yeah, yeah. Talk to all the associates and just look over the shoulder of how they’re working.

Aydin Mirzaee  23:05  

Yeah. And I, you know, I’ve heard this, uh, you know, in different formats, you know, I’ve heard some people, they call it like, management by walking around? Just like walk the floor, and then just like, show up at someone’s desk and like, what are you working on?

David Cancel  23:21  

It’s so underrated, just like this power of, you know, I always say like, we get wound up about technology and software, in the world that we’re in. But all the answers are people, issues, you know, people kind of psychology, they’re all like people-based systems. These are people these systems that we’re in. So like, all the stuff that you need to learn and that kind of stuff. And so I spent all my time really trying to zoom in and figure out like, and observe how our team is doing.

At my last company. I used to, we used to have, we have lots of little small teams, just like we have at Drift. I used to just observe teams and people, you know, when I would tell them that they think I’m crazy. They’re like, what do you mean? And I said I just look at him sometimes all day, just look at them.

And what I’m looking for is when they’re at lunch or whatever is like, it’s very simple thing that people like, neglect. For some reason they’re too logical, which is like, how are the interpersonal relationships looking like on a team that’s working well? They kind of look like this. And over time, I can see like how people interact with each other. Now, some stress happens in the system, whether it’s, something’s wrong, you know, or maybe we introduce a new person into the team, or we make changes within the company, then I’m observing the team and I can see how the team is doing, are they doing okay? Or is the team look totally chaotic now?

And these are, when you think about it, very natural. These are human patterns. Like you can tell like, if you’re close with a group of friends, if they were at that table across from us, if they were all mad at each other, you wouldn’t need to survey them to figure out that they are mad at each other.

Aydin Mirzaee  24:50

It’s like watching TV on mute.

David Cancel  24:52

Yeah, exactly. And I think some of that came from for me because I’m naturally pretty introverted personality one, and two, you know, when I grew up I only spoke Spanish. And I taught myself to speak English watching TV.

I was, like I say I always say like, if there was ESL when I grew up, I never heard of it. That’s a modern invention now when I was a kid, but so I taught myself watching TV. So I had spent the formative years just observing people trying to understand what they were talking about, because I didn’t speak the language. And I got used to just observing and kind of understanding what someone meant without literally understanding what they were saying. So it is almost exactly what you said, like watching TV on mute just watching that. And if you watch a TV show on mute or movie, you could guess a lot of the emotional things that are happening or probably all of them without having to hear anything.

Aydin Mirzaee  25:40  

Yeah, that’s interesting. So a lot of it is observations, I’m assuming like, I mean, you’re a pretty friendly guy. I don’t know at work, what it looks like, but on the outside… Do you have the situation where you’re in a group setting with you know, skip-level setting or whatever, and like, you’re the CEO, and you’re sitting there and everybody is quiet, like, how do… What are the questions that you start asking to get people going so that you can go into observe mode?

David Cancel  26:12  

That barely happens to me because I design, I spend a lot of time thinking about the people who are going to be in the meeting. And so even though we’re doing, it’s random, we never have true random right? So it’s really I’m thinking about, like, making sure there’s the right dynamic of like, I need some people who are firestarters who can talk and get the meeting going, even though even if I don’t know them, right now, that’s their personality type. Because you know, I would do total true random, yeah, random before, and sometimes you’d end up with a meeting where like, nobody talks. Yeah, cuz everyone is pretty introverted. And like, no one will talk. Now I not only a mix tenures and levels and roles, but also personality types. So I know that the conversation is going to get started without me having to interject.

Aydin Mirzaee  26:59  

That’s very You’re clever, like, by design.

David Cancel  27:02  

Totally by design. And so like, once I started to do that I never have to really start the conversation. I just hang back and just like listen throughout the session and having it over a meal also helps.

Aydin Mirzaee  27:14  

Yeah, yeah, definitely. And what about, like, you know, from a skip level perspective, when you are meeting with an individual person now, it could be that you were doing this from the get-go. And so people are just used to this. But what’s your advice for someone who has not been doing skip levels? It’s scary. Like, if you book something in someone’s calendar, they’re gonna freak out, like, am I going to get fired?

David Cancel  27:36  

I think the way to do it is one, you know, I’ve made it, I would always make it public and say, announce it of like: Hey, I’m doing these meetings or write something in our wiki internally of like, here’s what this meeting means. Here’s what happens. And, I would also, like all the meetings I mentioned, I would keep a log of all the past meetings, of like, two weeks ago, I had the meeting and here are all the people that came and so like, it’s transparency and people know this is a normal thing. So that’s one thing.

And then I’d say the advice I’d give to people is, and this goes for general one-on-ones not only skip-levels is don’t do them in front of a computer. Don’t do them in a, you know, huddled in a room with a notebook in front of you like, because I always say that’s, that’s an interrogation. That’s not a one on one, you’re sitting there and like, and you know, people are doing it because they want to remember what’s going on. I understand. But like if you’re sitting there looking at someone and writing every word that they’re saying down or worse yet typing it, in a closed room, in a conference room that everyone can walk by and see. Like, that’s not a natural state. That looks like a police investigation. Right? it looks like you’re being questioned by the cops. That’s not a good meeting. So what I do is like, I try to force them to always be outside of the building And so like, let’s go for I do mostly walks. Let’s go for a walk. Let’s go for a coffee.

Aydin Mirzaee  28:51  

Even in Boston.

David Cancel  28:52  

Yeah, in the middle of cold. So we are next to a big kind of shopping mall clothing. And so we run to that shopping mall and then walk and loop inside of it when the weather is pretty bad or Yeah, but I forced them always to be outside and never to be in this kind of conference room kind of setting.

Aydin Mirzaee  29:10  

Right. And so for like a traditional one-on-one, I mean, the most ideal scenario you walk in and you know the person you having one on one with, ideally, like they have stuff and things that they want to talk about. How do you think about that, in terms of skip-level? Like is it still the other person’s meeting from that perspective?

David Cancel  29:32  

I kind of guide them to be to think about it that way, but I don’t expect them to prepare much for it. And so I say that to them. But then I just ask them random questions. You know, like, if I need to get going, and it’s pretty simple, you know, it’s like, Hey, what do you do this weekend? Hey, Oh, you like skiing? Where do you go skiing? I’m just trying to, it’s a pattern that I learned from interviewing hundreds of thousands of engineers over time. I come from an engineering background. And so like, And so basically interviewing people who are naturally introverted, and you know, some of them painfully shy. And so like in those meetings, I had to figure out basically coping mechanisms to get them to talk because they wouldn’t talk and so right, I would start basically doing just random, questions, anything.

Basically what I’m looking for is like even the most introverted, shy person, if you get into a subject matter that they’re passionate about, then they’ll start talking forever. Right? What I would do in the meeting is just throw in anything, crazy. I must have looked insane top the person because it’d be like one thing skiing, Okay, it didn’t work. Okay. Do you like biking, do you like this? You have gone hiking? This person. I’m just throwing out like random all over the map. And then finally, I’m like, okay, eyes lit up. All right, they just woke up. They’re like into something. They start talking. Okay, let’s go on that And what it did for me was not only one, get the person talking, but two give me an idea of what does that person look like? What do they look like physically when they’re engaged.

Now I have a way to understand that’s what they look passionate. This is what they look like when they were disengaged or shy. And then I’ll go and then I’ll find another one. Okay, they’re engaged again, I saw it again, boom, light up the eyes. They’re rolling into something. And I don’t try to talk to tell many people about this at work, because then they know that I’m running like a psychological test on them. And so I’m like, boom, boom, boom. So anyway, I came up with that. So I use that same method in this kind of skip level one on one, so if I can’t get someone talking. I’m just like, anything random, random, random, random. And then I finally find something. Everyone has something they start talking about. I’m really into music. Okay, cool. Let’s just talk about that.

Aydin Mirzaee  31:37  

But you know, what’s interesting to me about this is like, you’re actually doing this very interesting thing, which is you’re trying to get to know every single person on a super individualized level. I’m assuming obviously like the same, you know, for everybody who reports directly to you. You probably know the things that get them excited. And you can tell like if they’re not, you know, engaged in like, they don’t enjoy whatever thing like, probably just look at their face.

David Cancel  32:03  

And, you know, I do it because it’s the only point of leverage as a manager, right? If you can’t, if you don’t know what, how someone reacts or what motivates them intrinsically, like if you don’t really know them, then how can you get the best out of them? How can you manage them? You can’t, right. And so like management by metrics, or you know, just a standard way, like, that’s not going to tell you what the potential of that person is, and where they need to be pushed where they need to grow, where they’re feeling pain, you’re not going to learn any of that just by measuring metrics.

Aydin Mirzaee  32:33  

And we know you as a metrics and data person. So for you to say that is like an epic state.

David Cancel  32:39  

Yeah. I was the most data-driven person for so many years. And then I figured, like, you know, the problem with data, though, is that the last company like data-driven like, well, it all depends on what data like if you have a system where we’re a company where there is no limit on what data someone can use, right to make a data-driven argument, then those are like pretend arguments, because I can pick any three pieces of data and make any argument that I want out of it, I can tell you any story that I want, if you allow me to pick the data, and so like you have to have tight controls on, what are the data that we’re going to react to what are the metrics that we’re going to react to and then you can’t just pick uncorrelated metrics and put them together and tell me a story.

Aydin Mirzaee  33:17  

Right. You know, David, this has been awesome. As someone in you know, what’s fascinating to me is, you know, obviously, I mean, you mentioned how you had to teach yourself English by watching television Gilligan’s Island, you started as an engineer, you seem like you figured out all of the people side of things and gone from data-driven to people-driven, how have you learned all this stuff? Like how can other people emulate and become better leaders?

David Cancel  33:45  

So you know, I would say don’t follow my method. It took me you know, I’ve been doing this for 20-somewhat years. And so first 10 years or at least 10 years, maybe a little longer of my career was just brute force pain. Basically, what I mean by that is like, I didn’t try to learn from anyone else, I didn’t seek out mentors. I didn’t seek role models. I didn’t think about the people aspect of things. And so I learned or everything that I learned through brute force, aka pain, and learned the hard way. And so what I would advise everyone else, which is what I’ve done for my second half of my career, which is learn from other people, don’t try to learn everything on your own. There are things that you need to learn on your own. And Mother Nature will teach you those things. But that is the last resort because those are going to be the painful lessons. Instead I look for I would advise people like study psychology, I wish I would have done this earlier. You should study psychology, you should study human decision making. There’s tons of books on human decision making from economy into easier stuff to read, about cognitive biases that people have related to decision making.

You know, social psychology like those are the areas that if I was a new people manager, I just say just spend all your time doing that. And even us as a marketing company like I had, you know, I had our marketing from day one only study those things. Ignore everything else. And then the implementation of those things in the form of copywriting and kind of those kind of triggers. That’s what made all the difference for us in terms of marketing, not by studying what other people were studying, right? It’s really decision-making pattern. And so if you’re a new manager, go read those kind of books on decision making. Forget everything else that you’re reading, like domain specific stuff about your SAAS, whatever. And this stuff like that stuff doesn’t matter. This is all just people based systems like, you know, it took me in other words, you know, I’d say the first half of my career, it was I thought 99% of it was product, pricing, packaging, go-to market, all the stuff that we talked about, and geek out every day. And then the second half of my career, what I firmly believe is like that is 1%. And we spend 1%. That’s 1%, 99% is people and those people are, your team. Those are your investors, they’re the community, like your market, those things are insanely difficult and you will never master those things. That’s what you should study. Study the 99% don’t study the 1% SAAS metric Who cares? That doesn’t matter.

Aydin Mirzaee  36:03  

That’s incredible. That is incredible. And you know, you mentioned a bunch of cool books and people should should read: Sam Waltons book, made in America, Daniel Kanehman’s book, thinking fast and slow. Any other recommendations?

David Cancel  36:19  

I have so many book recommendations. And so if you just search for David Cancel books. I have many, many lists for different types of people.

Aydin Mirzaee  36:26  

Awesome. We’ll make sure to include all that in the show notes. David, thank you so much. This has been so awesome.

David Cancel  36:30  

Thank you for having me. We finally did it up in Ottawa.

In this season

We interview leaders from all walks of life to tease out the habits, thought patterns, learnings and experiences that help them be who they are.