How to scale your career alongside your startup: Mike Boufford’s lessons after 10 years at Greenhouse

Mike Boufford - Edited - First Round

Brett: [00:00:00] Mike, thank you so much for joining us today.

Mike: Thanks so much for having me.

Brett: So one place I thought we could start you're one of the few non founder CTOs that has made it a decade at one startup through the transition to, a very large business. And I'm curious, why do you think that's been the case for you?

Mike: It's a good question. I don't know that I have the complete answer, but I do get asked this question sometimes and I think I have some perspective. Number one, I think actually aligning with the right founders in the first place probably plays an outsized role. Are you going to be the right type of person that they wanna partner with long term?

So I think that's a thing that maybe is, a combination of luck and good intuitions at the beginning. A lot of the other stuff I think there's maybe two different lenses I'll apply. One of which is the lens of, what kept me there so long because I think, when you end up building a successful business, you have more and more options over time.

What, caused you to stick around and continue investing there versus putting your energy towards [00:01:00] something else? And the other one was maybe like the survival lens, which is, every single role in Greenhouse has had at least a couple of other folks go through the executive team over time.

And frankly, I fully expected at the beginning that, I would be replaced by the right person at the right time. And I had that in my mind the entire time. It was like, the best thing for the business is to hire the right person for the job. And the only thing that's really within my control is whether or not I.

Am the right person for the job at the right time. And so maybe I'll actually start there, which is I think at the very beginning I felt like, all right, there's, this business that I can go join with these two founders who have actually done stuff before and I can learn from them. And that's my worst case.

My worst case is I show up, I've taken a salary, cut and done all of that, stuff that you have to do in the early days of startups. You're working for a company, no one's ever heard of. And then I thought, I'm in it for the learning experience and in a year or two I'm gonna go off and I'm gonna found my own business.

It turns out 10 months later, after writing the first line of code, we made our first sale and actually had our first customer. if you flash [00:02:00] forward about six months from that moment, we had built a business that looked like it was gonna take off.

 I think we had Airbnb, Pinterest, Uber, and Snapchat. We're four of our first 20 customers. And so some of the fastest growing biggest potential most interesting startups had placed a bet on us. And so I started changing my own perception of what the reality could be with this business and what role I wanted to play.

And so I started getting into my head the things that I didn't love about other workplaces, I could actually change here, we're building it from scratch. I could make this the workplace that I actually want to be at every day. And so when I saw that opportunity, I felt I can create my own environment.

 You don't get to do that when you go join a thousand person company or you join an already established culture. that was a motivating factor and that kept me grounded in okay, I need to Build out, fairness and respect and, growth and, the ability to make changes and all of those things into the culture 

And then I needed to always look maybe a year and a half out and say, okay, what is it in 18 months? Cuz I always say [00:03:00] that, maybe an executive is bound to survive 18 to 24 months in a startup. What is it in 18 or 24 months that will be expected from my role? And what can I do to make sure that I'm actually ready for those things?

And I think one of the big readiness things that people often forget is you have to stop doing the previous job. , this is like a key survival thing, if you're the first level engineering manager, and then what's really required is that you build a recruiting brand and level up the technical stack and make sure that the site gets stable.

Those are maybe some early responsibilities the sort of head of engineering role. You have to stop doing a lot of those things and hand it off to someone else and then focus on the next job. So maybe the next job is something more the VP job where you have to operationalize processes across a growing group.

You have to make it function autonomously. You have to keep employee engagement high and do all these things at scale. You have to communicate at scale, and so you have to shift a lot of how you. You have to hire the right people and make sure that they're doing the right things and you have the right sort of processes and meta processes for iterating on your processes baked into the team's [00:04:00] culture.

And when you have all those things, you can step into this next role, which is an open space. And I always felt like I did that over and over again every year and a half or two years and occupied the different job. And so now we're 10 years in, I And a lot of my job now is like corporate strategy and product strategy and m and a stuff, and, being an internal figurehead and, an external voice to, to customers and to the market.

And so that job is obviously totally different from right the first lines of code. Set basic sort of infrastructural requirements about how to keep things up and how to build out processes for a team. And so I always saw what is that next job and what do I need to learn? And around that point, when I saw what was coming, that's when I would really start focusing my learning.

And so I'm doing whatever the job is that needs to be done today, but I'm making a plan for who I need to hire. I'm reading books, so like when I knew the strategy thing was coming oh, I gotta know what I'm talking about here and actually have some good opinions on it. I read three or four strategy books, , for example.

 that helped give me a grounding and what is the [00:05:00] language that needs to be used? When I realized I was gonna be part of an exec team for the first time, I read two books on every other person's area of the business. So I read like two marketing books and two sales books and took like a finance course.

I just tried to make sure I understood how the whole thing worked together. And I think that was transformative. And then I relied a ton on, Intros from maybe people like you , to, venture capitalists or other board members or people I knew in the community who had already been there and done that.

And, you don't have to experience every pain from scratch. You can learn from other people. And so I found a lot of the things that I needed to tackle other people had done before and even failed that and had some good insights and wisdom that I could take with me. 

Brett: that's a good framing. Lots to dig in on there. I guess one piece that you left out is I like the idea that for someone to be successful in a role, they need two things. They need to be competent at the thing, and they need motivation to do the thing. 

what did you figure out about motivation? And did you want to be doing that thing 18 months later versus what you were doing 18 months previous?

Mike: I think my motivation [00:06:00] changed over time, to be perfectly honest. At the very beginning I think my motivation was I need to learn how to build a company. , if I go, way back to when I was like 18 or 19 years old I had been programming like in my room and trying to dream up products and make things for a while.

And I went out after high school and actually started two companies, both of which didn't particularly go well. 

And at that point I had actually hit like a low in my life where I, maxed out all of my credit cards. And thankfully they only give you like $7,000 worth of credit limits when you're like 18 or 19 and have no real income of any sort. And so I'd, run out of money.

It was 2001. I was, nine 11 happened. I was, unable to raise more money and I fell into a little bit of a funk around it. And I think the funk was, Interesting when I pick it apart. And this does relate, back to your question, which is that part of it was this feeling like, maybe you can't do this.

Like maybe you are not someone who can make, your dream happen. You're not someone who can make all these things real. And I [00:07:00] decrease the scope of my ambitions for a little while. And I like, did my undergrad and I ran my consulting business and just focused on plotting through there, assuming I'm going to, need this degree, That was not quite the, fantasy that I had as a kid and I started writing off the idea of building something as a little bit of a fantasy. And I think I had this realization while I was traveling a bit in in my mid twenties where it was like, you know what, maybe that fear I have about not knowing what to do is rational.

And that was a moment. It was like, okay if it's rational that I, I know I don't know how to build like a billion dollar business from scratch. What can I do in order to close that gap and, actually learn what it takes in order to succeed? And I started thinking about like an orchestral, performance, right?

It's if you've never seen an orchestra play something before, it's like you've maybe you don't know about the crescendo. Maybe you don't know about how songs end, or how songs begin, or what needs to change over time, and all of those things I felt were analogous to company building that I didn't really know enough to be able to improvise [00:08:00] successfully all the way through from beginning to end.

And that motivated me to want to join greenhouse and join two founders that already knew what they're doing. At the very beginning, to get back to your earlier question, it was really about learning. I felt like I want to learn from people who really know what they're doing.

What it takes to build a company. And I still feel 10 years in that I'm learning about how to build a company. And they're improvising at this point as well. This we're almost a thousand person company. It's the biggest company that any of us have ever been a part of building.

But, I think I learned a ton about what the early movements look like. I learned about the struggles and how to reason about the next stage and how to make it successful along the way. And I think that's actually been, one of the core motivators. Now. There was also this big identity shift I had to go through, maybe even several times in a couple of different phases through my time at Greenhouse, where towards the beginning it was like, okay, I'm gonna come in, I'm gonna learn, and then I'm gonna leave as soon as possible so I can go start my own.

and that lens, I started challenging a little bit, so I [00:09:00] was about four years in greenhouse, had raised its series C I think it was maybe valued at 250 million or something at that point. And so I put a ton into it and I started talking with the founders and I was like, I want to stay this is exciting. I have this other dream, I've been focused on.

And I basically, gave them the challenge on some level of what do we need to do in order for this to be my best? And that, I think involved a bunch of different things. It involved the level of autonomy I had, I was treated like a peer I think in many ways.

Throughout that time. And engaged in all aspects of running the business. So I got to have something that was more like a co-founder experience, even though I was not a co-founder than a functional area leader experience as the company was growing. Of course there's like, how do I participate in the upside of this thing that's going really well? That's just of course an implementation detail, like necessary, but but not sufficient on its own. And then and I think I went through a, a few different waves with it about, when you hit your lows, like when Covid happened and we had to do a layoff of, a bunch of people and a quarter of your friends and [00:10:00] colleagues yeah, disappear in an instant.

Those types of lows. I think a lot of people are like, am I doing the right thing with. Right now is this is this going to scratch all my itches? And so I think I had a few different moments where I reassessed does the identity I want to have in the future line up with the future I'm expecting to have here?

And as I inspected those questions, the answer just kept being yes. And so here I am, 10 years later having both survived and not been topped by someone more qualified yet. Although I fully expect that to be the case at some point whenever I'm no longer the right person for the job.

And I'm still feeling intrinsically motivated to to build this thing. And, maybe the last note on that is I know that I am not a co-founder of the company. I wasn't in the, room sitting there. When the idea for structured hiring and how to layer it into the recruiting market was formed at the same time I think the shift in identity from this is somebody else's company to, this is my company.

Actually really helped because it changed the relationship I had to the work in a way that allowed me to feel like, I am building my own business.

Brett: When? When did [00:11:00] that happen?

Mike: I think it happened in a few different phases. Like I definitely felt that way with the engineering culture at the beginning.

This is my team, I can build it how I want. When I think maybe this is an interesting topic and I don't know how shared this is, but I think it's often true that in these early stage startups, cuz you have less product than market demand for it, you end up with the engineering organization being one of the first larger organizations.

And of course eventually you get really big and like engineering shouldn't be the biggest organization anymore and in most companies. But I got to be the first one with no HR person to go create like the people pay practices and what cadence we, set up for growth conversations and all these different things.

And I think a lot of that imprinting of what we did in engineering got. Brought into the rest of the company made me feel like, oh, this is a company I shaped. I helped make, all the culture and processes and all of this stuff. It's lots of people all working together, but I could see my imprint on it.

And I think that was significant. And then again, I think, that moment after [00:12:00] the Covid layoffs when I was thinking about, is the trajectory still gonna be good? What's happening in the world? I think all of us had some level of existential crisis around that time period.

As I thought about it more and more, it was like, you don't have, I don't know, you don't abandon your kid kind of thing is almost what it felt like.

It was like, no, this is this is my company. I helped feel that I need to steward it through through the rough times and, to the degree that I'm still the right person for the job. It's, both my responsibility and my desire to, to be there and show up.

Brett: You touched on sort of the conditions that the founding team created to enable this 10 year career that you've had at Greenhouse, but I'd be interested if other founders wanna create the conditions such that there are more career trajectories that look like. what would the advice that you have for them, maybe outside of the generic that everyone talks about, which is, give people opportunities, support them. What are the sort of levers that come to mind if other founders wanna create an environment such [00:13:00] that there are more people that, that look like you?

Mike: Maybe I'll break it down into Innate Plus environment, cuz I think the intersection of those is probably where the answer lies. maybe these are personality traits that I believe are central to my identity and were only reinforced by my experience at Greenhouse, probably number one was adaptable.

 I don't just say like growth mindset, like adaptable, like I could actually fundamentally change even how I'm processing and thinking about the world a bit depending on the conditions. And startups being incredibly dynamic environments, I think usually the failure mode is that people don't end up changing fast enough at the right moments.

So I think I was always proactive in adjusting myself and that. Difficult thing to interview for, but that might actually be a good thing if you were hiring early employees.

Usually I think it's just will someone please join my brandless moneyless venture? That is my idea. As the first employee and help me make it real I think in that desperate situation, there's often not a ton of scrutiny on adaptability, [00:14:00] nor is there an expectation that whoever they end up hiring is actually going to be the person who would continue scaling.

And so there's maybe low emphasis there. So that might be an area for high emphasis if you actually wanna hire someone. It's more, more like hiring your co-founder maybe, right? Is this somebody who has unlimited potential to scale? Is it someone who can participate in the creative and strategic process and are they going to be able to change over time in the ways that the company is going to demand?

 And then in terms of environmental conditions I think I. Let's get into I'll probably get get killed for this, but one of the co-founders of Greenhouse, is my direct manager, John STRs is really a product guy and, he's helped build some pretty great products.

Obviously Greenhouse included over time. He was also I think first product [email protected] and, if anyone who's had kids you you've probably used that at some point. He's done call center performance management stuff, all of these things. And the way that he manages, because he hates management as a, like an activity.

Let's sit down and do a performance review and all of those types of things. Not that anyone, particularly loves having those types of [00:15:00] conversations, he tended to almost automatically manage by. . And by that I mean he would just express something he was worried about. He would be like, I'm really worried about, whether XYZ thing is going to succeed or happen, or whatever it was.

And I think that allowed me to be really autonomous in solving big important problems that the founders saw without ever being assigned a task. And I think he would almost broadcast some of these anxieties. He would, go chat with all of his direct reports, other people in the company and just say, I'm anxious about xyz.

And if it was appropriate for me to pick up, if I was the right person to go drive some sort of change I would just say, okay, let me go look into that and, go try to work on it. And I think that allowed me to both work on the right stuff and feel deep down that I.

Discovering and finding and solving for all the right things in the business as it went. So the autonomy was a big part of the environment. Another one that maybe they, they didn't do specifically with me, but I think probably would be helpful, and it's something that I definitely do with my direct [00:16:00] reports, is try to help them envision the future.

 the thing I do with my direct reports is I'll, draw out like, True of our future plans. what does the business look like in five years? If we sustain growth, how many people are in the company? How big is our team? What shape might it take? What are the things that it's going to, need to be able to do that it can't do today?

What's gonna take a long time? What's gonna take a short time in order to realize? And so just talking through some of the long term planning stuff and how that future of the company intersects. The demands on the org helps you break it down almost like stepwise refinements, like how do I refine my way to the specific next thing that I need to do?

If you can see in two years what we're going to actually need is multiple VPs and we're going to need to restructure some of the teams and do this or that, That helps provide a clear picture for, both direct reports.

And I think people who are in a position like me, whereas head of engineering to imagine that future if they haven't done it proactively on their own or didn't have enough information to even do so on their own. And then collaborate with them to try to figure out like what it would take for them to get there at the right time.

It's [00:17:00] okay, what if in 18 months you need to be doing this strategic role? you need to understand finance well, you need to understand how the whole business works better. You need to understand our partner ecosystem. You need to have enough free time to be able to focus on those things and not do all the sort of day to day operational stuff, which means, the person reporting to you needs to be able to do that really well, or they're not the right person for the job.

 for the environmental stuff I think helping them see the future and helping them figure out what the specific plan is so that they can be ready for the future as it comes is probably the most helpful thing I can say.

Brett: So another thing that you shared a little bit about was the other part of the equation, which is how did you approach your own growth in each chapter of the company's life? You talked about reading other books on functional areas developing new muscles like strategy through reading, leveraging members of your extended community.

But I was wondering if you could you could share more about that, maybe share some stories or your [00:18:00] approach that allowed and enabled your success in all of these different roles over the last decade.

Mike: one area in particular that I think is important for anyone who's trying to grow and adapt I have this specific theory around one's identity and like what you should absorb and what you should deflect and what you.

Work on proactively. And so by that there are probably core parts of who you are that you don't wanna change and are positive attributes. And they might very well be two-sided coins in certain cases. Many personality attributes are.

But same time you want to have that identity. And for example, part of my positive identity attributes are one that I talked about already. I'm adaptable. Whatever situation I'm in, I'm pretty sure that I will be able to learn what I need to learn and change at the right pace in order to be able to do the thing well.

 Another one is that I try to be kind to everyone.

Now is that always true? Am I always kind a hundred percent of the time? No, but it's like a personality attribute that I want to have, and I think [00:19:00] strengthens who I am and how I show up in the world But I try to take any of those sort of positive things that I think are really, fundamental to who I am and absorb them and take them in and accept them as an identity.

Now on the other side, there's all the negative stuff. There's the times when you screw up. There's the times when you don't meet your own or other people's expectations. There's the times when somebody has an opinion about you. That is potentially labeling you as one thing or another, you're incompetent.

You don't these are not necessarily things that people are saying of me, but you're incompetent. You don't, you're unreliable. You don't complete things on time. You are a real jerk in that meeting, whatever it is. All of those types of things. I very much intentionally will absorb the behavior and deflect the identity.

And so the behavior might be that I didn't show up as well as I could have, or somebody asked me to do something and I didn't get it done until three weeks later and, that created some harm. All of those things are like observational data to me. It's like I can. How I'm behaving. [00:20:00] And then I need to devise some way in order to take those negative labels, turn them into behaviors that I can observe as actions, and then turn those negative behaviors into behaviors that are no longer part of how I'm operating day to day.

And so I think that requires a fair amount of self-reflection and depth. So sometimes I'll literally sit down and take something I've screwed up and do my own retrospective. So it's not like literally sitting up there with a whiteboard with, happy mass, sad or something along those lines.

But it's like sitting there and writing with myself and it's, a reflection exercise of how did I feel like, how did I make this other person feel? What was the context What other things were going on for me that caused me to behave in that way? What is it that I believe to be true that caused me to make the assumptions I made that caused that interaction to go badly?

Just like tearing all those things apart and trying to surface them so my conscious mind can process them. And so that it doesn't all just happen to me subconsciously, I think there's like this default of. Victimhood almost of you're a victim of the [00:21:00] worst attributes of yourself.

And it does feel that way sometimes, cuz you're like the version of myself that I identify with would never have behaved in that way. But there it is. You did, 

And so sitting down and reflecting on it and coming up with a plan for how to make it better, I think is actually a key, learning approach that's allowed me to go through some of these cycles and iterate on myself over time.

Brett: I think that's a good foundation. Can you go into a little bit more detail in terms of techniques, tactics, things that you did that sort of sat on top of that, that enabled it? You talked about some of the reading that you've done and how that influenced you. Maybe things like when you leveraged other CTOs or other people that were maybe farther along, did you engage with them in a certain way to maximize your own learning?

Mike: Yeah, I think one thing I've actually done with my peers is even asked them for feedback. And so I'm in, a few different little CTO pods where, [00:22:00] people meet up once a month and some of them I've met with for a really long time and they've gotten to know me and so usually you bring up some topic and everyone discusses it over breakfast And so periodically I'd bring up instead of a topic, the question of what is it that you. see about the way that I'm thinking, the way I approach problems whatever it is that I can learn from. And so I've gotten some interesting feedback that's usually very specific and specific to that moment that I can act on really quickly from peers who are sometimes a step ahead.

Just to I guess name drop a, a friend of mine who gave me a specific piece of feedback at just the right moment It was Yi Fang who's co-founder and CTO of Peloton.

And helped build that company up. And it was a few years ago and I think. He was going through like super, super hyper growth. The first time I met him, I think he was he was still building the first prototype of the bike and we were at some like 2013, CTO conference.

And I was like, oh, that sounds really cool. And we stayed friends over time and the wisdom he gave me was, I think you're trying to control things a little bit too [00:23:00] much, and that was a key learning moment just to reflect on, which was in years, let's say five through eight, Where I think I transformed into big team leader where you have to, lead teams of, 60, 80, a hundred, a hundred plus people, and you start transitioning into broadcast mode and you start really focusing on process as opposed to like specific decisions, right?

You're trying to figure out how do I create the framework for decisions. I was actually so productive in creating process probably in that first year and a half that I got into this default mode where I just kept adding more and more. Process. And thought that was my job. And I think the company wasn't quite ready for me to paradigm shift at that moment either into more of the strategy role stuff.

So I felt like I was wedged into the sort of VP of engineering type job of create process. And I was going too far. And I think what I didn't realize was that structure, part of which was very much intended to create empowerment, created a level of disempowerment where people felt like because I was so engaged in every process detail, that [00:24:00] processes needed to be run by being.

or that they needed to do it in the way that I was prescribing and not necessarily change it. And I think that was the right wisdom at the right time for me to absorb. Other times, I got I would be talking about some operational details. This was maybe the same era of like, how did I transition from, doing the VP of engineering type job to doing the, bigger company CTO type job.

Someone was like, I haven't heard you take huge swings. You always make measured decisions, and so like little moments like that where I have to interrogate myself and say is that true? Does that jive with who I think I am? Does that jive with the behaviors I, I have?

And a lot of times like, I get, get that feedback from someone who's been there and done that. It rings true. And that helps me realize at the right moment that I need to get better at. or identify a void that needs to be filled in in, in the growing business.

Brett: So I wanna loop back to strategy and some of the things you figured out there. But before we move on to this growth thread, a couple other things came to mind for me. One is that you seem to be quite self-aware that you're able to understand yourself and how you fit into the broader company strengths and [00:25:00] weaknesses, et cetera.

Is that just a way that you were wired or is part of the journey developing your own self-awareness?

Mike: I think it's probably both. I think I'm in some ways wired for it, but I do remember when I was really young, this might sound slightly unrelated, but I think it's actually deeply related. Every time my parents screwed something up, they would almost always admit it and then say if there was anything that you think should have been different about how we handled that.

Cuz we don't really, always know what we're doing. You can do that differently with your kids. And so I think that kind of put in my. That You're not a fixed person, In terms of other ways of reflecting on myself and where I fit in the broader context. I don't even know if I'm thinking about myself on honestly all that much.

I think it's more there's this like dynamic system of a business in a way, and it has a bunch of inputs and outputs and needs that are met and not [00:26:00] met. And and I think I usually wedge myself into a place where, I have the ability to express creative energy, and I think it's because I can get really interested in something that seems important to me.

And so I think the task is identify something that feels important to me, get really interested and like hyper focus on that thing. And I think that lets me leverage my superpowers. And so I think when I feel bored or I feel like I don't have anything that I can uniquely make a difference in doing that's like stagnation sets in a way that feels bad and I wanna go find something that makes me feel good, which is like the next interesting problem to go solve that I'm uniquely suited to solve.

Does that make sense? It's almost like painkiller. It's like the painkiller is go find something important to solve.

Brett: In continuing to build on this learning journey, what specific books or essays do you think have stuck with you or maybe had some sort of outsized impact?

Mike: yeah, I think, some of [00:27:00] them might sound standard. I'm gonna turn around and look at my bookshelf, so hopefully the microphone is still picking me up. I think things like thinking fast and slow and, identifying how, how your brain works and makes decisions is probably a big part of it.

I think like computer science books are actually interesting, especially things around data structures where you start learning how to visualize abstract things and then manipulate them in your head. And I think that was actually a fundamental thing in, in, my own learning journey.

And then, I think I read really broadly. I don't read probably enough pure fiction fantasy and things like that, that I think actually have an incredible place in, human interaction and expanding your mind I tend to read books that teach me some type of or provide me with some type of contextual information that I feel like really, enriches me as a person. Examples of a couple of ones that I've just, read very recently. Thanks for the feedback, which is one of those books from the Harvard.

Program on negotiation. A couple of other [00:28:00] great ones I had read before were difficult conversations, which is really interesting in getting to. Yes. All of those books I think are fantastic in thinking how you communicate and relate to and interact with the world.

Another one I read recently, was the power law, how, which is really like the history of venture capital. So that's like an ecosystem thing, right? Like I'm not a venture capitalist. But I'm interacting in an ecosystem where venture capitalists play a very significant role.

And so understanding like the fundamental mindset, the, the sort of history, who the players were, all that stuff I think gave me one little bit of extra context. And that's what I'm always probably seeking the most is how do I understand the dark corners a problem that, that I'm working on or, a space or environment that I'm in.

The exception to that would be professional sports. As a typical cto, I know nothing about professional sports, I couldn't possibly know much less about sports ball

Brett: Yeah, I'm not into sports either, and it, and I feel like maybe I'm missing some important part of humanity. I don't know,

Mike: I, I actually [00:29:00] I think I am. There's , there's definitely that bit about sportswear. There's the, how do you get the team excited during a down moment? How do you get everyone working together and playing their own roles? How do you coordinate a plan? Like I think all of those things pretty interesting to me.

And I always think it's like amazing to see the performance of all of these athletes. But the knowing which trades happened and the personality of each player and how they won one particular game. That's the type of stuff I haven't gotten fully immersed in, but maybe one day it will become an interest.

Brett: Yeah. I don't let my lack of sports knowledge keep me from using sports metaphors at work, so I feel good about that.

Mike: gotta use the sports metaphors at work,

Brett: One of the things that's been woven through our conversation is topic of strategy or being strategic. And I'm interested, like what does that word mean to you? Given I think it's so screwed up all of the time, and particularly at scaling companies, I think a lot of people are allergic to the word.

 and maybe related to the classic book, good, bad, good strategy, bad strategy. Like how would you articulate good strategy and bad strategy in the context of building a rapidly [00:30:00] growing software business?

Mike: So that's a great question. And I think, although I might be conflating them, cause I read four strategy books in a row I might actually use some of his example. And I think, right at the beginning of that book, I believe he's talking about how a lot of people think they have a strategy when they have a.

they figured out where they're going on some level or some numerical target that they wanna achieve, X percent growth. And then they hand off all of the details of the plan to somebody else to figure out. And so then you potentially have people who are even in individual contributor roles in a lot of startups who have to make strategic decisions.

And the way that they break it down in that book, I think is the strategy is a combination of figuring out which hill to take that in the context of the broader war advances your goals towards the broader objective of win the war. You don't just take a hill to take a hill, 

So you have to have clarity on what war you're fighting. You have to figure out which hill to take. And the part that I think is often missing and is a little bit [00:31:00] intention with and requires some reconciliation with empowerment ideas in management, is that you actually have to have a plan for how to take the hill.

And so the plan doesn't necessarily have to come from the same people. It's not necessarily that like the CEO says this is the war we're fighting. This is the hill we're going to take, and here are the 4,000 Jira cards the developers need to do in order to get there. I don't think that's the sort of right level of plan.

But to collaborate and say, here are the specific wedges that we've identified that we think are going to help us to take this hill successfully. And this is the sequence in which we should do them and these are the sacrifices we're making in terms of other things that we could be doing because we think this is the best choice against all of our other choices in order to achieve this strategic objective.

 I think that complete plan, Cascades all the way to the people then doing the work. And they can. Follow a road that's actually been cut where they know what to do.

And I think you can take more ownership when you are involved in at least signing off on and potentially influencing some of the plan. And I'm [00:32:00] using some of that tentative work cuz like a plan needs to exist, but it doesn't need to come entirely from the leader. And so I think the worry about being too prescriptive and saying do all these things is a valid one.

And I think the worry about being not prescriptive enough where there's nothing written down is another valid one. And I think somewhere in between is figuring out how do I do the hard work of actually engaging with the data and all the people that are going to need to make this thing happen.

And, any any other stakeholders I have and align on a plan that feels like it's gonna actually get. So to me there's probably 50 different ways to spin it around, but, from that book, I thought that was a pretty good description. 

 but that just, gives you probably the terminology and like a basic mental model for how to do it. Then you actually have to put in the reps. Apparently, as I've discovered, reading a weightlifting book does not make. Jacked , you can read a weightlifting book, but then you actually have to, go lift some weights in order to make your muscles bigger.

And as I've been using that more of let's figure out how to actually answer the question by, in addition to setting an okr, you set some gold [00:33:00] says improve the SAM to TAM ratio in Germany from two to 15% is totally made up a goal.

The plan in order to actually execute it requires that you have specific actions you're going to take. So maybe it's I'll translate the product, I'll integrate with, all of these job boards or other systems that I need to deal with in, in the local market in order to be properly localized.

So you've got some set of activities and then you have to presume that those activities will produce the result. So you might have to do a little analysis like if we do this, Will that create the result? What are our other options for increasing SAM to TAM ratio in Germany and how do we prioritize among them?

So we're maximizing our bets towards that strategic end and, zooming out one level higher. How do I know that, by improving SAM to TAM ratio, it maybe gets me to whatever the laddered up objective is, which is to expand international market share. And again, the same level of scrutiny might apply to, should we even go to Germany?

 or should we go to, China or Australia All of those types of decisions also require those strategic trade offs and [00:34:00] thinking, and it's a lot of work. And I feel like part of it is that not everyone always knows what the work is to do. And once you know what the work is to do, then it's accepting, oh, it's a lot of work to actually figure this stuff out in a good way.

Brett: continuing down this strategy conversation, you made a great point about implementing knowledge. You gave the example of you, you read a weightlifting book and you all of a sudden don't get jacked, so what in the context of developing the strategy muscle to mix metaphors here, if weight lifting gets you jacked, what is the thing that you are doing in this realm of strategy to make you good at it or to make you strategic?

Mike: I think it's, you have the opportunity to make decisions and you get some feedback loop on whether they turned out to be good or. And sometimes the cycle times are kind of long, so probably whether or not you're actually good.

Did you make, let's say 15 decisions and, could be just, randomness, that something ends up striking 10 outta 15 times and you got lucky, but most of the time, [00:35:00] probably if you were right, 10 out of 15 times, it was because you.

Have learned something gotten better. So do you see improvement in your ability to reason about these things? So that's actually the execution lens. Like I've done it. I see whether the result actually worked. The intermediate thing that I think I've actually been leveraging quite a bit is, you put something out there I'll take an m and a example.

So some company comes in opportunistically and they say, I would love to sell my business to your business. And you have to go find out more and figure out like, would this actually be a big fit? One question is how do I then reason about those things in a way that is, going to resonate with other people.

Let's say we actually wanted to buy the company. We would have to make a case to the board. What would be the components of that case and why? What is the overall framework of what makes sense for our company? So maybe there's like a scorecard for acquisitions generally.

 Does it go against the hiring or recruiting? so it would fit into our existing go to market engine, or would it actually be like a big change to our distribution engine, we would have to build a totally different machine, and that's too high a hurdle [00:36:00] to reach. And then if you then also are evaluating companies you can, write up little emails and share it with the CEO or board members and say, this is how I reasoned about this decision. Does this resonate or not?

And those stakeholders can then provide feedback. It's I totally think that you were right about what would happen to gross margin if we went and did, XYZ thing. But I, I.

Don't totally agree that it wouldn't be worth it because of Yeah. Some other thing, right? And I think that helps you learn and converge on a model that at least maps to what a lot of the other experienced folks think.

And so I don't know if it always gets you to the optimal answer, cuz sometimes the group consensus is actually wrong for some important reason. You have to keep an eye out for those times when that's true. But most of the time if you're surrounding yourself by people who really know any domain and know it well and have gone through a bunch of reps, they're probably going to have some good thoughts that you can learn from.

And so I think it's actually like rubber meets the road. Write the email, expose your reasoning, be vulnerable for a minute. Ask for feedback, take the feedback and [00:37:00] do something with it so that next time your reasoning is a little bit better and do a bunch of reps and you'll be better at it. Okay. So I'm not the greatest strategist in the world, but I think that's how I developed some of my strategic muscles.

Brett: I think in studying a lot of companies in the way that they operate to a slight degree, I think that strategy and sort of another word might be direction is slightly overrated and rate of execution is slightly underrated. And part of that is that I just think the future is hard to predict.

Reality is very complicated and the amount of learning that happens when you do a thing is so substantial relative to trying to pick the exact right direction.

Do you agree or disagree with that line of thinking?

Mike: I strongly agree and all things that I might answer. I would it, it probably depends a little bit at the beginning. Like you probably have to pick the right overall direction and then execute. Without spending tons of time just philosophizing on the edge of a cliff, like that's not gonna get you anywhere.

So I do think it's, very execution focused as long as you're moving in the right direction so that you [00:38:00] can have the best product be first to market. Wow. Your users do all the things to establish yourself from zero to one. Going towards where we are now. We can still be agile with certain decisions, but we can't be agile with every decision.

 it's a cruise ship and so trying to steer it from one place to another is taking longer and longer. And so I still think speed of execution matters, but there's always a trade off with speed. So is the trade off that the decision quality goes down?

 Is the trade off that it leads to burnout? There's usually some type of other side to whatever that coin is that may or may not make it actually worth it to go super, super fast. But I think trying to map out a little bit further out how are we gonna make a five degree turn in the business?

So we actually land on a different island than we were planning. I do think that becomes more relevant. And so you're not just expending energy in lots of directions that don't actually change things. You don't wanna tug left and tug right and end up going to the same place that you were going before, having spent a bunch of resources.

If you're spending, hundreds of millions of dollars a year on, on, building a business I think, the dollar [00:39:00] numbers and the consequences and the number of people required in order to get somewhere are so large that it is important to at least have a couple of people thinking far enough in the future, slowing down, doing some analysis, and then making the hard decision of focusing the efforts in some directions instead of letting it go in a bunch of different directions.

And the frenetic early startup energy I. Is useful and helps for, innovation and building a brand from scratch. But I do think at the very late stages of a startup Then a little bit more sort of thoughtful analytical steering and then try to execute as quickly as you can without sacrificing the other sort of critical things to make it successful at scale.

Brett: Switching gears just a little bit are there mantras or things that you tend to say over and over again when you're developing or coaching people on your team? Or if I were to just watch you at work over the last three or five years there's things that you tend to come back to, frameworks that you teach, or things that you say all the time that, that people might be sick of hearing you [00:40:00] say.

Mike: Yeah, I have one that I think people actually feared for quite some time. Which I think was actually maybe the most useful thing I did as an early-ish startup team builder. Which was to make whatever people were complaining about their problem and to find out what people were complaining about

And so I would spend lots and lots of time in one-on-ones with everyone. It doesn't totally scale to the team size that I have now to, go have one-on-ones with every single person in the team on a regular basis. But I was doing that, especially when we were, 20 or 30 people.

I was still meeting with everyone once a month. And I would try to ask specific tactical questions about where the pain was. And I found some really weird ways of finding it, like saying, if I were to ask all of your teammates what the biggest problem is that you all are seeing, what would it be?

And that just allows that person. Explain somebody else's opinion instead of their own, which can feel risky when they're talking to like their manager's manager. So that little trick, I think, it may not actually be the consensus opinion [00:41:00] that same person holds, but it helps bubble up some of what's happening inside the teams.

Another thing is that, they often broadcast retro notes. Okay, we had a retro, we complained about a bunch of stuff and said some things were good, and then it gets emailed out to the whole team. And so then there's like a list of things to go work on. Usually there's action items assigned.

Sometimes it's just dangling there and you notice it over and over again. So the specific trick of what I've, do, which I don't think is magic but does require that you get your managers bought into if you're a leader and you do have some layer involved, which is to say if somebody sees a problem with, let's say, how the interviews are being conduct.

How the, on call rotation is going, the lack of a policy for xyz, whatever the thing was. I would always challenge that person to go do the work and then I would not have them do it in addition to their day job. I would defend their time, I would say, to their manager, Hey, for the next week this person is going to go.

 tried to solve, problem X and assign them the task. So on the upside, people definitely felt you know [00:42:00] what, it's not on management to fix everything. It's on us. And I think they, they felt like they could take some ownership over the changes that were happening in their culture.

 I had that whole theory, I laid out in my first round review article which kind of culminated and, people don't feel fairly treated or respected or like they're growing. Those were often things that contributed to people leaving their companies, but the nail in the coffin is always that they don't feel like they have the power to change their environment if they felt like they could change it so that it was more fair or change it such that it would be a good place for them to grow.

 Then all of those things led to more engagement, more retention, and frankly more action whenever problem surfaced inside of the team. And I think that habit probably played a pretty big role in, in setting the culture 

Brett: So I wanted to wrap up by talking a little bit about hiring and and the area that I wanted to spend time on is how do you approach recruiting people like you? And what I mean by that is I assume, [00:43:00] given your own journey, one of the things, and maybe it depends on role maturity, et cetera is that you wanna hire people that have this sort of steep trajectory, that have the ability to really grow with the company in profound ways.

And at the beginning of our conversation, you talked about the idea of adaptability but I'm curious kinda specifically in the box of hiring people for slope or people that you can bet on that you think can have a really big career in your org. What are you looking for in those people and maybe just as importantly, when you're sitting down with them or you're referencing them, what are you doing to increase the quality of that forecast and that hiring decision?

Mike: I might answer first by saying it's easier to observe probably in advance and be right about people with slow slope than people with fast slope. Sometimes fast slope is obvious. But I can give a couple of examples. So someone with a slow slope sometimes will interview someone and they're super [00:44:00] nice and they've been a software engineer for 10 years and they have, let's say weirdly lower than average pay expectations for somebody with that experience.

And they go through the interview process and they test as like a software engineer, three who's, someone we would expect to let's say be a few years into their career. If it's taken 10 years to get to the level of someone who's about three years, that's probably a slow slope. It doesn't necessarily mean that they're bad.

It doesn't prohibit them from being good in the future. It could have been their environment, it could have been their motivation at the time, But when I observe that, I see that as let's draw the line out and imagine if that slope continues. Do we end up with someone Great.

And the answer I think is often no going the other way. Sometimes you see someone, and I'm sure you experience this constantly as a, venture capitalist, but you see someone who just looks like they have unbelievable slope, it's practically vertical.

They, double Stanford, went and worked for BCG or, Bain or something had a impressive chief of staff role at some big company or something. And [00:45:00] they're like, okay, I wanna go found. . So that person has probably a steep slope, 

And I know some of those people turn out to be amazing founders but some of them, that whole experience that they've had, put them on a really fast slope towards something else and not necessarily the slope that you would need in order to be successful at something as unstructured and volatile as starting a company from scratch.

And so I think maybe I'm just adding a layer to the question, which is you can find fast slope and realize that it's still going, the vector is still going in the wrong direction. For startup success the fast slope towards startup success I do think it's like adaptability, versatility.

Are they somebody who can, reason across the board, are they good at the quantitative stuff and the communication stuff? Are they someone that is like naturally attractive to be around? Like I'm not a big fan of the charismatic leader, prototype where they have all charisma and nothing else.

But can they be someone. People like, and they wanna be around and they wanna learn from. If that's not true, then they're probably not gonna do a great job of hiring. Are they somebody who [00:46:00] is intellectually flexible enough that they can walk off their own ideas through logical discussion of something and are they curious and interested in other people's ideas?

All of those things I think are pretty high slope for startups. But you take that exact same person, you put them in, let's say an analyst or banking job at a place like Goldman, and 90% of what makes them amazing for a startup doesn't apply.

And so they might actually be like the bottom 25% in that job, but our top 10% or top 1% in the startup world. So I think the, the vector is different not just the sort of slope of line.

Brett: So with that outline, adaptability, versatility attractive to be around intellectual flexibility those kind of attributes, how does that show up in the way that you interview someone or get to conviction that you think this person exhibits those traits?

Mike: first of all, this kind of goes against the structured interviewing ethos is is that they're [00:47:00] observable.

So if we take something like. Is this someone who I want to be around who I think can recruit other talent? You get some of that from actually sitting down and talking to them. It's not just you ask the one magic question that, tells you whether or not that's true. But if the thing that you're really trying to figure out is, are they someone who knows how to hire well and hire effectively as opposed to just do they have the personality where that might translate to that?

Then you can get more specific and, ask both behavioral interview questions or in past experiences, how did you actually go up and, build the team that you built and do some top grading, which is, where you go deeper and deeper on some topics.

So it's yeah, not just how you interview, but can you tell me about a time within that where you hired the wrong person, where you attracted the best person ever and developed them? You keep going down some of the paths that they lay out in terms of something like versatility.

You probably wanna see some evidence in their lives that they actively seek and choose different types of experiences. Like I think somebody who is interested in jazz and cooking and [00:48:00] strategy and a million different things 

That's probably somebody who has a bit of a versatile mindset. Somebody who gets hyper focused and is great at one thing. Is probably someone who is less of a versatile and is probably somebody who is more of a focus master. 

And then in terms of adaptability, Yeah, I think I actually have an opinion on this, but I don't know how easy it is to interview for other than to ask about their life experiences. But have they put themselves in lots of different uncomfortable settings where they've had to actually adapt. that probably helps support them in being adaptable when they join.

Brett: When you think about these sort of steep trajectory type people, is there a nuance in is there trajectory and ambition oriented around themselves or oriented around the company

Mike: My God, yes,

Brett: and what have you learned about that? Because in some cases there's overlap, right?

If I care about growing in a certain way, for me, [00:49:00] maybe that can be leveraged for maximal kind of impact at a company. At the same time I often find that nuance is hard to pick apart and that if somebody truly cares about company first themselves, second really great things happen.

And in a lot of the language you used about your 10 year journey, I feel like you are that type of person that is steep trajectory, very ambitious, applied to the company, first person second. And I often find that the inverse one is it's just the nightmare to manage this type of people. It's just very unpleasant.

But you can also create some really nasty, unintended consequences, anything in that area.

Mike: Yeah. I'm gonna borrow a quote that was repeated over and over again. in the early days by, by Dan Ch, who's the CEO and co-founder of Greenhouse. He would always talk about build a great company. You have a lot of great options. And I remember in the very first year, I'd be like, so when are we getting ipo?

It's like we have one customer and [00:50:00] it's like your dad, and like that. It's not a real company yet. the core was, just be great and you'll have a lot of options. And I think that is true in individual careers. Just show up and do your best at whatever the thing is.

And people will probably be knocking down your door to, to do it with them. So I think it's maybe that simple, the people who get too into their own head about what's really gonna work for me? I think they should have that at the career level. Is this an environment in which I can become the self I need to become?

I think that's a really good, valid question and I think it's a good question to even bring to a manager, which is. I have aspirations to become these things, not this title or this amount of money, but I have an aspiration to go become this in my life. Those are not things that feel like offensive or like an allergic reaction to a manager If you're not able to have that conversation and then get to a place where you believe that being at this company and, providing value is going to be the thing that actually, gets you where you want to go [00:51:00] then you can make a career decision for yourself and, figure out like whether it's the right environment.

But I think if you're getting hyper focused, it's almost like this, desperation to achieve this extrinsic. Expression of I've, got a ton of money. I got a fancy title. I have a lot of power. Those types of things. I think they're like toxic motivators.

And I think that they also do have a sort of polluting relationship with all the other people around you. The best teams are all focused on how do we get the company to win? And when someone's in there, trying to empire build do it for themselves.

I think I think that person often ends up an outcast and has trouble achieving those goals.

It's like the cherry picker, , in, in sports, let's use that analogy,

Brett: Got, got another one of those metaphors in there. So to wrap up, maybe an interesting place to end you. You shared this really great conversation, I think it was with the CTO of Peloton that you had relatively early in your scaling journey. And he gave you this perspective that maybe you need to give up control and that was an unlock for you.

Is there another one of those stories that come to mind, a conversation, a pivotal conversation you had that sort of [00:52:00] set you up for a lot of success? And maybe we could use that as an ending point.

Mike: Yeah. I actually am going to get two different mentors of mine to intersect But these comments were many years apart. I was, totally lucky to have randomly gone to Jewish Youth Group with this guy Dan, who I became, good friends with.

And his older brother is this guy Mike Afgan. who is the 26 year old CTO of. And I was like, 19 or 20 years old, and we wound up on the same bike riding team. 

And so I used to go bike riding with him like, three or four days a week in the morning. And we talk about business and computer science and all this stuff. And I was always in awe of him, honestly. It was like, you're 26 years old, you got PhD from MIT in 10 months. This guy's a, super genius.

And I got to, spend time with him. And so one of the things he said, which sounded like a super small comment, was, whatever you think you can get done by yourself, you can do more with the team. And I was running my own independent consulting business at the time, and that really landed for me.

He was like, oh, if I get, good at building teams than I can accomplish these much bigger [00:53:00] things now, nothing then really happened. I, Take that advice immediately and go do something with it. But then years later I went from having run my own consulting business to joining a small startup that had gotten, acquired by Lending Tree, I think a week after I joined or something like that.

And when I showed up, I think I was used to feeling like I just needed to do the best I could do and just be a rockstar. And so I would get all of the work assigned to me done by, the middle of the day on Wednesday, and then I had the rest of this other half a week to do whatever I found interesting.

And so I would do things that I thought were also super impactful for the company. Make the site faster or, refactor some code base or whatever the thing was. And I remember that I got asked out to breakfast by, or Schnapps, who's he's now a director at Facebook, but he had been been CTO of this startup.

 He took me to breakfast and he said, you're screwing up. And I'm like, in total shock. I'm like, what do you mean I'm screwing up? Like I, got all of my work done by the middle of the day Wednesday, and I just added all these other capabilities.

 And I'm like what do you mean? And he was like, when you get [00:54:00] to that point where you've finished all of your work, you had the choice. You either worked on something you found interesting or to work as part of the team in figuring out what the team needed to get done and helping all of your colleagues actually accomplish what it is that they're trying to accomplish as a whole.

And as a result, the team resents you. Like they resent that you're not. Participating fully as part of the team. And so those two things intersected for me in realizing both the role that somebody plays in a team and how important it is to put the team above the individual fundamentally. And that I hadn't been doing that and that was damaging to the relationships around me and potentially even the success of the company to have, tried to be the consultant type star instead of be a great team member.

And and then that other sort of echo from my conversation with Mike Ahan about, whatever you can do you can do more with the team really landed for me and I internalized it before scaling a lot of the teams at Greenhouse. And I think that put me in the right mindset to be able to, keep.

And to, build it up into what it is now, [00:55:00] which is a fantastic team. So I'm shocked and proud by the company and team we got to build.

Brett: Thank you. Thank you. What a great conversation. Thanks Mike.

Mike: thank you.