#194- Personal growth as a CEO in different stages of a growing startup | Sam Corcos & Ben Grynol

Episode introduction

Show Notes

Over the lifespan of Levels, the company and the CEO role evolved drastically. Sam Corcos went from coding the initial product to CEO, and he experienced a lot of personal challenges and growth along the way. Listen as Sam chats with Ben Grynol about time management, strategy versus people ops, requirements at each startup stage, and taking time to reflect through quarterly Think Weeks.

Episode Transcript

Sam Corcos (00:06):

I knew what the correct answer was, but I let the loudest voice in the room determine what happened. I was too afraid of hurting somebody’s feelings, and I just let something bad continue. And it didn’t really do them any favors and certainly didn’t do me or the company any favors, because they kept working on something. They were basically wasting months of their life working on a thing that I knew wasn’t going to deliver value. They thought that it was, but I knew that it wasn’t.


But I didn’t want to hurt their feelings and tell them to stop what they were doing. And that’s the responsibility of a leader. And I think just coming to terms with that and just recognizing what your role is as a leader, it takes a lot of practice and repetitions to get comfortable with it.

Ben Grynol (00:51):

I’m Ben Grynol, part of the Early Startup team here at Levels. We’re building tech that helps people to understand their metabolic health. And this is your front row seat to everything we do. This is a whole new level.


When you’re early in a startup, maybe there’s one, maybe there’s two, maybe there’s five people, a handful. It’s pretty easy to see the work that you’re doing every day. It’s easy to see what everyone else is working on. Whether you are a founder, whether you’re an early team member. It doesn’t really matter what you do. Everyone’s very much an individual contributor in some way, shape, or form.


Well, that was very much the case for Sam Corcos, co-founder and CEO of Levels. When Levels started, it was just him and Josh Clemente. The two of them together started getting traction. And over time they built up the team. Dr. Casey Means, one of the co-founders, Andrew Connor and David Flinner. The five of them came together and they started to form a talent pool around them. Well Sam, until about April of 2020 was very much an individual contributor as much as he was the CEO of the company. He was writing code, he was shipping product, and it felt very different than his role now. And what he works on today three years in, is very different than what he worked on in the early days. As he puts it, it’s very much about having context, being able to make decisions, and being able to connect the dots cross function.


So we sat down and we discussed this idea from engineer to CEO, what his journey’s been like and what are some of the learnings over the past three years as things have evolved with the company. It’s really fun doing these conversations, talking about culture, talking about how even personal things change. What are some of the things that he finds hard, and how does he think about getting around these challenges? Anyway, no need to wait. Here’s the conversation with Sam.

Sam Corcos (03:01):

I’ve had a couple stints operating as basically an IC engineer at Levels. I think I had three pretty defined periods in the early days of the company where I basically worked under David who was leading products and just delivered the things that he was proposing. And yeah, I really enjoy software development. It’s really fun. It can feel magical, just the amount of leverage that you can get. And I think being a software developer today in particular is just so insanely leveraged. It has to be the most leveraged job in the world, just in terms of the amount of stuff… like one human with access to Amazon Web Services can do more stuff than teams of God knows how many people even 20 years ago. It’s remarkable just how much leverage people have to do stuff. So yeah, I really enjoyed that time as an engineer.


And the conversation with Josh, some of it was about liking, but mostly it was just about being good at certain things. The skills that I have are more aligned to the role of CEO than Josh’s skills. And that was the biggest part of the conversation was what are the skills that are needed? If you’re a CEO, you need to have venture capital contacts, and I have a lot more of them. You need to have a lot more management experience. You need all of these things that we had talked about. It just made more sense for it to be me.


But at the same time, there are definitely parts of engineering that I still miss a lot. And the early days when I… basically after I fully gave up writing code at levels which was, I think the last time I wrote substantive code would’ve been April of 2020 maybe. So quite a while ago. I talked to a bunch of other former CTOs, former technical leaders who took on the CEO role. And I was asking, “How do you get satisfaction in work? Because I feel like I’m just shuffling papers and I’m not delivering anything.”


And what was really interesting is every single one of them without exception said, “You just aren’t going to. You just have to accept that and find ways of making your current role more enjoyable, because you’re not going to get that same delivery cadence. You’re not going to be able to ship stuff like you could before.”


I think for a lot of these things, people look for solutions. And there were certain types of problems where you should really just be looking for how to manage it, not for a solution. And that was a pretty clear recognition from all these conversations. This is not a solvable problem. The only way to solve it is to find somebody else to fill the role. And if there is somebody better, then I would be more than happy to hand it off. But short of that, this just is something that I have to manage, not something that I can solve. So it was helpful to hear that as a piece of contact from other people who have been through it. And just realizing that I have to find ways of making it enjoyable.

Ben Grynol (06:55):

Yeah. It’s a weird feeling going from shipping work where as an IC, you’re moving the ball forward in some way. And then accepting, coming to a point because it’s not sort a binary like today you do this and tomorrow you don’t. It slowly evolves as more people come on board and things get more complex. But the idea of being comfortable with, especially after having those conversations with people in your network where they’re like, “No, your job is just air quotes ‘pushing paper.’” That’s the job. Your job is to create cohesion across the team and do make sure all the parts are moving properly as opposed to shipping things.


But it always feels weird because it doesn’t feel like the same type of work. And so wrapping one’s head around that, it’s entirely okay not to ship work even if we want to and not thinking that we’re not contributing at our best. Because your best contribution is being the glue and the cohesion. And without that, you almost take it for granted. Oh yeah, the house of cards falls apart pretty quick. If you don’t have great leadership in place and you don’t have everybody communicating and collaborating properly, there’s a lot of inefficiency.


So making that transition, I think it’s always hard whether it’s like you go from in your case, let’s go back to that. You wrote, we always referenced it the pork tacos version. That was the first actual version of the app. And then I think it was April ’20 that you said, and that’s when you moved into doing ops work. I think you were doing ops for a bit there. It’s a weird thing to go through that transition whether you are in a leadership position or even just somebody who’s going from IC to people manager at any scale of a company.

Sam Corcos (08:43):

Yep, sure. This is true for really all managers at some scale is you become a context machine where your job, the leverage of making the right decisions and trade offs based on context is greater than the output of your work as an individual contributor.


And I think there have been several pretty distinct transition points in the company’s history where my role has changed pretty substantially. When we were about 12 people was when I did a lot less individual contributor work as an engineer. I think that was roughly the time when I basically entirely moved off of IC engineering work. When we hit 25 people was another inflection point where we needed to solve a lot more around hiring an organizational design.


When we hit 50 people, which was pretty recently, we’re about 60 people now. That was another interesting inflection point in my role in that my involvement in projects usually creates more problems now than it solves. This was especially true in engineering, when it was almost always the case as an engineering leader, when I would get involved in a project, it would go better and it would be done faster. People would learn things, and everyone was happy.


It is now the case as a CEO where when I jump into a project, it often causes a project to lose focus and go in wrong directions. And this is another one of those things where every person I talk to who has been in this role says, “Yep, that happens and you just have to figure out what the right strategy is.”


One of the other CEOs that I talked to recently, similar stage company, similar in many respects, similar industry was saying how I think there were just over 50 people. He said it feels like he’s shouting into the void where he isn’t able to do the things anymore and he’s basically fully reliant on his team to deliver things. And so he feels like, I think somebody mentioned that around this stage, this might have been Ale Resnik in the conversation I had with him. But around this stage is when the CEO role shifts from execution to influence as the primary mechanism for leverage. So that’s something that I’ve been trying to better understand at each of these stages.

Ben Grynol (11:52):

One of the things that is so hard or so interesting though is the, let’s go into the product thing. Granted, I’m removed from product. I’m going to use the mental model of Sam as part of the organization, because I think you can extrapolate it to product. I wouldn’t suggest that the reason the projects go off the rails is because you’re coming in and you’re team rolling a project. What happens is because of organizational scar tissue from past experiences, we get to a point where we get a case of the emperors close. No matter how much you’re like, “Hey I promise, please say no to this and it’s going to make me quite happy.” You’re throwing little input or feedback into something and everybody almost freezes and they’re like, “Does this mean Sam wants us to do this thing? What’s the timeline?” And no matter how much you frame it as, “There is no timeline for this. This is not a priority.” You can frame all these things. He always brings it up where he’s like, “Man, Sam would suggest an article and I thought I had to do it.” It took me six months or a year. It took him some amount of time till he was like, “I’m allowed to say no.”


Because his past experience, his past experience at PopSci specifically, if the CEO came in and said we should do an article about X, it was like drop all other priorities. And I think that’s the context is that gets to be hard for any leader in any organization is no matter how much we frame this, we always have to be very conscious of the feedback that we give to any project. Because it can steer people off course, where all of a sudden they are deprioritizing the most important thing. So I would suggest it’s not anything that you are doing in particular. This is thematic across organizations. It’s just really hard for leaders to be careful about how involved they are in any project. And it gets harder as you get larger.

Sam Corcos (13:51):

Yeah. It’s something that I’ve noticed, and this is reinforced by almost everyone I talk to is that as a CEO, people take what you say a lot more seriously than you intend no matter how much you hedge. I wish I could remember who mentioned they said, “Beware your power.” And just as the organization gets larger and these dynamics change over time, just be very aware of how hypothetical would be I have a casual conversation with an engineer and I mention like, “Oh yeah, it’d be really cool if it did X, Y, and Z.” That person could very easily take that as a directive from the CEO to change their priorities, drop what they’re doing, and fix this problem now. And then that creates problems for them, and their manager, and everyone else. And so just being super cautious with that.


And it’s something that again, this is another one of those things where people, this is often the case in startups. And I’m sure you’ve seen this as well because you’ve been through these growth stages where a lot of people lament the early days, “It was so much better when our velocity was super high and it was just me, and John, and David working on stuff, and we could ship things super fast.”


The reality is that that is a different universe, and that is a different stage, and that is not repeatable, because there are so many things that are different. It’s like, “I missed the days when it was just the five of us in a room.” It’s like well, that is a stage and now we’re at a different stage, and it’s necessarily different at each stage. And so it’s not useful to lament the days when it was me, Josh, Casey, Andrew, David, a few more folks, and we would have open conversations about prioritization, and nobody would misunderstand anything. And that changes over time, and you just have to accept that as a reality. And again, it’s something that needs to be managed. It’s not something that you can solve.

Ben Grynol (16:11):

Yeah, it’s okay to not like certain stages too. We talk about this all the time on different podcasts. Comes up probably once a month, but it’s okay to not a stage. That’s entirely fine. You don’t have to like the stage. It’s that don’t work at that stage if it’s not fulfilling anymore. And so it’s like that might be some people aren’t super interested in the earliest stage when it is five people in a room because that is as risky as it gets. And there might be people who are on the opposite end of the tail where it’s like, “I’m not a huge fan of being a publicly traded company and everything’s very buttoned up.” Totally fine, but don’t trick yourself into enjoying the stage because you think you should. Totally fine.


The hard thing though, I think what happens is when it is a few people in a room, so let’s use the example of you’re actually writing code and you’re making poor tacos, you’re doing that app. As things grow, and this is a personal thing that things like coaching can help, things like having open and transparent conversations across the org can help, but just saying, “We’re not going to have full control of things anymore.” And that’s what feels good I think when it is five people is you have control over it. And the more people you bring on board, it’s like there’s more decision making involved and we’re not directly involved in each one of those decisions.


So it feels, even using the word, maybe it’s a little too strong, but threatening. It feels like threatening that you are no longer needed for that thing. It feels bad inside that you didn’t make the decision, you weren’t involved in making the decision for the tooling that was chosen for some operations like triaging messages and that can feel really bad. But if we wrap our minds around it and flip the switch and go, “Wait, we’re doing so much more than we ever were before. We have such high volume of inbound messages, this is solved.” And what I have to do is make sure they’re supported and that I’m not steering the decisions too much, but I’m here to support. And that’s always this hard thing to do at every stage is to say, “I understand there’s going to be a lot of people involved and we have to default to trust and default to positive intent,” and all the things we talk about. But that can feel really bad as we go through different stages

Sam Corcos (18:31):

And the requirements at each stage are different. When we were something like 12 people, we tried to do OKRs. And it was really a complete waste of time because the amount of overhead that it took to put them together, everyone knew what everyone else was doing, everyone knew what all the metrics were. So we did this big effort to produce a result that didn’t increase alignment.


Once we hit about 50 people, that actually became quite important to get that alignment because once we hit 50 people especially as a remote team, you can go nine months without even interacting with somebody from another department. So knowing what it is they’re doing and feeling confident that they’re hitting the goals is really critical. And other things like we’re thinking about implementing PR/FAQs, which we had tried to do a couple years ago, but it doesn’t go anywhere because we weren’t doing release notes. We weren’t doing product marketing, so there was no real value in it. It felt like we were doing it was performative. We were doing it because it’s the thing to do not because it added value, but now we’re experimenting with it again because we’re at a stage where that might actually end up being a useful effort.


Similarly with change management is a whole category of work where you have to inform people of changes, teach them how to use the new thing. When you only have 10 customers, you can literally call each of them on the phone live, just walk them through it. You don’t need to worry about change management because it’s really simple. But once you have thousands or tens of thousands or hundreds of thousands of people, that becomes its own initiative all in and of itself because the scale is just different.


Some people can lament the days when you didn’t have to think about change management or OKRs, or PR/FAQs, or any of these systemic questions. Because they do add overhead and they slow down velocity, but they are necessary once you reach a certain scale is to figure out what system to solve the problems that you have.

Ben Grynol (20:51):

Let’s talk about one of the biggest misconceptions, or maybe something that is surprising yet not surprising to you, which is this idea of strategy. So the misconception I think externally for anyone is, “One day when I’m a CEO,” or I’m like, “I want to start my own organization. I can’t wait till we have more people. I’m going to spend so much time on strategy.” And when you do your time audit every quarter or every month and you’re like, “I spent that much on strategy and that much, this huge delta on people ops.” And it’s the nature of being in any leadership role where a disproportionate amount of time gets spent on people opts, ensuring that there is symbiosis within the organization and less time is spent on strategy.


Now it’s not to say don’t free up time to spend on strategy. It’s a matter of prioritizing the right things. But I think people think that the asymmetry is weighted in favor of strategy and way less people ops because that’s what the rest of the management team or the rest of anybody that actually has direct reports will do. And so why don’t we go into that? Because it’s such an interesting one to what we think will be true versus what is actually true are juxtaposed in every way.

Sam Corcos (22:07):

Yeah. The time allocation for CEOs is interesting because I’ve talked to a lot of CEOs about this. And for one, they don’t keep rigorous track of their time. So when I hear how they spend their time, how I think they perceive themselves spending our time, and it’s probably weighted in terms of how emotionally burdensome is the time that they’re spending. Writing down strategy feels like real work. So your brain might weigh that at 5X in terms of cost, maybe 10X. And what’s interesting is we have so much strategy written down as a company. I think we have hundreds of memos that are deep strategic pieces, five to 10,000 words. I’ve written many of them myself. And it’s only 5% of my time on a really solid strategy month. Which makes me think that most companies, the CEO’s probably spending a rounding error in actual strategic work.


A lot of them talk about spending a much time on recruiting as well, which I feel like I spend a lot of time on recruiting, but it’s really a lot less than I was anticipating. So I’m not totally sure where the delta is.


But I think on the time on people ops thing, I think over time, these things tend to come in cycles. And I think I was talking to another CEO who their company’s more than 500 people who was spending basically all of his time on people ops. He had way too many direct reports. He was spending a lot of his time with people on the team. He felt like he was treading water. He didn’t like the role anymore, and he had an honest conversation with one of his investor board members. Said, “I don’t like this anymore. I don’t like being here.” The board member said, “It is important to the company that you like working here, so let’s figure out what that looks like and let’s just do that.” And I don’t think had ever given himself the permission to be happy at work, which is kind of a strange statement. But he felt like he just had to do it because that’s what needed to be done.


And the next week, he basically announced to the team, “I am no longer taking any meetings. I only have three direct reports now, and this is just the way it’s going to be.” And there was a couple weeks of people getting really upset, and then everything went back to normal, and he started working on stuff that he liked again, and he was really happy. And I think there’s something to that which is you have to know what your own boundaries are. As the CEO, there’s nobody looking out for you to make sure that you don’t burn yourself out. So you have to be super aware of your own limitations and feelings, and make sure that you stay productive, and that you’re motivated to wake up in the morning and do your job effectively.

Ben Grynol (25:50):

So if you’re breaking down two buckets as far as technical challenges and personal challenges as things have evolved, what have been the biggest technical challenges to making the transition into being a leader three years in? And then what have the biggest personal challenges been?

Sam Corcos (26:11):

I can’t really think of any technical challenges. There were surprisingly few new skills that I needed to learn. I’ve been a pretty aggressive generalist for a long time. So I’m 80% good at most things, but I’m not by any means actually good at just about anything. So I wrote our first content strategy. And you know what? I read it again recently. It’s okay. It’s an okay strategy. And then we brought in Mike Haney who wrote the real content strategy, and it’s probably 10 times better than the one that I wrote.


But the strategy document that I wrote wasn’t wrong. It was just kind of juvenile in its understanding of how content actually operates. And that kind of spans across every org. It’s like when I needed to jump in and do growth stuff, I knew enough to get the wheels turning. But then once the wheels were turning, I thought, “All right, we now actually need to find the person who knows how to do this.” When I jumped in and did engineering stuff or when I jumped in and did operations stuff, once we got the wheels turning I thought, “All right, now we need to hire an actual operations person to manage this.”


There weren’t really that many technical hurdles. There were a lot of personal hurdles, where it takes a lot of discipline around for me, I found that I’m relentlessly novelty seeking. So I know my own limitations that if I’m stuck doing the same sorts of tasks on a regular basis, I’m going to burn out, and I’m going to get bored, and I’m going to not want to come into work at that point.


So making sure that anything that I start working on, I have an exit strategy for handing it off to somebody else. Or just the project is complete, and it is now no longer being worked on. Because if I’m stuck with all of these ankle biters, it’s going to really demoralize me and reduce my ability to be effective.


So those were the biggest personal hurdles. And I found that in much the same way that I get real satisfaction from shipping code, I get a lot of satisfaction from writing strategy. Having these big meaty deliverables where I feel like I’ve solved a really big problem and I have something to share, I get a lot of that same sort of feeling of accomplishment that I would get when I was as a software developer.


It’s not quite the same and the cadence is not quite the same either. Neither is the leverage. But it still feels like I often come into these sessions… This is one of the misconceptions about writing is that I often come into them with only a faint idea of what the actual solution is to the problem. I think many people approach documentation and writing as if they already assume that they know the answer, and this is just a process of memorializing it. And my experience is exactly the opposite. Because I have what I think is the idea, but it’s usually not correct. And so as I’m writing, the idea often evolves as I learn more. And I outline, I do some more research, I talk to more people, and the ideas usually end up very different by the end. So I found that on a personal level, I get a lot of that same satisfaction in work from doing my think weeks and spending more time on writing.

Ben Grynol (30:12):

The exploration docs are very fun to write because it’s exactly what you said, versus a reference doc. Like, reference is here are the facts and I’m putting this down so that I don’t have to rewrite this to somebody else. I can just send them the link. But the exploration of where is this going to end up.


Some of our best docs have been those exploration docs where they start out as, “I’m just going to start writing generally about this topic.” And sometimes the entire topic, it doesn’t shift to another planet, but laterally it might just move a couple degrees over. And then the way that we start to form some framework around it, you come out and you’re like, “It’s pretty interesting.” And we start doing some of the tactics, you’re like, “Wow, this thing’s kind of working.” Those are really interesting things, because everybody across the organization learns when we do these tests. And you can’t go into it and just say, “Hey, I’m just going to write this thing so that it’s a means to an end.” And we’ve got a document to put in notion that’s meaningless unless the point of the document is reference, which is an entirely not just okay, but appropriate use case. It’s just a different document to have. And reference docs in general shouldn’t take as long. It’s the exploration ones that take long because you’re using so much horsepower. Your brain is just on overdrive to really squeeze out those thoughts. So they’re fun to write.


If you’re reflecting on areas of opportunity or gaps, if you are introspective and you say, “Right now I feel at this stage my biggest personal gaps are,” or personal professional gaps, how would you label those? What do you think are these gaps that you think, “Man, I really want to get better at this one thing to take us to the next stage”? Or where you are in your life. Also just personal life. Everyone’s at different stages of life and can work in different ways at different stages.

Sam Corcos (32:16):

I think I do reasonably well with this, but I think one of my biggest gaps are still around conflict avoidance. Where there have been times even just in the last year where I avoided something for longer than I should have, and then it created a much larger problem than if I had just directly addressed it earlier. Or bad communications, a less than direct communication that led to a cascading series of misunderstandings between other people. Or not taking action quickly enough when I knew what the answer was, but I was just so hopeful that things would correct themselves, that I let it drag on for a few months longer than I should have. These are all things that I’ve improved on a lot.


I remember the first time I had to let somebody go, which was years ago at a different company. It was like a year after. It was way later than I should have. The next time, it was a little bit shorter. But still, way beyond what was reasonable. I was avoiding having that conversation because it was uncomfortable. And each time I have to do these things and I get a rep in, that time gets shorter and shorter until hopefully at some point, I will be able to make the right decision in a timely manner instead of way too late. I do think that the right decisions still get made. But I think that a lot of chaos could have been avoided had I taken decisive action earlier.


I found that people in general, and I’m guilty of this myself, often overestimate the cost of errors. All of my biggest errors when I look at my life over the last 10 years professionally, all of my biggest errors were errors of omission rather than errors of commission. They were mistakes of not making a decision, or of not taking an action, or telling somebody that they have to do something a different way, even if they don’t want to, or firing somebody who is creating problems that I was concerned for whatever reason that it might have negative consequences in other parts of the org.


So that’s something that I found is really helpful to reflect on. The think weeks that I do once a quarter are really, really helpful. And I strongly encourage every person who is in a leadership role, especially CEOs, to take some time to just not be in the hyperactive hive mind of communication and activity. Being able to see the forest, seeing the forest and not just the trees, it is a critical part of the role. And you can’t do that when you’re plugged in. So I’d say those are probably my biggest areas of opportunity is really on a lot of that interpersonal stuff, which I’ve gotten a lot better at over the last five years. But those are probably the biggest gaps currently.

Ben Grynol (36:23):

Why do you think you’re conflict avoidant though? Because from what I’ve seen, I would suggest you’re not. So is it that you are in edge cases and not in others? Like others, it seems to be like, “Let’s hop on a call. Let’s figure this out.” And that to me is the opposite of being conflict avoidant. It’s, “Let’s address this, let’s move on.” Do you feel conflict avoidant with everyone, and you find it’s just easier to take care of it with some people? Or is it sort of like when you really feel that internal turmoil of being conflict avoidant, it’s on these edge cases where you’re like, let’s just say with your brother, you’re like, “Yeah, I just call him up. I’m like [inaudible 00:37:12], I’m kind of bummed about this thing,” and you resolve right away. Whereas with other people it’s a lot harder to even get to that point and to have that clear and direct conversation. What is it that makes you feel that avoidance?

Sam Corcos (37:26):

Yeah. I mean these are something that’s on some kind of a spectrum, which is 10 years ago I was I don’t know, an eight out of 10 on conflict avoidance. It was really a huge problem, and it created all kinds of other problems. Today I might be, I don’t know, a three out of 10. Where it still causes problems, but I can identify it. I can manage it. So I would say it’s still a problem because it’s still something that I feel and have to overcome.


A similar example is when people have asked me what I struggle with, another thing that I know that I struggle with is being present. That’s something that I really struggle with. When I’m at a dinner table, when I’m with people, I struggle to just be here now. And when I tell that to a lot of my friends, they think I’m crazy because they would often describe that as something that I’m really good at. And I know that I struggle with it. The only reason why I am capable of being present is my phone is permanently on do not disturb mode. I’ve turned off all of these tools that can distract me. I keep a piece of paper, a notepad in my pocket so that when I need to take a note, I don’t look at my phone. Because I just accepted that these tools are more powerful than my will. And so I just have to bake in processes that don’t suck me in.


And this is something that my wife [inaudible 00:39:12] helps with as well around, just I was talking with Sam Parr about this when we were in Austin because he has a similar problem around self-control with junk food. And his wife has no such problem. And so they have an agreement that all of their junk food is in a locked cabinet that he does not have access to. And when he wants it, she has to open it for him. And [inaudible 00:39:39] and I have a similar arrangement for a lot of these things where it’s like I just know that if there’s ice cream in the freezer, I’m going to eat the whole pint in one sitting. It’s just going to happen. If I have access to my Twitter account, I’m going to spend way more time on Twitter than is healthy or productive. So I don’t even have access to my Twitter account. My assistant LJ has all of my credentials. She manages all of it. If in the event I need access, she will send me the password, and then she’ll cycle it the next day so that I get logged out.


So it’s just recognizing that some people don’t have these issues. They just don’t feel compelled to do these things. I recognize that I absolutely still feel those pulls. And so I don’t have any issue with conflict avoidance when it’s easy, which is good. It’s better than always feeling like you can’t engage in these sorts of direct conversations. But I think it only really matters when it’s hard. And that’s when I feel discomfort in my body, and I feel like I don’t want to do it. I recognize it as such, which is a step in the right direction. But it’s still very hard for me to just engage in direct conversation about things that are difficult,

Ben Grynol (41:03):

Hard because it’s a hard conversation? There are different levels of conversation, but hard because it’s a hard conversation? Or when you say easy, is it because that trust battery is so much higher that even if it was the hardest thing, you’re just like, “You know what? I know no matter how hard the actual topic is,” the thing that you want to say or need to say, that might suck and might not be good, but if the trust battery’s high, it might feel maybe easier because you’re like, “I know we’re going to come out the other side and there’s going to be a common understanding of whatever it is.” So is it both or is it more the trust battery thing? When is that what feels hard when you’re like, “Man, this is not making me feel good inside to have this conversation?”

Sam Corcos (41:51):

Yeah, some of it’s trust battery. I think a lot of it is you don’t want to hurt people’s feelings. The conversations get harder when performance is not up to par. And it’s especially hard when you see it and they don’t see it. And you have to be the bad guy and say, “This is not working.” And they say, “What are you talking about? These things are going great.” “Well, I don’t think they are and it’s my responsibility. So I have to make this change even though you disagree with it.” And those are not fun conversations to have. It’s like, “Nope, I know that you think we have to do X, but we are going to do Y. And I will take responsibility for it if it doesn’t work because this is what I think needs to happen.”


And those are the things that I struggle with personally is. But like I said before, most of my biggest failures as a leader in my life have been times when I knew what the correct answer was, but I let the loudest voice in the room determine what happened. Or I was too afraid of hurting somebody’s feelings, and I just let something bad continue. And it didn’t really do them any favors. I certainly didn’t do me or the company any favors, because they kept working on something. They were basically wasting months of their life working on a thing that I knew wasn’t going to deliver value. They thought that it was, but I knew that it wasn’t. But I didn’t want to hurt their feelings and tell them to stop what they were doing. And that’s the responsibility of a leader. And I think just coming to terms with that and just recognizing what your role is as a leader, it takes a lot of practice and repetitions to get comfortable with it.

Ben Grynol (43:55):

If you’re thinking through takeaways as far as what other founders or anybody that’s maybe a CEO at a starting or a growing company, based on this evolution, this three year evolution of how things have evolved, what’s the one thing? I know we always talk about culture, we talk a lot about having difficult conversations, act of communication. If you were to give one concrete takeaway and say, “To be effective you have to be X.” What is that X in your mind?

Sam Corcos (44:28):

I’ll just throw out a few words that are coming to mind. I think a big one is humility. Another one is around trust, which is you have to be able to give away your Legos.


I think another one is talking to other people who have been through the same sorts of situations. Get advice from people. I think reflecting is always really helpful. Doing retros on your time. Focusing on strategy is incredibly important. Knowing where you’re going. Being able to zoom out and develop context to make good decisions.


This is going to sound extremely non-tactical, but I think the most important thing for a CEO to do is whatever is necessary to make good decisions. That is the ultimate responsibility of a CEO is to make good decisions. And that spans strategy, people, everything. And for me, what I need to be able to make good decisions is I need space. I need these quarterly think weeks. I need time to write about strategy. I need to be able to talk to lots of people to learn from them. So whatever you need in order to be effective at making good decisions.