Long Strange Trip: CEO to CEO with Brian Halligan
00:21:18 · Brian Halligan
[00:21:18] S1: Okay, I love that advice. I get a lot of blind references when people do that to me. Think it's brilliant when they, is that the best person that's ever worked for you? I'll no. And they say, why? And that opens things up. I want to talk about you. You're the twentieth CEO I've interviewed. It's been really fun. And honestly, my thesis when I started this podcast was, I'm gonna figure out kind of the common thread, what everyone's doing, and I'm gonna write it down, I'm gonna kind of standardize it. The truth is there's not even close to a common thread. Everyone does it differently and there is no playbook. And the playbooks are changing extra fast right now. And my last two interviews are emblematic of it. I interviewed Tarek from Kalshi and he and his co founder have, I forget, 200 employees. There's no levels of management. They all report to those two. And he referred to it in the podcast as management by chaos. My last interview was with Ali Yodse from Databricks, and he's got eight direct reports. It's very structured. His direct report team, he has three meetings a week with his direct reports. He has a QBR once a quarter, and then he has an off-site strategy session once a quarter. Like polar opposites, both doing extremely well. Where do you fit in that spectrum?
00:22:47 · Luca Ferrari
[00:22:47] S0: Probably somewhere in between. I think these things are generally like, is more formal approaches to management, I think they are they're greatly overestimated in the impact. Think if you, you know, in a company's outcome, I think almost all of the outcome depends on essentially your strategy, what people sometimes call product market fit, but also the motes you have. And you know, that's overwhelmingly what drives it. I always ask myself if for me, a business is a good business, if it would do well, even if management was mediocre, maybe not awful, but mediocre. So that's, know, that's the first thing. The second thing that matters to me is talent levels and culture, which culture is really like, you know, how do you make decisions? What matters? What doesn't? What do we value? What do we not value? Then everything else, you know, lines, whether you have OKRs or you keep it fluid and informal span of control. I'm sure it does matter on the margin, you know, making things a bit better or a bit worse. And I'm sure different solutions will be optimal depending on the people involved. Because ultimately, a manager, a CEO is some sort some sort of a leader or should be and, and, and the same strategy, the same approach to working with others depends on the human capital you have different people react differently from the culture you're trying to foster. But I think that within reason that doesn't make a huge difference, maybe like a plus minus 10% kind of impact. So I think you're much better off obsessing over what first and foremost strategy, but then once that's in place, the qualities of the people and the culture you establish. So if you know, if the 200% organization kept chaotic, super high, I don't know them, assuming, you know, super high talent density, a culture of business orientation, rationality, hard work, you know, even if a little extra structure, theoretically could be helpful. I think, you know, the talent and the culture will mostly trump any such gap, or close any such gap and vice versa. You know, maybe in the other extreme, a little bit more fluidity and flexibility with ideal. But if you have very good people and a great culture of let's get it done for the benefit of the business, will not get stuck because there is a little extra structure. I haven't thought a lot about these things.
00:25:07 · Luca Ferrari, Brian Halligan
I'm convinced they're not the most important thing to be honest in excelling in business. [00:25:13] S1: Fascinating. When I was the CEO, I tried to get better and evolve as the business scaled. And I got a lot of feedback. And one of the pieces of feedback I got a couple of times was, Brian, you're a very good leader and a very bad manager. Are you? Where are you on that? [00:25:32] S0: I don't know. I get a lot of feedback. I don't think anyone kind of rated me on those two against archetypes for job descriptions, [00:25:46] S1: but a little self reflection here.
00:25:46 · Brian Halligan, Luca Ferrari
[00:25:46] S1: but a little self reflection here. [00:25:50] S0: I don't think yeah I, I'm not sure if I'm a good leader or a good manager, to be honest. I generally feel that I'm pretty privileged that I work with very good people. And my, I tend to be more self conscious and, and question whether I'm, I'm doing enough and I'm living up to expectations. So I'm I see I tend to see the whole the glass half empty. So my instinctual reaction would be I'm, I'm probably not terrible at either. Would be disingenuous if I told you I think I suck. I but I will probably rate myself something like, okay at both, but but not necessarily amazing. I'm probably a better leader than manager if I understand what you're hinting at. I think I've generally done okay at setting a vision that made sense and a compelling vision and communicating that reasonably well. If I've succeeded as a leader has been mostly through what I would call servant leadership, like be just working super hard and helping people as much as I could. I don't think I'm the kind of William Wallace kind of leader, someone making a grand speech and everybody, know, get their heart and get get their hearts pounding and everybody, know, gets to work. But when you work with someone who's walks to talk and is in the trenches and does their best, I think you tend to be inspired. So maybe that kind of person, I try to be that kind of person. I don't think I'm a great manager. I don't think I'm the best at running one on ones or anything like that.
00:27:23 · Brian Halligan
[00:27:23] S1: Okay. One of the things I used to say to myself is actually I got this quote from Eleanor Roosevelt of all people. I wanted to keep my head in the clouds, but my feet on the ground. And by that I meant I wanted to be okay, a JV, William Wallace painting a picture of the future, getting everyone excited about where we're going, looking over the horizon. But feet on the ground, it's like, holy crap, there are a lot of problems and we have to deal with all these frigging problems. And my glass was very half empty and I spent a lot of times a little negative looking at the problems. Where are you in the Eleanor Roosevelt quote?
00:28:02 · Luca Ferrari
[00:28:02] S0: I want to give myself a little pat on the shoulder. I think if there's one thing I tend to do reasonably well is being able to see the big picture. You know, I guess head in the cloud kind of thing. Maybe I'm not the best at say articulating it again with the grand speech, but I think I'm pretty good at you know, in the substance understanding what matters, what doesn't, where the opportunity is, what logically we should be doing and what's just noise. And I think I've historically been very hands on in the details in the trenches. I think it's a good quality that you want to have as an entrepreneur and CEO. Don't think it's a it's not super widespread in the population, but it's quite commonly found, I think in entrepreneurs and CEOs. And I think it's quite powerful because if you if you don't have the big picture, you can't really set a direction of strategy. That's that's the winning strategy, unless someone else bring it brings it to you, which is always nice, but you can't count on that happening. It's a, know, hope is not a strategy as they say. But if you're not in the details in the trenches, feet firmly planted in the on the ground, then I think you're unlikely to be able to inform that big picture properly, you're unlikely to be inspiring to your colleagues, very few people like working with with people who are in an ivory tower that they don't get their hands dirty, doesn't really scale. I think it's not good. You're not in a position to assess others to coach others because you don't really know anything about the work at some point. So I do believe you need both to be successful. And you know, finding some sort of equilibrium, I find it's easier to sequence those activities and trying to run them in parallel. So I try to have times where I'm very much in the clouds thinking, Okay, what are the big problems or big big opportunities? How should we go about them and be more of an architect and then long stretches where I just get into execution mode. And I'm, you know, mad head to toe, just getting stuff done, blood, sweat and tears. I think it's quite difficult to be both at the same time, but you can be both in sequence.