Lenny's Podcast: Product | Career | Growth
00:00:50 · Brian Halligan, Lenny Rachitsky
[00:00:50] S0: I look for four things, I call it my lock algorithm. [00:00:56] S1: Today, my guest is Brian Halligan, co-founder and longtime CEO of HubSpot. I asked Brian to come on this podcast because he is, more than anyone I've met, a student of the job of a CEO. After leaving HubSpot last year, he became the in-house CEO coach at Sequoia, where he brings together dozens of top CEOs to learn from each other, he does one-on-one coaching with some of the world's top CEOs, he also hosts a popular podcast, called Long Strange Trip, where he interviews some of the world's most successful CEOs. In this conversation, we unpack what it takes to be a successful CEO in today's era. Let's get into it, after a short word from our wonderful sponsors. Applications break in all kinds of ways, crashes, slowdowns, regressions, and the stuff that you only see once real users show up. Sentry catches it all. See what happened where and why. Down to the commit that introduced the error, the developer who shipped it, and the exact line of code, all in one connected view. I've definitely tried the five tabs and Slack thread approach to debugging, this is better. Sentry shows you how the request moved, what ran, what slowed down, and what users saw. [00:04:02] S0: Thanks for having me, Lenny. [00:04:04] S1: It's my pleasure. I want to start with something that I've heard your board members, the way they described you, is someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational trait of successful CEOs, successful leaders?
00:04:04 · Lenny Rachitsky, Brian Halligan
[00:04:04] S1: It's my pleasure. I want to start with something that I've heard your board members, the way they described you, is someone with a perpetual state of constructive dissatisfaction. Do you think this is a core foundational trait of successful CEOs, successful leaders? [00:04:21] S0: By the way, I like that description, when she did, a woman named Lorrie Norrington, who [inaudible 00:04:26] said that. I like it, I took it as kind of a compliment, and I liked it. So, I spend most of my time these days coaching very fast-growth CEOs. They all are kind of like that. They're all in kind of a state of perpetual dissatisfaction, but in a positive way. One of the things, by the way, I like about the current crop of CEOs, they don't really take stock of what they've done and feel it, they're always a little bit dissatisfied with where they are, and very focused on the end state. And I've been surprised at how humble this generation is of CEOs. And I think of my generation of CEOs as being, I don't know, humble wasn't the first word that would come out of your mouth when you describe my generation. But this generation I feel like is different, and I've been impressed with it.
00:05:25 · Lenny Rachitsky
[00:05:25] S1: Okay, I have a bunch of questions along these lines, because one, you've been a CEO of an incredibly successful company for a long time, for about 20 years, before you moved on to this new chapter, now you work with a bunch of CEOs, you're Sequoia's in-house CEO coach, there's a few things that I've heard you do. One is you gather groups of CEOs, and what I've read is that you have kind of two tables. You have the kids table and the adults table. The kids table is CEOs that are companies that are about under 100 employees, the adult table is over 100 employees. So, let me ask you just, when you look at CEOs that move from the kids table to the adult table, other than just they scale and grow, what is it that these CEOs that graduate from kids to adults table do differently?
00:06:11 · Brian Halligan, Lenny Rachitsky
[00:06:11] S0: The adults are really focused on, all they really want to talk about is their exec team. Their direct reports, how do you build our exec team, that next level down, org design... You would be surprised how much they think about that. And on average, I would say the adults are spending half their time just recruiting and interviewing. It's pretty all consuming. And I remember that from that phase in HubSpot's growth. And it surprises people like, wow, my job is really just to interview and hire, I didn't know that was going to be the case. So, that is one that they are making that transition, and I would just say in general, people are very bad at this, and HubSpot was too. I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference. And I interviewed Dave, the CEO from MongoDB the other day, and he had an interesting [inaudible 00:07:22]. On average over his 10-year lifespan as a CEO of Mongo, there were two C-levels turned over per year. That's a lot of turnover at the top, and I didn't keep track of it like Dave, but I think HubSpot was kind of similar. And all of these startups are kind of similar too. And so, people are working on that, and struggling with it, is one thing in common with all of them. [00:07:49] S1: What do you do when you coach someone on that? When you're like, okay, you think you're amazing at interviewing, you think you know who's going to work out, what advice do you give them to help them develop that skill?
00:07:59 · Brian Halligan
[00:07:59] S0: I think even me, I've been doing this for 150 years, I still think I overrate my ability to interview someone, and really know if they're a good fit. I give a couple pieces of advice. Parker Conrad has a good hack that I liked. Before he's got a C-level interview, CFO, chief product officer, whatever, he has some sign an NDA, and sends them the last board deck, or the board memo, or some important doc, and he schedules a half hour interview with them, and he just has a chat about the decks. And if they're just very complimentary, and it's so great, and you're doing this amazing thing, it's a major red flag to him because he wants someone that will challenge him and not a yes person. And I thought that was a pretty good hack to get inside someone's head and how they think and how they'll interact with you. Getting on a whiteboard and working through a problem I think is always a good thing. I think the standard interview of walking through your background, I don't think is all that valuable. And I coach people to do blind references, find someone you know that work with them... VCs are good at this by the way. And I get a lot of these, and you can tell some of them are like, we've already decided we're checking the box, versus they're asking me hard questions about this person. And one of my favorite questions people ask is, would you enthusiastically rehire this person for that role? Which I think is a really good question. On a scale of one to 10, how likely is it that you'll try to rehire this person back from me down the road? I think those types of questions are good, so not mailing an in on those blind references I think is really good. My other piece of advice, and no one listens to me on this, is hire slow and fire fast. People hire fast and fire slow. If I had to guess, Lenny, with 18 months after you hire a C-level exec, at least 50% of the time they're gone. High mortality rate on them, it's harder than people think.
00:10:10 · Lenny Rachitsky, Brian Halligan
[00:10:10] S1: And so, what you're saying here is there's only so much you can actually do to increase those odds. [00:10:15] S0: I think you can, I think the blind references are key, I think doing real interactive, working on a project together is key. I'll tell you one of the things we learned at HubSpot about this. We would have a candidate come in, let's say a head of engineering, and we'd have eight people interview them. And our scale's one to four. And let's say four people were four out of four, and four people were two out of four. So, that's candidate A. And then the next candidate comes in, eight people interview them, and everyone's a three out of four. Almost every time we hired the three out of four, the person with the least amount of weaknesses. And we changed it, and we went with the spikier people, we went with people with weaknesses, we with people who would challenge stuff, and that has worked out quite well. Our hit rate at HubSpot's improved. We also have shrunk the pool of people on that interview panel from eight to four. We just hired a head of product, and there were just four of us that interviewed them. I think that worked too. So, I think there's things you can do to get better at it, for sure. [00:11:21] S1: Okay. This is incredibly tactical and useful. On the references piece, the toughest part is getting people to be honest because there's very little upside to them to say negative things about people. Is there anything that you've learned to help get real honest answers from folks you call for references?