Lenny's Podcast: Product | Career | Growth
00:57:56 · Brian Halligan, Lenny Rachitsky
But I do think companies have one center of gravity or another. [00:58:00] S1: There's a really interesting thread throughout this conversation of just, when do you want to change how you operate you have to go really far to a whole other... And to almost over-correct to... Yeah, it's a really interesting of just how much work it takes to change culture, to change your norms. [00:58:15] S0: Yes. And the bigger it is, the more obvious you have to make it. And the other thing about being a CEO, Lenny, is you got to say the same thing over and over and over and over and over again. It just doesn't sink into people's heads, you have to just be incredibly repetitive on it before it sinks in. Same thing with marketing, but internally, and that happens. The other weird thing about being a CEO, Lenny, is as it gets bigger... When it's small, everyone's giving you shit, and you're all on the same level. But as it gets bigger, you didn't interview everyone, you have thousands of employees, you don't know everyone, and people put you on a pedestal that you don't deserve. And let's say you're in the hallway, and you're just kind of shooting the shit with a bunch of people, and you're like, ah, it'd be cool if we had a product that did... Somebody inevitably would go home and build that thing, and be like, Brian wants this as a big initiative. So, people really lock in on what you said. And it turns out you have to be very repetitive and you have to be very careful what you say.
00:58:15 · Brian Halligan, Lenny Rachitsky
[00:58:15] S0: Yes. And the bigger it is, the more obvious you have to make it. And the other thing about being a CEO, Lenny, is you got to say the same thing over and over and over and over and over again. It just doesn't sink into people's heads, you have to just be incredibly repetitive on it before it sinks in. Same thing with marketing, but internally, and that happens. The other weird thing about being a CEO, Lenny, is as it gets bigger... When it's small, everyone's giving you shit, and you're all on the same level. But as it gets bigger, you didn't interview everyone, you have thousands of employees, you don't know everyone, and people put you on a pedestal that you don't deserve. And let's say you're in the hallway, and you're just kind of shooting the shit with a bunch of people, and you're like, ah, it'd be cool if we had a product that did... Somebody inevitably would go home and build that thing, and be like, Brian wants this as a big initiative. So, people really lock in on what you said. And it turns out you have to be very repetitive and you have to be very careful what you say. [00:59:12] S1: Dharmesh was on the podcast, your illustrious co-founder, and he developed a whole system to avoid this sort of thing. Flash tags, where it's like, this is just an FYI.
00:59:12 · Lenny Rachitsky, Brian Halligan
[00:59:12] S1: Dharmesh was on the podcast, your illustrious co-founder, and he developed a whole system to avoid this sort of thing. Flash tags, where it's like, this is just an FYI. [00:59:22] S0: We had a whole system. Because we would say something on an email to the management team, or Slack, and everyone would be like, okay, this is what they want, let's do it. And sometimes it is like, you need to do this, and sometimes it is like, we should talk about doing this, and sometimes it is, this is just kind of an FYI, we're thinking about it. And because it got big, we came up with that rubric of, we needed to tag each email with, do you want me to get this done this week, or is this something we should talk about, or is this something that's just FYI, I'm thinking about? [00:59:51] S1: I love that... One of them is plea. Pleading you to do it. I'm not telling you to do this, I'm just pleading that you do what I ask. Oh man. Okay. This all connects. And by the way, you guys were co-founders for 20 years, you shared something before we started recording. So, Dharmesh famously did not ever want direct reports, he's just like, Brian, I want to start this with you, but I don't want to ever manage anyone. And you were talking about how you had to take on engineering, which didn't make any sense.
00:59:51 · Lenny Rachitsky, Brian Halligan
[00:59:51] S1: I love that... One of them is plea. Pleading you to do it. I'm not telling you to do this, I'm just pleading that you do what I ask. Oh man. Okay. This all connects. And by the way, you guys were co-founders for 20 years, you shared something before we started recording. So, Dharmesh famously did not ever want direct reports, he's just like, Brian, I want to start this with you, but I don't want to ever manage anyone. And you were talking about how you had to take on engineering, which didn't make any sense. [01:00:19] S0: No, I'm an engineer and I can code, but it's not good. So, when we started the company he's like, "I was a CEO before, I was terrible at it, I don't want to do it again, you're going to be the CEO." I'm like, "Great." And he's like, "And by the way, I'm not going to have any direct reports." I'm like, "Well, it's just the two of us so don't have worry about it." He's like, "No, ever, never." I'm like, "Yeah, yeah, yeah." And then we get 10, 12 people, we're starting to hire engineers, and onboard them, and making up big decisions, and I would go to him and be like, "Well, can you manage him?" He is like, "Don't you remember I told you I don't want to have any direct reports?" It's like, "Surely you were kidding when you said that?" He said, "Nope." And so, Dharmesh Shah has never had a single direct report at HubSpot. [01:01:02] S1: Incredible. I don't, it's just like a dream, a way to operate, I love that you made it possible for him, and it created all this opportunity for him to tinker and innovate.
01:01:02 · Lenny Rachitsky, Brian Halligan
[01:01:02] S1: Incredible. I don't, it's just like a dream, a way to operate, I love that you made it possible for him, and it created all this opportunity for him to tinker and innovate. [01:01:14] S0: Yes, yes, it freed him up to really think and be creative. [01:01:15] S1: Yeah. I'm excited to get him back on the podcast someday, we're going to link to that episode. Maybe a last question, I'm curious if there's anything else you think we missed? As a company grows and scales, the job of a CEO changes. You've written a bit about this, of just how different the job is when you're a starter versus a scale up. What are some of the things that most change where your time goes as a CEO, as the company grows? [01:01:38] S0: Well, you clicked on this earlier, but that inspiration thing. I have a little rubric where it's like, in the startup phase it's 90% perspiration, 10% inspiration. When you get the scale up phase, it's 90% inspiration, 10% perspiration. And over time you're doing every job in a startup, and you still need to be very attached to it, and you still need to talk to customers, you can't give it up. But man, you have to let go of so much stuff over time in order for the organization to scale, and I have trust issues. I only trusted a small number of people at HubSpot to be a DRI, and to really drive something important. It drove people crazy, that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem. And that's a scaling limit, that was a limit for me. I wasn't trusting enough.
01:01:38 · Brian Halligan, Lenny Rachitsky
[01:01:38] S0: Well, you clicked on this earlier, but that inspiration thing. I have a little rubric where it's like, in the startup phase it's 90% perspiration, 10% inspiration. When you get the scale up phase, it's 90% inspiration, 10% perspiration. And over time you're doing every job in a startup, and you still need to be very attached to it, and you still need to talk to customers, you can't give it up. But man, you have to let go of so much stuff over time in order for the organization to scale, and I have trust issues. I only trusted a small number of people at HubSpot to be a DRI, and to really drive something important. It drove people crazy, that I didn't have a larger trust surface. Every one of the CEOs I work with has the same problem. And that's a scaling limit, that was a limit for me. I wasn't trusting enough. [01:02:33] S1: Brian, I feel like I could chat with you for hours, there's a whole list of Halliganisms I'm going to link to that we didn't even touch on. But before we get to our very exciting lightning round, is there anything else that you think we should chat about? Anything you want to leave [inaudible 01:02:48] with?