The Exchanges

Q What are two or three books that you've recommended most to other people?

A Uh, the two that I probably recommend the most are crossing the chasm by Jeffrey Moore. The current edition still has some things that are a little bit older now as, as examples, but the core of it is still very, very amazing. The other one is essentialism. And that is really about saying no to the right things and finding the thing that you really need to do to get the job done. And then not a book. But Jeffrey Moore created this, uh, there's the critical core context framework. And if you've read both of those books, it really helps you frame in what is the critical part for your business? What is the core of the expectation? And what are the things that you can say no to with, with, uh, the little amount of risk. So those things together, I think are really powerful.

AI assessment note: “the two that I probably recommend the most are crossing the chasm”

Q You mentioned Slack as a tool you use. What other tools do you find really interesting that people may not be thinking about for working successfully in a remote environment?

A I, I'm gonna be biased here and say GitLab as a product. You know, we, uh, we call it dogfooding, but we use it for everything we do. And that's become key because it makes sure that the product we're shipping is going to work for our customer and our end user. But our policy here is like, Hey, if you have the idea, like open an issue and then tag your team, and then that issue becomes that single source of truth. And we can then turn that into an Epic, or if it's gonna become a work for the engineering team, it can be converted into one of those types of issues. And we do it that way. We also encourage people to use Zoom if you have too many back and forth. So like, say like, like Lenny, You ask me a question, I answer it, and you go, but I understand, like, you ask it a different way, and then I answer it again, and you're so confused, like. Practically reach out and get on Zoom because maybe it's just something in writing's not translating. And so between those three main communication tools, that's what we use. GitLab is very anti-email in a lot of ways. Obviously we use it for external communication, but internally it's on an issue. It's in Slack or it goes into the handbook, right? So like if we've made a decision together, whatever you and I were going back and forth on, we think this is really important. We go update that part of the handbook or add a new handbook page …

AI assessment note: “I'm gonna be biased here and say GitLab as a product.”

Q To convince someone that this is worth doing, what do you find are the biggest benefits of operating this way? Because it sounds like, it sounds like more work and it sounds like there's more risk. And so what do you find are the benefits and also just like maybe second order benefits that you didn't directly expect? Yeah.

A So I would say the big thing I've seen is, uh, focus on results, especially for our customers. We are a global company. We weren't always as big as we are, but you know, GitLab is over 2000 people. It allows people to asynchronously consume what happened while they were offline and it gives them both more engagement as well as that lack of feeling of like FOMO or fear of missing out. And To me, those are really the top level items that come out of it. The secondary benefits of those are, of course, teams are better aligned. You find things that you may not find till the end of a software release or beginning of a go to market campaign. You have to redo something. And so I just think really And I say this with encouragement to people, pick one project and try it. And if that's successful and doesn't feel like a lot of additional work, try it with another one. And before you know it, you might find out that it's actually a lot easier to be transparent than it is to not be transparent. Cause now you don't have to worry about tracking things you may or may not have said. Think about, well, did this person hear it or were they not in that meeting? Like it just becomes that that's a lot of data that people can consume and then they can make informed decisions quicker. Cause they're not being siloed out of the conversation.

AI assessment note: “The secondary benefits of those are, of course, teams are better aligned.”

Q you're working. It's hard to do a lot of times, because in this sort of work, it's like, I don't know, this, like, what should I expect of this person to achieve? Maybe this bug takes a week, maybe it took a day. Do you have any, just advice to help figure out and nail, like, here's how we can Create outcomes that connect well with people actually working fully.

A Fixing a bug is kind of like a, uh, is more of a deliverable than like a business outcome. And so we're, we try to make them things like we want to have. 60% of our customer base using this part of the portfolio. Now what do we do to get there? And that allows people then have a measurable outcome. That does tie back to how many hours they're working to a degree, right? Cause you're scoping it, but it's not about the ship 20 features next month. That could take you more than a month. That could take you a day and a half if you break down your feature into tiny little features, right? Whereas it's more like celebrate the adoption, not the, the shipping. And I think that's really where we've tried to move. GitLab as a company has always been very focused on how fast we ship software, but that's not really how our customers use it. It's more about what pain point or use case did we solve? And if you're now framing it in that way, you begin to move away from the deliverable and the hours and you get into the, did the customer adopt it? What was their outcome? Like what success did they have? What are you trying to do with that? And by the way, I think that's the biggest challenge for people who move from a different role into a product division or product role is changing that dynamic to not be like the bits and the bytes, but be the use case, the pain point. Cause sometimes you ac…

AI assessment note: “Fixing a bug is kind of like a deliverable than like a business outcome.”

Q strategy, breadth over depth. Also, one of their core values is transparency. They share all of their financials with everyone, salespeople, everyone. They see everything. So it's so interesting that there's, these companies are very different and have very different markets, but there's two really similar elements here. And I've worked out for both. I guess, does that bring up anything? I don't know how much you know about HubSpot.

A I mean, I, I know the company and know some people who worked with me in the past that have gone there. I think what, what you're touching on is that there's some like product frameworks that are universal. You know, I occasionally will have founders reach out and ask the question, when do I make that pivot? And it's really like, have you found your fit in the market? And have you done the whole, and I'll, you will use like, you know, Jeffrey Moore's book, the crossing the chasm, like, have you found that? And if you have now, you know, to put all of your wood behind that arrow to use a saying, right. And then you're able to get that differentiation in that market presence. And you know, well, we go back to breadth over depth when we're looking at new investments. So it's not like it's left GitLab. It's currently part of our AI strategy that we're finding the, the Spots for DevSec Office for AI makes a lot of sense. But we also know that if those five things I shared with you are leading and we see them as leading in the industry, it's going to give us the ability to do more of that breadth over depth as we try to expand our SAM or try to go after a new market.

AI assessment note: “what you're touching on is that there's some like product frameworks that are universal”

Q meeting of your product team a while ago where they're talking about a book club of Barney Kagan's recent book. I was watching engineers talking about some scaling challenges they were having. There's a video of you being introduced to the UX team from a year or two ago, and maybe it was like after a reorg or something. Uh, what's just like the policy on which videos go online?

A Yeah. So that's a great question and you're actually correct. So about two years ago, we moved UX from engineering into product to make them a much more strategic part of the company. I knew a lot of UX, but didn't know everyone in UX. So we took the time to let me introduce myself to them if they weren't familiar with me or hadn't talked to me at all. Um, but to your question, like our policy is like be as transparent as possible. So if it's not customer data, it's not vulnerability information. We heavily encourage the team to put their videos, like record their videos, sometimes even live stream them onto our YouTube channel. So for those not familiar, you can search for get live unfiltered on YouTube and there's more content there than a human being could watch. You know, in a single day or even everything that's recorded during the day. Uh, cause there can be multiple meetings happening at once that are also showing up there. But a good example of that is my bi-weekly product meeting, where we kind of go over things we're working on, things we're excited about, troubles we're having, challenges in how we can Work better together. I can tell you that it was a change joining GitLab in 2019 to have that much content just be available. You also learn how to be better on meetings because of it. Uh, my first meeting was like my first day and I spent a lot of time looking all ove…

AI assessment note: “our policy is like be as transparent as possible. So if it's not customer data”