TT: Take Control of Your Career Growth with Jason Warner, Former CTO at Github

(Intro Narrator at 00:00:00) Today, we're bringing you an episode of Tech Titans. Jason Warner, former CTO of GitHub, joins us in this episode to share his best advice on taking control of your own career path. You are listening to Joel Beasley, Tech Titans.

(Joel Beasley at 00:00:20) I'm curious how you grow and develop your next generation of leaders, like technology leaders. I saw you write a lot, and you're very smart about culture and leadership. But how do you sort of, how do you do that on a tactical level?

(Jason Warner at 00:00:37) So the one skill I find that you need to be remote more than anything is the willingness to pick up the phone, as I say, which is you've got to be able to jump on a Hangout or a Zoom or a phone call midway back when to be able to do it. And video has changed the game entirely for remote. When you were just doing audio conferences, it was much, much, much harder, and I don't think it was nearly as successful. And no matter what anyone says, IRC and Slack and all the other ones are not accessible alternatives for video.

(Jason Warner at 00:01:09) And I find that if you're not willing to do that, do you want to stay async entirely and just use text-based communication? It is very, very difficult to do that. You have to make some modes. So you've got to be able to write. You've got to be able to async write and consume, and you've got to be able to jump on video to do this, to hash things out.

(Jason Warner at 00:01:29) If you're able to do that, I find that all of them kind of wrap together, allow you to have a pretty good experience. Every once in a while, I think you should get together in person, but I don't think it's necessary to be doing that every week or even every month. And, you know, your mileage may vary, but your willingness to get on a video call like this is key to doing it.

(Joel Beasley at 00:01:49) So you mainly coach your leaders through one-on-ones where you're on video and communicating one-on-one?

(Jason Warner at 00:01:54) We do Slacks back and forth just to do check-ins. And, you know, the first time you ever send any sort of miscommunication on even a back-and-forth of a text-based communication, you're like, yep, got to jump on the phone. Let's go right now. Let's jump on the video Hangout because the most important thing is to clear up small issues before they can become the big ones, and then also talk through scenarios. And if you're going to do the scenario stuff, talk through them live because nuance is very difficult to text. Talk to them when you can see the other person.

(Joel Beasley at 00:02:26) What sort of advice would you give or share, or story you would share, about stepping outside of your comfort zone?

(Jason Warner at 00:02:35) Oh, wow. This I could go on for days in a kind of meandering, probably no real point at the end of it type of thing on this one, and I do like to talk about this stuff.

(Joel Beasley at 00:02:47) One good story. One good, you know, stepping outside your comfort zone story that yields a positive result.

(Jason Warner at 00:02:53) Oh, well, I would say for me, obviously, the acquisitions one. It's not very often that you try to talk about stuff like that stepping out of my comfort zone, but obviously the payout was huge. I would say the first time I really jumped into management is kind of one of the first ones. I'm more, you might call, a reluctant leader. If I look back on my career, I jumped into management really, really young. I went back to IC, jumped again, went back, jumped, went back, kept doing it over and over again.

(Jason Warner at 00:03:19) And finally, there was a point in time when I was kind of burning the boats on engineering leadership and just went all in on it. And I remember the time I did it was because I was so incredibly frustrated with what was going on around me. And it was one of those moments where I love the company, I love what we were doing, but everything was a mess. And, like, generally speaking, most things are on fire or, you know, there's some degree of emberness, smoldering, if you will, that is happening at all times.

(Jason Warner at 00:03:47) But this one felt particularly on fire. And I stepped up, and I said I wanted to go help. How can I help? And I went and I had a very uncomfortable conversation. This is the stepping out of the comfort zone part.

(Jason Warner at 00:04:01) I was young, and I had a very uncomfortable conversation with the CTO at the time. And you could see that this person almost had this sense of relief because this person was like, "God, I know everything's on fire, and I have no idea what to do. What can we do?" And you can see that there was this guard-let-down moment where I was like, "I don't know. You don't know either, so let's just talk about some of the things and prioritize top five that we should go after." And that was my first real jump into management professionally without just kind of dabbling at it, which led to executive management, you know, six, eight months later, and then the rest is history.

(Joel Beasley at 00:04:41) I like that because what you're describing is you saw an issue, and you looked around, and you're like, "Hey, nothing's happening." And then you stepped up outside of your comfort zone, and you made some changes and figured out how to solve the problem.

(Jason Warner at 00:04:55) Well, in that, and now in particular, the uncomfortable conversation with a superior was the really stuff outside your comfort zone one. But there's a way in which you can do those. I like to say that every conversation is a chance for net improvement or decline in a relationship. And there's a way to have a conversation, a difficult conversation with someone, where you need to become closer and stronger, form bonds outside of it, even if it's like you're not going to work at this company anymore. Or you can have that same conversation, and next thing you know, you've got a villain for life that's coming after you.

(Jason Warner at 00:05:27) And the skill is finding out how to have those conversations. And most people don't know how to have those conversations, and I think it's an actual skill to develop, difficult conversations.

(Joel Beasley at 00:05:40) We had this little inside conversation at the office. It was a small debate, but I'm curious to get your perspective on it. We were discussing personal development, like professional development, like improving yourself, and whether that's the responsibility of the individual or the company to improve the individual.

(Jason Warner at 00:05:59) So I find that this is actually quite an interesting conversation because I think it goes to two mindsets all around the individual as well as the corporate body. So here's what I say: assume that no one is going to be responsible for you the way that you can be responsible for you, and assume that you have to take your responsibility into your hands. However, look for places that care for you the way that you would want to be cared for. And if I look at it that way, my job as an executive leader is to try to provide opportunities or things, growth opportunities or forms in which people can do those things.

(Jason Warner at 00:06:36) But I'm also looking for people who are going to own it themselves because, one, that shows a drive on their own and a more assertive attitude or approach to general care and cultivation. That's how they're going to care for themselves. I like that it transfers to other aspects of the job as well. And there's a statement I live by. The longer I've been getting into my career, I like to look for people this way. I forget who said this one, but he said, "You try to find people you need to rein in, not people you need to motivate." And, you know, I think my job is actually to motivate and inspire. But if that's my job—that's my job—but if I'm looking for a trait in a person, I should be looking for a person who I don't need to do that for as much as you might think you need to.

(Jason Warner at 00:07:28) And if you combine those two things, magic can happen because you find, you know, leadership that might care, but you also have people who are really self-driven. There's a lot of stuff that you can conquer in that approach. So to answer the question more directly, I think it's both parties. If I were to lean, it's going to be, probably I'd say, the individual should do it because there's very few people in my book who care about them the way they care about themselves.