Lead Time Chats, Episode 1: Will Larson

Will Larson, CTO of Calm, speaks to Jean Hsu for Lead Time Chats

Note: Lead Time was recorded to be watched and listened to in video format. We recommend you watch the video if you’re able to. Our transcripts are automatically generated using transcription software and include limited human review so they may contain some errors.

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Jean Hsu: Hi, Will. Thanks for joining us. The topic I wanted to talk about—and we'll just dive right in—is really the path of the senior engineer. That could mean different things at different companies, but I think you're really well positioned to talk about it because you've written the book, the Elegant Puzzle, which is about engineering management and then more recently your book on staff eng, called Staff Engineering came out.

One thing I noticed you wrote about was how the senior engineer is, at a lot of companies, the sort of role where you can just hang out. You don't necessarily need to progress or get promoted in that role. So I'm just curious what was your own experience when you were in that place or in that role?

Will Larson: So it's interesting. My personal experience as an engineer is pretty unusual in the sense that I went into engineering management, like pretty early, but basically I was teaching English in Japan and I was writing a ton of my blog. I somehow got hired at Yahoo to start next year and I went in just like literally knew nothing. And to the extent of how little I knew about being a software engineer, I got an offer from them. It was like my first salary offer. There was like $90,000 a year entry level.

And I was like great; accepted and they, the recruiter called me back and he's actually like, we think the offer's too low even though I already accepted it. We're actually going to bring it up to a hundred thousand.

Jean: This exact thing happened to me at Google too. When I joined at 70 and then it got bumped to 80 before, after I signed the offer letter, I guess this is a common thing.

Will: How did you feel after that happened?

Jean: I didn't know anything. I was like on the East coast, knew nothing about tech companies, so it's just cool. I guess I was going to accept anyways. So yeah pretty young and naive. I don't even know that I really thought about it much other than okay. Sounds good. Yeah.

Will: It's funny. I, in retrospect it highlighted, like I just didn't know how to negotiate a job offer. I didn't know. You didn't know? I didn't know what a reasonable salary was. I didn't do any research on what a reasonable band might've been. It was my first job, like the first non strange job that kind of professionally, I just didn't know what I was doing, but so they gave me this offer I accepted, they increased it because they thought I was just, they’d never seen someone negotiate as poorly as I did.

Jean: [laughs] Still accepted.

Will: Still accepted. I was like so then I started and Yahoo didn't really have titles at that point for a lot of the engineering levels.

It was just technical. Yahoo is what it was called. And it was only once you got to architect on, which was the fourth role or went into management that you actually got a title. So I was technically Yahoo, but I was like the first level and LLN or whatever. And then some of my peers were , but we didn't have any architects on the team I joined. So everyone was technical. I was there about a year then I got promoted. I think, fortunately, I definitely knew how to work a lot, even if I didn't know much else. So that was like a great opportunity. But also what happened at that point is that Yahoo sold its search business to Microsoft Bing.

And so there was a mandate to not ship anything for an unknown period of time. So the team that I was on had actually finished our products, the feature was complete, like the week before that, then we went into this like contract period with things. So we just didn't know what to do. We started building the V2, but we never launched the V1. And actually by the time I left a year later, we just never got to launch the thing that we built. Then from there, one of my coworkers who I enjoyed working with, a product manager named Josh. He went to Digg so he was like, “hey, we're hiring. Worst case, you're going to make a quarter of a million dollars. If you join; easy.”  The classic Silicon Valley story that people will tell you.

So I accepted the offer. Our CEO gets fired the Friday before I joined on that Monday. But again, like I had already accepted, I was going. And like the biggest perk honestly at that point was not working meaning to Sunnydale everyday because I was actually walking like 40 minutes to a Yahoo shuttle an hour and a half on the shuttle and then doing that same commute back. So I was commuting, like three, three and a half hours a day. If it rained, it would maybe take four and a half hours or something. Cause the one that wants a nightmare. So just not doing that was this amazing perk of the job in the city.

Jean: What a different world we live in today. Huh?

Will: I know. Did you ever go from having a long commute to having a short commute?

Jean: Oh yeah, I was commuting from Mountain View. When I started at Medium, I was commuting from Mountain View. I would drive,  park, run to catch the last bullet train, like California bullet train, and then get to Fourth and King and then walk 15 minutes to get to the Medium office and then do the whole thing in reverse and then I moved to San Mateo and moved to Berkeley. I'm was circling SF and getting closer and closer. And I did that while I was pregnant too. I was just like walking and smelling fumes and feeling like I was going to throw it. I just get to work and throw up; is was really bad.

Will: Yeah. That sounds terrible. That sounds really awful, but like that  first three months after you go from having a long commute to having a really short commute or no, can you, it's just like the best three months of your life then like the time rebalances and you no longer realize you have another three hours a day, but it's like a beautiful moment.

Jean: The relative being in that comparative condition moment is a good time.

Will: So Yahoo. Went to Digg, hired as a mid-level. Humorously enough, again, I didn't know what I was doing. At Yahoo, I got a pretty big raise, I think I got up to 113 or something and Digg lowered my salary. I was like I guess I'm going to do it anyway. So then I went and got like undercut on salary again, which is finding on just really pretty stupid at that point in my career about negotiating.

And I went to the CEO's fire the day before I started. And they were actually in like year two of a death March to launch this like dig V4. And so the, most of the experienced engineers, like had I later realized like quit and that six months before I started. So it was just like the people who are too loyal to the cause for whatever reason to leave are still there.

And they're like desperately trying to backfill. And so on it turns out it's like relatively easy to get promoted to senior and in that case but actually I. I moved into management and less than six months after I was there. So this is only two and a half years into my professional career in software.

I was in an engine management role. And then we had a series of layoffs. So I was the only manager who left the company after about 12 months. And so I, they gave me a shiny director title because literally they. We're trying to retain people. And then they were trying to make it like an attractive acquisition target.

And so having like higher titles, created that perception of some sort of seniority but really I effectively spent no time as a senior engineer and really had an accelerated appearance of a career due to that, just like what a tire fire took was at that point.

Jean: When you were considering or being offered this move into management, was that a choice where you're like, Oh, I could either do this or take a more technical path. Cause that's the path you're talking about now in speaking with a lot of senior engineers, I think.

Will: It's interesting. I can talk to that in a couple of different ways. So first I think that this was a company where there really was no people management happening. Everyone was just trying to ship code and the managers were just trying to like align people to ship code that there wasn't like career planning happening there.

Wasn't, like a development budget that there was just desperately trying to figure out how to get to a feature like this, launch out the door. And so even the manager was more like a tech lead or something like that. And so the first product I was first like the NG manager for the API platform, which was just.

Like basically some tornado servers for the Python ecosystem that was like a proxy to our Python backend. And I was like a team of three people. We had a mobile contractor that we had given like a six month commit to, so he was one of the three engineers on the API team and was just our iOS developer because we didn't have an iOS app to build anymore.

He joined the API team. And two other folks both of them left fairly shortly after that. So that was like my first exposure to more of a tech lead role. And I think they just saw someone who was willing to irrationally take personal responsibility for these kinds of things.

And I think that was, it's a strength, I think, to take a lot of responsibility. It's also like a bit of a trap where you end up taking responsibility for a situation that's a little bit on salvageable. And that was the beginning of it. But I did later go to the CEO, the new CEO, the third CEO of my, like a two tier period and say Hey, I really want to go back into the technical path.

I don't want to be. I'm not a manager. I don't know anything about management.

Jean: It's only two years into your professional career that feels like you don't want to get siloed and never really develop that technical depth.

Will: Absolutely and basically they just didn't have anyone else to do the people management well, and again, the amount of people management, I was doing a sort of comically low.

Like I think if I now look at what I was doing, I really was doing like some sprint planning and then trying to write code or something like that. I really didn't know what I was doing. But it just structured the company needed someone in this like director role is really, again like a manager role at best.

And so I just. Couldn't get out of it but really I did want to go back to it. And if you want to think about career regrets, I want to give advice on this topic to folks. I think don't leave the technical role path until you're done doing what you want to do, because I do think it's, sharing majors has her a great key sound like the manager into your pendulum, but I think something that, that piece doesn't address is that as you get deeper into one of those two, I think the switching costs do go up.

And the kind of the economic rewards of getting deeper on them is extremely high. And so I think it's like the opportunity cost of switching, I think is actually a lot higher as you get further in your career than than it might appear. Early on.

Jean:  Yeah, that's something I learned I had gotten that advice from a coach too.

While I'm not too senior, I like to learn as much as I can because that's when people accept or tolerate this sort of more junior mindset in a bunch of different areas, but once you're more senior, then it's what you're working on. And of course it depends on the company depending on your manager, but overall there is that increased cost to switching and switching back and forth.

Will: Absolutely. And so I really, that's like the biggest thing I tell people is just make sure you're done before you tried to switch. I think when you're an entry level manager or when you're like a staff engineer, you can still switch back and forth a bit. The roles are quite similar. But if you look at what a director does or what a VP of engineering does versus what, like a principal engineer does, they're quite different and it, the skills are less transferable than I think folks sometimes think they are.

Jean: What piece of advice would you have for someone who's in this sort of senior engineer role and is. Contemplating or looking down these two paths of, more management track and more headed to her staff engineer. Like how do you help them decide which path is what

Will: I think there's definitely a lot of different ideas I have on this one.

I think maybe I can give some advice about where I see folks who are trying to go into the staff role or where they stumble in particular. And that's helpful for folks to think about, I think there's the perception that like management is soft skills. It's dealing with ambiguity.

It's, never know what you'll do on a given day as a manager waking up. Whereas if you stay on this technical track, there'll be like more predictability, more consistency of the work. You have a clear direction but actually like my lived experience is like the complete opposite of that.

Where I think for managers, there's a ton of resources at your company you'll have a peer group almost necessarily almost certainly you have a peer group of like probably a dozen or at a larger company, like a medium or a Stripe or something you'll have probably like 50 other managers who you can go to and be like, Hey, like I have this problem.

Or how did you deal with this? And like at the

Jean: Like at the general company management training as well.

Will: Yeah. There's a good people team trying to support people, managers to success. But on the staff side, none of that, like the people team doesn't really think at all about how we make staff engineers or principal engineers successful. That's just not a problem they think about because structurally the people team doesn't see like staff engineers as company leaders in the same way.

It sees people managers as company mirrors because. Functionally it's true in engineering, but in most other functions that just doesn't exist. So they just don't structurally. They just can't think about this problem that much.

Jean: They're trying to solve for the whole org and there's management and the whole Orrick retina.

There's not these like staff engineer equivalents.

Will: Exactly. And so I think the staff engineers actually often end up in the spot where Oh, my manager will be able to help me as a staff engineer and they will, to some extent, but most managers have never been a staff engineer. And most directors, I've never been a staff engineer and most VPs of engineering.

I've never going to staff engineer. And there are often, far more directors of engineering or the company ratio wise, and there are staff engineers. So your peer groups are really small. So people are like, Oh, I don't like ambiguity. I like having clarity in my work, somebody on this staff path. I think it blindsided that just like how little structure and support there is when in the actual role itself.

Jean: How have you found that? People are able to get that support externally.

Will: Yeah, I think there's a couple of different things that I found. So first there's like the classic Lara Hogan manager of Ultron. And when I interviewed Michelle do for staff and she talked about the Frankenstein manager, which is the same idea with a slightly more grizzly metaphor.

But I think like finding the different pieces that can be helpful to you. And to your point about going externally, I think going externally is incredibly important for these folks and these staff roles, because I think these people usually are really defining what that even means at their own company, even companies that think they know what a staff engineer is often don't. And so I think these peer groups like learning circles like that, you can put together. I found that people in staff and principal roles have this immense thirst for kind of like peers and like folks in that community. And so there's a lot of openness.

If you just reach out to folks like, Hey, like I want to talk about this, or I want to do like a learning circle to participants. Cool.

Jean: Then I wanted to ask you so you've published her elegant puzzle book. You recently published staff enj. No in the pandemic with a newborn, which I thought was really funny.

It's like the Taylor Swift of NG management released two albums. But What do you, how do you think about your work? Like where do you find the time to do it? What does your week look like?

Will:  I think so first I think a really important point, maybe the most important point I would make on the idea of like work or kind of supplemental work is that most of the most successful people you've ever spoken to don't really do this.

And so I think in the Bay area or in technology in general, there, there is such a. Strong online presence of folks who are doing these, like God forbid like side hustles, or like whatever you want to call them where they're like turning up content. They're writing a lot. They're like doing a YouTube channel.

They're like on clubhouse, like talking about their deep clubhouse, you think Tik, TOK, whatever. And I think it creates this competitive pressure to like, be there. Yeah. I just think it's an important round that sounds like the most successful people, don't do any of this and you don't need to do any of this.

If you don't want to do it, just please. Don't

Jean: I do have that feeling. When I saw it, I started to see leadership content on Tik TOK or clubhouse. I'm like, God, I got to do that too. I'm just trying to keep my kids alive.

Will: Yeah. It's wild. And I do think conversely, like I think if you do it.

It's really helpful, but it's just one form of privilege. And so I think, privilege is like universal lubricant that helps make everything easier in your life. And so if you went to Stanford and you have a Stanford degree, people just think you're smarter, no matter what else you do, even if you like to try to prove them wrong they will see that degree and they're like really smart people.

Do you have an MBA? At some company or some business schools, people would think highly of you. And some people hate MBA. So not every case of privileges, like universally applicable but really if you go work at Google people like, Oh, super smart works at Google or, and so you just have to figure out like, what are these different ways you can build privilege?

And so I went to a really small liberal arts school in Kentucky. There were I think six people in my computer science class that went that the year that I graduated. And I think that was like one of the larger classes and no one's ever heard of this. And so when I was teaching English abroad, I was trying to think about how to actually build some sort of privilege so that it's easier to find these jobs when I, no one knows what I've done.

Jean: They get the right signaling and credibility.

Will: Yeah, exactly. Like it's a shame on some hand that like signaling that's a great word. Just so important to these processes, but I think we also have to just recognize the reality of it, but signaling is incredibly important. And then figuring out how to like, create some of that.

And I think like writing online the books all of these are really seeking out a couple of conferences, like just doing a small amount in each of these is like this incredibly powerful signaling tool. You don't even need to do much of it. You don't need to keep doing it, but just having for popular posts. You've written like two, like a conference talks up on YouTube just a little bit. I think it is a really powerful way to accelerate your career if you want to do it, but you certainly don't have to.

Jean: So it sounds like you're not doing it like all the time, but writing a book and, writing books is not, it's no walk in the park.

But it sounds like those are things that you don't have to do, but it's things that you were motivated to do.

Will: I think writing a book isn't and people have different experiences. I enjoyed writing my second book. It definitely more than I enjoyed writing my first book.

I think my first book, I created a timeline that was helpful for me finishing it, but also that was unpleasant to execute within. So I definitely regret how I timed that one. And I think one of the joys of self publishing and the second book I did self publish is you own your timeline and you own the quality level. I think that to me was really powerful when Jerry Weinsberg wrote this book called the Fieldston method for writing. And it talks about basically writing where you have energy. And that really appeals to me where I like to work on projects as long as they're energizing for me. But this is a hobby.

And if it's not energizing, like I just want to stop doing it. And the problem with working with the publisher is you can't just stop. You'd have to keep going with it. And so to me, that's where I'm self-publishing was great the second time.

Jean: It sounds like really genuinely finding this adjacent or any area stuff that maybe I called work, but stuff that qualifies as a hobby is how you found time and found time for it.

Will: Yeah that, that is what worked for me and I do think the experience of releasing a book when it goes well is I think just there's a lot of just like in Doerksen highest to it.

And they keep going where. It was really rewarding for me to do it. I don't know. I don't know if I really have another book in me in the next couple of years. Like maybe going to be a little bit slower on that one, but I really enjoyed it. It's really cool to have something that you've created that you can like physically holding that is not squirming out of your hands, trying to get away from you.

So I, I really enjoyed it, but I definitely think I could have accomplished the same, career outcomes, like faster and more simply then, and you didn't. I really think to me, starting with a hobby and then reasoning forward from that, and not, it has been important for just sustainability for it.

I've been writing for like over a decade and if I was doing it, cause I had a clear business goal or something I would absolutely give up like probably nine years ago. Yeah.

Jean: Cool. I have your staff enj book. I think it's being delivered as we speak. So I'm really looking forward to reading it and seeing how I can better support people on my team who are in that senior and staff level. Thank you so much. Thank you so much for joining me today. Have a good rest of your day.

Will: It was a pleasure.

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Lead Time Chats, Episode 1: Will Larson
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