The Exchanges

Q Never one's ever mentioned Top Chef before, so that's fun. Do you have a favorite interview question that you like to ask candidates that you're interviewing for a job?

A A lot of my interviews now are trying to help people decide if they actually want to join a company. And so my, my favorite, my favorite company question I ask now is like, Hey, We've really loved you. You're going to come through. I think you're going to get a lot of offers from other companies too. I bet you'll have three or four really compelling offers because you're a fantastic candidate. How are you going to figure out really specifically which of those options are right for you? And I think it forces people to tell you what they want. And then you tell them why you have that more than anyone else. And then you can actually like pitch them on what matters versus pitching on things that don't.

AI assessment note: “my favorite company question I ask now is like, Hey, We've really loved you”

Q Awesome. I'm excited for that episode with Richard where we're going to go real deep into strategy, but maybe just as a lasting topic around there, if someone listening wanted to get better at, say, end strategy specifically or a strategy in general, is there anything you recommend they do? Is it read these books? Is there anything else?

A If people want to get good at strategy, there's, there's a lot of different types of strategy, right? But here, here are some things I'd really recommend. First, I think the Richard Rumelt book. I think good strategy, bad strategy is probably the right starting point. I think the crux also, also quite good, but maybe I would read that 1:02. Great overview of how to think about strategy. I also think thinking in systems, I mentioned that before related to systems thinking. A big part of strategy is being able to model the reality so you can improve your diagnosis, and so I think that that one's really quite good as well. If you get into the engineering side of things, There's a lot of interesting books here. Um, there's, uh, Technology Strategy Patterns by Evan Hewitt. There's The Value Flywheel Effect by, um, Anderson, McCann, and O'Reilly. The Phoenix Project by Kim Burr and Spafford, um, which is kind of a modern rewrite of the goal by, um, Goldrat. But I think there's like, still the missing canonical book is kind of missing on this one. So I, I took a stab at strategy and my upcoming book, um, which is coming out, the engineering executives primer coming out early next year. I also took a stab at it and staff engineer my previous book, but I still think there's like a missing book here. So I, I sort of am like dreaming of writing like a, a engineering strategy book for my n…

AI assessment note: “First, I think the Richard Rumelt book. I think good strategy, bad strategy”

Q it'd be fun to start with just what is changing in engineering. It feels like there's been a lot that has changed over the past few years, especially from kind of the ZERP zero interest rate era to today's market, which is very different. What have you seen most change from an engineer's perspective? And then just also what are you telling engineers about how to handle all this change?

A I think it's a pretty, a pretty strange time in the market. So I think that, you know, I, I started working and, you know, the right before the 2008 kind of crash. And so the first few years there were, were not so good. When I joined Yahoo, there was a layoff basically every like four months, there was a layoff of some sort. It's pretty chaotic, but then we got into the last decade and it was just smooth. Right. And so, you know, numbers went up, revenue went up, headcount went up. And people started learning how to build really large teams. People started learning how to hire a lot. When I was at Uber, some days I would do like six, like interviews back to back. I would just be in a conference room. And at some point you can't even remember who you're talking to because you talk to so many people, one after another, after another, you just have some like scrambled, scrambled notes you're trying to like decode afterwards. Pretty, pretty different now. Like a lot of engineering managers are spending half their time or more hiring like 18 months ago, and now they're doing like two interviews a month or, or less, maybe zero interviews a month. So there's a real shift in just the amount of time people are putting into hiring. Instead, like all these different competencies that have kind of become more critical or a really great engineering director might have just been spending th…

AI assessment note: “So there's a real shift in just the amount of time people are putting into hiring.”

Q to spend some time on is measuring engineering, velocity, productivity. I think it's probably one of the most common and also maybe the most annoying questions engine leaders get is just how do I know if my engineers are moving as quickly as they can? How do we help them move faster? What advice do you give to engine leaders for an engine teams just for how to measure productivity?

A Well, this is a question that's coming up even more right in a moment when we're kind of reducing a lot of the size of teams from the industry on the venture capitalists that are on the board for these like Venture backed companies are pushing on the efficiency of engineering. Engineers are trying to figure out like, how do we like, how do we represent this? Um, how do we prove that we're appropriately productive for the amount of head count and funding that we have as an organization? And man, that's hard. And so the, the, the first way that people kind of focus on trying to answer these questions is just like benchmarking by like the amount of funding that you have. And that's pretty straightforward to do. It's a mechanical exercise. You look at like, you get a data set from your, your, your venture capital funds or whatnot. And you figure out like, okay, how much should we be spending in R&D? How much should we be spending in engineering? How much should we be spending on, you know, infrastructure engineering in R&D? And you can like benchmark this all out and figure out what the correct numbers are there. The problem is this is like a very mechanical and not very like insightful driven way. Like it will get you a defensible answer. It's like the old, like no one gets fired for buying IBM, which definitely hasn't been true in my, my career ever, but You know, this idea that …

AI assessment note: “the first way that people kind of focus on trying to answer these questions”

Q We'll control ourselves. So then getting very tactical, I think this is what a lot of people are always wondering. How do you, how do you make time? What's your workflow? How do you make time for writing so that you keep at it with knowing you have an intense full-time job?

A I used to do things differently before, before I had a kid. So I have a three and a half year old and, and just your, your timing, your, your life just like really shifts a lot once, once you have kids. Um, but the, the biggest thing that I found is finding things to write about that also directly relate to what I'm working on. And this is where I can do something that helps me at work and helps me write at the same time. Cause I think it's, it's, it's incredibly hard to find time to write about stuff that has nothing to do with your work. Cause it's all, and just distracts you from, from your work. Cause these, you know, particularly if you're in like a senior role, like these can be like pretty demanding jobs, but they're not demanding because you're responding to a urgent DM on Slack, like every, every five or six minutes they're demanding. Cause you need to make some really difficult decisions really well. And I think writing about like related topics is a great way to refine your thinking and improve your performance. It's not like a, not like a conflict and, or you do one, you either write or you do your job. Well, I think you can find a way to like align. And so a lot of podcast folks, um, do interviews with folks who are related to what they're thinking about at work. And that's a great way for them to like learn, to build their network, to refine their thinking, to tes…

AI assessment note: “finding things to write about that also directly relate to what I'm working on”

Q Wasn't there a value of no, of toe stepping, encouraging toe stepping, something like that?

A Let builders build, uh, toe stepping. There, there, there were a number of values that, that could be interpreted in different ways. And, and sometimes they got weaponized in various ways as, as, as all values do. But, but these, these are both interesting in different ways. And so number one is honest, then two is applicable. Um, three is, I think the last thing for a good value is this idea of reversibility. So there's some values that Aren't actually like usable. And so here's a good example. Um, we build good software, like, okay, but like, why would you ever not build good software like that? That doesn't, that doesn't make sense or, um, We solve customer problems that matter, right? Good. What, who would ever say their, like what, what company doesn't think they're solving customer problems that, that matter? And so there's certain like values that just, you can't apply. And so like, I think of these as like identity values. Like these are really just you describing like who you want to be. Like we care about our customers. Great. But like who would say they don't care about that? They're just like, there's certain values that I think of it just like identity values and they're not like, They're not wrong to have identity values. They just aren't very useful. You can't actually use them for anything. And so I just always push people not to spend too much time on these bec…

AI assessment note: “Let builders build, uh, toe stepping. There, there, there were a number of values”