Career growth for engineering leaders in the AI era: Building your thesis, the “running framework” & developing technical depth w/ Chris Chiu #251

We're doing a special in-episode feature on the future of AI-powered incident management with our friends and sponsor X Matters. People as a primary integration layer is really fragile. With multiple people and all of that coordination, you become slower to find the root cause. The slower you find the root cause, you then don't know what action you need to take to resolve it. Getting to that fast is the goal.

Later in the episode, Mike Bennett, who leads the engineering team at X Matters, shares why human-driven coordination creates outage risk and how AI-powered orchestration can dramatically accelerate your path from event to resolution. There's this concept. Uh in running progression. You shouldn't ever increase uh your workout along more than one dimension. Uh if you are going to be running further than you usually do. Do it at the same speed or

even slower than normal. Uh and if you're gonna be having a workout where you're trying to run faster than you normally do, do it at the same distance that you're used to or even uh reduce it. And I found this to be a really good framework. For thinking about career moves as well. I'll tell you this. I I've regretted every time where I've made a change that

changed or or increased uh or stretched me uh too far in too many dimensions. So a larger team, a bigger scope, a different tech stack. It always left me with Too little ground uh of expertise for me to expand from uh and get early wins. And instead, lately I've been thinking, I've been a lot more conscious about only stretching myself in a

few areas when it comes to changes. Hello and welcome to the Engineering Leadership Podcast brought to you by ELC, the engineering leadership community. I'm Jerry Lee, founder of ELC. And I'm Patrick Gallagher and we're your hosts.

Our show shares the most critical perspectives, habits, and examples of great software engineering leaders to help evolve leadership in the tech industry. To properly introduce this episode, I want to start with a quote. Daniel Kahneman of the famous book Thinking Fast and Slow has Has a great quote that pertains to what we talk about. Everything makes sense.

In hindsight. Career progression is rarely a straight line. And very much like this quote, it oftentimes only makes sense in hindsight. In this episode, Chris Hugh, VP of Engineering for Agent Force at Salesforce, joins us to deconstruct. How to navigate these nonlinear career paths.

We talk about identifying the mismatch in your current role and building a personal career thesis to help provide guidance and clarity when you're on this nonlinear career path trajectory. We also talk about how to engineer a productive exploration phase.

and leverage your relationships or VC networks to understand the market, plus how to apply the running framework to ensure success in your next role and why technical depth is no longer optional for modern engineering leaders. Let me introduce you to Chris. Chris Chiu is VP of Engineering for Agent Force at Salesforce.

He was head of engineering at Moonhub, acquired by Salesforce, and was director of engineering teamwork at Figma. Chris previously led product engineering and platform teams at Flexport and OpenGov. He's been a longtime friend of the community, and he's been a longtime friend of mine. Enjoy our conversation with Chris Chiu.

Chris, it's been too long. We get to catch up today. It has been a while. We were chatting regularly when you and I were were part of the same peer group, uh, which was a wonderful experience. I've I left Figma, went to a startup, now got acquired and

Been it's been a pretty wild ride. Well, I yeah, I was trying to think about how do I walk up this conversation for for everybody listening in here. We met right when you started at Figma. Through the course of that time, like we we spent a lot of time talking about leadership and wrestling with real people problems, but also we spent a lot of time talking about family and how things sort of change over the years and

And those are conversations I really valued. I blinked and then I missed a few major milestones in your journey from that point. And so I was like, well, we have to catch up and talk about that. You know, from Figma to Moonhub to now Agent Force at Salesforce. And, you know, I want to frame one thing for everybody listening in here to kinda guide like where are we gonna go and why.

To allude to some of Chris's journey, like part one of our conversation is really like career decision making and building your thesis for your next step. And we're gonna spend a lot of time talking about that. But then also too, it's like sort of

remarking on some of the observations that you've had uh about the changing role of being an engineering leader and how that kind of played into the thesis and career decisions that you were making. And so it's gonna be part reflecting on how things are shifting, but also then how people can make decisions on their own.

Maybe we start at the beginning, like you transitioned from Figma to Moonhub, like bring us into that moment. Like what was going on? What were some of your considerations and like what were driving your decision to make that transition? Yeah. It's a great question. Um, you know, I ha I had gone to Figma when it was

I don't know, engineering team of about fifty. Uh, and so it wasn't the very, very early days of Figma, but it was still before it it hit its inflection point. And I spent four years there, uh, helping build out the collaboration teams as well as some of the the billing and community teams. And after four years, uh I realized that the company was just at a much later stage.

Uh the company was much bigger. The problems that we were solving, both technically and organizationally, uh were much bigger. Uh, and it wasn't something that I was as interested in. I I was really thinking about what my next steps were. I knew that it was going to be something that was pretty different uh than it was at Figma. I didn't quite know what, uh, but I knew I wanted it to be quite a bit of a change and so

Some people are very comfortable interviewing while working and exploring these questions while working. I I I felt like I needed a time and so you know I put in my notice, I took some time off uh and really spent a lot of time exploring. exploring different opportunities that I had, thinking about what I wanted to do next. You know, through that process, I think I really honed in on wanting to go.

To a company that was smaller and earlier. Uh, AI was just starting to become a really big thing. I knew that that was something that I wanted to dive. Uh head first. And then, you know, every company, even at the time, was like, oh no, we are AI, but not many of them were yet. built foundationally on top of it. And two, not many of them had AI expertise in it. And so for me, like those were two big big important aspects. Finding a startup and then finding one that had an AI expert in it.

Moonhub's founder was Nancy Shu and she was an AI researcher at Stanford and uh just overall very much an expert in the field. And I knew that I could come in and help her build the engineering team while uh being able to learn a a a lot about the domain from her.

So part of the patterns behind this, I think, are really interesting is it takes a lot of self-awareness kind of at each of these different moments. Two. I think one, recognize maybe there's a difference with where you're at and where you wanted to go. I think two, the self-awareness required to like identify them, like what is it, the things that you want to learn or what are the types of environments or experiences that you want to get. And like that self-awareness and like that initial piece.

It's not a default pattern for people to develop. I I I like I like I appreciate how we kinda laid out some of the big milestones here, but I wanna dig in deeper into a couple different a couple different things.

So one when you were kind of going through the reflection process of identifying, you know, the mismatch between your role and what you wanted to do, were there certain questions that you were reflecting on? Like what did that kind of moment look like where you were like, okay, cool. Like, Like it's now time for me to transition. Like what led you right to that moment to to identify that this was the right time?

This has become a a topic that it's a little bit more talked about, but there's this concept of energy, right? And it's like what do you get energy from? I think for me Figma got to a point where I felt like I I wasn't getting uh a lot of energy from day to day. And and there's a lot of factors that go into it, like you're you're

spending the time doing the things that you wanna do. Uh, you know, you're energized about what potential next steps there are for in the opportunity that you're currently in, uh or about the things that that you're working on. And and like I said, I I think it came down to

Having having the self-awareness to be like, hey, I I'm not enjoying this as much as I used to. I think that there is a few things that would allow me to optimize more for the things that I I I would enjoy, but I will just have a lot more success.

uh if I looked for something that is more natively that. Uh, you know, and so I spent some time exploring some opportunities with my manager at the time, but I think we we both agree that, you know, I I would probably have more more luck finding something external.

I was talking to a a career coach friend of mine and we he kind of helped me see it as like a Venn diagram of like you start to identify like what do you do? What are the things that you know you get energy from? And like the Venn diagram is like when you're starting to assess either new roles internally or externally.

Like how can you kind of increasingly shift that Venn diagram where it's starting to converge more and more around the things that you know you get energy from, you're uniquely good at or um wanna continue to build? So I can see kind of your your thought process sort of shift in that direction. I wanna get into this exploration period.

I know you and I know that like part of this was was such an intentional choice to explore and I want to learn all about like what was it like to take this time off? So first off, like how long was it and then how did you spend some of this time to start to answer this question of what's next?

One of the things that I I wanted to open with, you know,'cause I I get this question sometimes around like, hey, how do you plan around your next career move? And like, what is the right frameworks and everything? And and one thing I wanna say is like It's okay not to have a plan. And if you're pretty happy with all your careers going, it's like don't get stressed out because you don't have a plan. I've talked to a lot of extremely successful people who never had a plan.

They just sort of like went with where their heart was sort of leading them. Uh and they found ways to be impactful at every place and and as a result grew. Uh, you know, and and it wasn't sort of this charted out thing for them. I think it It's part personality, part, I don't know, uh something. But uh I d I just wanted to say it's like not everybody needs a plan. I needed a plan. It was something that uh would would help me sort of think through it. I agree. I need a plan.

But I think that that that you know, that's something to to consider. Uh and then something that's, you know, attached to this as well is, you know, career growth and pathing doesn't follow the normal laws of physics. Uh I think a lot of people are worried that they basically only have a limited number of steps. to take in career progression. And so they wanna make that line as straight as possible. And they feel like any deviation, any like

sidestepping will basically mean that they don't get to go as far, uh, in the direction that they want. I've seen many, many times that that's not the case. I've seen directors of engineering who went back to being NIC And then within a couple of years became VP. You know, I've seen people who are engineers go into program management and eventually become head of engineering. Uh, you know, there there's no kind of paved path. I think, you know, many people are just like,

Like I wanna manage a team, I wanna manage multiple teams, I wanna manage managers, I want to become head of engineering. But the reality is there's there's many sort of paths. To the end and sidesteps doesn't signal inefficiencies. Yeah. I think that's a really a really great disclaimer for right now because I think more so than

Like more so than ever, like there is that churn and then there's the re resulting emotional discomfort with that type of churn. And I think particularly because of the Shuffling that AI and AI driven development are sort of introducing. And then you have sort of these workflow models where inherently in the company, when you join, companies are having people shift to to be more of an IC first before managing. And there's these are some of these like trends coming up.

It's it's no longer as linear. It is much more of this sort of revolving sort of journey. So I I just think that disclaimer right now, in particular, if people do feel that discomfort where it's like it's not going in the direction that I want, right now is the time where things are going to zag quite significantly, I think. Yeah, I couldn't agree more. We're taking a quick break for a special feature on the future of AI-powered incident management with our friends and sponsor, X-Matter.

Mike Bennett, who leads the engineering team at X-Matters, shares why human-driven coordination creates outage risk and how AI-powered orchestration can dramatically accelerate your path from event to resolution. We're the ones that are correlating the alerts across the platform. We're the ones that have to remember that a similar issue happened six months ago and this is what we did about it. We're the ones that have to figure out this is a symptom in service A.

But it has a dependency in service B that we need to know what that dependency is and how that could impact this thing. We decide on who is going to be page based on some informal knowledge. It's it's not scalable. I mean that all of that works in a in a very small scale environment. But as as systems grow, as teams grow, people as a primary integration layer is really fragile.

So the outage risk is with with multiple people and all of that coordination, it you become slower to find the root cause. The slower you find the root cause, you then don't know what action you need to take. to resolve it. The risk there is not knowing immediately what the problem is, so you don't know what the route for that mitigation is. With all of the information that is out there, getting to that fast is the key

goal and is the key problem when you've when you're relying on people to do it. When a signal comes into X Matters, the first thing that you can do is based off of that signal, you can then make a call out to the right people.

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to the signal that comes out to say, okay, this has happened, do a rollback and I can just Touch my phone and go back to bed without even getting out of bed. All of the automation, the flexibility of the tool and all the the things that you can build in along with the data that you've got with the service catalogue, with your on call, with your who's on duties and get you to get the right people at the right time on the call if you need to get to a point where you're in a conference.

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dot com. You know, during that time I explored a lot of different opportunities. I think one thing that I knew is that um I wanted to go smaller uh and I wanted to go in AI. And it it it took me a little bit to figure out those two things.

I'll start with the latter because that's easier. There are these times uh where a lot of technology changes and as a technology leader, uh, if you don't keep up with it, You you just don't have as many opportunities ahead of you and then you have uh a little bit less of an ability to sort of see where things are going.

Me me and a friend of mine used to talk about it's it's the same thing that happened to a lot of security people. Cloud came around where they were v very, very well versed in on prem security. Uh, and then all of a sudden everything shifted. Uh and I just knew that as an engineering leader, um, if I wanted to have opportunities to compute can continue to build amazing products or platforms.

Uh, I just needed to be on that edge of AI and force myself to learn it so that as it permeated through the industry and through the way that we build products and build companies. uh I would feel well versed in being able to navigate that. I think that that was a really important uh aspect for me. And then the other one was I knew I wanted to go to a smaller company. And that came from the energy conversation. One of the things

That I knew I was going to be energized by was by being the head of engineering somewhere. And I wanted to get into an opportunity where there was less of a safety net. You know, there was less of well, my boss or my boss's boss is the head of engineering and ultimately uh they're the ones held accountable and and I wanted to be in that position. I wanted to understand what it's like to be an executive. Uh because frankly uh at the time and still now I'm a

exploring like do I want to go found a company at some point? And if I do, you know, I'm gonna have to play a role as an executive. And is this something that I enjoy thinking about uh the company in much broader terms than you do as a director of engineering or even a VP of engineering and cell.

Uh, I wanted to explore that. I also knew that, you know, I was very energized by being in the details, by building products with the team, by thinking about the, you know, specific decisions uh that all Sum up to make a great product. And there's only really one company size that allows you to do both of those things, which is, you know, a seed stage or a series A startup. Because after a while, you just end up having to specialize either at that executive level.

or at that like detail line manager level. That that combination I knew I could only find at an early stage startup. Uh and then adding the AI bit, uh, it really narrowed down what I was looking for.

So then what was the structure like to explore these questions? So you kind of gave us an idea of like, you know, here's what I ended up looking for and why. So what was the structure or the process like to discover this? Like did you have self-imposed constraints? Who were you talking to and why? And like what did that look like? Like, bring us into some of the mechanics of what this structured exploration time was like. Yeah, I I I ended up casting my my net quite wide.

Thankfully was able to leverage a lot of my network to explore um any of these ideas. And so I connected to a lot of VCs, you know, because I was looking for a startup, I was like, all right, these are the VCs that I generally respect. Let me go look at their portfolio companies. Uh, and got to talk to a few partners in those VCs and Uh, you know, they were able to help me zero in on the types of companies that I was looking for and what the market was looking like and everything.

Um, so I think that that was uh a really big part of it. Uh also connected to a lot of uh other engineering leaders that I've worked with in the past, uh, went back and forth with them on uh their experiences and uh what are the the kind of opportunities that that they sought after. I don't know if I have a a a specific structure here. I think that that it just took time, uh and it took a lot of iterating and thinking through to get down to uh, you know, this this specific set of companies.

There was a principle that I was looking at that that has really guided the choices that I've made in my career moves in the past couple of years. For the VC conversation, like were these pre existing relationships or were you looking at portfolio companies on the website and then reaching out to a partner there and be like, Hey, I'm I'm kind of curious about getting involved in these companies? Like

Like was it what was the specific mechanism there for that outreach? Like was it cold or were there relationships? Like and if you had advice for somebody who was maybe going to pursue exploration conversations like that, what advice would you have? The easiest way to get an introduction to a VC is to like know another VC. Once you're in it,

Uh it's like very easy to go from one to ten. Uh and it is hard to go from zero to one. Uh I would say that the the best places to to do it is to basically find the like head of talent. at a VC uh and find a way to reach out to them via LinkedIn, via email, via you know, introduction from somebody. They're basically tasked with finding talent for startups.

uh anywhere anything from an IC to a a head of engineering to a co founder. Right. And so uh they're very motivated to meet people. That's basically what they do. It doesn't take a lot to get on their calendar. They're basically a recruiter at heart.

Uh and so I think the the same way the same things that will open your door to talking to a recruiter or getting past a recruiter, uh, is the things that will will enable you to to talk to them. And so having worked at one of their portfolios will help a lot. Yeah, you know, having some recognizable brands uh on your resume will will open doors as well. But if you know any connections um and you can get an intro, you you usually get a conversation. All right. I like that.

So you tease some career principles that are shaping a lot of this. Like why don't you bring us into those? I would love to spend a a little bit of time uh actually on on this previous part around like, you know, having some brands. In talking about careers, I think one of the things that's that's really interesting and I've thought a lot about is status and you get a lot of advice which is like don't chase status. Go for the things that interest you. And then status here usually is

some brand name for a company, you know, some like recognizable hot company that everybody wants to work at. Or a title, you know, it's like, oh, don't chase that VP title. Just like find a job that you want to do. And I do think that status is overrated and so I I'll generally agree with that. But I will say that there is a utility to status uh that folks frequently don't talk about, which is it does open a lot of doors.

uh when it comes to opportunities that you can have. My advice around status has evolved over the years. The status symbols of of a brand name or a title. can be really useful, uh especially if you don't have any.

On your resume. And so, you know, there's been a few folks that I talked to and mentored over the years where I'm like, you know what? If you just did a two year percent at a fang company or at that hard mid-size company, it would really open a lot of opportunities for you in the future. There there's a little bit of nuance here, uh, where I think status

Uh can be overrated, but I think it can open a lot of doors. I saw this for myself. I didn't graduate from a university that is, you know, uh particularly flashy, but I saw that once. Once I got a few logos on my resume, uh, it really opened doors. A lot of VCs, uh, you know, when I would connect their talent. teams, you know, their partners would come in and be like, actually can I pitch you in starting a company and everything? And I think a lot of that

uh was due to the history uh and the companies that I've worked at, some of which are are just recognizably very good. That being said, I also had an opportunity in this search. To go work at, you know, major AI model company. And even though it's very enticing uh from a status perspective, uh I realized that I didn't really need that logo and it wouldn't add much.

approach to what I already had and it wasn't what I was looking for. Being very pragmatic around this approach, uh, you know, of not chasing status, but recognizing when it's valuable and if it's valuable for where you are in your career can actually be really helpful. I think the that last point is is really powerful. It's that it's like once you kind of recognize what is the intent of that next step and the role it's supposed to serve within your career journey.

And maybe it is like, oh, something that provides a sense of security or provides like a that signals the type of scale that I can work at or the type of caliber, like one that like makes it easy for people to translate that, like that's really good. And so I I definitely appreciate that last that last remark.

So you did mention some career principles. Yeah. Yes. That you were also thinking about. Are there other things that you were reflecting on through this that you were kind of honing in on? Patrick, one of the things that I've recently started doing is running and it's been great. In running, there's multiple dimensions. And the main two ones are speed and distance. And there's this concept. uh in running progression, you shouldn't ever increase uh your workout along more than one dimension.

Meaning. Uh, if you are going to be running further than you usually do, do it at the same speed or even slower than normal. Uh and if you're gonna be having a workout where you're trying to run faster than you normally do, do it at the same distance that you're used to or even uh reduce it. And I found this to be a really good framework. For thinking about career moves as well. I'll tell you this. I I've regretted every time where I've made a change that.

changed or or increased uh or stretched me too far in too many dimensions. So a larger team, a bigger scope, a different tech stack. It always left me with Too little ground uh of expertise for me to expand from uh and get early wins. And instead, lately I've been thinking, I've been a lot more conscious about only stretching myself in a

few areas when it comes to changes. So let's talk about this like Figma to Moonhub move. Who because I knew that I wanted to one, try my hand at this executive role and think about strategically uh, you know, about the company and its direction. and two go towards AI, uh, which is is a domain that I wasn't familiar with and have no expertise in. Because I knew that both of those things were new to me, I very consciously targeted uh team size that I knew was uh relatively easy.

for me to manage. Uh, you know, it was a team size that I have managed multiple times uh in my career. And as a result, something that I wouldn't have to spend as much time and effort doing. so that I could focus my attention on these net new unfamiliar areas and be successful in them. And so this has really become a bit of a career principle for me. Uh and I think that

But sometimes due to uh ambition and and the the desire to get ahead, people will basically say yes to an opportunity that just stretches them in too many directions. And and just like running, sometimes when you do that. It just results in injury. Uh, which from a career perspective looks like

failure or really crumbling of a person's confidence uh to do well at their job, uh, which I think can be very, very debilitating. I I think that is such a Elegant way to break down the different dimensions of a new role and to really kind of consciously enter into it with like, I'm going to test.

and gain these new skills. And I know I'm going to be successful because these elements or are sort of my bets for what's gonna be really familiar. Yeah. I think that this connects to two other principles that that I really believe in. One of them is is something that I touched on. I think that a lot of people basically feel like uh the right thing to do is is to basically always

take on as much as they possibly can. And I I see it particularly in in very hot kind of companies and the employees that it attracts. Uh, and sometimes people end up stretching themselves very thin and they don't have enough mastery over what they're working on. And really I think this contributes a lot to this sense of like imposter syndrome, uh, where So much of your work and it's such a challenge and struggle and it's so much of a stretch.

that there just isn't a lot for you to feel confident around. And as a result, folks are just really stressed out. And they feel like, hey, this is the right thing. I'm being uncomfortable and I'm really growing. But it comes at such a cost. uh, I think for their work life balance, for their mental health. And I actually don't think that you actually build up that much speed, right? Is it's just like the running analogy, is like pushing yourself

faster and further doesn't make you become a better runner. Uh it just increases the the low the tax on your body in a way. Uh and I think that that something that that I had to learn a little bit and I I hope that others can learn as well, which is like going for the the m the most amount of growth, the most amount of stretching is not always the best thing. And and this really connects to, you know, a lot of research that has been done on flow, this idea of like flow state.

And, you know, researchers will say flow state is when you are basically at the edge of your ability or just beyond. And I think that a lot of people basically put themselves Too far beyond the edge of their ability. for them to ever get that flow state. Uh and as a result, flow state is basically uh characterized by uh this idea of being able to really enjoy and execute, you know, and and operate without a lot of thought.

With putting yourself so far beyond, you basically never enter flow state and everything takes so much effort and it's so taxing mentally and physically. Uh I really appreciate how you connected it to career flow state. It's almost like using this principle to create career longevity in terms of being able to develop mastery, build skill, and then also at this point like enjoyment and to find that sense of flow and in doing these new things. I think that's really great.

I wanted to go deeper into joining a company that had a competency and expertise within sort of the AI space. One of the questions you were asking is like, how should I think about developing skills with this as an engineering leader? And so you you know, you said you wanted to join something, you know, related to AI and gain mentorship and expertise from there because it felt transformative and it was one of these big industry inflection points.

How did that shift your thinking about being an engineering leader as you're starting to get involved in that space? AI is is is very much new. Um and The reality is there there's not a lot of expertise uh anywhere, really. Uh, I think that uh obviously there is there's folks who are very academic and and know a lot about

the domain, but I think nobody really knows where things are heading. That being said, it has been revolutionary and and you could argue the place that AI has disrupted the most is actually in engineering, uh and development. Uh that's where it's been most successful. Uh and so it it is a very disruptive t uh technology. For me, I I again I was specifically looking to go somewhere that would basically provide me both the forcing function and mentorship. To really learn the domain.

every company is is trying to get into AI. But I I you know, the metaphor that I use is they're basically trying to sprinkle AI on top of what they already do. Uh and I knew that that would never be enough pressure uh for me to learn it. Because if I knew that the core of what my company did was something else. And I think that uh I was looking for some somewhere Where it was like either this this is basically gonna make or break uh on top of this AI bet.

The second thing, and I think something that is often underappreciated when thinking about careers is person that is going to be able to mentor you. You know, it would have been easy for me to join a company that that was taking a bet in AI. And at the time when I was talking, most of these companies were basically built by engineers.

Uh, and it it felt a little bit like it was gonna be the blind leading the blind. It was great for me. It was very important for me uh to find a place where uh somebody would have that expertise, somebody would be two or three years ahead of me. uh in terms of that knowledge, uh it would be guided uh and well directed uh as opposed to just scrambling for insight.

You know what's it's so great, but this reminds me of uh you remember a couple of years ago when we were doing a lot of the like career growth uh and like skill acquisition blog post writing uh from like the the famous Wade Chambers Conscious Career Growth Conversation? Uh I was like, this is such a great example of like

Finding somebody two to three years ahead of you to accelerate your career growth. What's so cool is how you've internalized a lot of these practices and like are directly applying some of these principles and frameworks. to your life, Chris. Like the fastest way to learn is by finding somebody who is like a a couple of years ahead of you who can help shepherd you into that that new skill acquisition.

This is something that I've shared with you before and I I think it it's definitely one of the principles when I'm looking for new opportunities is this idea that like when it comes to leadership, humans ultimately learn it. through imitation. You know, most things that you and I know how to do in life came through imitation. It didn't come from a textbook, right? It didn't come from like reading a blog post.

It really came from watching people do something and be successful and then imitating it. I have really over the last probably two or three moves in my career, really optimized for that. I set out to really look for somebody who I wanted to become like in three, five, ten years.

Uh, and I found that in the the at the time VP of engineering now, CTO of Figma, Chris Rosmisson, who uh is is one of the best engineering leaders I worked under. And he had the the right combination of people, leadership. and technical acumen uh and humility that I was like, man, if if I get to become him and like

two or three years, uh, I would be really happy. I I still am trying to become like Chris uh to this day. But I think that uh he really ended up shaping a lot of how I think about engineering leadership and engineering growth, particularly the technical leadership part of it. And and it's a principle that I I've applied. And and so again, like go going to Moon Hub and working with Nancy uh was similar in terms of this is somebody who's

Really good at uh learning this new space. Uh and that's something that I wanna learn from as well.

I I think that that line of who do I wanna become and who do I wanna learn from is such a powerful filter for those next opportunities. And I think the way that you relate that to Chris, I think is is such a powerful example of that.

And I know one of the things that you've been reflecting on right now is sort of the shifting role of being an engineering leader and the trend that is pushing people to be more in the details now than five years ago or so. And so I was wondering if you could talk a little bit about

That shift and what you've been doing to uh around that and like how you've been sort of focusing in on on technical leadership and being more in the details. Like I guess first off, d I guess like just tell us about your observation there and then w how that's been changing your approach to leadership. Yeah, I would love to connect this um or start. this discussion by connecting it back to Chris.

Who was the leader uh is the leader of Figma. And Chris really taught me the value of being very involved in the technical details. There's a few things that he set up at Figma that were unusual at the time, but I'm seeing it more and more now. Uh oftentimes, senior engineer is a transition level between IC to manager. Uh and Chris elevated that. He was like

You need to be a staff engineer actually to go into management. And the reason behind it is that he really, really value technical leadership from his managers. Uh and this is uh honestly something that I think has been developing in the book. Career path.

There's this concept as well where the author is talking about the technical level for an engineering director is higher than for an engineering manager. And there's a lot of people who make the shift too early and stop their technical learning and get Stuck uh at engineer engineering management because they they aren't technical enough to go to director, nor did their job afford them time to grow technically. It was a trend.

before, but I think has become a lot more true now. Uh and I think in some ways it really started with Airbnb when during the pandemic they had to let a lot of people go. To set some context here, prior to that when you know multiples were really high and every company was hiring. There was a big

power dynamic between employers and employees and more on the employee side. And so what that meant was that as an engineering leader at all levels, a huge part of the job was can you attract and retain talent? And it shifted a lot of the focus. Towards people leadership. How well could you motivate your individuals? How well could you inspire them? Uh how well could you build connections and support them?

uh and help people foster a place where people felt really great about work and really liked their managers. And it was good. I think it was a a good and necessary chef. uh in engineering leadership. But right around the pandemic where Airbnb had to do a round of layoffs, uh, and then other FANG companies had to do multiple round of layoffs.

You really started to shift, I think Ben Horowitz would put it. Uh the shift from peacetime CEO to wartime CEO. And what that means was that companies and teams Now started looking to their engineering leaders.

for a different set of things. Uh and it was a lot around, can you get down in the trenches? Can you make us successful in the face of adversity? Can you lead from the front uh instead of leading from the back? And Uh as a result, I think it really emphasized a lot more of this technical leadership. as a core skill. And now we have AI coming in, uh, which is a brand new space. Uh and again, the roadmap for many teams is not a given. We're not building the five hundredth

checkout flow anymore. Uh instead there's a quite a bit of technical leadership required. A lot of new technologies, uh like changing paradigms and libraries and technologies and I think it's extremely important now for engineering leaders. to be very technically competent, uh, in what their team owns. And so this is a value that I have for myself. It's a value that I have for engineering leaders under me.

Spend time understanding the details of what your team is working on. And the litmus test that I always give my leaders is this. If every time the discussion gets a little bit technical, you need to go call an engineer from your team to come represent the team, you are a leafy abstraction. You are not technical enough to properly represent the team.

Uh you need to go deeper. And there's a ton of benefits to going deeper. One is this ability to be able to represent the team properly. Two, the more technical you are, the more your team will trust Your judgment when it comes to who is doing good work and who isn't doing good work and is is that getting recognized?

Uh, because if you aren't technical enough to recognize that, then people are going to start optimizing for things that are showy instead of things that are necessary and hard, but not Very visible. A technical leader, especially during these times, can be very, very inspiring. Surprisingly, it's an underappreciated. Skill. It's something that a lot of engineering leaders feel like it's optional or maybe further down in their priority list. But to me there are not too many more things.

that are as high leverage uh for an engineering leader, uh, as making sure that they're technically in the details and aware of the day to day and decisions that the team is making. I see this trend pop up in a lot of different places. So that I I really what I like the way that you distilled this too is that they're changing priorities to different skills and that's leading from the front.

And that technical leadership is now a core engineering management or engineering leadership skill. Leadership in AI is technical leadership. So if you're trying to build your career capabilities in that space, like your technical leadership is at the forefront of this. The the last thing I'd want to cover here is

I I'd love to get into just like a s your story for how you started to make this shift and to to refocus on technical leadership. Cause I I know you had told me that, you know, you'd gotten some feedback when you were at Figma around more technical leadership and that you use that as a catalyst.

to to really refocus and reorient your leadership there. So I think maybe it's like the question of like how do you make that shift and what did that look like for you? Yeah, absolutely. And and I'm so glad that you asked this and and that you're familiar with my story and we've chatted because I definitely don't want to come across as like

Hey, look at me. I'm the most technical leader of them all and you should all be like me. Uh, because it it it actually was an area of weakness for me and and I did get feedback on this, uh, where My manager at Figma uh was like, Hey, I will need to see you leading from the front more. I need to see you getting into the details more. And, you know, and it was at that time really that I uh started to notice how high leverage and valuable that.

um who had strengths in those areas and I'm like, they're so effective. Like I I enjoy working with them so much and and realizing that a huge part of that uh was that they had that context and they had that strength. And so uh it's definitely been a a big shift. for me. And and again, part of m me going to Moonhub was that and and you know, I as I said earlier, going to a place where there was no backstop, you know, where like

Well, if I wasn't gonna be that technical leader and get into the details, then the team would just fail. Uh and and obviously we don't want that. And so part of that was was forcing forcing myself to do it.

Uh and and it's definitely been something that I think has been hugely rewarding. We did we didn't even dive into the acquisition between Moonhub and and Salesforce. And so I guess like maybe if you could just tease, you know, looking forward, like where are you looking to grow in this next phase? Now that you're at Salesforce, you're working on Agent Force, like where where's sort of the next area that you're focusing on for career and leadership growth?

Well, I I'm I'm definitely not an expert in this area, right? Uh Figma was the largest company that I have worked at and it was about a thousand people and now I'm Salesforce and it's eighty thousand people and It's given me a lot of appreciation for the type of problems and scale uh that companies solve at this size and and just the complexity of organizations.

You know, w one of the things that I've I've been really appreciating is, you know, when you're a startup, you're building an entire company out of a single piece and you get to shape that piece exactly how you want it to be. Uh and when you're part of a large company, you are now You know, a piece in a puzzle. And so much of what you have to spend time doing is like drawing the outlines of how you fit uh with the pieces around you.

Uh because that's more important than anything else and it m it might sound like just negatives. I have a huge amount of respect for leaders that are able to now take a thousand pieces and make them effective, uh and and you know, get get a complete puzzle out of it with that amount of complexity with that amount of people and and their own motivations and directions that they want to go and everything. I'm trying to learn that right now.

Taking it back to the running analogy, optimizing for scale, complexity of just size, but also customers. I I love it. Chris, we've got some rapid fire questions. Question number one. What are you reading or listening to right now? I am reading uh a book that uh you all sent me uh called Turned a ship around, uh, which has been really great. I'm still just starting, so I I can't say too much about it. Uh I also enjoy reading a lot of fiction. Uh and right now I am reading the last book

in the Sun Eater series, uh, which is uh sci-fi fantasy. Question number two. What tool or methodology has had a big impact on you? You and I were having this conversation around analog hobbies. Uh and I have really gotten more in touch with analogue things in my life.

Especially when it comes around productivity. I I have so many chats with the clots and the chat GPTs of the world that I really felt like in other areas I wanted to get more analog. And so um I've been doing a lot more notebook writing. Uh my own task management system has has come down to sticky notes in a jar and I crumple sticky notes to when I'm done and put them in a jar. Uh I've just really enjoyed this sort of like this kind of physical presence.

Right, uh, of of objects, uh and even task tracking uh that I think can't r easily be replaced by even the the smartest uh AI assistants out there. Analog productivity systems for the visceral physical satisfaction. I'm such a fan of that. I love that. Okay. Next question, Chris. What is a trend that you're seeing or following that's been interesting or hasn't hit the mainstream yet?

I I don't I don't know if I have a good answer here. I'm obviously following a lot of the personal assistant agents uh that have been going around like Open Claw and thinking about how those will impact. different platforms, uh, like your you know, iPhone or Android phone and everything. So I've been playing around with it, but I you know, i it's clearly not

I I guess it hasn't hit the mainstream as like most people, but I'm sure everybody who's listening to this podcast uh is well aware of it. Um and so that that's the main thing that I've been following recently that it's been really interesting. Final question, Chris. Is there a quote or a mantra you live by or a quote that's been resonating with you right now? I've been thinking a lot about the idea of having a growth mindset.

I think something that has been really interesting in my life lately, and especially now that I have kids, is really instilling in me and my my kids and my family. uh the idea that very few things are permanently true about people, uh, and that many things can be changed by just changing behavior or attitudes.

uh or where we spent time. Uh and that can be for anything from uh sports, you know, I I'm not good at basketball, but I I can become good if I choose to spend time in anything, really, like in including non professional, like interpersonal.

uh things that that you might feel like might have been true about you for for a very long time, but maybe aren't that optimal in the context that you're in right now. And so it's something that I think has permeated a lot of my life from both professional to personal, keeping a very loose uh handle on like who am I as a person. Uh and not being so attached.

Two things uh out of a belief that these are kind of permanent things that that can't be changed. Uh, and instead uh having this growth mindset. Uh and this uh uh this willingness to to change and and knowing that you can, uh, if you just make different decisions uh or spend effort in different places.

Chris, thanks for taking the time. Uh I've I've really enjoyed being able to catch up and hear more about your journey and the lessons that have shaped you along the way. Like it was a long time coming. And so uh I'm glad we gotta really, really have this time together. So thank you. Absolutely. Thank you, Patrick. It's always a pleasure.

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