Building Trust as a First-Time VP at a New Company

A conversation with Michael Stahnke, VP Platform, CircleCI

Michael Stahnke took his first role as a VP of Platform at CircleCI. After building relationships and trust over eight years at his previous company, Puppet he found the transition jarring. We talked about why he took the role, what he found most difficult, and how he built trust with different parts of the org — the engineers, his engineering peers, and the rest of the exec team.

It's so great to have you today. Can you introduce yourself?

Yeah, sure. I'm Michael Stahnke, I'm the VP of platform engineering at CircleCI.

You were at Puppet for eight years. Some companies have very distinct cultures, Puppet is an example of that for me. There's something there where the team just really gels in a way that I don't see at every company.

I think it's easier for me to see in hindsight but yeah for sure. I think a lot of that was the cult of personality, founder and leader, Luke Kanies. He was the reason I went there, no question about it. People learned a lot working under him and with him. I think he learned a lot along the way. So we all got to kind of learn together at our own different rates, but he was pretty open about what was going well, and what wasn't going well, and that created a lot of trust in the entire company.

What was it about the CEO that made you want to join?

I felt like he really understood the problem space that our customers were facing. He understood the space, and wanted to solve it because he knew that there was a better way for real, like it wasn't just a, "Hey, we could do this too." It was, "I'm going to..." He created the market of that toolset, in my mind anyway. I mean, there were a few precursors, but they were more academic projects than software companies that were making money, or attracting revenue, or whatever the metrics are that you want to use. He was very driven to build a business, and solve customer problems, have a great product, but use an open source business model. Like it was, it was all just the things that certainly in 2009, 2010, like that was what I wanted to do. So that’s why I went there.

How big was Puppet when you joined? And how big when you left?

The company was about 35 people when I got there. It was maybe 550 when I left.

Yeah, that's quite a different company. Were you planning to stay at Puppet for eight years? Are you the kind of person who loves to have a job and stay for a long time?

Yes. I really wanted to see it through, like I wanted to see are we going to IPO? Are we going to get bought? I didn't make it that long, but we had had several fits and starts down those paths, and market conditions change, and things like that. I wanted to be there for a long time. I think once some of the founders and leaders stepped away at certain points, it was like, "Okay, I'm free to go look elsewhere."

What made you leap to Circle?

I mean, I wasn't really looking, but I wasn't saying no at that point. So I got some recruiter emails, and I guess I can tell this story now because neither of us works at Puppet anymore. They recruited one of my peers and then he was like, "Hey, this doesn't look like a thing for me, but this looks up your alley." I talked to them a couple of different times. It was a long process, I will say. I think I first started talking to them in November and my first day wasn't until April. That wasn't because I needed like three months' notice or anything like that. I think I gave two weeks in the end.

It was a growth opportunity for me. It was the first time that I was going to step into a VP role officially. I had kind of been defacto running engineering at different times at Puppet, either through an interim role or through, maybe there was another engineering leader, but they were more focused on a different division. I ran the enterprise business, and the open source side and they ran innovations or things like that. So I had done a lot. I had worked with the executive team.

I felt like I really understood open source, business models. I felt like I understood Puppet's business model. What was really attractive to me about CircleCI was just being a software as a service company, or a cloud company where if we make a mistake, we can fix it in 10 minutes. At Puppet, if you ship a mistake, okay, you can ship a new fix in 10 minutes and maybe you can put it up on the website in another hour, but now you have to wait for those customers to download that fix, apply it, go through change control, all that stuff. So that fix could be out in the wild for a year and a half or two years by the time it's all done, and 10 minutes versus two years, there's no argument which one's more fun to work with.

Well for sure. There was also being a VP of an engineering organization. Was that something you had been seeking or was that sort of a nice benefit of moving?

It was kind of something I was looking into. It was kind of one of the next steps, I had been a director for seven plus years at that point and running an organization that was basically responsible for 95% of all the revenue that Puppet had, all of those things. So I felt like I had hit a lot of the metrics that were kind of business oriented around leading and then it was, “Well, what's it look like to be a VP or what other opportunities are there?” Working with an executive team, to me, was kind of the interesting thing because I had gotten glimpses of it, being an interim executive at times at Puppet through different, different scenarios. I learned so much every time I was in one of those meetings about how the company ran. I thought I understood engineering fairly well. "Okay. Here's how the bits get from one end of the page to the other." Things like that.

But what I really wanted was, how does this plug into finance? How does this plug into accounting? How does this plug into the go-to-market motion for the entire company? I didn't have a deep understanding of that. I had a pretty decent understanding of it at Puppet, but it was also, I was there for eight years to gather context on it. If I was at the executive level, I could help learn those things from the ground up or understand them as they change or even provide the inputs, engineering, we can see this, we've instrumented it in this way. Our users are doing this, this, and this, therefore the impact on the business is this other thing. That was something that I had no experience doing, and so that was really exciting to me. And just meeting new people, working with new people, I mean, eventually, you're there somewhere for eight years, there's always kind of a, "I wonder if the grass is greener somewhere else."

So you liked CircleCI’s ability to see changes much faster. And then also it being a growth opportunity for you to challenge yourself in a leadership role in a different way that you hadn't.

Yeah. The other big thing was that Puppet had kind of plateaued so we weren't really hiring. We were kind of just backfilling and we weren't growing out and building new things, and CircleCI, it was like, "Hey, we're about this 200 people mark, we just got a bunch of funding. We need to get a whole bunch of engineers. We need a leader to go recruit them and sign them." I was like, "Oh, sign me up, get me on this. It sounds great."

CircleCI was about 200 when you joined, how big is it now?

About 650.

What were those first 90 days like?

Yeah. I mean, it was scary. I wanted to take a bunch of time off between the two roles, because I was like, hey, I've been burning as hard as I could for years at Puppet. We had, the early days especially, we had days where we were up till 2:00 AM and back at 6:00 to do certain things by certain times. Luckily that hadn't happened in the last several years, but I was just thinking about, wow, I've put my heart and soul into this. I'm going to need a little bit of time to decompress before I start something new. That didn't happen. There was an executive offsite to kind of redo a bunch of planning and they were like, "We really want you to come to this." It was in Napa and I was like, "Well, I’ve got to show up to a Napa executive offsite." Like, "What's the point of being an executive if I'm going to miss the Napa executive offsite?" So I went to that, and so I think I had had like a three-day break.

I mean, I think it was very, very little between the two jobs. And got there, and went to this executive offsite meeting with all of my new peers and there were many of them, I couldn't remember all their names, and confused a couple of them a couple of times, I think. We start talking about just having raised Series D, everything was changing to  usage-based pricing from  container-based pricing.

So it was all brand new to me. There were a lot of emotions flying high about all this because people have so much context for all these things that are happening. I was just like, "I don't know, I'm new here." I’m here to help with availability and some other stuff that was on the platform. And I was like, "I'll take care of it." And they were like, "How?" And I'm like, "Oh, well, do you trust me to do this?" Well, they're like, basically, the answer was, "No. How are you going to do that?"

Was that different for you?

That was very different for me. I had never had to show my work before to an executive team. So that was kind of a, "Well, how are you going to do these things?" That was a new set of challenges for me.

It took me a while to get over thinking, “Wow, they don't trust me”. I don't think it's that they don't trust you, it's that there's just a different work style than what some other people had, or what I had at my previous company. A lot of it was, "We should have some indicators. We should have more metrics." It was a shift from, "I trust you based on reputation." to "I need numbers to show me the work is actually happening."

That's fine. I don't even regret most of those changes. They were difficult to go through for me because it was just so foreign. Now it’s different. I was writing a job description the other night and I was like, I needed these results proved through metrics like I was literally writing that down in the job description because it's just such a better way to work.

It was a growth thing for me. I know that sounds really stupid when I say it out loud, like, "Wow, this person did a bunch without a bunch of numbers." It's true. I did a bunch without a bunch of numbers at my last job. I got here and that wasn't acceptable. So that was a new thing to learn and work with. By default, I'm not a person that slices and dices data and overanalyzes it. I have people that I hire that do a lot more of that than I do, just because it's not my forte. So it felt like stretching a new muscle and learning how to use it. Even today, I wouldn't say I'm nearly the best at those kinds of things, but I can apply it appropriately across getting the function of my job done.

How much of that was a culture shift, wanting the data versus starting as an exec at the company with a trust bank that's zero?

I think it was both. The expectations for how things operated were very different, so that was a culture change, no question. When I’ve hired people that I worked with in the past, they usually ask, "What's really different about this culture?" And I'm like, "You better show up with numbers." That's pretty much my default answer when somebody asks about the culture. From a trust perspective, I didn't realize how much I had leaned on these relationships that I had built over eight years. And some of these people I knew before that and worked with even before that eight years. So I knew some of these people for 15 years. When I went to this new company, I knew zero people at this company. Which for me was a weird jump.

It was just, I'm jumping right in. I had almost no trust with anybody other than, "Okay, they thought he was good enough to hire as an executive." Winning over the execs was one thing, but winning over the engineers was tough too. I had written some of the code at my previous company. I had stepped through that with them. They knew, "Okay, this guy knew this product in and out. He had done everything in those roles at various capacities at various times and helped people along." I had so much trust from those people because they'd seen all the work I had done over the years and the culture that I brought, and I like to have fun at work. I think they saw that and appreciated that. At CircleCI, I get there and they're like, "Oh, got a new VP. Cool. Another guy up in the boardroom telling us what to do."

Building trust with the engineers as a VP was a lot tougher than I would've ever guessed. 

So I tried to connect a lot more with the people, tried to understand their problems from like a technical standpoint or talking through kind of the outcomes that they could receive with the right technical changes, or whatever. I mean, even today, I don't think I'd ever be accepted as, "Hey, that's one of us up in the executive suite." I just don't think that's how they see it.

When I was at Puppet, I was a leader, but I think it was like, "Yeah, that's one, that's our leader. That's our person." It was a very different setup than what I have today. I think it's changed and I've gained a lot of trust over time at CircleCI, but I think it's still mostly with members of engineering management primarily or very, very senior ICs. I think the average person, probably looks at me like, "Hey, there's the guy who manages things through spreadsheets and just thinks we're rows in a sheet, and makes some changes here and there." And I understand if that's what you see from the way that I have to work.

I hate that part of my job. I think of what I would think if I was in their chair. And I'd be like, "Wow, I hate what this guy's doing right now." I try to keep that level of self-awareness and empathy for where those people sit. If this is your first engineering job, what do you see from this team versus if you've been around at many different companies through different ups and downs, and things like that? So I try to keep grounded in, what do the people doing work think about their leadership team?

It sounds like you when you took a leadership role at a new company you didn’t realize how much you had relied on your past to influence the team?

Oh, I hadn't really thought about it. My experience in those eight years, I was in an office for a while and then moved away, and so then I was remote. At CircleCI we were 100% remote. So even just in that, I had rapport built up in other ways, like the water cooler talk, the going to a bar, whatever. I didn't have any of that to start with. When the executive team got together, I would take very big advantage of meeting people, whether it's in the morning prior to an offsite, getting coffee, or it's at lunch, or it's at dinner, or it's happy hour, whatever, it was like, I just needed that face time with people. Not too long after that, a couple of quarters in, we hit a pandemic. So all of that stopped. I don't know how to operate where I don't at least get some kind of face-to-face touchpoint here and there. That was really difficult for me, and honestly still is if I don't get those touchpoints.

What feels different about being in person as it relates to the work of leadership?

To me, it's all about trust. When it comes to my career, the word trust would come up more than any other word. You trust somebody more by talking about the non-important things, or doing, sharing an activity, whether it's literally walking to a restaurant, having dinner, or walking back, that builds more trust than a Zoom call for three hours, talking about a problem will. That's just how it works. Sometimes you need that trust and have somebody see you as human and not a business process.

Well, right. It's about seeing people as humans. People do coffee chats and things like that to bring humanity into a remote-only connection, but that can sometimes feel awkward.

Well, anytime you basically have to schedule your water cooler talk, it just doesn't come off as authentic. I know some teams do it and sometimes those things are great like I have teams that have kind of a weekly happy hour, or a weekly social time, or whatever, and that's fine, I don't have any problem with them, but I still think they would all be like, "Wait, if we could get together in person, we would do that tomorrow." I think they all are pining for it.

Yeah, in a three-hour business meeting, we're talking about the problem, but we're not really talking about how we interact with each other and the relationships that are omnipresent, but we're not really addressing.

Right. Right. We end up all business all the time. I think that's why Zoom burnout became a thing for a lot of people. It was different than traditional leadership burnout, engineering burnout, or whatever it was. It was like it was a whole new level of different symptoms, different occurrences. I caught that many times, when it was, wow, I spend 8, 10 hours a day on calls, that's just my job a lot of days. Some days that was okay and some days it sure wasn't.

I want to go back to what you said about the first 90 days being pretty hard. When did it start to ease for you? When did you feel like, “Okay, I've got a trust bank and I understand this new culture?”

It was a pretty gradual process. I focused on being a great teammate to the other engineering leaders — the chief architect, and the VP of product engineering. I wanted to make sure they were in my corner and I was in their corner 100% of the time. I worked really hard to make sure that if I was in a meeting where decisions were being made or discussed, they would get notes or output from it. Particularly the chief architect didn't quite have the same level of access that the executives had to certain things, and so I would take notes and share them with him and things like that. That's the first thing I need to build trust. Can I trust the two peers that I'm working with constantly, all the time, and them me?

After that, some of it I imported because I hired some people I had worked with before, which comes with free trust and that's a great way to do certain things. Then I hired different people and worked with them to set goals and we accomplished some things together and that worked out really well. Luckily when you're at a company that's growing super quickly, people have all sorts of opportunities to demonstrate what they can and can't do, or even, and even something they couldn't do six months ago, they can do now because they've learned it. You can establish a lot of trust through all these opportunities you have. I got to hire different people, hire different managers, bring in different engineers, and satisfy new criteria.

Ultimately when it comes to trust,  can you own your results? I was brought in with a set of results in mind, I hit those very clearly the first several quarters I was there, they moved the, we move the, what the expectations are of those. They get more difficult over time. Now it's definitely not a slam dunk to hit all of them anymore. But when I got here, even hitting them at the numbers they had set was seen as a tall order.

The number one way to build trust is if somebody says, "I count on you to do this." You better do it. There are more nuances than that, but a lot of it is say what you're going to do and then do what you said. That's the easy way to build trust.

It also seems like you did lots of small things to build trust.

Yeah. I think some of the other stuff I tried to do was talking to all of engineering shortly after I got hired. There's a stage and you're doing presentations. I was really trying to say, "Hey, I'm pretty new here, but here's how I think about the problems that we have." I tried to go over the principles that I approach things with and talk about the value of the customer having to come before our own problems. Things like that.

I had some pithy sayings on some of that. Some saw that as a big problem. They were like, "Wow, this guy cares more about the customers than he does about his employees." And I'm like, "Well, I don't want to say that's totally false." It's not that I want to say, "You need to kill yourself to satisfy a customer." But if we don't satisfy our customer's needs, none of us are going to have jobs anyway. It was just such a weird thing to get in an argument with certain engineers, and they wouldn't even come talk to me about it. I would only get it through back-channel feedback.

Yeah, they're not coming directly to you. You’re the new VP.

That was another really interesting thing I learned. People wouldn't actually talk to me about the problems they had with me once I'm a VP, or at least a VP coming in greenfield into a new environment. At my last job when people had a problem with me, they'd walk up and be like, "Dude, you screwed that up. You’ve got to go talk to this person and make sure they're okay." That's easy to fix. When you have  a rumor mill swirling that you're only tangentially aware of at best, it is very difficult to work with. So there was some of that that I had to learn how to work with in one way or another.

People see you as an authority figure. No matter how hard we try to be personable and human, there's something about it that can put a barrier for people to come and talk to you directly.

Certainly, certainly. That was something I had just dismissed in my previous life.

Meaning you weren't aware of it or thought that wasn't going to happen to you?

I just thought it didn't happen to me.

Was it the presentation and conversation afterward that made you realize or was it a series of moments that lead to realizing you needed to build more trust?

It took a little bit of time afterward. I heard feedback from some other people that I trust quite a lot. They were like, "Hey, this did not land as well as you think it did with certain groups of people." And I was like, "Well, why not?" They kind of talked me through it and it was just like, “Huh”. What I realized was people were not starting from a place of, "I trust this person and therefore I can build upon those ideas in my mind." It was, "You are an executive, you're the man, you're the person I'm selling out to." Whatever it was in their mind. So anything I said could be construed kind of in the other direction, it's not just like, I kind of hate to phrase assume good intent because I think it has so much baggage behind it, but I didn't have good intent that people could start with and I didn't have trust to build upon. I didn't. So some people took the opposite approach of like, "I am going to parse every word this person says and pick it apart for the evil bastard that he is." And that was just what happened.

I had a similar experience. I realized that sometimes people get scared and so they want to look, they look at the worst because they're scared. As a leader, you’re the easy target.

Right, right. And they connect dots that were not connected in any way from the way that we were, I was operating, but because this thing went wrong and this other thing went wrong, therefore in two weeks from now, this other thing's going to come down and I'm going to get fired on Tuesday. It's like, “Wow, that is not even close to what's going to happen.”

People have their own narratives that they build, and so a lot of that was, “How do I set more context for the way that I'm thinking and talking?” For a long time, I wrote an email out to everybody that was in my organization every Friday to kind of say, "Hey, here's how I spent my week. Here's what I learned this week. Here's what came up as top of mind as a discussion as we worked with the exec team or as the engineering leadership team worked together." Or whatever. Eventually, I got away from that because I felt like the context didn't help a lot of the engineers that much.

I still send that weekly to my engineering management staff. I have 35 people in engineering management under me at this point, so that's a sizable group. Whereas at that point it was like 35 ICs originally. So I've kind of tried to keep around the same number of people on those distribution lists, but it's, that's one of those things I can do to build trust. I can tell you, "Well, here's how I spent my week." Of course, I don't talk about every single thing because certain things are confidential, but try and share context of how is your VP spending their week? What are they doing? What are they learning? What are they thinking about? What's top of mind? I get a lot of feedback that people really appreciate that. If I miss a week, which happens pretty rarely, sometimes people will notice. I get an email from one or two people being like, "Hey, where's that email this week?"

You started with 35. How many are in your org now?

200ish.

That's a sizable increase in folks.

Yeah. We got to grow engineering, which was one of the things that I was sold when I got here. Totally planned out to be true.

I want to go back one more time to that moment when you gave that presentation, you'd been at the company 60 ish days. You got feedback that maybe it didn't go as well as you would like, did you have that moment of like, "Oh shoot, I have to build trust."?

I don't think it was one moment. There was a lot of, "Oh, I have to work differently here to build the trust of these people, because it's not like automatically granted." It wasn't, "Oh, here's how I would've reworded that presentation." Or, "Here's how I need to talk to these engineers directly." It was just, "Wow, this is starting from a different position than I'm used to. I need to think about how I work." 

It was around that time that I started asking around people that I've worked with before, "Hey, how do you do this? How do you work with other execs that don't have all your trust? How do you work with new teams that don't have all your trust?" And I remember sitting down sometime that summer with the founder of Puppet, like we were sitting out in front of a bar, having a drink, and talking about it. He goes, "Man if you figure all this out, let me know." Because, he's like, "Because this is terrible. It's really hard." And I was like, "That's classic."

That's encouraging. (laughs)

Yeah. (laughs) I remember him saying, "It's really hard to gain trust with certain people and certain individuals." I think I asked him about interactions with other executives and he's like, "Sometimes you need to figure out their motivations a little bit, because you think it's all, 'Hey, we're here to solve company problems.' And other times it's very personal, and other times its very ego driven." There was just this whole, like a bunch of cynicism, and he's a cynic by design, but I mean, like it was like amped up. And so it was just a, it was a bunch of, there's a lot there, and so shortly after that, I think was when I went out and found a coach, because I was like, "I'm going to need more help with this. I'm weak in this spot."

That shift is really hard. Getting a coach is smart. It’s not like you grew up through the organization and then became a VP. You sort of choppered in as a VP, without trust. It’s a different experience.

It's totally different. You just don't have that organic trust that you've built over time that you can call in or say, "Hey, people, this is this." I think people think I'm authentic and I deliver things with, I think generally now people believe what I say, or want to believe it, or think that I'm not trying to pull something over on them, but they're also like, "Well, he's still phrasing things like an executive and trying to paint the picture the way it's supposed to be painted, maybe how then, how I would see it if he just showed it to me without talking about it." All those things are true, that's just how it happens. So I guess I say, I do understand, the little bit of cynicism that a lot of people do carry from an executive team, and being an executive, sometimes I'm mad at myself for it.

What about building trust with other leaders inside the company? What was that process like?

It took a long time for a couple of different reasons. One of them was there was kind of a hierarchy of two tiers of the executive team. There were the people that reported right to the CEO and the people that reported to some of those people. And so C-suites versus VPs kind of thing. In certain cases, I felt like I could say something and it didn't matter unless the CTO also said it, then it would matter. It was kind of like my voice didn't carry a lot of weight. That was when I was like, "Oh, I need to work on this trust thing with them because I don't know how this works."

So I tried to make it a point to connect to each of those executives in smaller groups, because at a meeting with 10, 12 people, that's not, and it's over Zoom, like it's not, that's not going to be a great, a great situation for building trust. It's kind of, "Let's get the work done and carry on." So I tried to connect to those people one on one, or talk to them, or get smaller things that we're working on together. That was pretty easy to do with certain executives because our work just happened to overlap in nice ways, product management, and engineering, not too hard to get closer together to connect. You may not always agree with things, but your work overlaps all the time.

The customer engineering kind of customer success side was really easy for us to connect to because of their support and they have the kind of some of the intake process from customers that I need to learn about. So that was really easy to build a relationship there. Marketing was pretty easy, maybe not with, not necessarily with just the CMO, but like even with a lot of that team, because I do a lot of public speaking, I do some blog writing, it was just, I had different stuff that could easily inject into the processes that they had. So sometimes you just volunteer for that and that helps. I had to make a lot more effort for like legal, how often do I interface with legal? Not a ton if I'm doing things right.

Then some of the go-to-market revenue side of things, sales, which was different for me, because in my last job I was pulled into sales calls all the time, and here I wasn't, and it was just like, "Oh, well I'm available. You can get me in front of the customers. That doesn't bother me." Finance, accounting, and things like that was the space where I think I was just like floundering. I didn't know how I was going to connect to these people at all. It was because it was definitely the weakest in my toolbox of like things I understood. I never took an accounting class in college or anything like that, so I just didn't know anything about this space. Accounting seemed like fake math to me because I know what the balance is on the account and this has all sorts of different numbers, and they're colored funny with parentheses around them. It was a whole bunch of stuff that I didn't really understand. How do I engage in this? Because a lot of times they're also telling you what already happened. It's like, "Hey, you had this much money, now you only have this much." And you're like, "Cool." Like how do you have a good conversation to build trust around some of that?

So it took a while and it kind of came down to when we started negotiating things like giant AWS bills of, we're going to do a commitment on AWS and things like that. Okay, now I actually have a really good thing to go work with the finance planning and accounting teams on.

It took a lot of time to build relationships with other leaders. I don't think I could overstate how long some of that take. I mean, it was more than a year for certain areas, certainly.

Yep. We all talk about how important building trust is, but we don't talk about how hard it might be and how long it takes.

Yeah. I mean, a lot of this stuff comes down to, I mean, classic relationship psychology, and trust takes a long time to build, you can lose it instantly. That's just how it works. So you have to figure out, okay, if you lost trust or if you didn't start with any, how do you build it? And that's just tough. It's not even unique to business. Personal interactions or whatever, it's all the same.

What about HR? That must have been an important partnership because you were scaling the business. So lots of hiring, onboarding, people stuff. Was that another one where building trust was easier because you had projects to work on?

We definitely had to work a lot because of this, when you're hiring constantly, you are in constant contact with the recruiting team, who rolls up through HR. And then you have people that have leave or benefits questions. We were talking with HR literally every day for months, months, and months. The other thing is HR, when I talk about trust, I think about my position and then I think about HR. I think HR would be way harder to build trust in, just because there are people who are super cynical about HR.

They really can be.

They kind of come at them with like claws out in a lot of ways. It's just a very, and so sometimes I would have to step in and kind of be like, "Hey, can we all assume that everybody's trying to do good work here for a second?"

Retract the claws. (chuckles)

Yeah. (laughs) No one's out to get you like, "Let's, can we talk about this?" So sometimes I would have to step in and help with some of that. Other times I would be just as mad at HR because something I needed to happen didn't happen the way it needed to happen. So I'd go over to the VP or leader at the time of HR and say, "Hey, I needed this. Didn't get it. What are we doing about it?" That kind of thing.

I love too how you said that you build trust with them, but that also that you help build trust between the rest of the team and HR.

Right. Sometimes you have to lend your credibility, where it's if you trust me, know that I trust this person. I know that's not necessarily like a one-to-one pass-through, but maybe it gives you a 10% boost or something like that. I try to do that when it's genuine. I won't do that, I won't do that if I don't trust somebody, I'll say that. Like, I can't lend my credibility out if it's not real.

I've been in a people role, I understand. People came at me that way, and it was hard to build trust, yet you have to work together all the time. As a leader sometimes we have to let people go or there’s organizational debt. We have to work with HR to sort that out.

Yeah, that’s all true. When I first got to CircleCI, HR, I think was about two people, that 200 mark. A lot of it was, "Hey, we did this. Go make the paperwork true." So it was simple in certain cases, it was like, "Hey, I'm going to retitle this person." Or, "This person doesn't work here anymore." Things like that. That was really easy. Then as we got more formal with HR, I think that's when the frustration grew a lot more where it was like, oh, this process is a multi-week, step thing. And like, and that's all the right thing to do. It's the right level of maturity to go through. It was just sometimes it was like, "I kind of miss the days where it was like, I just made a decision and told somebody to now update the paperwork."

There wasn’t a lot of organizational debt when I got there. It was more that after I learned a little bit about who was in what roles, I was like, "Hey, here are some adjustments that I think we're going to have to make." Almost everybody stuck through it, they were like, "Yeah, that role probably wasn't the best for me." A few people opted out at different points, and that's fine too, but I didn't, I don't think I had to fire anybody in like my first six months or anything like that.

It sounds like things were in a good place.

Yeah. I mean, to me, it was, I'm going to talk to people about what I expect out of the role and see if they can do it. And they're like, "Wow, that's not really what I thought this role was." And I'm like, "Well, the thing you want is actually this other title, can I interest you in that?" And they would usually say, "Yeah, let's do that."

You talked about like getting trust from other people. How are you at giving trust to the team and other leaders?

I think I grant trust really easily. I have a lot of faith in people. There are times that has caught me, where I've given too much trust and stayed a little too hands-off, given too much autonomy to other leaders and had to circle back. 

Once I turn over that rock, I'm like, "Wow, there's a lot of stuff under that rock." That's a thing I'm still trying to balance today — how do I grant the right amount of trust to grant someone to feel like they can operate with autonomy and some ownership and empowerment, but it's not so hands-off that they're empowered to do the wrong thing over and over again? Or the wrong direction at full speed?

So that's still a balance. I mean, I'm still growing as a leader. I think most of us are, no matter what your role is, you get new scenarios and new applications. Humans aren't computers, they're non-deterministic. A scenario that worked yesterday may not work today. I think by default in a lot of cases, I've granted too much trust initially. I think maybe I need to grant it more provisionally a little bit, or I need to still empower people, but maybe have a little more checkpoint set up and say, "Hey, I'm going to let you totally own this space, but you're going to have to tell me how this is all working with these criteria filled out in five weeks, or four weeks." Or whatever it is. Then we're going to talk about it again, and again, and again because I've had some misalignment issues before with my directs and even with other people that I work with like peers. Like, how do you manage your peers when they're not doing the things you need to do? That's another trust relationship. You’ve got to build trust and then talk to them about what you need. So it's a fascinating thing that I, again, I keep working on and I, sometimes take the right steps, sometimes I step right in it.

That's called leadership, right?

Yep. Yep.

What advice would you give to somebody else who is navigating a VP role for the first time at a new company?

Learn your business inside and out. I know my department inside and out. I know how to run an engineering team, but understanding the business, what are the critical metrics that this company cares about and why? Do they care about them because they cohort them with other teams, with other companies of their size? Do they care about them for investor relations? Do they care about them just for their... Like, what do they care about? Why? Is it net dollar retention? Is it gross margin? Is it revenue per employee? How are all those calculated? When are they calculated? How do you recognize revenue? If you understand all of those things as a leader of any department, you are way more effective.

I will say that some of my favorite things are when I get praised by our CFO or accounting because I'm talking about gross margin or I'm talking about the cost of goods sold inputs into the gross margin, or net dollar retention based on cost acquisition for this type of a customer cohort. I like when I can participate in those conversations for real, that is, that's trust. Like that's just being like, wow, my engineering leaders are 100% invested in this business. So to me, really learn the business. It's hard, but sit down and do it. That's the hard work that'll make you better, for sure. I thought I had a lot of that, and I had a good foundation, but wow, there was so much more to learn that I totally did not, did not have yet.

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