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“Finding Flow” in Engineering Leadership

with Rob Zuber

February 8, 2022
“Finding Flow” in Engineering Leadership
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ABOUT ROB ZUBER

Rob Zuber is a 20-year veteran of software startups; a three-time founder, and five-time CTO. Since joining CircleCI, Rob has seen the company through its Series F funding and delivered on product innovation at scale while leading a team of 150+ engineers distributed worldwide.

Before CircleCI, Rob was the CTO and Co-founder of Distiller, Continuous Integration and Deployment platform for mobile applications acquired by CircleCI in 2014. Before that, he cofounded Copious an online social marketplace. Rob was the CTO and Co-founder of Yoohoot, a technology company that enabled local businesses to connect with nearby consumers acquired by Appconomy in 2011.

Rob holds a Bachelor’s degree in Applied Science from Queen’s University in Kingston, Ontario, and lives in Oakland, California with his wife and two children.

"When you start a company or you end up leading a very small company, the decision about how many people you end up managing is external forces on the company. The company just grows and your team grows to support it. And no one is saying, ‘Hey, it looks like you're ready for this...’

And so I think so often what you see is early leaders end up exiting because that transition happens faster than they were prepared for. To me, that's a really fascinating dynamic because a lot of people coming into organizations are both opting in and getting selected in for the stage of the organization that you have...”

- Rob Zuber   


SHOW NOTES

  • Rob’s reflections on recapturing the “first-time coding” experience (3:08)
  • On finding flow as an engineering leader (6:48)
  • How Rob thinks about his role as CTO & why he brought on an SVPE to support (10:48)
  • The “One Thing” moment & finding flow leading engineering teams (15:21)
  • How do you intentionally protect maker-time (20:14)
  • Balancing challenge & support to create flow (24:21)
  • Frameworks for personal discovery or delegating executive responsibilities (29:35)
  • On introducing resets & retro-ing your org (34:41)
  • Rapid-Fire Questions (38:37)
  • Takeaways (43:28)

LINKS AND RESOURCES

  • “The One Thing: The Surprisingly Simple Truth Behind Extraordinary Results” by Gary Keller (book)
  • First Team concept (definition)
  • How CircleCI modeled its security training after DEF CON’s capture the flag (article)

TRANSCRIPT

In this episode, we have a conversation with Rob Zuber CTO at CircleCI who shares some of his thoughts and musings on the quest to find flow as an engineering leader,

We cover the challenge of recapturing the first-time coding experience. How Rob thinks about his role as CTO and why he brought on an SVP of Engineering to support him. What it's like to find flow leading engineering teams, balancing challenge and support to create flow, and a bunch of different frameworks for personal discovery to help you find what brings you flow as an engineering leader.

Let me introduce you to Rob...

Rob Zuber is a 20 year veteran of software startups, a three-time founder and five time CTO. Since joining circle CI Rob has seen the company through its series of funding and delivered on product innovation at scale while leading a team of 150 plus engineers distributed worldwide

Before CircleCI, Rob was the CTO and co-founder of Distiller, a continuous integration and deployment platform for mobile applications acquired by CircleCI Before that he co-founded Copious and was the CTO and co-founder of YooHoot.

Enjoy our conversation with Rob Zuber.


Wonderful. Well, Rob, just to begin, Jerry and I both just want to say welcome to the show. It's so great to have you here.

Rob Zuber: Yeah, thanks for having me. I'm excited.

Patrick Gallagher: Awesome. The purpose of our conversation: we're on the quest to find flow. And, as I'm sure you've known through your life and career, that moment of flow is absolutely elusive to find. So we figured the best way to enter into this conversation was with a big question, knowing that it's likely going to open up a lot of doors where we could take this and all the different elements in your life that have helped you find flow with engineering leadership.

So I was wondering - and we could start at the beginning of your time at CircleCI - I think the interesting part of that story is you start off having managed about 8 people. And since that time you've gone to manage over 200 people.

Can you tell us a little more about that story of growth? And what was that like? What did you learn? And what are the big moments you reflect on from that period?

Rob’s reflections on recapturing the “first-time coding” experience

Rob Zuber: First of all, I want to be very clear. I haven't figured this all out. Like I think flow is a really interesting thing. And I think that as a software developer, it's one of those things that experienced and absolutely loved, right?

"Oh my, is it five o'clock in the morning? And all I've eaten is like these Cheetos or whatever. But I just, I don't even want to go to bed still because I'm loving what I'm accomplishing right now?"

And I do think there are other places I've experienced that in life.

I just want to be really clear. I've been thinking about this concept with respect to leadership lately of, what would that feel like? And can you capture that? And I do believe it's possible. But it has to look a bit different.

And so, to answer your question, going back to the early days of CircleCI. I don't know what the exact numbers are. I think there were 14 people in the company, or at least I've said that enough now that I believe it myself, and there were three of us who got acquired through an organization called Distiller.

We were doing CICD for mobile. CircleCI was, obviously very small back then or relatively, but was doing really well. I had a great customer base and we felt like standalone mobile wasn't going to be as interesting as packaging that together and bringing the bit that we have built to what CircleCI was doing.

And of those three folks. One of my two other partners in the business also with CircleCI, Jim Rose, who's the CEO and has been the CEO since sometime in 2015. So we joined mid-2014, August 2014.

And it was a very different place. Unsurprisingly, CircleCI was primarily engineers. Unsurprising for a company of that size, particularly their company building products for engineers. There was a lot of intuitive sense of this is what our customers are looking for. This is where the opportunity is. You know, it wasn't a lot of focus group necessary to just say, okay, we're software developers. This is the problem we have. Can we solve that problem for other folks?

And so it was fairly flat, I would say. I mean also probably unsurprising. Paul, the founder was the CEO at the time. And just a bunch of folks doing great work, trying to solve the problem of the customer that they understood.

But there was a desire, a need, all of those things to grow and to continue to build the business or to start building the, what I'll call the business, which I hate that word, but I don't have another one for a second...

All of the other elements of what does it mean to build an organization like the organization we have now? Right. marketing, sales, G & A, like, basically anything that wasn't just people with hands-on keyboards writing code and starting to think about putting some management structure in place.

And, you know, there was sort of just some fortunate timing, I guess, in that we had joined because we had built a product that was interesting to the organization, like to CircleCI on the folks that were there. But Jim and I had both, we had been working on a different business for a few years and it was only the tail of that that became Distiller.

And we had been in the industry for a pretty long time. So it had a decent amount of experience, both building small companies, growing those in some cases, working in slightly larger organizations, just bringing a lot of different dimensions to the table.

And effectively Paul said, "Hey, you know, I'm actually interested in getting some support doing this. I don't know if building a company is the thing that I'm really excited about right now versus just building product and like, thinking about where the product is going..."

It was very, just sort of this realization from Paul, "Hey, this isn't really what I want to be doing. It seems like you might be able to help us out here," whatever. And so it was a bit of an opportunistic moment to just say, "Okay, sure. Let's try this and see how it goes." Right?

And I think that the number eight, that I had joked about, was actually eight prior to this organization had, you know, had eight people I think was the largest team I had ever managed.

Cause that's what happens when you build a bunch of startups as your career, right? Not a lot of people around to manage. And so, we just started on the path. And sorta like, it sounds absurd, but like one thing leads to another and then you just, you have a lot of people, all of a sudden. Right?

On finding flow as an engineering leader

Rob Zuber: And I think one of the things that I was reflecting on with respect to that is when you sort of get promoted through roles, there's a whole bunch of "external governors" on the rate at which you do that, right?

"Oh, it feels like you're ready now to manage 20 people, or 40 people, or manage some managers because you have a department..." or however you want to think about it. Right?

But when you start a company, or you end up leading a very small company, the decision about how many people you end up managing is external forces on the company, right? How much are we succeeding? How much revenue do we have? How many people do we need to fulfill the needs to meet that revenue?

I dunno if I've explained that well, but... The company just grows and your team grows to support it. And no one is saying, "Hey, it looks like you're ready for this." You know what I mean? “It looks like you're ready for this.”

And so I think so often what you see is early leaders end up exiting because that transition happens faster than they were prepared for. And I'm not saying that I was perfectly prepared for that. I'm just saying like, to me, that's a really fascinating dynamic because a lot of people coming into organizations are both opting in and getting selected for the stage of the organization that you have.

When you look at these, I mean, pick it. Zuck? Right. That guy just thought he was going to run an organization of three people. And I have no idea how big Facebook is. But... so you have to find different models to deal with that because the "I'm just going to stay at this level" is not an option.

I guess it's an option at some point. You could just say, you know what, we're going to hire someone to come in and take over whatever. But If your question is what was that like? That was like a lot of learning.

You know, we love expressions, like "beginner's mind", but if you want to go from 10 people to 250 people, you have to know that every day is going to be different, right? Your set of problems is going to be new and different and you probably don't have the answers.

And so if you feel like you have to have the answers, you're probably going to put yourself in a worse position than if you build the frameworks to get the answers. And just openly acknowledge, like, "Hey, I don't necessarily have all the answers here, but I'm totally willing to put in the work and figure it out. And I know how to get answers. I know how to get ideas. I know how to work with the people around me and bring them in to find people outside and bring them in."

And if you love to learn, there's really no better experience. If you feel like you have to show up with everything it's probably not going to work out that well. That'd be my take.

Patrick Gallagher: I feel like the quote you just shared about "build frameworks to get the answers" epitomises your approach from just our previous conversation. When we were going back and forth and sharing a lot of frameworks that have been so important to you.

And a part of all this, talking about is when you think about flow and achieving this sort of sense of ease as an engineering leader, the conditions that create that state as an engineering leader - and as I'm sure as you're growing so fast dependent on these external actors that you don't - the source of that sense of fulfillment in flow is different than as you're coding, and as like the beautiful image you mentioned, of like the Soylent staying up late and just like trying to survive, but loving what you're doing, I think there's a lot of people that relate.

So now, you know, here you are. CircleCI has grown to over 250 engineers now in the organization. And so you're making a new transition now and there are some very, I think, important frameworks that you're sharing with us about that.

So can you tell us a little about your current transition now? How you're thinking about that and some of the frameworks that are shaping your thought process around this next step of organization-building?

How Rob thinks about his role as CTO & why he brought on a SVPE to support

Rob Zuber: So, let's acknowledge the transition first. So yes, I grew the organization to about 250 members of the engineering organization. That's the 250, you know, ICs, but the overall organization, including management structure, et cetera.

And then made the decision to bring in an SVP of Engineering who reports directly to our CEO, has management responsibility for the entire engineering organization, and then shifting my role specifically to... if you're watching this, I'll have to say air quotes, you know, for people who aren't watching a video, but "More CTO things" because CTO is such a fascinating title that everyone does it differently.

And I think that actually, the fact that everyone does it differently is reflective of the kind of thinking that got me there. Which is people do it differently because they bring different strengths to the table and finding the right balance in your organization is probably more important than what any one person will put on paper about what a CTO should be.

And so, I think when we were talking, I referenced this earlier. I happened to be reading this book, maybe a year or two ago at this point, called "The One Thing."

When I read books, they tend to inspire new ideas that maybe aren't even the things specifically in the book. Although I think that the book is great. And there's this concept in the book of a clarifying question, like "What is the one thing that I could be doing right now that makes everything else either easier or unnecessary?"

Which is a fantastic question to ask yourself. If you don't ask yourself that question often, please do. So let's just leave that one there.

The thing that came to me out of that was bigger picture, "What is the one thing that I should be doing for this organization? Like what am I uniquely qualified to do on behalf of the organization to make us successful? "

And then as soon as you apply the context of your organization and yourself, whoever might be listening to this, your answer is going to be very different from my answer. And that's totally okay. That's why people do this job differently.

I talked a little bit earlier about the rapid growth of organizations and people who adapt and sort of find ways to continue to contribute. And those who struggle, a lot of that is being willing to ask, "how can we be successful as an organization? What do I contribute to that versus what does the world expect of me based on the title that I've been granted?"

Or however you want to think about it.

And so I was really asking that question, like, "What is the thing that I am most uniquely qualified to do in this organization?"

And so to apply the CircleCI context, again, we are building products for people like me, right? Like in some grand, sort of hand-wavy, "people like me" or "people wearing shoes that I have worn" however you want to think about that. I've been a software engineer. I've done product management. I've done engineering leadership. So, we do different things for each of those folks.

And of course, different people have their own organizations. But within our organization, someone who has the "executive context," let's say like understanding of where we're trying to go as an overall business and the personal experience of having lived a huge part of what our customers live every day and trying to do puts me in a great position to really connect the dots for folks around exactly that.

"Where is the market going overall? How do we help enable that persona, that user, customer, however you want to think about it within that market? What are they trying to achieve and how can we help them do that better from my own personal experience? And then how can we support that kind of product experience with the right technical investments?

And linking all of that together is generally hard, not because honestly, it takes a special brain, but rather because it's being in the right place. Again, the executive context, the business context, the product context, the personal experience, having all those pieces is unique. And I've been in the organization for seven years. So I know a lot about this biz, like this specific CircleCI organization business.

And so contrast that to... coming into this organization, having run a team of eight people in the past and looking at the challenges of scaling an organization. Those are two different sets of problems really. Or can be two different sets of problems.

And so saying, "you know what? I bet there are people out there that know how to do this, have done it really well in the past, and can bring some of that experience and shaped that experience by our context."

Like I'm never a big fan of the, "I'm just going to execute the playbook that worked somewhere else..."

But bring a set of those experiences, be better positioned to help with that set of challenges. And then allow me to focus on something that's much more about the customer and the market and how we meet those needs. There are tons of intersections there. We all know that in engineering leadership. But really that was what led to this transition for me.

The "One Thing" moment & finding flow leading engineering teams

Jerry Li: Yeah, that's really helpful to have that context and journey. If we are able to going back to the overall theme of finding flow, since we're exploring. So I'm curious to learn from your perspective that you've been in engineering before and have been leading teams...

Do you have a few moments to remember that exemplify "Oh, this is the moment I feel the flow again?"

Rob Zuber: I'm trying to think of somebody. So I'm going to start by just explaining how I think about that. I think that some of the key elements that I was telling you before that I just started reading the Art of the Possible.

But one of the, some of the description that they use, the language that they use in that really resonated with me was around sort of everything else falling away, Having this clear sense of, this is important. This is priority. You know, all the rest of this is distraction. And I think that's, to tie a couple of things together. I think that's what appealed to me so much about that book "The One Thing."

And I remember now that you mentioned it, this element in one of the closing chapters, I think where the author is describing, "if you do this... if you adhere to this set of principles or this principle is highly complex, if you adhere to this principle, a lot of stuff is going to look like it's on fire around you. And you have to be okay with that, right? Because as soon as you stop to put out all those little fires, then the big raging one in front of you is going to keep going. And the whole point is identifying "If I put this out, these other problems get smaller."

And to me, that relates a lot to how flow feels.

When I look back on those moments in engineering. It was, "I know I'm ignoring everything around me..." like, I don't know if I want to say this by probably even ignoring my personal health at some point in here, because I'm so invested in what I'm doing. and it's so fulfilling and rewarding that, it's easy to put those things out of mine. I think it's finding that balance.

And so, as I try to think about that in the context of leadership. I think one of the places that we're challenged to get that same state is feedback cycles. Right? Like feedback cycles in software development can be in seconds. "Oh, I wrote the thing. It did the thing I thought it was going to do. Great, I'm on to the next one."

As you get to large organizational scale then it can be years. So feeling like, "okay, I'm moving, I'm making progress, I'm making progress."

And it is that sense of momentum, I think. That really supports the feeling of flow.

So, the best examples I can come up with, unfortunately, are probably firefighting because like incidents or whatever, you know, when something big comes up that makes everything else between what's important and what's not important, so big and so obvious that everything else falls away. Those are some of the easiest examples to come up with. But I certainly don't want to be advocating, like," just create more fires" because then you'll have this calming sense of flow. Right?! That's not really what we're going.

And that's, what's so fascinating to me. You know, another big part of that is you know, what do you enjoy? What are you curious about? What motivates you every day? And if you can find the right combination of those things, does that give you the opportunity to get back into that state more?

And I would say when... I probably can't come up with a concrete example because I'd be too complex to try to explain, but at the points where decisions feel easy and it feels like people are really well aligned. And I don't mean aligned because you told them the same thing a million times, but aligned because they all share the same sense of purpose. That is the closest feeling I think that I would have that I would relate to that sort of "personal I'm just up all night coding flow, which is we're all working together on something and it the coordination is easy. And the coordination is easy because we understand the goal and we all know the role that we play in it, and we're executing against that."

And I think that's always easier in the small, and I am personally in pursuit of attaining that in the large, Like, the bigger you can get that sense of coordinated execution in the sense that like, we don't need to talk a lot because we have a bigger picture that we all understand the more likely we are to feel like we're just moving and we have that momentum.

Jerry Li: Yeah, that's one of the important sense of momentum, because the team could have more aligned and more productive. Everyone knows there where they're going. I can resonate on some of the moments that I have that feeling.

And going back to the firefighting example, I think that's really fascinating. It says that it is forced focus. But it literally can not focus on anything else, but on the fire. And I think that links to the notion of the book, The One Thing because a hallmark of being a leader is that your time is being demanded by meaning people like you have a lot of messages, a lot of meetings, a lot of asks. So it's really hard to have more sort of the maker-time.

How do you intentionally protect maker-time as a leader?

Jerry Li: How do you intentionally protect your maker-time as a leader? Because I feel that ties directly to the flow state.

Rob Zuber: I think the maker moniker in there is really fascinating to be at again, deconstructing this on the fly. So like, let's see how this goes...

But... one of the biggest challenges, certainly that I've had personally through the whole period of the growth of this organization is the feeling that. Or maybe not the feeling, but the definition of maker, right? Like what is it that I make and can I carve out time to do that? Right. I'm well past this point, I think, but one of the classic struggles that CTO has always have is like, "how much do I still code?"

Yeah, like sure. I mean, I could probably go write some lines of code and run our systems and the PR would get rejected. Like that would not be a good use of it... I could carve out time to do that. Right? That wouldn't necessarily be a good use of time.

So then what does that look like? What's a product that you can create that's helpful or high leverage? Or whatever that might be. And that could be anything from clearly articulated statements about direction or contexts, like things that actually move for a lot of people.

And I will say there was a period, unfortunately, it wasn't didn't last, but for about half a year, I crafted email messages to much of the organization like, "Hey, this is what's going on this week. This is what I'm seeing. Here's how you can take that and think about it in your space."

Like, not details of how we're doing things, but just, "here's what you need to know about this part of our business that might help you do your job better. Right.

And that was like a little bit of that maker. Like I can sit here and write an email and I enjoy writing. Right. Which is not necessarily true of all engineering leaders. I enjoy writing. And so I've produced something, but it's probably more valuable than code that I could write for that same amount of time. Although oddly, I think I'm fussier about my English writing than I am about my code writing, which is ... I dunno, says something.

So that sense that I can create, yes. But what is it that I create that's of high value?

And so, even that example is still a single-person product, versus, do I have the opportunity to grow, mentor, coach? I don't actually love most of those words. I feel like it's more balanced than that. They sound very one-directional. But you know, I typically learn more than I teach, I think in most of those conversations.

But can I enable people to do their jobs more effectively again, by providing context or understanding or additional framing? Or, whether it's, here's how you can structure this in a way that it will be more valuable to the rest of the organization will be received better or just take into account this other thing that's happening, because that will give you an opportunity to do this more easily. Like those sorts of things, helping people see more, right. It's not sitting here, headset on, listening to music, and cranking out code. But it feels productive, right? It's not, it's also not a status meeting. Right. It's not just ingesting information about what other people have done and then leaving. I've never felt a state of flow around listening to other people tell me numbers that I could have read. Right.

So I do think, you know, it shifts and we keep throwing this word around, but it's really about, "how do I feel like I'm generating momentum and how do I feel some sense of feedback around that" that says, "Yep, this is working well. I'm going to keep doing more of that. It's engaging. And it feels like I'm sort of doing something that's fulfilling to me and valuable to the organization."

Balancing challenge & support to create flow

Jerry Li: I love that email example you just provided. That's really inspiring. That's a way to spend your time as an outlet for your creativity, but has a much different and probably bigger impact on the organization than writing code. So, feels like the intention to find time like that, where you can focus. You can get into single-player mode to create, but in a different form than code. That's one way to find flow in engineering management. So, really like that example.

And another way people need to balance sort of the time flow state is the level of challenge. If it's no challenge, you feel bored. If you're too challenged, you feel stress.

So any insights you can share on that? How do you at least ways you attempt to find those balance?

Rob Zuber: Yeah that's a really fascinating question because I think that, you know, one of the things that happens whether you want it to or not: at a certain level of leadership the level of ambiguity is extremely high. Right.

And so what I think about what challenges folks like as they grow in their own careers, that's typically one of the key dimensions that I would think about. what is your ability to handle a level of ambiguity.

Am I handing you a very specific task? Or am I giving you basically an open space and saying, I think there might be a problem over there, right? Like, those are pretty different in terms of your growth and the size issue, like at a CTO level, you don't get a lot of choice in how much ambiguity you're going to be facing. if I turn around and say, I can't handle this, then I'm out shopping for a new CTO, so I, I don't get a lot of options, I guess?

And so I talked about like compensation frameworks earlier, And I think. It probably balances out in other ways. So I'm not really answering your question directly, but it's sort of like, "Well, this is the level of challenge that I have to operate at. So how do I dial the rest of my life for my own personal balance?"

It feels analogous to decision fatigue, like there's this classic example of Steve Jobs wearing a black turtleneck every day, Or, I think Barack Obama just had one suit. I mean, probably totally misquoting these things because they have to think so much or in Steve's case had to make so many decisions all day long about just like anything that they can sort of clear off their plate is valuable. So I wonder, I wonder if there's something like that from a challenge perspective, I meter that a little bit differently and just try to find ways that I can do things that are challenging, but not necessarily thinking in the same way. I mean, keep talking about guitars, like creative outlets that are just very different in the use of my brain. Right?

So my brain is overly taxed on a particular type of challenge. Oddly, I pick activities that are really frustrating. And like, playing guitar frustrates me. Cause I want to be better at that too. Right. But it's just a different kind of mode. And being able to shift modes maybe brings me balance?

I feel like I'm totally not answering the question, but that's, how I think about the challenge because again, I'm not sure that you can say I'm not going to accept this challenge. It's too hard for me.

You might say "I have an executive team and I may be titled the CTO, but these people are all really smart. So how am I going to get everyone to help me?"

And I think that's one of the biggest transitions that good executive teams go through is realizing. Wait a second. Your title is CTO and mine is CRO or CMO or whatever. But we are the team that needs to solve this problem. So if there's something I can do to help you, because just in the case of marketing or revenue, like I know a lot about the customer as I described because in their case they know a lot about being very numbers-driven, right? Like marketing and revenue are very analytical organization. They're very good at that sort of thing. How can we take some of those tools and apply them to, you know, other parts of the business, right. Is there something we can learn from that?

So everybody has something to share. And so, not saying we're not going to solve this problem because it's too hard or I'm going to like, there's no one up to go, right? Like your CEO is probably really busy. But can we, as a team, work more tightly, be open about the fact that we don't necessarily have all the answers? Work on it together, get outside help, whatever that might be?

Jerry Li: On the flip side though. So we often hear from people that I am so ready to go next level. I feel bored. I'm being many, a team of this I've been for a while and I don't find it challenging anymore.

And these are Patrick you hear some of the stories in the peer group discussion Maybe you can put an example or maybe we can shed a light on that side of the challenge. Like, feel bored as a leader, where do I find new challenges or upward a challenge?

Patrick Gallagher: Well, I don't know if it's the quest to, I feel bored. I need more challenges, but I think it's more relevant of recognizing that the challenges that I'm facing are either at a class level that maybe I'm not personally ready for, or like, as the question where I've introduced, like somebody might be uniquely positioned better to solve those for the organization.

So like specifically, I mean, a small peer group of startup CTOs. And the question that they're ultimately have been wrestling with the last few months has been sort of recognizing that to get the company and the engineering organization to the next level, and to better align or answer the question of doing more of the things that I love or doing more of the things that I gained fulfillment of. I need to figure out how to carve that out or how to divide that with somebody else.

And so a lot of them are sort of contemplating bringing somebody else into the organization at that senior level to, complement and augment the work. So they're also in this discovery process of what do I actually value and love about this role? And what do I want to do more of? Or what am I uniquely positioned to get involved with?

Frameworks for personal discovery or delegating executive responsibility

Patrick Gallagher: So I think that's kind of a big windup to explain that context and Rob, like I was wondering if you had other frameworks that were helpful in that self-discovery process that helped them answer that question?

Or other areas you would help them look at it. And having that conversation of when you bring somebody in to augment the role, how do you think about that from a mental framework perspective or from a carving out responsibility and time?

Rob Zuber: It's such a huge question. And, I think the most important thing to say in there, and I'm not trying to dodge the question or how I would try to help someone else think about it. But it is very personal, very context-driven right.

Like that's the thing that I think is most important in all of this. What's going to make your organization successful is not what's going to make someone else's organization successful, right?

Like, just because someone else in your peer group who you know really well, and you think in similar ways has decided to bring in a director under them. And that's how they're going to split up the work. That doesn't mean that's the right answer for you.

And so, I think we always struggled to have these conversations in a very, open and personal way. Like I think it's easy. And I acknowledge like the fortune that I have to be able to think about this pretty openly. But it's easy to let outside pressures, outside expectations come in.

I would say, probably one of the most important things would be to go get the real outside expectations, right. I already told you my Jim our CEO, like we came in through an acquisition together. We've worked together for 10 years. Like I generally know where he's coming from. But I'll still go ask him like, "Hey, this is how I'm thinking about this problem. Like, what's your input on this?"

There's a reason we work well together because we have different perspectives, right? Like, why wouldn't I, share that? So, or look for that. Right. And so, don't project onto other people, their expectations of you. Go find out what those are.

They might not align with what your expectations are. But wouldn't, you rather know that now than after you decided to make a really big change.

Of course, I have no idea who's listening and what size anyone's company is or organization. But like, I talk about this a lot because this is where we are as an organization. And I think it's really valuable for us in terms of our stage of growth, but, you know, at 20 and 30 people, I was slamming out code and rebooting boxes and figuring out how to deploy security groups and everything else.

Like, I wasn't sitting around and saying Hmm, what would be personally fulfilling for me?

It's like, how do we get this company to a stage where I get to ask that question? Right? Like, don't lose sight of that. It's such a weird... I feel like I'm giving both pieces of advice at the same time. Like pay attention to what motivates you. Burnout is real right. Understanding how can I contribute? But at the same time, know that certainly in the earliest of organizations, everybody has one job. That job is product-market fit. If you don't have product-market fit, none of these questions matter, right? Like it doesn't matter how much you want to do one thing or another, you're going to do whatever it takes to get to that point. I guess weigh that against kind of where you are in the evolution.

But then as you start to think about it, like, understand outside expectations. You know, understand what's real and possible for you as a business, right. Or for you and your business, I guess.

Like where are we from a funding perspective? What kind of person could we bring in right now? Like if you're really talking about... so if we narrow the focus to just augmenting your role, I think understanding where you are is a really important exercise and probably less obvious than it sounds... Meaning, what do we value right now?

to me, that's really interesting because values were probably set or if you're past product-market fit and scaling quickly... values were set earlier on the growth curve than you are right now.

And so. If you are talking to folks who think that a company of your current size is interesting, but your values are all set back here, right? "Like we're young and scrappy and we stay up all night..." I mean, young company, I'm not young by any stretch, but I still think this way. Well, you know, we stay up all night and we like code into the wee hours and we live off Soylent. but we want to bring in this really mature person, who's going to pull us to the next level.

And someone who's coming from a much more mature organization, right, who has structure and like process and ways of thinking. And you're... the first day is just going to be clashing. Wait a second. This is totally not what we wanted... sort of thing. So just be really honest about where you are and what you need, if you're considering actually partitioning the role in that way.

And I think you can be a little bit ahead, right? You want someone who helps at the next level. But if you're three levels ahead, right? I think when you're small, there's always the humor about the person who comes in and then the first job is to hire five VPs and you're like... that was the job you were supposed to be doing.

You know what I mean? Like, like that you need to manage all the people so we can get the work done.

I would imagine going through that process, you would learn a lot about yourself. I guess I, I feel like I'm totally rambling, so I'm just going to close that by saying every form of self-reflection... that's really valuable.

Patrick Gallagher: I think that's an incredible disclaimer.

On introducing resets & retro-ing your org

Patrick Gallagher: So you mentioned about the values and it's made me think about one of the headline topics that are like, oh, it'd be kind of fun to talk about this, was about the idea of introducing resets or retro-ing org structures.

So like having that sort of organizational assessment to take stock of "did this work, did this not what's the next evolution of what we need here?" What's your mental framework around introducing resets or retro-ing an org?

Rob Zuber: I think I'm interested in this, you know, in your use of the word reset, because in the early years, of CircleCI. I mean, I was three years in when I joined, we made more big organizational changes than we do now where we sort of have settled into a groove and we're growing. I mean, we grow, grew significantly in the last 12 and even 24 months. And so, had to see that evolve.

And I think reset makes me think of some of those earlier, like, "Oh, this isn't working, let's try something totally different."

And as bold and exciting as that sounds, it was generally a highly disruptive with minimal positive impact or a long time to realize impact, I think?

I think at a smaller scale, I could envision doing sort of organizational retros. But when I think about the scale that we operate at now, particularly if you're talking about structure I would want to see that done at smaller levels, right?

How are things working in this part of our design? How are things working in this part of our design? And I think the opportunity to increment your way towards better operation is probably greater than the opportunity to just be like, "we're tearing it all down. This is a mess, you know, let's just start over with a new sort of approach."

Part of that is just who ends up working in organizations at larger scales, right? Like when you've got a company of five or 10 people, like you're used to things that. That's the name of the game, right? whatever we're about to try it's probably not going to work at all.

We're going to be a hundred percent wrong and you get to the level that we're operating at. We know what our business is, right. We know who our customers are. We can be better. There are lots of places where we can improve and tweak. But saying wholesale restart on kind of how we think about running engineering or running the organization.

Like those things just aren't they're not going to have... It would take you like a year? Even to make that, you know, to execute that a really significant change. Sorry. I mentioned the kinds of people, right? Like you bring in people who want to operate in a more stable context. Right. And that's good because you go from a few superheroes to people who really know how to build teams.

Right. And you have more resiliency in your overall organization, all those sorts of things. Like you get a lot of positives that support being big... I mean, we're not big, we're like bigger. you know, those don't support, "Hey, let's all do different jobs today. Let's all just swap jobs with each other, cause that'll be awesome, right? Or 10 people, like everyone knows everyone else's job and uses whatever else work on anything. Doesn't matter."

You know, people need some space to really be focused on their piece of the puzzle. And the puzzle has gotten so big that, jumping around and shifting, I think would be... anyway. I really keyed off your recent word. Maybe that wasn't even what you meant, but do everything smaller work on increments?

Patrick Gallagher: as I was just about to say, like, that part was a big mental shift for me, because I'm just an email, anything like, oh, it just really simple to redesign the larger,

But like, that's ultimately the summation of those small interactions in those small moments. And if you can transform those, that has a more of that exponential compound effect on the organization to get to that level of trends.

Rob Zuber: I mean, if we take "The One Thing" framework just for a second, like what's the one change that you would make at your organization? Like, thinking about organization, you know, reshuffling, the whole thing is like throwing all the cards up in the air and hoping they land in a different house.

They don't! They're all over the ground. Right. And then people have to start picking them back up. And so, you know, but there might be one really big thing that's getting in your way right now. Find a solution to that problem. Right? Not start over. That's my take.

Rapid Fire Questions

Patrick Gallagher: Rob, we're coming to the end of our time. We have a couple of quick, rapid fire questions. already shared with us what book you're reading right now, the art of impossible... Is there another book that you would recommend or is there another book or something you're listening to that you would want to share it with folks?

Rob Zuber: I also started reading the, art of doing science and engineering. And I can't highly recommend it because I'm only early in it. But I love the concept. And it's basically how types of thinking have led to great innovations.

Patrick Gallagher: What's a tool or methodology that's had a big impact on you?

Rob Zuber: I feel bad saying continuous deployment. Well, it changed my life. So I'll stick with it. I mean, I remember the day that I started doing continuous deployment, I've never looked back. So I totally acknowledged that I worked for CircleCI and I'm really proud of what we do, but changed my life.

Patrick Gallagher: There we go! Is there a trend that you're observing right now that you'd think is really interesting or something that hasn't hit the mainstream yet that you're really fascinated by?

Rob Zuber: Well, the funny thing is no one knows what to call it, but I'll say what we are now rebranding as "Testing in Production" or I guess for taking "testing and production," which was a terrible idea before and making it into a real thing, which is... "My systems are too complex to be able to validate everything before I put them into a production environment. So I want to mitigate the risk of putting those not perfectly tested things into a production environment."

And I think people are getting their heads around it, even though it sounds terrifying. And I think there's a lot that we can do to make that good. And I think it actually allows us to be even better at software delivery.

Patrick Gallagher: You already shared a life-changing question with us earlier today. What would you say is your favorite or most powerful question that you've ever been. Or love to ask.

Rob Zuber: Oh, man. I feel like I should have a rapid fire answer to this one...

I'm going to try to make it the rapid fire version of the answer but someone asked me. Well, what I learned through my growth at Circle CI and then they had a follow-up question, which was "What have you done to enable other people to go through that growth more smoothly?"

And I was like, now I have to think. And that, that doesn't feel good. Like, I should have a really good answer to that.

You know, so you learn this lesson and turning that around and saying, great, what are you doing to help others learn that lesson? I think was a really insightful question.

Patrick Gallagher: I had to sit with that one for a second Rob. Is that when, like, totally just like disrupts your pattern, like instantly the moment you ask that I'm like, what have you done to enable somebody else to think about that? And I that's never occurred to me.

Rob Zuber: Right, but as soon as someone asks you, you're like, oh, Am I that terrible, I mean, it's a fantastic question. So yeah. I mean, write that one down. Ask yourself. Daily.

Patrick Gallagher: That's great. last rapid fire question. Is there a quote or a mantra that you live by, or just a quote that's really resonating with you right now?

Rob Zuber: I have two. Number one. My guitar instructor is a jazz musician. And he told me once that "improvisation is just composition in real time."

I have to explain this for a second...

The reason this is so fascinating to me is when I think about, when we say we're going to make it up as we go, or like there's a crisis situation and we just have to figure it out on the. What experienced people are doing is taking this massive base of knowledge and set of patterns that they have and just adapting them to the situation, which is totally different from an inexperienced person who is just guessing at everything.

Right. And like... you probably know what that sounds like in music, if you listen to any music, but that concept that "I have a set of building blocks and I'm just recombining them in the moment."

Was very enlightening and powerful to me. And in particular, over the last couple of years where we've all been like, "what is even happening in the world? And what tools do I have that I can bring to bear?"

And it allows me to feel less unprepared, like, which I guess would be more prepared to know actually what I'm doing is just recombining these tools that I already have. So that's one.

The other that I've been joking a lot about lately. It's like a running joke in my family. I don't know if you're a Ted Lasso fan, but there was a reference in that show to the use of the word unlucky.

And if you play soccer or in my case, I have kids who play soccer... To me, it is the most, it is a blameless postmortem in one word. It's like, "Let's move on. Okay. What did we learn from that? Learn it now because the ball is flying down the field and we need to get."

Not "We're going to sit here and be frustrated and disappointed and point fingers at each other" and whatever.

And I just love that word. I literally, my, my wife dropped a dish on the floor the other day and it shattered. I was like, oh, lucky. Like we just keep rolling through life. It's I don't know. It's to me, it's very excited by it. Anyway.

Patrick Gallagher: Improv is composing on the fly and I think it's so apparent... what immediately comes to my mind is you were sharing all of these frameworks with us that you've committed your whole life to learning and how you've been taking different parts and composing them to different elements and making them work for you in different parts of your life.

And so I think it's sometimes really hard to see how does somebody take what they learn and then integrate it into different decisions that they make in different applications of leadership.

So, Rob, just thank you for sharing your story with us and opening up the box to how you've composed your leadership.

Rob Zuber: Thanks so much for having me. It was, tons of fun.

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