How To Effectively Manage Your Co-Founder with Mike Julian

Besides his duties as The Duckbill Group’s CEO, Mike is the author of O’Reilly’s Practical Monitoring, and previously wrote the Monitoring Weekly newsletter and hosted the Real World DevOps podcast. He was previously a DevOps Engineer for companies such as Taos Consulting, Peak Hosting, Oak Ridge National Laboratory, and many more. Mike is originally from Knoxville, TN (Go Vols!) and currently resides in Portland, OR.

Announcer: Hello, and welcome to Screaming in the Cloud with your host, Chief Cloud Economist at The Duckbill Group, Corey Quinn. This weekly show features conversations with people doing interesting work in the world of cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.

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Corey: Welcome to Screaming in the Cloud, I’m Corey Quinn and I’m having something of a crisis of faith based upon a recent conversation I’ve had with my returning yet again guest, Mike Julian, my business partner and CEO of The Duckbill Group. Welcome back, Mike.

Mike: Hi, everyone.

Corey: So, the revelation that had surfaced unexpectedly was, based upon a repeated talking point where I am a terrible employee slash expensive to manage, et cetera, et cetera, and you pointed out that you’ve been managing me for four years or so now, at which point I did a spit take, made all the more impressive by the fact that I wasn’t drinking anything at the time, and realized, “Oh, my God, you’re right, but I haven’t had any of the usual problems slash friction with you that I have with basically every boss I’ve ever had in my entire career.” So, I’m spiraling. Let’s talk about that.

Mike: My recollection of that conversation is slightly different than yours. Mine is that you called me and said, “Mike, I just realized that you’re my boss.” And I’m like, “How do you feel about that?” He’s like, “I’m not really sure.”

Corey: And I’m still not entirely sure how I feel if I’m being fully honest with you. Just because it’s such a weird thing to have to deal with. Because historically, I always view a managerial relationship as starting from a place of a power imbalance. And that is the one element that is missing from our relationship. We each own half the company, we can fire each other, but it takes the form of tearing the company apart, and that isn’t something that we’re really set up to entertain.

Mike: And you know, I actually think it’s deeper than that because you owning the other half of the company is not really… it’s not really power in itself. Like, yeah, it is, but you could easily own half the company and have no power. Because, like, really when we talk about power, we’re talking about political power, influence, and I think the reason that there is no power imbalance is because each of us does something in the company that is just as important as the other. And they’re both equally valuable to the company and we both recognize the other’s contributions, as that, as being equally valuable to the company. It’s less to do about how much we own and more about the work that we do.

Corey: Oh, of course. The ownership starts and stops entirely with the fact that neither one of us can force the other out. So it’s, as opposed to well, I own 51% of the company, so when I’m tired of your bullshit, you’re leaving. And that is a dynamic that’s never entered into it. I’m also going to add one more thing onto what you just said, which is, both of us would sooner tear off our own skin than do the other’s job.

Mike: Yeah. God, I would hate to do your job, but I know you’d hate to do mine.

Corey: You look at my calendar on a busy meeting day and you have a minor panic attack just looking at it where, “Oh, my God, talking to that many people.” And you are going away for a while and you come back with a whole analytical model where your first love language feels like it’s spreadsheets on some days, and I look at this and it’s like, “Yeah, I know what some of those numbers mean.” And it just drives me up a wall, the idea of building out a plan and an execution thing and then delegating a lot of it to other people, it does not work for my worldview in so many different ways. It’s the reason I think that you and I get along. That and our shared values.

Mike: I remember the first time that you and I did a consulting engagement together. We went on a multi-day trip. And at the end of, like, three days of nonstop conversations, you made a comment, it was like, “Cool. So, what are we going to do that again?” Like, you were excited by it. I can tell you’re energized. And I was just thinking, “Please for love of God, I want to die right now.”

Corey: One of the weirdest parts about all of it, though, is neither one of us is in a scenario where what we do for a living and how we go about it works without the other.

Mike: Right. Yeah, like, this is one of the interesting things about the company we have built is that it would not work with just you or just me; it’s us being co-founders is what makes it successful.

Corey: The thing that I do not understand and I don’t think I ever will is the idea of co-founder speed dating, where you basically go to some big networking mixer event, pick some rando off the street, and congratulations, that’s your business partner. Have fun. It is not that much of an exaggeration to say that co-founding a company with someone else is like a marriage. You are creating a legal entity that without very specific controls and guidelines, you are opening yourself up to massive liability issues if the other person decides to screw you over. That is part of the reason that the values match was so important for us.

Mike: Yeah, it is surprising to me how similar being co-founders and business partners is to being married. I did not expect how close those two things were. You and I spend an incredible amount of time just on the relationship for each of us, which I never expected, but makes sense in hindsight.

Corey: That’s I think part of it makes the whole you managing me type of relationship work is because not only can you not, “Fire me,” quote-unquote, but I can’t quit without—

Mike: [laugh].

Corey: Leaving behind a giant pile of effort with nothing to show for it over the last four years. So, it’s one of those conversation styles where we go into the conversation knowing, regardless of how heated it gets or how annoyed we are with each other, that we are not going to blow the company up because one of us is salty that week.

Mike: Right. Yeah, I remember from the legal perspective, when we put together a partnership agreement, our attorneys were telling us that we really needed to have someone at the 51% owner, and we were both adamant that no, that doesn’t work for us. And finally, the way that we handled it is if you and I could not handle a dispute, then the only remedy left was to shut the entire thing down. And that would be an automatic trigger. We’ve never ever, ever even got close to that point.

But like, I like that’s the structure because it really means that if you and I can’t agree on something and it’s a substantial thing, then there’s no business, which really kind of sets the stage for how important the conversations that we have are. And of course, you and I, we’re close, we have a great relationship, so that’s never come up. But I do like that it’s still there.

Corey: I like the fact that there’s always going to be an option to get out. It’s not a suicide pact, for lack of a better term. But it’s also something that neither one of us would ever entertain lightly. And credit where due, there have been countless conversations where you and I were diametrically opposed; we each talk through it, and one or the other of us will just do a complete one-eighty our position where, “Okay, you convinced me,” and that’s it. What’s so odd about that is because we don’t have too many examples of that in public society, it just seems like there’s now this entire focus on, “Oh, if you make an observation or a point, that’s wrong, you’ve got to double down on it.” Why would you do that? That makes zero sense. When you’ve considered something of a different angle and change your mind, why waste more time on it?

Mike: I think there’s other interesting ones, too, where you and I have come at something from a different angle and one of us will realize that we just actually don’t care as much as we thought we did. And we’ll just back down because it’s not the hill we want to die on.

Corey: Which brings us to a good point. What hill do we want to die on?

Mike: Hmm. I think we’ve only got a handful. I mean, as it should; like, there should not be there should not be many of them.

Corey: No, no because most things can change, in the fullness of time. Just because it’s not something we believe is right for the business right now does not mean it never will be.

Mike: Yeah. I think all of them really come down to questions of values, which is why you and I worked so well together, in that we don’t have a lot of common interests, we’re at completely different stages in our lives, but we have very tightly aligned values. Which means that when we go into a discussion about something, we know where the other stands right away, like, we could generally make a pretty good guess about it. And there’s often very little question about how some values discussion is going to go. Like, do we take on a certain client that is, I don’t know, they build landmines? Is that a thing that we’re going to do? Of course not. Like—

Corey: I should clarify, we’re talking here about physical landmines; not whatever disastrous failure mode your SaaS application has.

Mike: [laugh]. Yeah.

Corey: We know what those are.

Mike: Yeah, and like, that sort of thing, you and I would never even pose the question to each other. We would just make the decision. And maybe we tell each other later because and, like, “Hey, haha, look what happened,” but there will never be a discussion around it because it just—our values are so tightly aligned that it wouldn’t be necessary.

Corey: Whenever we’re talking to someone that’s in a new sector or a company that has a different expression, we always like to throw it past each other just to double-check, you don’t have a problem with—insert any random thing here; the breadth of our customer base just astounds me—and very rarely as either one of us thrown a flag on something just because we do have this affinity for saying[ yes and making money.

Mike: Yeah. But you actually wanted to talk about the terribleness of managing you.

Corey: Yeah. I am very curious as to what your experience has been.

Mike: [laugh].

Corey: And before we dive into it, I want to call out a couple of things that make me a little atypical for your typical problem employee. I am ADHD personified. My particular expression of that means that my energy level is very different at different times of day, there are times where I will get nothing done for a day or two, and then in four hours, get three weeks of work done. It is hard to predict and it’s hard to schedule around and it’s never clear exactly what that energy level is going to be at any given point in time. That’s the starting point of this nonsense. Now, take it away.

Mike: Yeah. What most people know about Corey is what everyone sees on Twitter, which is what I would call the high highs. Everyone sees you as your most energetic, or at least perceived as the most energetic. If they see you in person at a conference, it’s the same sort of thing. What people don’t see are your lows, which are really, really low lows.

And it’s not a matter of, like, you don’t get anything done. Like, you know, we can handle that; it’s that you disappear. And it may be for a couple hours, it may be for a couple of days, and we just don’t really know what’s going on. That’s really hard. But then, in your high highs, they’re really high, but they’re also really unpredictable.

So, what that means is that because you have ADHD, like, the way that your brain thinks, the way your brain works, is that you don’t control what you’re going to focus on, and you never know what you’re going to focus on. It may be exactly what you should be focusing on, which is a huge win for everyone involved, but sometimes you focus on stuff that doesn’t matter to anyone except you. Sometimes really interesting stuff comes out of that, but oftentimes it doesn’t. So, helping build a structure to work around those sorts of things and to also support those sorts of things, has been one of the biggest challenges that I’ve had. And most of my job is really about building a support structure for you and enabling you to do your best work.

So, that’s been really interesting and really challenging because I do not think that way. Like, if I need to focus on something, I just say, “Great. I’m just going to focus on this thing,” and I’ll focus on it until I’m done. But you don’t work that way, and you couldn’t conceivably work that way, ever. So, it’s always been hard because I say things like, “Hey, Corey, I need you to go write this series of emails.” And you’ll write them when your brain decides that wants to write them, which might be never.

Corey: That’s part of the problem. I’ve also found that if I have an idea floating around too long, it’ll linger for years and I’ll never write anything about it, whereas there are times when I have—the inspiration strikes, I write a one- to 2000-word blog post every week that goes out, and there are times it takes me hours and there are times I bust out the entire thing in first draft form in 20 minutes or less. Like, if it’s Domino’s, like, there’s not going to be a refund on it. So, it’s kind of wild and I wish I could harness that somehow I don’t know how, but… that’s one of the biggest challenges.

Mike: I wish I could too, but it’s one of the things that you learn to get used to. And with that, because we’ve worked together for so long, I’ve gotten to be able to tell in what state of mind you are. Like, are you in a state where if I put something in front of you, you’re going to go after it hard, and like, great things are going to happen, or are you more likely to ignore that I said anything? And I can generally tell within the first sentence or so of bringing something up. But that also means that I have other—I have to be careful with how I structure requests that I have for you.

In some cases, I come with a punch list of, like, here’s six things I need to get through and I’m going to sit on this call while we go through them. In other cases, I have to drip them out one at a time over the span of a week just because that’s how your mind is those days. That makes it really difficult because that’s not how most people are managed and it’s not how most people expect to manage. So, coming up with different ways to do that has been one of the trickiest things I’ve done.

Corey: Let’s move on a little bit other than managing my energy levels because that does not sound like a particularly difficult employee to manage. “Okay, great. We’ve got to build some buffer room into the schedule in case he winds up not delivering for a few days. Okay, we can live with that.” But oh, working with me gets so much worse.

Mike: [laugh]. It absolutely does.

Corey: This is my performance review. Please hit me with it.

Mike: Yeah. The other major concern that has been challenging to work through that makes you really frustrating to work with, is you hate conflict. Actually, I don’t actually—let me clarify that further. You avoid conflict, except your definition of conflict is more broad than most. Because when most people think of conflicts, like, “Oh, I have to go have this really hard conversation, it’s going to be uncomfortable, and, like—”

Corey: “Time to go fire Steven.”

Mike: Right, or things like, “I have to have our performance conversation with someone.” Like, everyone hates those, but, like, there’s good ways and bad ways to them, like, it’s uncomfortable even at the best of times. But with you, it’s more than that, it’s much more broad. You avoid giving direction because you perceive giving direction as potential for conflict, and because you’re so conflict-avoidant, you don’t give direction to people.

Which means that if someone does something you don’t like, you don’t say anything and then it leaves everyone on the team to say, like, “I really wish Corey would be more explicit about what he wants. I wish he was more vocal about the direction he wanted to go.” Like, “Please tell us something more.” But you’re so conflict-avoidant that you don’t, and no amount of begging or we’re asking for it has really changed that, so we end up with these two things where you’re doing most of the work yourself because you don’t want to direct other people to do it.

Corey: I will push back slightly on one element of that, which is when I have a strong opinion about something, I am not at all hesitant about articulating that. I mean, this is not—like, my Twitter is not performance art; it’s very much what I believe. The challenge is that for so much of what we talk about internally on a day-to-day basis, I don’t really have a strong opinion. And what I’ve always shied away from is the idea of telling people how to do their jobs. So, I want to be very clear that I’m not doing that, except when it’s important.

Because we’ve all been in environments in the corporate world where the president of the company wanders past or your grand-boss walks into the room and asks an idle question, or, “Maybe we should do this,” and it never feels like it’s really just idle pondering. It’s, “Welp, new strategic priority just dropped from on high.”

Mike: Right.

Corey: And every senior manager has a story about screwing that one up. And I have led us down that path once or twice previously. So—

Mike: That’s true.

Corey: When I don’t have a strong opinion, I think what I need to get better at is saying, “I don’t give a shit,” but when I frame it like that it causes different problems.

Mike: Yeah. Yeah, that’s very true. I still don’t completely agree with your disagreement there, but I understand your perspective. [laugh].

Corey: Oh, he’s not like you can fire me, so it doesn’t really matter. I kid. I kid.

Mike: Right. Yeah. So, I think those are the two major areas that make you a real challenge to manage and a challenge to direct. But one of the reasons why I think we’ve been successful at it, or at least I’ll say I’ve been successful at managing you, is I do so with such a gentle touch that you don’t realize that I’m doing anything, and I have all these different—

Corey: Well, it did take me four years to realize what was going on.

Mike: Yeah, like, I have all these different ways of getting you to do things, and you don’t realize I’m doing them. And, like, I’ve shared many of them here for you for the first time. And that’s really is what has worked out well. Like, a lot of the ways that I manage you, you don’t realize are management.

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Corey: What advice would you have for someone for whom a lot of these stories are resonating? Because, “Hey, I have a direct report is driving me to distraction and a lot sounds like what you’re describing.” What do you wish you’d known sooner about how to coax performance out of me, for lack of a better phrasing?

Mike: When we first started really working together, I knew what ADHD was, but I knew it from a high school paper that I did on ADHD, and it’s um—oh, what was it—“The Overdiagnosis of ADHD,” which was a thing when you and I were at high school. That’s all I knew is just that ADHD was suspected to be grossly overdiagnosed and that most people didn’t have it. What I have learned is that yeah, that might have been true—maybe; I don’t know—but for people that do have any ADHD, it’s a real thing. Like, it does have some pretty substantial impact.

And I wish I had known more about how that manifests, and particularly how it manifests in different people. And I wish I’d known more earlier on about the coping mechanisms that different people create for themselves and how they manage and how they—[sigh], I’m struggling to come up with the right word here, but many people who are neurodivergent in some way create coping mechanisms and ways to shift themselves to appear more neurotypical. And I wish I had understood that better. Particularly, I wish I had understood that better for you when we first started because I’ve kind of learned about it over time. And I spent so much time trying to get you to work the way that I work rather than understand that you work different. Had I spent more time to understand how you work and what your coping mechanisms were, the earlier years of Duckbill would have been so much smoother.

Corey: And again, having this conversation has been extraordinarily helpful. On my side of it, one of the things that was absolutely transformative and caused a massive reduction in our interpersonal conflict was the very simple tool of, it’s not necessarily a problem when I drop something on the floor and don’t get to it, as long as I throw a hand up and say, “I’m dropping this thing,” and so someone else can catch it as we go. I don’t know how much of this is ADHD speaking versus how much of it is just my own brokenness in some ways, but I feel like everyone has this neverending list of backlog tasks that they’ll get to someday that generally doesn’t ever seem to happen. More often than not, I wind up every few months, just looking at my ever-growing list, reset to zero and we’ll start over. And every once in a while, I’ll be really industrious and knock a thing or two off the list. But so many that don’t necessarily matter or need to be me doing them, but it drives people to distraction when something hits my email inbox, it just dies there, for example.

Mike: Yeah. One of the systems that we set up here is that if there’s something that Corey does not immediately want to do, I have you send it to someone else. And generally it’s to me and then I become a router for you. But making that more explicit and making that easier for you—I’m just like, “If this is not something that you’re going to immediately take care of yourself, forward it to me.” And that was huge. But then other things, like when you take time off, no one knows you’re taking time off. And it’s an—the easiest thing is no one cares that you’re taking time off; just, you know, tell us you’re doing it.

Corey: Yeah, there’s a difference between, “I’m taking three days off,” and your case, the answer is generally, “Oh, thank God. He’s finally using some of that vacation.”

Mike: [laugh].

Corey: The problem is there’s a world of difference between, “Oh, I’m going to take these three days off,” and just not showing up that day. That tends to cause problems for people.

Mike: Yeah. They’re just waving a hand in the air and saying, “Hey, this is happening,” that’s great. But not waving it, not saying anything at all, that’s where the pain really comes from.

Corey: When you take a look across your experience managing people, which to my understanding your first outing with it was at this company—

Mike: Yeah.

Corey: What about managing me is the least surprising and the most surprising that you’ve picked up during that pattern? Because again, the story has always been, “Oh, yeah, you’re a terrible manager because you’ve never done it before,” but I look back and you’re clearly the best manager I’ve ever had, if for no other reason than neither one of us can rage-quit. But there’s a lot of artistry to how you’ve handled a lot of challenges that I present to you.

Mike: I’m the best manager you’ve had because I haven’t fired you. [laugh].

Corey: And also, some of the best ones I have had fired me. That doesn’t necessarily disqualify someone.

Mike: Yeah. I want to say, I am by no means experienced as a manager. As you mentioned, this is my first outing into doing management. As my coach tells me, I’m getting better every day. I am not terrible [laugh].

The—let’s see—most surprising; least surprising. I don’t think I have anything for least surprising. I think most surprising is how easy it is for you to accept feedback and how quickly you do something about it, how quickly you take action on that feedback. I did not expect that, given all your other proclivities for not liking managers, not liking to be managed, for someone to give feedback to you and you say, “Yep, that sounds good,” and then do it, like, that was incredibly surprising.

Corey: It’s one of those areas where if you’re not embracing or at least paying significant attention to how you are being perceived, maybe that’s a problem, maybe it’s not, let’s be very clear. However, there’s also a lot of propensity there to just assume, “Oh, I’m right and screw everyone else.” You can do an awful lot of harm that way. And that is something I’ve had to become incredibly aware of, especially during the pandemic, as the size of my audience at this point more than quadrupled from the start of the pandemic. These are a bunch of people now who have never met me in person, they have no context on what I do.

And I tend to view the world the way you might expect a dog to behave, who caught a car that he has absolutely no idea how to drive, and he’s sort of winging it as he goes. Like, step one, let’s not kill people. Step two, eh, we’ll figure that out later. Like, step one is the most important.

Mike: Mm-hm. Yeah.

Corey: And feedback is hard to get, past a certain point. I often lament from time to time that it’s become more challenging for me to weed out who the jerks are because when you’re perceived to have a large platform and more or less have no problem calling large companies and powerful folk to account, everyone’s nice to you. And well, “Really? He’s terrible and shitty to women. That’s odd. He’s always been super nice to me.” Is not the glowing defense that so many people seem to think that it is. It’s I have learned to listen a lot more clearly the more I speak.

Mike: That’s a challenge for me as well because, as we’ve mentioned, my first foray into management. As we’ve had more people in the company, that has gotten more of a challenge of I have to watch what I say because my word carries weight on its own, by virtue of my position. And you have the same problem, except yours is much more about your weight in public, rather than your weight internally.

Corey: I see it as different sides of the same coin. I take it as a personal bit of a badge of honor that almost every person I meet, including the people who’ve worked here, have come away, very surprised by just how true to life my personality on Twitter is to how actually am when I interact with humans. You’re right, they don’t see the low sides, but I also try not to take that out on the staff either.

Mike: [laugh]. Right.

Corey: We do the best of what we have, I think, and it’s gratifying to know that I can still learn new tricks.

Mike: Yeah. And I’m not firing anytime soon.

Corey: That’s right. Thank you again for giving me the shotgun performance review. It’s always appreciated. If people want to learn more, where can they find you, to get their own performance preview, perhaps?

Mike: Yeah, you can find me on Twitter at @Mike_Julian. Or you can sign up for our newsletter, where I’m talking about my upcoming book on consulting at mikejulian.com.

Corey: And we will put links to that into the show notes. Thanks again, sir.

Mike: Thank you.

Corey: Mike Julian, CEO of The Duckbill Group, my business partner, and apparently my boss. I’m Cloud Economist Corey Quinn, and this is Screaming in the Cloud. If you’ve enjoyed this podcast, please leave a five-star review on your podcast platform of choice, whereas if you’ve hated this podcast, please leave a five-star review on your podcast platform of choice along with an angry comment that demonstrates the absolute worst way to respond to a negative performance evaluation.

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