We’ve got some big news… 🌱 Know Your Team is now Canopy →

Episode 11: Interview with Michael Lopp, VP Engineering at Slack

As the VP Engineering of Slack and prolific author on technical leadership, Michael discusses why being busy is a bad thing as a leader and how to delegate well.

Claire: Hi everyone. I’m Claire Lew, and I’m the CEO of Know Your Company, and today I’ve got a very special guest. I have with me Michael Lopp, who might be better known to some of you on the internet as Rands, and he is the VP of Engineering at Slack, and is someone who… we met at, what, a conference, I think we’d both spoken at, maybe a few years ago and spoken at the same conference a few years ago. Yeah, I know, it’s been a while.

Loved what you had to say, and Michael has done some just incredible writing and he’s written a book on managing people, I believe it’s called “Managing Humans,” in addition to just being a real advocate about thinking really thoughtfully for how to manage teams, especially engineering teams. And so, a real pleasure to have you today, Michael, and I’m excited to ask you this one question about leadership.

Michael: Absolutely. Thanks for having me. It’s a lovely Friday and looking forward to talking with you too.

Claire: Cool. So the one question I have for you, Michael, is what’s one thing that you wish that you would’ve learned earlier as a leader?

Michael: It’s a really easy question. I thought you guys would make it a hardball here.

Claire: Oh good, whew.

Michael: But it’s a really easy one.

Claire: Good.

Michael: The thing I wish I’d learned and it’s something that I look for in all emerging leaders — it sounds really simple but it’s a very complex action — is delegation.

The act of delegation for a manager or a senior manager or an experienced manager is just this real solid power move because it’s about giving up something that you might love to do.

And we are trained as individuals to like, “This is my thing, I got to deliver on it, and I got to know about it,” and this sort of thing, and you become a manager and suddenly your job is to give away your Legos and give away your toys. And that’s just hard. It’s just hard because you know you can do great on it if you were hands-on, and you just see a lot of really strange, really backwards leadership behaviors of people, who half-delegate or try to micromanage. Micromanagement is the act of not delegating.

There’s all of those things that go on, when someone’s not really delegating well. That, I’ve just been screwing up for decades by the way. That it’s really interesting to see that moment when I watch a manager or someone just say, “Hey, I know I can get an A on this doing it myself, but I’m going to give it to the team, and I’m pretty sure it’s going to be a B, but that’s okay. Because I’m not responsible for getting it back to an A.”

Because they’ve never done it before, or whatever the reasons are. And maybe they get an A, who knows. But, watching them do that, it’s just a fundamental move of selflessness. And it’s a fundamental move of trusting the team. And they know that you’re giving them the thing, like “Whoa! I’m not really ready to do this.” And that’s cool. That’s awesome. That’s like my job is to help you to do that incredible work.

So that delegation thing, is one of the first things I look for in managers. And I say this answer many times, because I’m just like, this is how I will know that you are … you understand a job of management and leadership.

Claire: Absolutely. I mean, you said that it’s something that sort of took you decades to learn. Was there a moment that caused you … or something that happened where you went, “Wow, I’m messing up my role as a manager because I’m not willing to delegate.” And what do you think is the thing that holds people back from giving that … passing something on to the team?

Michael: Yeah, the first question is, “When did I know?” I had this that, it’s just really in the last couple of years I realized, and being a leading indicator that I’m not delegating enough, and it’s when I’m busy. When someone sends me an email and says “Oh, I know you’re super busy.” I go, “No, I’m not.”

And if I ever am busy, I’m failing as a leader because I’m shouldn’t be busy. My job is to run the team well, and me being busy, it’s a fundamentally inefficient state. When I feel really busy, it means I’ve got too much on my plate. There’s something upstream from what I signed up to do or something where I’m like I am doing too much.

And it’s not that I don’t like being busy and getting things done. It’s that I’m setting the example that I don’t have time for my team, or that I already have stuff to do. And that’s bad, and they start to thing that’s the way you’re supposed to work. And that’s not a go to way to work.

So that’s how I know, is when I’m like, “Oh, I’ve got too many things.” But the thing is, even with experience comes doing too many things. It’s like, “There’s just certain projects I love to do.” It’s why engineers struggle sometimes with management because they just love coding because it’s such a satisfying act of building.

So the thing that I messed up is, “Oh, God this is such a Lopp-shaped task.” And like, “It’s perfect, and I will have great coding doing this for the next three weeks.” And it’s selfish. Because someone else should learn how to do that same thing. And learn that joy that I got when I did it. But when I screw it up is almost always when I’m like, “I’ll just do this one thing.” No, you should give that to Julia, you should give that to Ross. And let them run with it.

Claire: Absolutely. I think what you’re describing, the sort of, awareness that keeping something for yourself is inherently a selfish act. I think that’s a hard realization for a lot of leaders. Because like you said, it’s fun. I reflect on things that I do at Know Your Company where we’ve hired other folks on and I’ve been like, “Do I want to give that to that person, because I actually kind like it.” Right?

Or something I think you eluded to earlier is this fear about quality. ? And when do you know that something is going to be good enough, but I think something that you also touched on is that, it’s the role of the leader to make sure and say, “Okay, let’s get this from a B to an A.” Or even to be pleasantly surprised, right? That it is going to maybe turn out to be an A.

So as a leader what are things that we should be thinking about and doing to, when we do delegate, to put that person into a good position? To put that person into a position of success. I’m going to safely assume that you’re not just saying, okay just assign out task. And then just leave people to the wolves. There’s some coaching involved and some context that you give. Tell me a little bit about that.

Michael: It’s another early leadership move you got to know, which is read the room. Understanding the people that you have, the team that you have, and the individuals that you have. I have a profile for everyone one of my direct reports. And it’s something we’ve talked about. I have a leadership rubric and these are the things I’m looking for out of my leaders. And these are the clauses, and we have an understanding. We talk about, “Hey these are the things you’re amazing at, and things we’re working on.” So lesson number one is, know the people and teams that you have.

And number two is, as this work, just kind of flows across your desk, it’s like okay, is this a Ross thing, is this a Julia thing, is that a Frank thing? Whatever. And going on okay, who should it go to, who’s going to get the most learning out of this. And then, based on what I know about the person and the teams, it’s like okay well what do I need to do in terms of framing, in terms of coaching, in terms of setting expectations.

And, obviously that varies from just throw it over the fence because Julia, she’s got it. I just trust her to do those things. Or give it to Frank. And this is going to be, I’m going to weekly touch ins. Or I’m going to write up a spec right out of the gate and be a little be more directive. It just depends on what the person needs and how they need to grow, and where you’re at with them in terms of their professional growth.

Claire: Absolutely. I think sometimes, something I know a lot of CEO’s and founders that we work with, and that I speak to, sometimes find difficulty in that line between delegating effectively and providing context, so that person doesn’t sink and drown. Versus micromanaging. And maybe checking in too much, or telling the person how to do it. Or imposing their own processes or tastes on how this person is going to do something. How’s a leader, especially when maybe you coach other managers … do you try to let people know, here’s when you give enough information, here’s when you need to back off and give people that space to at least do the job.

Michael: Let’s first concede that micromanagement has a leadership skill of super bad. And regardless of how things were set up or how things were staged, what the relationship is … if you’re on the receiving end micromanagement, you’re just like, “Oh, I failed.” It doesn’t matter. It’s like, “I failed.” They feel that, the boss is showing up all the time, duh, duh, duh. So let’s put that over there. Micromanagement, bad.

Highly directive and constructive feedback. Intense involvement. I realize it sounds like I’m saying exactly the same thing as micromanagement. It’s not. Because it’s around the intent. Micromanagement is, like I know you failed and now here I come to save you. What I’m talking about these other words is, “Hey okay I’m dialing it up because I sense directionally, we are headed in the wrong direction here.”

Or it’s a subjective thing, it involves tastes, like you say. And I see we’re kind of headed in this other direction, and I want to weigh in on this sort of thing. There’s this nuance of intent to be pulling in the different kinds of direction you going to go to.

If you’re in a really good state with a team and you have high trust. When you come in there and act like a micromanager or something like that, they’re not seeing, “ This is failure” and “Lopp is mad” or blah, blah, blah. They’re seeing, “Oh he’s here to help. I’m going to come and coach folks. I’m going to come in and be there.”

It’s how you’re presenting that highly directive leadership, that I think is the demoralizing situation, or this coaching situation. It’s totally different and you know when you’re giving hard feedback to someone. You know this is a moment that you’re either going to demoralize or you’re going to build trust.

It’s super hard. Feedback is like one of the hardest things a manager can do. And it’s how you’re delivering it. Everything you said before that … the things that you’re saying there are sort of the difference between making a positive versus a negative interaction.

Claire: Absolutely. It’s such a hard balance to find. And I think your description of thinking about how you build trust versus how you avoid it being a demoralizing situation. It all, I think, comes down to, definitely intent is a huge part. And I also think, and I think this is implied in what you responded, the way that you provide that feedback, right? It’s not just telling that person this sucks, here’s why. You should’ve done it this way. But asking questions, that say, can you tell me a little bit about why. Do you mind if I share why I think it could’ve been like this.

Just different ways to build the person up versus tearing them done. So I think that’s really really helpful.

I guess my last thought here, or the thing that I’m curious to know is, for managers who are first time managers, and they’re flexing this new muscle of delegating. What advise do you have for them to get more comfortable with this? Because personally, it’s a very uncomfortable thing, as someone who you spend the majority of your career being the individual contributor, building pride in your craft, and now, your saying stop doing those things and actually give it up. What advise do you have for folks who are just getting into that, to become more comfortable with this skill?

Michael: That’s a really good question. I have this talk I give called “The New Manager Death Spiral”. And what I do is, I take any bad incident that I made and I stitch it together into this awful horrible story of … and it’s about delegation, but it’s really kind of about trust and respect. And I just walk you down as a new manager to the worst place you can be. And I wrote that talk just because I’ve seen all these new managers struggle with parts of that, not the whole thing. They would never do it in this cascading series of awful steps.

But the reason I do it, is to describe, and I exaggerate it a bit, to describe the consequences of not doing well. And to also put the … and I talk a lot about how the team is seeing you during this death spiral, to kind of, both remind them of what they were like when they were an individual. And also, how they see managers and some of the trials and tribulations and the assumptions there. Just to give them that other perspective.

Because I think what new managers, myself included when I did this long ago, is they assume there’s power that you’re granted, when you become a manager. And there’s some things there, like comp or performance reviews or whatever.

But nothing is granted. It’s all earned. It’s all responsibility to be earned. And you earn them by them trust you. So delegation and some other things as well, which are these things that are these trust building maneuvers.

And when you understand that that’s the currency that you’re building, with these folks, and it’ not a switch that says “I’m a Manager.” This hat that says “Manager” on it. It’s the responsibility you build over time, this it makes it a little more approachable and little less scary. That’s one way to do it.

Claire: Absolutely. No, I love that. I think focusing on trust and thinking of it as this currency to people to delegate well. And that’s really the means of which how well that situation is actually going to go, how well are you building trust, how well are building that rapport. That makes total sense.

Well, Michael, thank you so much for your time. This is incredible. I’ve learned a lot. Like I said, really respect your work and so thanks so much for participating.

Michael: Absolutely. Thank you very much.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.