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New Manager Death Spiral

Michael Lopp
VP of Engineering

In this talk, Lopp walks us through a story where a new manager successfully performs every single common mistake in their new role. The New Manager Death Spiral is a cautionary tale full of good advice.

little bit a dread there. Can you hear me back there? How are we doing in the back? Raise your hands. If you can hear me lovely. Okay. Funny as I was talking, he said very loud. I'm the VP of engineering and slack read a couple of books, Mandy cumin. I had this leadership slash you should go to not because I'm running it because there's 4,000 people.

They're literally talking about leadership all the time. So there's two things you need to know. There's a slack should go to that's about leadership and there's a slide about seven. And let's see another big thing, but I'm not going to tell you what that is enough about me. Let's talk about you. How many of you have been managing for in years?

Okay. Let's do three to seven years. Boom spot. Okay. And then one to three years. Okay. Yes. I think it's 25%. Your math is adding up. And how many are like, what the fuck? I'm a manager. Holy cow.

Okay, well, let's it's interesting. How many of you are extroverts? Introverts? Raise your hands.

I know that was hard.

Okay. That's a, that's a good thing. All right. Let's let's go back and we met, I'm going to need a little bit you have your own managers are about getting managers. I need you to change your perspective a little bit while you've been doing it for 10 years, 20 years. If you're just starting, the mindset that I've put you in is I think isn't the same slide from last time I did this, but it's a totally different.

Mindset. I want to put you in is you're now a manager. Congratulations. You're a manager. You got that promotion. You got that new role. You got that new gig and you're there and it's like, you feel like the progressed we're here and now you're a manager. So congratulations. Congratulations on this goal. I have bad news.

I will now explain the in 20 or 30 minutes how your good intentions and the well-trained instincts are going to erode your credibility with the growth of your team. And it reinforced theory that these manager types are power hungry, jerks working with all the authority, not all the information and woefully linked together.

It's going to be a rough 20 or 30 minutes. Why have we started with that? John wick two? Yeah. This is, this is a cautionary tale. This is a cautionary tale full of hardware device. Because everything thing that I talk about, some of them are like no way, no human being would ever do that thing. I'm down like three times, three times.

Like I didn't learn her in the first two times the third time. I'm like, wow, this is really a bad idea. I probably shouldn't do it. So the opening talk for the keynote. The new manager does I'm like that nervous, laugh. You shouldn't be nervous. It's going to be a rough 20 or 30 minutes. So here's the deal, man.

This is the worst case scenario. What I have done is that constructed a series of decisions and choices and the situation into a worst case scenario, chances are you would never do all of these things. At the same time or in this sequence, but it's here to prove a point of what happens when each of these parts, these decisions, these things happen, and you can do the worst possible thing.

Okay. So that's a synthesized version of a bunch of different stories. It combines all of the, me, all of your mistakes and it starts right after you go, congratulations. It starts with this affirmation that you tell yourself you're telling yourself, you don't tell anyone this.

I can do it. I'm the boss all rolls up to me and now I'm responsible for other things. All of the things they are mine. I'm going to do this. I'm the boss boss. Right?

So what do you mean. You do what you did as an IC, you want to make a good first impression. So you sign up for all of the things. Hey rod, can you do this? Hey Julie, can you do this? I'm on it. No problem. You're trying to do something very honorable. You're trying to do something very sensible, which is prove yourself.

You signed it. You work late, you do your very best to kick ass and make a good first impression. You sign up for all the things. This is the approach that work. One of you. Can you do it? Of course I can. Thing is you are now signing yourself up as well as your entire team. This is the beginning of the spiral because you didn't just say, I think you would all I'm the boss, what you actually say.

You didn't say, did you actually have the thought was I can do it all myself because I'm myself. This is your first failure as an IC. You had this wonderful, cool kid. You have complete visibility into what you're doing total ownership, because it's your thing. It's your keyboard. Don't touch my stuff. I'm working on that.

Work. Well, as you're you are instinctively reluctant to delegate your work because it represents this unfamiliar loss of power. I'm going to give you the thing and trust you. You're going to do the right thing with it. Like I'm going to be judged on it. So you don't naturally do this. You don't naturally

Compounding your poor judgment is your belief that you're the best person to do all of this, because you've always been the best person to this stuff, because it was just you and you were no longer this person, this your problem, isn't that you're asking effort to prove yourself. You signed up to do far too many things.

And it is again finding that work because it's the work of the team and not just. This leads to your very first failure mode, the quality of your work drops because you signed up, did you mention many things you liked that time to correctly complete it. Miss deadlines, cuff commitments have completed work path off and it's done.

I've done that. And you start to discover a couple of awkward situations.

Your job is no one can get things done. That's part of the job. Your job is to get things done at scale, to get many things done at the same time. And that means calling enter. If you were doing everything right, the moment that you sensed looked overloaded, you would ask for help, but you're not going to do that because where are we?

We want the new manager does not going to add a scrap guests.

So remember what you said in your head? I can do it all myself. I'm in control. I'm in the box. The spiral of stress could pick up a little speed right now because you have this moment where you've walked up to someone and you're like, Hey, great. How are we doing that thing in his eyes? You can see that trust has been lower.

He's suddenly a little bit nervous. Like I think it's something, Hey, you can see in the glimmer. And you got to go to, you've seen that before. It's a nice even now.

So you got to take your mom. Okay. I get it. I'm failing. I'm a little bit overloaded. I can do it all myself. I'm in control. Cause I'm the boss again. I'm gonna say it's like three more times. Worst case scenario. You, everything. So you do, as you're bad at delegation, you sign up for too many things is you start to not delegate.

You start that fake delegate. You're like, Hey citizen, I need you to do this small project. And you don't actually give her all of the context because you're bad at delegation. You don't get full control or full context. They don't need it right near the boss. Don't give it to him. What you mean? You tell them what things they need to know, but not everything.

And just like you were just casing around, same scenario occurs. They either start to fail because they don't feel they have authority to change the course of the work or the project for them to understand the context of what it looks like. Or maybe they had it pointed in the wrong direction from day one and they do the right thing.

They did the right thing, or you're not doing anything right. They say, Hey, what brands, wherever your name is? Hey, tell you that. Hey, sorry. We don't, we were really confused by this. They say, listen, we would like to live with, we would like a little bit more context. So they tell you, I think we're off by one of the speaker notes.

Thank you. And this is when it gets really painful. It's not already painful. You, I can see people missing in the audience, right.

It's painful every possible decision together. They say we didn't in the course of the project, which was important. And so we started over here, which in hindsight was clearly the wrong place. You think, do you think, but do not. It's obviously the wrong place to start. If I were running this project, we wouldn't be in this situation.

I think your notes again, please. Thank you. So you think this, but you don't say you're internally frustrated. You're like, I wish they would. We're getting better on this saying I think I know I could have been better at it. It's obviously one place to start, but you're, and you're right, but you're so wrong.

You would recommend that if your hand were hands on working on this project, your prior experience with it likely and the execution, but you're wrong because the strategy of building trust successful delegation is one of the greatest accelerant accelerants to the new manager, new manager that the spiral not building delegation and trust is what really gets the state.

Again saying I can do it all myself in control because I am in the OSS. You don't want to appear weak. You don't want to update your priors. You don't want to change your strategy because that's somehow an admission of weakness. You give the barest of correcting advice and you tell them something that you probably never ever said.

What again?

You'll figure it out.

You would never say this. You wouldn't never ever say this. There are lots of ways to sit out saying these words to be threatened. It gives people the source of the idea that there's consequence that you know, that they don't, your team leaves this interaction with the following impact. Like failing true.

You're mad. Add inflexible, unwilling to listen to their ends. And this is the point of this file where they stop talking to you and they start talking to each other.

This is the slide that is the most important stuff in the deck.

This is the one I know if you're managing and building a lot of it. The inflection point between being an IC manager, is this do one-on-one when there's a million other 40 50 hacks, you have to do, this is what I know the manager understand his, your job is to aggressively delegate. There is work out there that you are guaranteed to get an email you can vantage and get done.

And of course, You've never done it before. So when they do that work, they're gonna get a B and a B it's killing it for first time product. And at the beginning is actually veterans because you give them the work and they get to learn, understand how and where. And I got Indian. That's pretty good. Right?

You get to see the beat and then coach them to an end. Well, by the way, it wasn't me. Here's why this is how to actually get to a day. But the thing about this is when you delegate something big and scary that you both in agreement is currently beyond their means. It's this vote of confidence. You're devastating trust in these people.

We're going to figure this out. Whatever this project is, that's scary and big and large. You've never done before, but you don't do this cause like your honest, best, final thing. That's such good advice. I wish I took it at the time. So what do they do? They do the same thing that you did is they fail.

You're not listening. So the steam team starts to talk to each other and other teams they're not talking to you because you're mad and threatening. They are trying to self correct. And sometimes they do, but since it's the death spiral, they don't. So they fail. This is unfortunate because. They all have the data that they had the data to be successful and what they needed from you.

The leader was the nudge. Hey, let's just a little 30 degrees over that way. We don't start there and start over here. You didn't share that cause you weren't communicating well. So the project becomes a failure getting super bad. Now it's getting the bottom and then I'll bring it back up. Super bad. Now this is, this is when you're going to know you're going to bottom out.

I wouldn't say memorialized. Everyone feels like they failed including you, but since no one is truly communicating well, all sorts of opinions start to become. You're telling yourself a story. You might not have the right people. So lineal chef on the team. So I'll shuffle them around and get a better outcome, which leaks out.

And people start to lose their mind because there's a reorg. Or if it's just you thinking they think they fail because you didn't give them context because you were busy, withholding information, being proud and not listening by the way. If you worry about politics in this scenario, this is a cesspool of politics.

This is where politics gets created, where people divide and the little factions that aren't communicating. It's a nightmare scenario, and it gets a lot. Congratulations.

Congratulations through this death combination of poor communication. Crap judgment and systematic demoralization of the team. You and your team have failed at the task at hand, but you've also irreparably harmed your relationship with your, maybe your peers and your team, and your credibility is hurting really bad.

But when you know, it's awful, when you know you hit rock bottom on the new manager, death spiral is when someone comes to you that you trust and they say, hello. Horrible toxic thing, whatever that is someone that you trust is this is the mean about you or the project, and could not feel it could not be more untrue and it punches you in the gut and slaps you in the face.

And you're like, that's just not, that's not, I didn't, I don't even understand where that came from. It's a bad toxic. And you quietly tell yourself the following statement.

This is me.

How in the world did like this scenario, like come to true? Like how can I say that thing about me? The thing that this is awful, it's designed to like, make me feel bad. It's just, it's untrue. You're right. It's not really who you are. What you are right now is precisely the opposite of a leader.

All right.

Teacup, pig, timeout. I want to take a deep breath. Relax. I got a teacup pig. All right, so that one's better than the first one. Good. All right. I have just described obviously, a very personal thing for me because I've been through it before when you've received, like, oh my God, that's awful. And it is, again, all of the things that are constructed to like make it a worst case.


management is not a promotion. Anyone who thinks this is a promotion. Is woefully incorrect. It's not a promotion. One of the things I have done at slack with many of the wonderful people in the room here, how many slack employees in here? I should probably ask that now, slack folks. All right. With like sick of the people in here is we have a course landed there early on built a management track.

And of course, because there's this management track and we're saying, this is the management track I haven't gone to, this is what we should be over on that. So we're losing all these engineers to being managers, which is lovely because it is a different role and it helps us scale. And some of these folks, we have amazing managers, but some of these folks will not be good managers and they need to have that sense of progression.

That sense of how I'm going to develop as a leader, without doing all of this people stuff, or may not be equipped to do. So. We built a leadership path, which is the IC path, which has all the same pomp and circumstance and chance to opportunity for folks to grow. These are equally important. Because if you create one path, everyone's going to think that's the path towards promotion.

You are promoted when you were successful at your current job, it's equal parts, recognition and reward in many companies, the expectation is you're performing at a higher level for a period of time before you actually get there. If you're going into management for the first time, you are effectively starting over.

It's a restart. Management is a career restart. Now, you know, the company, the terms, the culture, and all those sorts of things, but you're moving to the other side of the brain. It's a completely different set of skills. The curse of the Silicon valley relative to engineering is that we have spent way too much time highlighting this management thing and not enough time tiling the leadership thing, because folks just jump into management and we lose some amazing folks that could be great leaders, but maybe not good, man.

The death spiral is not real unrealistic and deliberate construction. It is unlikely that you perform each of the steps in the spiral is equally likely that you nodded your head. I was as talking and I can confirm that many of you, many of you were nodding your heads and grimacing as I was talking. Yep.

I did that. Whether you perform one or all of the steps, the lessons are the same and they are the same lessons. I wish someone had given me when I was first. There are three.

This is a powerful, powerful thing. Let others change your mind. There are many, any more of them, then you, it stands to reason their network is collectively larger than yours, or it stands to reason, right? They have more information, listen to that information and let others change your perspective and your just.

Cal Henderson is a CTO at slack, and he's a little bit scary. He's kind of British. He's really smart. He's one of the founders and, and he's a guarded, I think is the thing I would describe her amazing partner in crime there. But the thing that I really appreciate about cow is when you walk in. Yeah, we had this meeting a couple of weeks ago.

Oh, count also has strong opinions about things. Okay. When we came into a meeting, my senior staff meeting and someone was presenting something that I was pretty sure was contrary to what Cal believed. So what did he do? He let the person present and then he peppered them with questions. What about this?

What about that? What about this? What about that? And this person had prepared cause they knew this is kind of the game that was played. And when he was done, when it's done peppering this person with questions, Cal said, and this is how you know, that you've changed his perspective. He says, that's perfectly reasonable.

It's kind of awesome because he is so strongly opinionated. But when you have passed the test of this is a reason, a defensible argument. He tells you yes. Now that's different than a lot of leaves with feel I have to dig in, but what did he do? He listened. He updated his priors and he built trust. Okay, here I was wrong.

He didn't say I was wrong. That'd be hard. When you update his priors, you want to show to demonstrate to your team. And when you receive information that you can update your priors and change your mind.

Augment your obvious and non-obvious weaknesses with a diverse team. You are bad at something. Do you know what it is? Not bad. Let's let's get a positive. You have areas of growth. Do you know what those are? If you don't and you're a leader. Go ask a friend, maybe someone at work and say, what am I bad at?

And it's like, Hey, you are so amazing. And like the first 30% and the inspiration. And when you can go to this thing, but when the work actually has gets done, you get bored instantly. So you lot need to be paired with great execution humans because they help that middle part. When you're like, this is boring.

I can already see the ending, which is three months away. So I am paired with execution folks. Cause I liked the front. I liked the design piece. I also liked the ending piece cause it's kind of like the opposite of the design piece. A diverse team is not, there's a social justice thing, which is very, very true.

It's it's choosing the path of least resistance to build a team full of humans who agree with you. And by the way, you're wired to do this because it's comfort, it's safety to have people say why. Yes, that's a great idea. Ideas do not get better with agreement, ideas, gather their strength with healthy discord.

And that means finding and hiring a set of humans with the widest spread of perspective and experience and to build a safe place to be. I'm arguing for more tension on the team. I'm arguing for arguments where it's a little bit charged, but that's okay because you're building things for other humans probably.

And the more humans that you have informing and debating your decisions, the better your ideas are going to be. This is not easy. Most teams, I would argue, hire people that are like. Because we are biologically wired to do that. And you need to inject chaos into the system to make sure that you're finding and attracting and building these diverse teams who, and this is the one I know I already said this, but it's the most important part.

I think you need to figure out how to delegate more than is comfortable though. I have a very capable. Don't tell the spotlight people is, as he streams on YouTube, I have a very capable leadership team. I have a very capable, I am. The reason I am so happy is I am partnered with an amazing CTO and my team is capable.

And what do I mean by that? That means 99% of the things that come to me, I'm like, oh, this is a big, scary, huge thing. I feel absolutely confident. And I can, I can hand it to someone, anyone on the team. That is the first time in my career. I've had that like calm confidence in the entire team. You need to build that confidence in giving folks other things.

And that means giving up your toys, getting that thing. That's like, oh my God, I can totally crush this. It's a culture people thing. That's my jam. Let me just like do this thing. Put me in the biggie. I, I really should give this to someone. Who's going to get a B on it. We're going to build trust. We're going to get it done.

And we're going to bill each other as we do it. This is the thing I want you to think about. Wow.

The role of management is already set up with a tremendous amount of pre-existing potential inks. You are their boss, you gauge their performance, you set their. That is an intense thing. Set of responsibilities. It's a powerful set of responsibilities. The burden is on you to prove that you deserve those responsibilities.

You weren't given to them. You have to earn them even after congratulations have happened, even after you already in the role. And you do that by building trust. By listening by over communicating all the time, delegating giving feedback, receiving feedback. It's a long list. There are books on this topic, but this is what you're working on.

This is the thing that you're doing teams that trustee Tyler, I bet you know what this feels like. I bet you've had a team that was high trust. You know, everybody on the team, you know, their names, you know what they're good at? You know, what they're bad at and you trust that they have your back. You're trusted.

They're going to tell you what's going on. These are highly effective high velocity teams, high trustees get shit done in a way other teams that are like, whoa, it'll be should we check that with the person? And I'll talk with Bob and I'll get back to you as opposed to like it's for Bob I'm outta here.

He's bested that stuff. When your, every action as a manager, this is another thing that's not in the slides, but I'm going to go on is being scrutinized in a way that you are underestimating every word that you say every action is percolating and amplified out into the system. So what you need to do is look at each action that you're taking and ask and ask, think their eyes reflect.

Am I building or eroding trust with this? If the answer is, yes, I am building trust. You can avoid the new manager death spiral. You build yourself by building others. You build yourself by building others. That is what a manager does. Thank you.

About Calibrate—

Founded in 2015, Calibrate is a yearly conference for new engineering managers hosted by seasoned engineering managers. The experience level of the speakers ranges from newcomers all the way through senior engineering leaders with over twenty years of experience in the field. Each speaker is greatly concerned about the craft of engineering management. Organized and hosted by Sharethrough, it was conducted yearly in September, from 2015-2019 in San Francisco, California.