How to Actually Build a Better Boss
I never thought I would be the sort of person with a massive stack of management books in their office. I would look at those books in the airport and think who reads those things? Well, there’s an answer: millions of people who want to be better at their jobs, or want to feel like the sort of person who is better at their jobs, or have been told that they need to get better at their jobs. They’re eager, they’re desperate, and/or they’re not actually interested, but feel like they should be. That’s the market for management books, but that’s also the market for all manner of self-help books — which are responsible for millions upon millions in book sales every year.
I generally want to be better at my job, but my job isn’t managing. I have these piles of books, many of them bought for approximately 99 cents off of eBay and various other Used Book Sellers, some of them from the last five years and others from fifty years ago, because I wanted to see both the perceived problems of management — as well as the advice for how to fix those problems — has changed. Charlie and I read, gutted, or threw a lot of these books across the room while researching Out of Office (pre-order that shit!) Some of it was interesting, most of it was quite bad, in part because most of it seems to profoundly misdiagnosis the problem in the first place — or, just as often, attempt to treat the symptoms of bad management without confronting the actual malady.
And then Charlie had a long, meandering phone conversation with two ex-Mozilla employees, Melissa and Johnathan Nightingale, in Toronto. I have a memory of Charlie coming down the stairs afterwards: we were in the real depths of trying to write the chapter on work culture, fumbling around to give shape to what was so profoundly wrong with management pre-pandemic. “These people fucking get it,” he said.
Instead of trying to describe what, exactly, they get, I’ll just invite you to read their answers below. If you, too, feel like the vast majority of writing on office/knowledge work and management misses the point, I can’t recommend their work highly enough. And if you’re interested in hearing more, they have a new book, Unmanageable, a newsletter (appropriately titled World’s Best Newsletter), and you can learn a lot more about them and their work with Raw Signal Group here.
I was immediately drawn to your work because you had lived what, in our book, Charlie and I call “add-on management” — when someone is very good at their job, and a company decides that their skill means that they should naturally be a manager. I’ve found this attitude all over the place in tech/start-ups in particular, in part because so many of them start without any form of management (we’re just some people making a thing!!) and then, when they realize they need some, they start scrambling. I get the inclination, but I also know that it can have pretty disastrous short and long term ramifications. Can you talk about your route to your current work — and how that experience influences the overarching way you think about management?
Melissa: Johnathan and I both started managing people at Mozilla, in the very early days of Firefox and the web. We started with the organization when it was around fifty people. And grew with it to up over a thousand employees. That experience of fast growth was really formative. But it wasn’t unique to Mozilla — this is the experience of a lot of people in startups and tech companies.
Johnathan started as an engineer. I started as the first PR hire. Over time, engineering grew. And so did the marketing team. The organization needed someone to manage those people and so, within a few months of each other, Johnathan and I both stepped into people management roles.
We joke that the full extent of the preparation we got was, here’s a new title, here’s a new box of business cards, off you go. But that’s what it was. There was no training. We were not only managing people for the very first time, we were leading large teams, doing complex work, across time zones and different labour markets.
At the time, we thought it was just a byproduct of being in a fast growing org. But the longer we stayed in tech and the more we managed and led teams, the clearer it became. This wasn’t a one-off. This was how we were bringing up new managers basically across the industry. And you didn’t have to look too hard to see that the ramifications weren’t slightly less productive orgs. The impact was unchecked harassment, workplace trauma, and a massive flight of marginalized groups from the sector.
Johnathan: When you talk about “add-on management” it reminds me of the conversation I had with my VP when I was promoted to Director of Engineering. I had a three week old newborn at home, it was my first conversation back at work. And my boss said, “We’re making you Director of Eng - you’re taking on another 15 people. I want to be clear that this is strictly additive.” He said it like it was a charming, self-aware joke. Ha ha, here’s extra work, and responsibility for more people, but no you can’t put anything down. That’s obviously unrealistic, but here I am saying it! Strictly add-on. Ha ha. Isn’t that a funny turn of events?
I really tried to live up to it. When you’re promoted it feels like people are trusting you with more, and you want to prove you deserve it, and it messes with your head. If someone asked me to take on a new job as, like, Chief Financial Officer or something, I’d like to imagine I’d ask for training right away. Because I don’t know how to do that job. But when it’s management, we treat it like it’s some natural extension of your individual work. Even though it’s totally different. It takes a pretty high level of self-possession to be able to say, “I am honoured but I don’t know how to do this job and I need help.” I didn’t have that self-possession until later, and can list several screw ups I made as a manager as a result.
In the intro of Unmanagable, you write that “people aren’t born knowing how to manage and lead groups in a work context. And if they aren’t born knowing it, that means it’s learnable.” I think people are increasingly on board with thinking about management as a discrete, teachable skill — but they also are thinking of it as something that can be taught through, like, a half-day off-site. (Or, in remote world, a couple of Zoom seminars) What does that understanding get wrong about what good management actually looks like? And if not a half-day off-site, what?
Johnathan: How hard could it be, right? We hear this a lot, and it’s a place where we make ourselves a giant pain in the ass at times because we don’t do “snackable.” It’s true that management is a learnable set of skills and I totally get why people want to treat it like a buffet. “I’ll take a bit of difficult conversations, and some compensation strategy, and maybe I’ll come back later to learn why my meetings are so hateful.” But it doesn’t work that way.
One key part of management is learning the skills, for sure. But you aren’t actually doing management well — you can’t be — without two other things: 1) You need to develop an awareness of, and do some reflecting on, your power in the organization and how you use it; and 2) You need to build systems of accountability for yourself and your peers in management.
Those are learnable too. But self-reflection takes time to set up, and time to actually do. And that group accountability, a shared, vulnerable place where we can say “we’re not doing the things we need to for our people or each other” also takes time. We talk a lot about how the skills training is a trojan horse. It’s not really fair: the skills are valuable all on their own, they aren’t a con. But the skills conversations let us pull a group of leaders into conversations around power and motivation and engagement and sense of purpose and values and identity. Important, essential stuff happens in those conversations, but they are a slow tool.
During COVID we had to build whole new programs, because all of our work had been in-person until March of 2020. Right now the shortest program we run is about five to six weeks long. That’s honestly as fast as we can go to give people the room to do work that will actually last. And even still we send them six months of follow up prompts.
Melissa: We talk to leaders about the Dunning-Kruger effect: this idea that humans, as a species, are super bad at estimating our own expertise. The sentence tucked in at the start of Johnathan’s answer above is a very famous marker of something called Unconscious Incompetence. The part where you’re so bad at a thing, you aren’t even able to assess what skillful would look like. “How hard could it be, right?”
Taking it out of the realm of management for a second. Playing guitar. Standing up on a surfboard. Driving. “How hard could it be, right?” If you have ever tried to learn any of these skills, you know precisely how hard it is. The minute you’re out in the ocean and a wave crashes on top of your head, you realize there’s more to surfing than the standing up part. The first time you try to play a chord and realize that the guitar strings cut into your fingers. And that first time you’re in the driver’s seat and realize you don’t even know how to put the car in drive. That realization. That shift from “how hard could it be, right?” goes directly into something called Conscious Incompetence. Which is to say “actually, really fucking difficult.”
Bringing it back to this idea of how we teach management in organizations today, many of the snackable programs are pulling from Unconscious Incompetence. I haven’t yet begun to grasp the complexity of the thing and so it seems simple. But the more I begin to engage with it, the more I understand that it’s a layered set of skills. Ones that I can understand. And practice. And overlay. And that yes, it’s all learnable, but it’s not gonna happen over the course of a single lunch & learn.
The book invites readers to revisit the places they were at various points over the course of the pandemic, from that initial flailing to that later extended slightly duller but no less acute flailing. I appreciate that you want the book to take people back to the experience of trying to manage — or just trying to be an employee, or trying to be a human — over the course of the last year and a half. But I also think there’s a real desire not to revisit those places. I was thinking about the process of writing our own book last year, the immersion and sameness of the days, a real revisiting of some burnout behaviors….and it was hard and weird and tender. Why did it feel important to throw people back into that early and mid-pandemic experience of managing?
Johnathan: Hard and weird and tender. Yeah. 18 months in that shit has not healed, has it? I feel that.
I have a polished answer and a childish answer for this. The polished answer is that everything about work has changed through the pandemic. And that we felt like it was really important, for anyone trying to lead in the next decade, to really sit with the depth of that change. To go through it, and process it, and integrate it into how they relate to their colleagues and their work. A thing I love about your writing through the pandemic is the way you’ve talked about grief -- that you can be gentle about it but you can’t skip it or hide from it. You have to feel the feelings to get to the meaning on the other side. That’s definitely part of the reason.
The childish answer is that it’s a fuck you. There are these bosses I can imagine, in the future, saying “easy for you to say, you don’t know what it was like, we had to make tough calls during uncertainty and fear and the survival of the company was at stake &c &c.” I am a twitter person, so I’m very skilled at being angry at imaginary people. We were there when it was hard. The bosses we work with were there. And I feel like it’s so important to say, “even in the shitty scary parts, it was possible to think about your company this way, it was possible to keep people on payroll at a loss, it was possible to run a good business without hurting people.” Each chapter starts with a calendar entry, and I feel like that’s the key to the whole book.
Melissa: We had this paranoia. One that I think you and Charlie probably saw with your book as well. That because of how books typically get written and produced, we worried that any book about the pandemic and work would be written as a retrospective. And that, with the benefit of time and space, it would be easy to gloss over some of the uglier and more tender parts.
It’s fine to want someone else to pre-chew the food and give you something with the rough bits sanded off. That’s an ok thing to want. But we didn’t want to lose the actual experience. Because the actual experience is what’s driving everything right now. People leaving work without knowing what’s next. People pushing for change because the old thing was untenable. The urgency of that push is in direct proportion to how shitty that year was.
On the back cover of the book, we say that if you want to understand the future of work, you have to start here. That’s because the strength of the shove going on right now won’t make any sense once it’s been watered down and repackaged and made palatable for a 2023 audience.
Starting before the pandemic and continuing now, there is a lot of focus on Diversity, Equity, and Inclusion (DEI) initiative in the workplace — but I don’t know that those conversations, internally or externally, are actually delving into what it means to hire and train managers in a way that doesn’t just recruit or retain “diverse candidates,” but reimagines the entire organization as diverse, with inclusion and equity fundamental to its operation. What’s missing from DEI conversations when it comes to management and leadership? And how do you encourage snow-capped organizations in particular to conceive of management and leadership differently?
Johnathan: We have a lot of friends who do DEI work in-house or as consultants but, to be honest, we have even more friends who used to. The burnout and exhaustion and sense of futility that they often have to deal with is brutal. And it’s because of exactly what you’re pointing to. Great, transformative inclusion work is about understanding and dismantling and rebuilding systems of power, right? I mean, it has to be. But the practitioners we talk to often find themselves talking mainly with the more junior employees in an organization, who are often marginalized and experiencing the shitty end of those systems. That’s important work! But they are totally shut out of the conversations with the people who actually hold power in the organization.
It’s not even that those senior leaders are cynically ticking a DEI checkbox -- some of them are, but not all of them. It’s almost worse. It’s that they just haven’t really given it much serious thought. Somehow, in 2021, this is a topic that they’re starting to think about for the first time. And they still feel like the whole thing is sort of peripheral to their core work.
So much of what we talk about in the book and in our newsletter is about this renegotiation that’s happening. That power is shifting in organizations and that new expectations and accountability are being pushed *up*, that bosses can either get right with, or get run over by. And for a lot of the bosses we work with, the hardest part is just getting them to actually see how power operates in their organization. Whether we’re talking about salary negotiation, or running a good hiring process, or giving meaningful feedback, there’s this underlying current of “am I treating the other person with dignity and respect”? Am I acting with empathy for them and their position, am I listening to what they’re saying or just managing a complaint? Who has power in this interaction and how do I feel about the ways it’s being used?
When it works, when it really connects with a boss or a team, we can tell because they start to get really curious. Like, they start to see it everywhere, because it is everywhere! Among other things, that’s when they start to ask us for DEI referrals: because they actually want to go deeper now, and they have a moment where they can glimpse how structural it is. I wish I could say that happened every time, but when it does it’s pretty great.
Melissa: There’s a fundamental shift in organizations when leaders view themselves as on the hook for culture. Middle managers, in particular, get caught in this trap where they view themselves as powerless. Which is a weird-ass thing for people who both by role and hierarchy, hold power. But they aren’t the CEO. And they aren’t part of the C-suite. And so they point upwards and shrug.
And that’s a punt. Bosses control how work feels for the vast majority of the company. If you think about a traditional tree structure for a minute, like the awful powerpoint org chart that’s sitting in an HR file somewhere, and you just imagine the lines that indicate relationships. Count up the direct relationship lines for the CEO and then put them side by side with the direct relationship lines for all the middle managers across the entire org. In most companies the bosses are holding the overwhelming majority of those relationships. They are the people who make shifts and move the org. It’s not that the CEO doesn’t get a say or have impact. But if you want to change the culture of an organization, it’s almost impossible to do it without the middle.
Johnathan points to this push from the bottom, on accountability and equity. That’s necessary but not sufficient. For every organization, both new and established, the big question is where are your leaders in this story? And how do they think about their role in it?
Why is it *so hard* for people to change the way they conceive of managing? I’m thinking specifically of leaders who want employees back in the office, no matter what: in so many cases, it’s a symptom of not understanding how to manage outside of presence, surveillance, and the *feeling* of power.
Melissa: I love this question. And if you really dig into the leaders clinging to dated and disproven notions of how to effectively manage and lead teams what you find is that they are two things. Afraid. And unskilled.
Afraid because I’m on the hook for the performance of this team. If they don’t do well, then I know that reflects on me. Either in terms of my own ability to advance within the organization. But also in my own ability to stay employed. So I reach for what I think might work. And even when it’s been disproven by decades of organizational behaviour researchers, most middle managers aren’t spending their days catching up on the latest academic research. Most of them are trying to get by and hoping no one will figure out that they don’t know what they’re doing. Which brings us to the second thing.
Unskilled. There’s a very sad stat that most leaders, not just tech but across all knowledge industries, go about 12 years in the role before they get any management training. And that’s pretty consistent with what we see out in the world. The vast majority of leaders have no formal or even informal training. And so, as a boss, I don’t even know the difference between a good tool and a bad tool. It’s not to make excuses. The folks who are getting paid to manage teams should possess core management skills. But if you look at how our offices are structured, many don’t. Either because they lack internal training programs. Or because they have them but are pulling from very dated or very dull material. And the overwhelming majority don’t have anything in place at all, outside of some legally-mandated harassment prevention training.
So the trick to getting bosses to change how they approach management is to give them a robust toolkit. Give them skills. And a cursory understanding of why those things work. And then have them build muscles using the new tools. From there, it’s much easier to put down the things that aren’t working. The tools that are undercutting your team's effectiveness or cohesion. Because it’s no longer a choice between “this thing that isn’t working well” and “nothing.” It’s a choice between the shit that is no longer serving the boss, the organization, or (oh by the way) the team. And actual, concrete skills that would. Once I’ve got some new tools and I see them work, I get more confident. And from a more confident place, I’m much more open to change.
Johnathan: This is also why you see so much snake oil in management. Every month there’s a new personality test or “management operating system” that gives everyone a letter, or a number, or an animal or whatever as a way to give people a framework to stop failing at this. That and true crime is basically all airport bookstores sell.
When you think about Melissa’s answer, you have a population that’s unskilled, and afraid, and has money. That’s going to attract every grifter in a thousand miles. They’re always super reductive, they’re always framed as “Finally a way to make sense of the chaos! Once you understand that there are only 8 kinds of people in the world, management is easy.”
What we tell bosses is, look, if Myers-Briggs, or Strengths Finder, Enneagrams, or DISC assessments, or Astrology help you gain clarity about yourself and do some of that introspection? Great. All models are flawed; some models are useful. Any tool that gets you interrogating how you show up for other people is a gift. But please do not inflict it on others, or believe that it constitutes thoughtful, nuanced, effective management when you do.
You offer advice in the book about how to quit a job with some modicum of elegance when you know it’s time. Burnout, deep disengagement or demoralization — those are signs that it’s time to start looking for another job, but how do you know the difference between when you need to figure out how to create a better relationship with work/your manager….and when it’s time to quit? When, in other words, do you know that there isn’t enough therapy in the world to fix the relationship?
Melissa: Sometimes you don’t. It would help a lot if the moment we’d tipped from fixable into unsalvageable, some glaring red light went off over our desk. But that’s not how it works. Often, we have a nagging sense for some time that it’s not quite right. Or something changes, a new boss, a new project, a different client account, and it’s not so much a nagging sense as a screaming in our gut. But regardless of how it shows up, for many of us, we feel the need to try to make it better. To ride it out. To be grateful for the fact that we still have a job when so many people have it so much worse. We point to the fact that we are still learning, and that we like our coworkers. And if we leave, we worry about how much work will end up on their plates.
Humans are very good at storytelling. And we’re very good at staying safe. And so we find creative ways to tell a story about why staying put is a good idea. Sometimes that conservatism is really helpful - it gets us through a rough patch where after that things start to improve. But other times that storytelling keeps us in a bad situation well past a healthy point.
The problem with prolonged exposure to a toxic or abusive workplace is that the longer you stay, the harder it is to leave. The more time you spend with a boss who thinks you’re incompetent, the more you internalize that message. And the harder it is to muster the courage and confidence to apply for other roles. This is a very bad spot and most folks in this position know it’s not going well. But they often hope that they can fix it single-handedly. That if they work hard enough, they can turn it around.
And the hard truth is that if your own boss is not on board. If that person doesn’t want to see you succeed within the organization, you’re screwed. You may luck into a spot where that person quits and suddenly you’ve got a new reporting structure that allows you to thrive. But if you are working for someone who doesn’t believe in your ability to learn and grow within the organization, you’re sunk. You cannot outsmart that problem.
So the question for anyone trying to figure out if they are staying or going is “do you have a partner in making it work?” Can you point to someone in a position of power over you who is actively trying to make things better? Is anyone adjusting a burnout workload? Introducing new systems or processes to make things run smoother? Communicating planned changes that have you optimistic about the future? If not, you have your answer.
Johnathan: I just want to underline where Melissa uses words like “toxic” and “abusive.” That’s a real risk: work can really wreck people. Lots of people can’t afford to quit, and that’s an awful trap to be in. But if your work is veering towards abusive, and you have any ability to leave, please leave. Don’t work on a relationship with an abusive workplace or an abusive manager. Even if you think you can endure it, it’s not worth it. The costs to your health, and self perception, and future happiness, are so high.
What mistakes or missteps are you seeing managers and organizations make over and over again right now — and what changes make you hopeful?
Melissa: Failing to train managers. I mean, perhaps we would say that. But holy shit does it keep happening. We promote people into management and we just hope that they figure it out. And then we stand, mouth agape, when things go sideways. And this isn’t just a problem for our new managers. We are 40 years into this strategy and now the overwhelming majority of the workforce came up through this same form of occupational hazing. Here’s a new job. It’s very high stakes. It’s totally different from what you’ve done to date. And the skill set isn’t intuitive at all. You’re smart. You’ll figure it out. And if not, you’re fired. Good luck.
That’s the summary version of how most of North America’s leaders stepped into the seat. And that they are now propagating that out is a huge problem, especially for a modern workforce that anticipates and demands competent management. That’s part of where you see generational strife in the workforce. Where folks who have been at it for a long time say, “Well, this is how it’s always been. Why are you complaining?” But when you ask them, “Were there downsides to that approach? Can you point to ways that it failed, both people and organizations? Oh yes, absolutely.”
OK then, let’s stop pretending we’ve got a working system for people stepping into leadership. Cause we don’t. And let’s get to work building something better.
In terms of what makes me hopeful, it’s that the folks just stepping into the workforce right now are correct. They are right to want something better than what came before. I talk to senior women in tech sometimes who want to complain that today’s new hires have no idea how bad it was. And I remind them, you don’t want that for them any more than you wanted it for you. Just because we’ve lived through the shitty version of work does not mean we need to gift wrap it for future generations.
Johnathan: I have another piece of hope to add here. It’s a thing I didn’t know when we started our company that now, in our fifth year, is obvious and reinforced every day. Most managers want to do a good job for their people.
This isn’t obvious to everyone, right? The popular writing about management is always a caricature: either a genius and perfect visionary, or a pointy-haired, micromanaging dictator. In our work, we have met very few of either. You can tell me that’s selection bias -- that we only meet the leaders who work for companies that invest in management training -- that’s fair. But we’ve worked with thousands of leaders now and we have seen a lot of bad management. We have seen “under-equipped”, we have seen “got some pithy-but-terrible advice”, and we have seen “hated a past manager and ran to the other side of the boat, making all the opposite mistakes.” I’m not giving those people a pass — that still sucks.
When you give those people some objectivity and some skill, though. When you pull them out of the worst of their Dunning-Kruger effect, they listen. They make connections, and ask vulnerable questions. The number of leaders we’ve had say, in one of our programs, “Shit. I’m realizing now how I screwed some things up.” That’s hopeful for me.
This will sound incredibly corny and I’m sorry but that’s what all of it is for. People talk about our books, or our newsletter, as marketing for our business. But the truth is: the books and the newsletter and the business are all just different ways for us to do the work. When bosses get better, work gets better. That makes us hopeful. ●
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