How F*cked Up Is Your Management?: An uncomfortable conversation about modern leadership

By Johnathan Nightingale and Melissa Nightingale

This book has swears. Any honest discussion of management today needs a few. And it’s just what you’d expect from the creators of the internet famous blog, The Co-pour.

If you’re trying to lead a group of people today, the bad news is that it’s harder than ever. Your employees have impossible expectations of you, an

• Language: English
• Publisher: Raw Signal Press
• Release date: Oct 3, 2017
• ISBN: 9780995964310

Johnathan Nightingale

Johnathan Nightingale has built and operated organizations from 2 people to 250. He was the Vice President of Firefox for Mozilla during a period of intense turmoil inside Mozilla and out. He helped build and launch the first Firefox offerings on Android and iPhone, and still cheers every time the open web wins. After Mozilla he joined Hubba as their Chief Product Officer, and helped that team triple in size while improving their diversity stats instead of watching them slide. He is proud to sit on the board of Creative Commons, and is a big believer in the power of mission-based organizations. He has strong opinions about your coffee infrastructure. You can find him on twitter: @johnath

Book preview

Welcome

Why are you here?

Did someone hand you this book? Maybe one of our blog posts was forwarded to you ages ago and you’ve followed us since? Maybe you spotted the cover on a shelf and picked it up because you like swears. You’re in luck—this book definitely has some swears.

However you found us, we’re glad you did. This is not a big book, but it’s an important one. We take this stuff seriously. Between us we’ve seen the insides of dozens of the world’s most innovative companies, and the results are bleak. Absentee bosses. Poorly run meetings. Ping pong tables and beer in place of culture. The modern office, with its open floor plans and free snacks, is failing to deliver on the most basic workplace essential: actual management. Even the devoted managers we meet tell us that no one taught them how to do this stuff—they’re learning it as they go, and they’re terrified that they’re fucking it up.

More often than not, they’re right. And it doesn’t have to be this way.

How to Use This Book

We should start by saying that this isn’t an end-to-end book. It’s okay if you need to hop around between sections or read the last chapter first. We kept the chapters largely independent of one another to make this easier. There are shared themes, but there’s no correct order.

We also expect that at different phases in your career, some of these sections will speak to you more than others, or that some chapters feel like they’re written for someone else in your life. That’s okay, too.

When a chapter pulls from a post we’ve written online, we used the same title so it’s easy to look up or share with a friend. But some of the stuff in here has never appeared online, and might never. The friends who need to read those chapters will have to buy their own copy, or borrow yours.

Our Origin Myth

The vast majority of this book was written in our living room. We’d take turns writing posts about tech leadership or startup management. Over time, we amassed something of a following. We’ve been in tech for our entire careers, and, at first, we assumed that was our only audience.

But we quickly learned that folks in other industries were reading, sharing, and commenting, industries in which we’d never worked a day in our lives. They emailed to say it was the first time in a long time they’d understood how to manage their teams, align their organization, or better understand what the heck their boss was thinking. These were people in health care, in agriculture, in law, and in mining. We started to get the sense that our writing wasn’t just about leadership in tech or startups, but about leadership in general. It’s a humbling thing. It was the first time we started to talk about putting this book together.

This stuff is hard, and it’s one of the areas where leaders need the most support but often get the least. When we write, we often think of ourselves a few years ago. We think about what we wish we’d known then, the mistakes we could have avoided, and the successes that would come in time. This book exists because of those comments and emails. If you’ve ever been unsure about whether to comment on a post you’ve enjoyed from some stranger’s website, now you know. Those comments made us believe there were enough people who gave a shit to make it worth doing. Thanks for giving a shit.

Signal and Noise

There are already a bunch of folks writing about this stuff. In a sense, that’s part of the problem. When you don’t know what you don’t know, everyone out there looks equally credible. Part of our desire to write this stuff down is the gap we see in the writing about startup life and leadership in general.

Social media is chock full of think pieces on management. But so much of what we read there doesn’t match our experience. The posts are well written and pithy, the headlines tantalizing, but they don’t cover the stuff that happens in our day-to-day. And in some cases they advance theories or propose systems that we don’t believe can help any company actually succeed.

There is good stuff coming out of some of the writers in the venture capital space. VCs have a rare vantage point: they get to sit on a bunch of boards, hear a bunch of pitches, work with a bunch of entrepreneurs, and do all of it simultaneously. They have access to a wondrous amount of context and, as a result, they tend to be great trendspotters. They write prophetic pieces about the state of the industry and what’s to come. They often have great insight on corporate strategy and product growth models. But they rarely touch on how to be a better boss or how to think about the organizational impact of scaling your company. And when they do, it’s clear that they are well out of their element.

It feels so different when you actually operate inside a business. The problems you are trying to solve are much more complex when you add humans to the mix. It’s no longer a matter of having a crisp vision or a well-articulated strategy. Those things definitely matter, but once you get a large team of people involved, all bets are off. The perfect vision, the defensible strategy—these are nothing if you can’t get a group of people fired up about helping you get there. This book is not about strategy; this book is about operating.

What We Mean When We Say An Uncomfortable Conversation

We didn’t set out to be controversial, but depending on your background and experience, some of what’s here may piss you off. A lot of what’s in this book is uncomfortable to talk about. We try to confront some messy power dynamics. We definitely disagree with some received wisdom. And a lot of what we have to say now was uncomfortable for us to learn about in the first place. We find that discomfort is generally a good indication of where there’s work to do.

Apply what’s useful, skip ahead to the chapters that resonate, and double back when something catches your eye. Spend time on what about it gets under your skin. You don’t need to agree with everything in this book, but if you disagree, you should ask yourself why. It might be that we’re wrong, or that we’ve said something that doesn’t apply in your world. But it might also be that we’re right and you just don’t like what that implies.

We’d consider it a failure if you made it start to finish through this book without wincing, without having some work to do. As leaders in modern organizations, we all have some work to do.

What We Mean When We Say Modern Leadership

We wrote this book to share more of what we learned the hard way. There’s a lot that we wish we’d known when we were starting out in tech twenty years ago.

The canon of management classics doesn’t have much to say on the management and leadership discussions that are happening right now. If diversity is mentioned at all, closely linked ideas like privilege aren’t. Books that talk about how to partner well with HR don’t have much to say about the modern trend of startups skipping on HR hires altogether. We now have companies crowing about how they’re entirely doing away with management. The classics don’t have much to say about that idiocy. We are in the midst of a major shift, not only in the age of the modern workforce, but in the expectations people have of businesses, bosses, and corporate accountability.

The fundamentals of leadership haven’t changed because people haven’t changed. Our job as managers and leaders is to make our teams more effective. Our job as humans is to add some compassion to the world and leave it more excellent and just than we found it. Modern leadership is the never-ending work to reconcile and integrate those things. What is different today is that we have access to so many more perspectives and exposure to so much more criticism. Our people expect more from us than the management classics ever anticipated.

That change is exciting for us. We’ve built our careers on it. But it means the management canon needs an update. What you hold here is what we’ve learned toward that so far.

ONE

Let’s Talk

A series of uncomfortable conversations

/1

How Fucked Up Is Your Management?

A quiz, an extremely boring manifesto, and a free drink coupon

> Johnathan

It’s taken me fifteen years in this industry to figure out how to be any good at what I do. I don’t know how to write it all down yet, but I’m going to give a piece of it away to you in the next five minutes.

It starts with an observation that is controversial to many folks, even though I think it’s like saying that water is wet:

Managing people is exceptionally hard to do well. People are complex, and organizations are just full of them.

I have managed many people at a variety of scales and worked with leaders of other organizations big and small. I’ve trained up new managers and watched them grow into strong leaders. I’ve sat with them through hirings and firings, and watched them struggle with both.

I’ve had members of my teams get married, get divorced, have kids, lose kids, attempt suicide and (mercifully) fail. I have had an employee die, and to this day the social network birthday reminders gut me. No one who takes management seriously and does it well finds this stuff easy. No one who’s been at it for very long imagines that there are shortcuts.

But, as P.T. Barnum probably didn’t say,

There’s a sucker born every minute.

The infatuation with management shortcuts, particularly in startup culture, is rampant. The charitable explanation is that a lot of classic management practice feels slow, and founders are trying to unfetter their people. I think the harsher, truer explanation is that many founders are inexperienced managers and don’t understand the trade-offs they’re making at their employees’ expense.

Let’s Try a Quiz

Score 1 My management culture is fucked up point for each of the following:

→ We have an unlimited vacation policy.

→ We don’t do regular one-on-ones, but we have open office hours or are super available if anyone wants to chat.

→ We don’t have a process for interviewing—we just hire awesome people when we meet them.

→ We super-care about diversity, but we don’t want to lower the bar so we just hire the best person for the job even if it means diversity suffers.

→ We don’t have defined levels and career paths for our employees—​we’re a really flat org.

→ We don’t have formal managers for every staff member—everyone just gets their work done.

→ We don’t have, like, HR HR, but our recruiter/office manager/only female employee is super good if you want someone to talk to.

→ We don’t do performance improvement plans for employees who are struggling. We just have a super-honest conversation about how they aren’t a good fit and fire them.

→ We would have some hard explaining to do if our salary list accidentally became public.

I’ll cancel out you your first point for free. I’ll cancel a second one because it’s hard to run a business and there’s always something you wish you could get to but haven’t yet. I understand that. And, if you’re on the bubble, I’ll cancel one more if there’s a thing on this list you are trying to change.

So how’d your company do? Fewer than 3 points? I’m happy for you and your colleagues. 4? 5?

More?

What a Waste

I’ve talked to people who score 7s and 8s. Sometimes they’re proud of it.

What I’ve learned is that a high score on that silly little quiz tells me two not-silly things about you: you’re wasting time, and you’re wasting your investors’ money. And what’s extra sad is that you thought you were doing the opposite.

You thought you were saving time by cutting needless process and especially needless meetings. Ugh, meetings, right? But a lot of these practices will increase turnover and lower productivity.

You know what costs a lot of time? When good people quit. You lose accumulated knowledge, you take a significant velocity hit, and you often have knock-on morale drag on the staff that stay. One-on-ones take time, but they let people get things off their chest. They also feed motivation and team identity. Defined levels and career paths take work to develop, but they’re a straightforward way to give people mastery goals and direction. A well-designed performance improvement plan takes longer than summary dismissal, but it can turn a struggling employee around and lift an entire team’s output.

Some of these policies do seem to save money. Unlimited vacation can be a useful way to avoid paying out accrued time when employees leave. And not hiring an HR person does save you their salary.

But a core value of good management is that your investment in your employees pays off as those investments grow in scope and impact. Well-managed employees make your company better. They mentor new people, take on new skills, and take personal ownership in the quality of their team’s work.

Ever look at some company getting it right and think, How did they hire all those amazing people? I’ll tell you how. They grew them. And they retained them. And that attracted more great people. People talk, and that flows both ways. Skimping on your people is a foolish (and gross) way to save money.

Don’t Take My Word for It

I try to manage well and thoughtfully, but there is certainly no shortage of disagreement out there on the right way to run things.

Valve software’s culture doc is near-biblical for many folks, yet it garners a pretty high score on my test. Valve makes more money than I do, and better games, too; maybe they’re right? I don’t know. Former Valve folk are not gentle with their description of a culture that felt like high school, with implicit favor-based power structures operating behind the scenes. I don’t want to work in that kind of place. Maybe you do?¹

Remember when GitHub was so proud of how they didn’t really bother with traditional management? Somehow, even with their unlimited paid time off, it didn’t go well.²

I hear they’re hiring more managers now, and I’m hopeful for them. My hope is not that they feel beaten and subjugated and pay their Manager Tax. My hope is that they realize how harmful their hubris is to the employees who helped them build such a central piece of the technology landscape.

An Extremely Boring Manifesto

Look, management may be hard, but this test is pretty easy to pass. And it proceeds from the first rule of startup club:

The First Rule of Startup Club: If you’re not planning to be the best in the world at something other people already do well, then don’t mess around with implementing your own version of it. Use theirs.

We usually cite this in reference to databases, or unit test harnesses, or snack providers. But it’s just as true here.

I don’t need you to be the best in the world at management. But if you’re not planning to be, if you’re not going to be really studious and dedicated to it, then for God’s sake stop messing with it. I promise you you can’t build a better management system in your spare time. Instead,

→ Set up every employee with a clear direct manager, and expect them to hold regular one-on-ones. Discuss their current work, but also