Be a Manager
This is my “manager origin story”. I wrote it in 2014 on Medium after I’d been a manager for a few years, during a periodic flare-up of anti-manager sentiment in the industry. (Medium itself was using a self-management system called “holacracy” until abandoning it in 2016.)
Managers as a group have been constantly under fire in the tech industry for my entire career. Zappos “got rid of their bosses” for a while. In 2001, Larry Page fired all of Google’s managers. And it’s no wonder. From Dilbert to “Office Space”, we all know the trope of the useless and conniving political player who’s managed to entrench himself into an otherwise well-meaning organization. He holds the keys to advancement, adds little value, makes other people miserable, seeks only more power.
But I’m here to say that the Bill Lumberghs and the pointy-haired bosses are not a natural symptom of organizations. Rather, they are a natural symptom of organizations that refuse to take good management seriously. They’re indicative of an organization that cares too much about what they’re doing and not enough about how they’re doing it. And this is especially prevalent in tech. Here’s what tech has effectively said about management: We can’t do this well, so we’re not going to do it at all.
This is actually a great approach to making it to your next funding round. Minimize distractions. Offload everything. Focus on the core problem. That’s a strength, but one of the best business thinkers I’ve ever encountered says this:
Whatever your strengths are, they will likely lead straight into your weaknesses. –Ari Weinzweig
Good startups are by definition great at focus, outsourcing, offloading, abstracting problems. It’s no wonder they look at this big messy problem of leadership and management and think first, “How can we avoid doing this at all?” And it’s fine to do that with your servers or your lunch, but not okay to do it with leadership.
The thing is, we don’t need to be innovative here. We don’t need to go back to, like, Sun Tzu and recreate management from first principles. There are tremendous resources available already, once we’ve taken up the challenge. How do we do that? We just need to understand that management is worth doing, and worth doing well.
I had my first and biggest life-changing insight long ago in the home of Chuck Newman. A close family friend, a wonderful host, and a longtime corporate and community leader, I grew up with Chuck as a non-related uncle, always a fun and energetic presence.
Eight years ago, at a Christmas dinner in 2005, Chuck said something that changed my life. At this gathering, I was rather rude to Chuck. He asked how things were going in my career at Google. At that point, the company was growing fast and hiring lots of top notch people, but above and around me I saw mostly conniving and striving. No one cared about the people “doing real work.” Everyone cared only about getting ahead.
Chuck asked if I ever wanted to be a manager. I waved my hand and said that managers were useless. That I’d rather focus on something important. I said this to a man whose wine I was drinking, whose success in management had paid for the standing rib roast I was eating. Chuck, though, was characteristically positive. “Really?” he said. “I’m surprised by that.” Then he said the thing that changed my life:
I’ve always thought that the hardest and most valuable thing in work is to get a group of smart people to work together toward a common goal.
Boom. Headshot. As soon as Chuck framed management as something that’s very hard and very valuable, I started to think of it differently. This was like telling a certain type of coder that Haskell is hard, a certain type of gamer that Dwarf Fortress is hard, a certain type of athlete that Crossfit is hard. I just couldn’t let it go. I left Google for a small incubator called Fog Creek Software and it’s been the smartest move I ever made. Fog Creek allowed me to grow into a servant leader while we created and shipped such products as Trello and StackOverflow.
So, that’s the “worth doing” part. If you’re not on board with the fact that this is difficult, valuable, and rewarding work, then you shouldn’t be a manager. But what does it mean that this is “worth doing well?”
For me, that means servant leadership. It’s really the only sane way to run an organization. See, the pointy-haired boss? Bill Lumbergh? He’s the default. He’s what you get if you don’t take management and leadership seriously and skeptically. He’s what you get when your managers are eager, rather than reluctant, to manage. And you can implement all the holacracy you want, but Lumbergh is always out there. A flat organization is a hundred-dollar bill laying on the sidewalk to these people. To a charismatic sociopath, or a good old-fashioned schemer, an organization without good servant leaders is like a field of wheat to a locust. Good management culture is your immune system against douchebags. (There, I said it.)
So what constitutes a “good” manager? Heck, if I could tell you in a few paragraphs, I could easily spin it out to a few chapters and have a business book annuity for the rest of my life. The best I can do is that they should first want to help people. Clayton Christensen says it best in How Will You Measure Your Life?:
I used to think that if you cared for other people you need to study sociology or something like it… I concluded if you want to help other people, be a manager. If done well, management is among the most noble of professions.
I chose to be a manager because in our very first session my career coach, Glenn Newsom, drilled down enough into my motivations. I was coding and enjoying it. He helped me to understand that I’d never be happy (only) writing code; what I really wanted to do was to help people. Specific people. Not humanity, not a disenfranchised class of people, but individuals I can see and understand. It’s the only thing worth doing to me. It’s the only thing I do professionally that gives me more than it asks of me (and thus is sustainable).
The people in my industry don’t need any other prompting to abdicate their responsibility to ensure good management. Many analytical types are already ill-suited to the task, given their distaste for messiness and gray areas. I felt this way when I was younger. But you know what? Suck it up. This is important. I see too many well-compensated and well-fed, but unhappy and unfulfilled knowledge workers to stay silent. These people are suffering needlessly (yes, yes, the poor coddled babies… but still).
Management is, frankly, not an attractive job to the people who should be doing it. But a good heart and leadership acumen is what’s needed most everywhere. Everywhere. Everywhere, but especially where good leadership has been left to the default, to the pull of charisma, to the machinations of the power broker.
If you care about the people around you and you cede the responsibility to become a leader, you are, every day, effectively promoting a new d-bag into management. I’m not saying you should storm into your boss’ office and demand to be promoted into management. That never works. But when good people start learning about servant leadership, something wonderful happens. People around them start sighing with relief. Finally! Someone has finally taken on the challenge. Go. Learn about it. Start learning to be a manager, and be uncomfortable about it. It’s exactly what we need.
You are exactly who we need.