I worked for each of these humans. They either hired or promoted me. I worked for them for many years. As is my way, I’ve vastly altered the details of each human, but the core issue I describe is the core issue. Also, each of these humans is very smart. No dummies.
Here are their introductions:
An Introduction to The Artist
They hired me. I could tell via the interview process that, like me, they were an introvert. The interview was awkward. Long pauses. Odd questions. No feedback. I got the gig because everyone else who interviewed told me I was a fit, but whether they thought I was a fit or not, I will never know.
First day on the gig. I was sitting at my desk, and they walked into my office, hands in pockets, stood in the door, and asked, “How was your first day?”
… because someone told them that is what you do with new hires.
They are The Artist. Burdened with creativity, all the vision. You could see it in the things they built. Inspired. Somewhere along the way, someone decided to make them a manager. Direct reports. The hope that the art they created would scale with the number of humans.
The challenges were many and diverse, but the core issue is the value of the things this manager was capable of creating, which blinded everyone else to the fact that they were reading books about being a manager, following the rules, but either not caring about what good looked like being a manager or not knowing.
“How was your first day?”
I told them. I walked through each 1:1 I had (five), shared my first very raw impressions (many), and asked them what they thought. The reason I knew someone told them to ask me about my day was that they had absolutely no clue what to do with my assessment of the day. Blank stare. They either didn’t understand or didn’t care. I couldn’t tell which.
Introducing, The Dictator
They promoted me. It took a couple of years of hustle, but they went for it. First meeting in the new role, and we’re in the basement for what is called a product review. Engineering, product managers, and designers. Small affair. Happens when it’s clear we’re at an impasse. A large enterprise customer is threatening to bolt unless we solve a critical feature issue. Not a lot of people — everyone here can contribute significantly.
Product kicks off the discussion with a timeline and three fact-filled slides. Framing the conversation. Small clarification questions, but everyone has been briefed beforehand, so we get to the heart of the problem. Cutting to the chase: it’s a design issue. We had the right requirements, we built it correctly, but our design is wrong. It is confusing the customer. The good news, Design is on it — Design vetted the deck with engineering, and they’ve got solid proposals. This meeting should be a formality, but the Dictator is here.
When we reach the discussion portion of the meeting, the Dictator starts asking questions. Does this mean this? Yes. Have they seen that? They have. If the feature is supposed to do this, why does that happen? Well, I’m glad you asked. We have… and that’s when it happens.
No, no, no, I know you have a proposal, I want to litigate some more. This back and forth goes on for an hour. Several of us attempt to redirect back to the proposal and do not succeed. Soon, we’re at the whiteboard designing a new feature, and the punchline is: the feature is wrong. It’s clumsy at first glance and bad when you’ve thought about it.
And no one says a thing. We leave the meeting, having agreed on building a feature that anyone who has read the deck knows is wrong. And we built it.
And last but not least, please welcome, The Knife
They promoted me, too. I’m not quite sure why.
After it happened, it took a month before we had a 1:1. I would get random requests for information or suggestions, but mostly I ran my show as I saw fit. When the 1:1 showed up on my calendar, I was one part relieved, one part excited, and one part nervous.
I walked into their office, and they were on the phone. Pointing at me to sit down. They were talking to finance people, and my recollection of the vibes of that call is The Knife thought the world was about to end, like that weekend, and they needed to act quickly to protect their assets. (Note to reader: the world did not end that weekend. In fact, while it might feel otherwise, it still has not ended.)
I sat for twenty minutes of a thirty-minute 1:1 listening to all the details regarding the end of the world, wondering why they had huge bulk boxes of granola on the floor, and then they were done.
I don’t know what we talked about. Not a clue. Not even going to invent anything because all I remember is that they pulled a hunting knife out of a drawer in their desk and started talking about something. Not the world ending, not about the granola, and not about the knife they were examining, twirling in their hands.
It wasn’t threatening. I was not in danger. It was just fucking weird.
Our Mind-Blowing Interlude
Ok, forget you read those introductions.
If you and I were at a bar and I explained the respective track record of The Artist, The Dictator, and The Knife in their respective roles, you would consider them good at their job. If I further explained objectively what they had done for their respective teams and companies in terms of generating shareholder value, you would vigorously nod, “Yeah, these are successful humans.”
It’s stronger than that, I can confirm that these are wildly successful leaders.
I can further confirm that each were very bad managers.
Let’s start with my belief that a manager’s job is to tell you where you are, and a leader’s job is to tell you where you are going. With this simple definition, The Artist, The Dictator, and even The Knife, as we’ll see, were strong leaders. They knew where we were going.
An easier way to understand the difference is that leaders are stronger at strategy and managers are stronger at operations. When do you need which? Depends an an endless set of factors, including team size, their place on the organization chart, company culture, and many more. The thing to remember is your boss likely leans strategic or leans tactical.
Let’s continue with the fact that you are going to end up with a bad manager at some point, and it’s not your job to change them — you can’t. In fact, the more senior the leader, the less you’ll be able to influence them.
Let’s finish with the fact that while I despise many of the traits of these humans, I learned essential lessons.
Ok, now remember those introductions.
They Are Bad Managers Because…
The Artist is bad because they don’t value humans. It’s not the part of the equation they care about. Maybe introversion? But mostly because they’re an artist, and what artists care about is the art. Not the essential humans who build the frame, find the right paints, brushes, and make sure The Artist can work in a clean, well-lit place. That’s just noise.
My approach with The Artist was education. I believe they understood the motivations and intent of other humans, but because they were so focused (and rewarded for) the art, they did not spend the time to understand the consequences. They did not appreciate why a team that understood the mission, how they were going to achieve it, and how each individual could meaningfully contribute made for better art.
I started with verbal explanations of complicated human situations. I got blank stares, so I started to write before 1:1s. When the stakes were high, I stared hard at the situation and wrote and rewrote the situation, my assessment, and my recommendation — over and over. The Artist saw the work, recognized how much work I was putting into explaining situations they were ignoring, and sometimes they’d engage. Sometimes not.
The Dictator is bad because this dictatorial approach was everywhere, not just in the basement. Our 1:1s started with less than 30 seconds of pleasantries before they started the rant. It was the dictatorial rant about the most recent interesting problem, and, wow, they had opinions. My initial job was to hold on for dear life.
My approach with The Dictator was one of the most important lessons I’ve learned. Yes, The Dictator used their position to bully the conversation, but I couldn’t deny that The Dictator cared deeply about the problem in front of us. The Dictator stared hard at the problem, the challenge, the opportunity, and they saw a single detail.
The Dictator cared deeply and had no time for anyone who did not share this belief.
In the next product review, I went hard on pre-game. I reviewed the deck, found the gaps, and had them filled. I spent 1:1 time with the product manager, and I walked around downtown San Francisco with the designer to hear the backstory. When The Dictator did The Dictator thing and started to shove the conversation in a useless direction, I told them, “This path has been explored. We understand this is a flawed direction, and here’s why.” I don’t remember what we were litigating, but I vividly remember the burning look on The Dictator’s face, Oh. You care, too.
This changed nothing about The Dictator’s approach. It still felt like a constant battle, but by doing the work of caring deeply, the battle was not one-sided. Yes, this is not how you treat humans, but this is how I developed my habits to see situations where my job was to be an expert.
The Knife is… just bad. Back to the beginning, no dummies here. This is an intelligent person, and they did a good job leading a team, but they had absolutely no business attempting to manage one.
Education didn’t work. Verbal explanations weren’t brushed aside; they listened, but then they responded… about something else. Written attempts went unread. Caring deeply didn’t work either. Seeking common ground… trying to reverse engineer what this human cared about was like trying to thread lukewarm lemon Jell-O through a needle.
The Knife could lead. When they spoke to the team about topics totally unrelated to the problems ahead, we somehow learned a lesson. Our 1:1s remained bizarrely off topic. Sometimes they called with random requests that I barely understood, but I acted on them.
But the lesson was stay the hell out of the way. Let them do their work, however inscrutable.
The Essential Lessons
As essential lessons go, stay the hell out of the way doesn’t feel particularly helpful, but this is not the lesson.
Everyone is an adjustment. The person you need to be with your boss, their boss, your team, and everyone else is slightly to significantly not you. You will need to adapt how to prepare, how you communicate, and how you act with each of them. Some adaptations are trivial and familiar, but others require you to find a different perspective to help build new habits. Yes, one would hope your leader knows when to manage, but you don’t pick your bosses; you decide who you are with them.