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Letter to a New Manager

Sixteen years ago, at 27, I was promoted to a managerial position at work. I was employee #197, and I had joined the company several years before the initial public offering (IPO). When I started, there were no more than a hundred employees, and when I was promoted there were more than a thousand. At the time of this writing, the company has over ten-thousand employees.

As far as I could tell, I was promoted because I had great technical ability; I guess I might have been considered a “rockstar engineer.” Not only was I able to understand what was going on with these incredibly complex systems, but I was able to set technical direction, make wise technical trade-offs, and I gave a real shit about what happened; I was conscientious and responsible.

I was tasked with reining in a challenging technical problem and engineering it into submission. At its largest point, while I was managing, my team consisted of fourteen engineers. In a company where each first-level manager had at least 50 direct reports, my little group was unusual.

Since that time, I have realized that perhaps one of the reasons for my promotion was that I was nearing the end of the four-year vesting period of my initial stock grant. Having gone through a successful IPO with tons of stock options, and with the stock price rising rapidly, I was rolling in cash. The daily fluctuation in my net-worth was many times my annual salary. Perhaps the senior management felt that I needed a different form of incentivization: authority and responsibility.

Shaken by the added stress of my position, the weak foundation of my personal life began to fall apart; I involuntarily moved to a different country and went through some other extremely stressful life experiences, including a very acrimonious divorce. I was only a manager for a few years. When I left the company to get a PhD in Clinical Psychology, I was an individual contributor again. I was still doing good work, but I was burned-out and wanted a change.

What follows is a letter from my current self to that twenty-seven-year-old self, and other new leaders that I have worked with. It expresses some of the experience, wisdom, and hindsight that I have mustered. This includes what I learned during those years as a manager, during time spent starting my own business, from my extensive experience in psychology, and from organizational consulting in management and executive leadership. This is my best advice to a new manager. It has been therapeutic for me to write it, and I hope that you too can benefit from it.


Dear New Manager,

Congratulations! You are now less important. The time has come for you to hang up your boxing gloves and put on your coach’s cap. Your days in the ring are over. You will never stand with your fist in the air again, sweat dripping from your brow, claiming a major victory. From this day forth, all your victories will be vicarious.

All of the skills you once prized, especially your technical ability, will now take a backseat. You have been amazing at what you have done. You have made it to the pinnacle of your career. Now you must start from the beginning.

You are a newbie again, and you have a whole bunch of people to serve. You’re going to be making a lot of figurative coffees. Whereas before your worth was measured by your ability to wrestle a technical problem into submission single-handedly, now your job is to stand to one side and encourage your team to do that.

You don’t get to code anymore. You don’t get to understand the details anymore. Your time should be spent getting to know yourself. Until now, you could get by being arrogant and dismissive of others, because you were not responsible for their productivity. Now you have to listen to them. You have to really listen to them.

Do you know how to listen? I don’t mean pretend to listen, or to pay lip-service to listening. I don’t mean that you should now tell people that you’re “open to feedback,” I mean are you really up for listening? Do you understand that when your employee is unhappy, you’re doing something wrong. You are doing something wrong. The data you’re looking for is right there inside that living, breathing human being in front of you.

You’re not there to “manage” people, or to control them. People are not machines, and the more you try to control people, the less control you will have. You’re there to facilitate greatness. You’re there to enable mastery. You have been put in charge of a world-class formula one driver. Don’t try to make her drive a Honda Civic on the track! Why would you do that? Put that world-class driver into a world-class car.

When she comes into the pit stop, don’t spend the whole time talking to her about how worried you’ve been while she was driving around the track. Don’t tell her that you’re worried that she might not be driving an ideal line! Don’t suggest that next time maybe you’ll ride with her to figure out where she’s doing it wrong. Do not, under any circumstances, suggest that maybe you should drive the track instead.

Instead, ask her: how’s it going? How’s the car? What could be done to improve the car, the track? How could I help you to improve? What would you like from me in order to take your mastery to the next level? How can I serve you?

Oh, and by the way, “Good fucking job! That was fucking awesome what you did on that hairpin bend! How did you even pull that off? It gave me goosebumps.” And she says, “Ah, but I’m not pulling the car round that slow, wide turn well enough.” And so you look her in the eyes, and with a deep seriousness and real understanding, you say “You’ll get it, I know you will. You’ll get it when it’s right for you.”

Your staff will come to love you. They will come to work deeply, intensely, passionately. You will unlock in them their full potential, because you will empower them. Other so-called “managers” might squeeze a little low-grade juice out of their “employees” before driving them away.

But you, you will nurture them, and you will feed them, and you will see them flourish into giant trees, trees that you can rest in the shade of. They will outgrow you, surpass you, and make your past accomplishments look like nothing. And you will be tempted to take credit, but you will lower your head, with a tear in your eye, and you will say, “I just didn’t get in their way.”

So, let’s get started. First of all, learn to meditate, and do it every day. Spend at least fifteen minutes watching your own breath. If you can’t become aware of your own breathing, then how will you ever become aware of your own bullshit?

Go see a therapist. I’m serious. Becoming a manager is one of the most stressful and challenging life transitions you will ever go through. You just essentially got a big demotion compensated only with a small increase in salary and some extra stock. Money won’t make you happy.

A good therapist will help you to chip away at the narcissistic veneer you’ve so assiduously developed over the years. That narcissism is going to make managing people like having sex wearing a hazmat suit: nobody is going to have any fun, and you won’t even make a baby. While it might have served you as a superstar engineer, narcissism is literally the largest impediment you could possibly have as a manager.

With that narcissism, you’re flying blind. You think you’re flying the plane, but the input that you’re getting—the horizon, the airspeed, the direction—all of that is coming from your own imagination. You can’t see reality for shit. If you don’t wipe that shit out of your eyes, you’re gonna crash the plane. I hope I don’t need to tell you that crashing the plane is bad.

Actually, maybe it’s good to crash the plane. Maybe it’s good to crash it a few times. Maybe there’s a lesson in that. Yes, that’s right, let your team fail. Let them fail and let them learn their own lessons. You are not a teacher. When you put yourself in a position of teacher, you disempower them. Guess what, they are teaching you. Are you taking notes?

I’m not talking about taking notes on what your narcissistic veneer is telling you. I’m talking about taking notes on what your staff are telling you. And then, are you asking questions? If you find yourself not asking questions, questions like, “How can I help?” “How can I serve you better?” “What do you need from me?” then perhaps you’re too caught up in your own bullshit. In which case, it’s back to the meditation cushion for you.

There are many ways that you can learn to build rapport and listen deeply to people. I’m going to recommend to you the training at NLP Marin. I wish that I had found it before I spent ten years going on a journey to find what they teach. Maybe I got other things on that long journey, but I can tell you that this is the most effective training that I have found for developing the ability to ask questions and be curious about the experience of others.

A great manager is indistinguishable from a great coach. Congratulations, you have become a coach. Go get some coaching training, and I’ll see you in a few months. In the meantime, please remember that I believe in you.

With faith and trust,

An Old Manager


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