There Is No Magic Leadership Book
Yes, You’re Doing It For the First Time. So Is Everybody Else
So this happens: we’ll be in a coaching session, ticking along, and you’ll get a slightly worried, perhaps bemused look on your face and say something like: “I’m doing this for the first time, you know…”, and then wait, expectantly, for me to say something. Probably I won’t. Or perhaps I’ll do a coaching thing and say “I hear you. So what’s the question you’re wanting to ask?”.
And then it comes out: “what is it that I don’t know? what are my blind spots? how do I compare to other leaders at my level? what do other people like me do??”.
Over time I’ve come to recognize this as anxiety calling, a cry for help from the part of you that doesn’t think you should be doing the job you’re doing, that badly wants some certainty: maybe a program of some kind, some tips, some kind of guarantee you’ll be OK in this scary, challenging position you find yourself.
It’s a call for The Magic Book: the book that has The Answers. A book that, if only you could read it, would reveal the Secrets of Being a Great Leader From Now On, that will elevate you to Elon-dom, or Jobsian insight or some other measure of CEO-brilliance. Or CTO brilliance, or middle manager brilliance — I have had this question from Ben Silbermann (Founder and CEO of Pinterest), first time CEOs of twenty person companies, Engineering Managers just wanting to be good at their jobs and everybody in between.
There is no Magic Book
Unfortunately, there is no Magic Book. If there was, I’d be out of a job, managers would get paid peanuts, and an entire industry dedicated to the publishing of the Latest Management Secrets would fold overnight (and we would be spared another thousand “Seven Ways Excellent Leaders Tie Their Shoes” blog posts).
So, why do we ask the question?
Well, Impostor Syndrome is one reason, of course. We have a view of ourselves that is out of kilter with the work we’re doing, with the person we think we should be. “A CEO is a tough, in-control person, doesn’t make mistakes” we think. “I’m just some person who got lucky so far”. Or “a manager? me? no, can’t be! I don’t know anything! I’m not articulate like those other people! it’s only a matter of time before I’m found out!”
So we look for a quick fix. Something we can read over the weekend that’ll make us the person we think we should be. Imbue us with some Gates-ness, some Horowitz-aura.
And reading will help, no doubt. But in the end, we need to take a look at ourselves. We need to look at our accomplishments, at what we do day in and day out, and learn that if we’re in the room, we’re in the room for a reason (old metaphor — maybe “if we’re in the zoom, we’re in the zoom?”). We need to spend some time challenging the “I don’t deserve to be here” voice with some facts: you got hired through a serious process, you got backed by significant people with money, you shipped products, people respect you. The voice doesn’t like facts. It’ll go quiet when you talk back.
Sure You’re Doing It For the First Time. So Is Everybody Else
“But I’m doing it for the first time!” you might say. “How can I be competent?”.
A little secret that sits in plain site in the tech world: pretty much everybody is doing it for the first time. Ben Silberman is, Zuck is, likely your boss or their boss is, some of your team are, your colleagues are. It’s one of the reasons I stay in the tech — we get to continuously make ourselves up. That makes for an interesting life.
And anyway, the stuff you’re doing now will be mostly different in three to five years. Even if you’re managing. Ten years ago, almost nobody managed data scientists. Now, integrating data science is part of almost every tech managers job. Five years ago, thinking about how to deal with widely distributed teams was a “nice to have”. Now, you’re doing it. Five years ago, providing a psychologically safe space for a racially and otherwise diverse team was unusual (unfortunately). Now you’re doing it, or learning how to do it.
Moving from a large company to a startup (seven years at Google, big team, lots of success)? You’ll need to have the humility to throw out at least half of what you know. New people, new pace, fewer resources, weirder challenges. Your experience will be valuable. But it’ll also get in the way. You will think you know how things work. And you’ll be wrong. You’re doing this job for the first time.
Constant exploration, constant receptivity to change is part of the work. It doesn’t go away. You will always be doing something for the first time.
Leadership is More Like Playing Music Than Making Widgets
If you were learning to play the violin, you might read books, but you wouldn’t expect them to help much in making you a better violin player. To get better, you’d have to practice. You’d play different pieces by different composers. You’d listen to the masters and try and imitate them, and you’d probably discover that some of them work for you — there’s a mysterious “click” with your inner musician — and some just don’t. You’d grow your style from imitating the masters that “clicked” for you.
The progress would be slow, and strangely unpredictable. Some weeks you’d suddenly master a particular technique, and from then on it’d be natural. And some months (or longer), you’d practice, practice, and… nothing. Or worse, you’d backslide, wonder if you were ever any good.
Learning leadership is like that. You have to do it, with different groups solving different problems in different situations, over and over again, and pay attention to what you learn along the way. Slowly, you develop some mastery.
And then you start with another group of people, in another situation, and some of that mastery works, but a bunch of it doesn’t. Great! More learning.
Because leadership is about people. And people are chemical, mercurial, endlessly different, endless complex in their experiences and responses. Put them together, and the combinations are enormous. Put them together with the goal of achieving something, and the possibilities become almost limitless.
The same piece played by a different orchestra in a different hall for a different audience at a different time needs the conductor to adapt, to learn.
So Relax. Take Your Time. Decide To Practice.
Well, “relax” might be the wrong word. Understand that, yes, you’re doing it for the first time. That, no, that really doesn’t matter — there will always be more to learn. That, yes, you deserve to be where you are.
And that, no, there is no Magic Book. There are many masters of the art, and some of them have written great books about how they did it, and you can learn from them.
But you get to master your instrument in the way your skill, personality and spirit guides you. (“Sprit? Really? In a piece on Leadership?” Yes, really. Leadership is about people. People are about spirit).
You get to make it up as you go along, build your style, play your own music.
Books That Are Not Magic, But You Should Read Anyway
High Output Management — Andy Grove
The Ur-Text of Silicon Valley management. Lays the ground work for much of the mechanics of our current tech world management style.
The Hard Thing About Hard Things — Ben Horowitz
Exactly that: why leadership isn’t cookie-cutter. Why things get hard and how to deal when they do.
A Managers Path — Camille Fournier
Gives a good sense of progression through the paths of Engineering Management. Practical and detailed.
The Leadership Pipeline — Ram Charan, Stephen Drotter, James Noel
A bit dry, and not tech specific, but may give you some clues as to the road ahead, and what happens at the jumps from manager to manager of managers etc etc.
Radical Candor — Kim Scott
Because if there’s one issue that every single leader has to deal with it’s hard conversations and decision, and RC is a great framework for approaching them (disclosure: I do work for the RC team).
The Mythical Man-Month — Fred Brooks
Written in 1975, a must read for anybody managing software development, for the central insight that despite all we have learned, the central issues in managing software development remain the same.
