Unintuitive Things I’ve Learned about Management — The Year of the Looking Glass — Medium

Unintuitive Things I’ve Learned about Management

I first started managing people seven years ago, three years after I graduated and got my first design job. At the time, I was woefully unqualified. I barely had any experienced being managed, let alone managing others. I remain grateful to my then-manager for her leap of faith in me. I don’t think I would have bet on myself in her situation. Then again, one of the things you learn is that a prescient manager can sometimes see things in you that you couldn’t, and push you to do achieve things that you didn’t think were possible.

In those seven years, I have mostly managed product designers, with a few UI engineers and researchers thrown into the mix. More recently, I now manage other design managers.

I love my job. I find it hard and crazy and wonderful because it is all about people. Interacting with people. Understanding people. Getting the best out of people. Realizing that everyone is imperfect but in our imperfections, we can still come together to do more than we ever could alone.

And yet, despite management being — like parenting— a certain kind of black art with no hard and fast rules, of course there are better and worse managers. A better manager gets better results. You can’t always measure this in weeks, months, or even sometimes years, but it eventually emerges clear as daylight.

I had a few things going for me when I first started managing. I was likable, I took my responsibilities seriously, and I always cared to know both sides of the story. But I also had my white whales: an Asian upbringing that taught hierarchy and going with the flow, a desire for perfection, a cavern of insecurities.

These are some of the lessons in my knapsack so far. Each year, I hope to collect more.

1. You must like dealing with people to be great at management.

One of the first things I now ask people when they tell me they are contemplating becoming a manager is this hypothetical question:

Imagine you spend a full day in back-to-back 1:1s talking to people. Does that sound awful or awesome?

If the idea of talking to people for 8 hours straight sounds awful, then you will probably not enjoy the day-to-day of management. I don’t mean to imply that every day is back-to-back meetings, but you can’t gloss over the fact that the pulsing lifeblood of management is people. If listening to and talking with people is not your cup of tea, then management will probably be an uphill slog.

Eventually, what will happen is that someone will come to you with a problem — they don’t get along with their coworker, they feel burnt out and need to take a month off, they have little faith the project is going to turn out well— and as you’re talking to them you will get a sinking realization in the pit of your stomach that you hate doing this and you just can’t anymore. You will long for the days when you were able to manipulate something directly — pixels, words, lines of code, bars of music — quietly and with headphones on, and in that blissful world nobody would need to talk to you and unload on you their burdens.

I know this lesson well because I have pushed people to become managers when I thought they had the right skills, only to burn them out and lose them down the line. It is crushing to have someone you asked to be a manager admit to you a year later that she is having trouble getting out of bed in the morning because the prospect of having to deal with her reports every day was that unappealing.

Unfortunately at many places, you’re roadblocked in advancing your career unless you become a manager. This sadly incentivizes the wrong outcomes, in which people who don’t love dealing with people become bad managers, and both they and their team suffers. In more technical roles, we are fortunate that many companies support separate but equal career tracks, where at a certain level of seniority you can choose to go deep into the craft of your discipline or go into people management. If you find yourself at this crossroad, ask yourself whether you’re interested in management for the right reasons.

The type of people who become great managers genuinely like working with people. They see problems of motivation, personal roadblocks, or unclear alignment as challenging but fulfilling to tackle. They like 1:1s. Their satisfaction comes from watching others thrive.

2. Having all the answers is not the goal. Motivating the team to find the answers is the goal.

Before I started managing, I thought that when people became managers, it was because they were one of the best in their specific discipline. After all, if a manager’s job is to give her reports feedback on what what they are or aren’t doing well, how can you do that if you yourself aren’t awesome at everything?

This is the reason why I was insecure about being a manager for a long time. No way did I think I was a better product designer than the folks on my team! And yet, I thought everyone expected me to be, or that I had to be in order to do a good job. To make matters worse, I applied this same view to my own managers. I’d be more inclined to think that they were right (it’s their job to be right!) which meant I didn’t often question their decisions (though this would sometimes turn to passive-aggressive resentment). If something felt off on the team, I’d bring it up to them as a problem they should go solve.

That line of thinking was destructive not only to myself and my team, but also to my manager. It’s exactly the kind of thing that contributes to our perfection-oriented culture, where people are afraid to admit weaknesses or failures, and we all pretend, like ducks, to glide gracefully on the surface of the water while paddling furiously underneath.

Look, nobody’s perfect. In some facets of our lives we’re heroes, and in others we’re shitty.

It’s unrealistic to expect that a person leading a team is better in most skills than every other person on that team.

As a manager, you don’t need to know it all. You don’t even need to pretend to know it all. The best coaches aren’t the best athletes. The best teachers aren’t the best executors. Your job is to get better work out of the team then they could have gotten without you, either because they are afraid of you, or because they are motivated by you.

I think we’ve all watched enough Game of Thrones to know what the right choice is.

How do you motivate a team? That is a longer topic for its own time, but I’d say first and foremost don’t be an asshole, and do the kinds of things you yourself are inspired and motivated by, not what you think others expect to see you do.

3. To evaluate the strength of a manager, look at the strength of their team.

I used to think there was some long checklist of manager qualities to determine whether a manager was great. Are they well-regarded? Strategic? Good at presenting? Can they knock out 20 important tasks in a day? Break up a fight? Mediate a peace treaty? Etc. etc.

I’m not going to say those things aren’t good traits to have, but the litmus test of a successful manager is quite simple: their team is awesome. Their team kills it on outcomes.

What does this mean?

At the most basic level, it means all the day-to-day things that you — yes YOU — personally accomplish don’t matter much in of themselves.

You can be the hardworkingest, smartest, most well-liked manager in the world, but if your team has 20 people and a reputation for mediocrity, then I’m sorry but there’s not a world where you can be considered a “great” manager.

On the flip side, sure, for a few quarters, a bad manager might be lucky. They might get exceptional results for a bit because they’re driving the team super hard. Or they might have inherited a great team.

In the long run, however, there is no getting around the fact that the best people don’t stay years and years to work under somebody they don’t respect or who doesn’t truly care about helping them or their teammates succeed.

These days, I have a lot of admiration for someone who has a killer team of unicorn ninjas, even if I don’t know anything else about her. There must be a reason they’ve managed to attract and retain such talent, after all.

This is also why the fastest path to becoming a 10x manager is hiring well. I remember when I first started hiring, I biased towards looking for people whose career paths I understood and had experienced myself. Unwittingly, I was placing a ceiling on the types of people I’d reach out to. As someone with 5 years of experience, for example, I couldn’t imagine that someone who had 10 years of experience would want to work on my team. Unfortunately, that kind of view meant that my team’s growth would be sluggish.

If you are the most skilled person on your team across multiple dimensions, then things might feel comfortable hierarchically, but trust me, you do not have a great team.

It is a thousand times better to have a diverse team with people who are strong in areas where you are weak, who can teach you new skills and challenge you to take on new perspectives. This is the quickest way to grow as a manager. If you are unsure of whether your team fits that bill, ask yourself whether you’ve learned anything meaningful from someone on your team. If you’re having trouble coming up with examples, it might be time to set your sights on more ambitious team-building.

4. The most significant advantage a senior manager has over a junior manager is an expanded perspective.

I sometimes get asked by new managers “What are the biggest lessons I can learn to help me quickly ramp up and become good at my job?” I used to ask this a lot myself, hoping for nuggets of insight that would speed up my learning process.

These days, however, if I’m to be totally honest, I don’t think a lot of management is learnable without actually experiencing it.

That is to say, I believe that it takes at least 3 years (and in most cases longer than that) to become a truly confident senior manager.

There is no shortcut where you can master this in a few months or even a year in by reading books, consuming articles, or asking other people for advice (although doing those things certainly helps the lessons you’re experiencing sink in more quickly.)

This is because management isn’t some skill like drawing where you can just practice in isolation for hours and hours on end. You need to have the opportunity to be stretched in certain situations in order to learn and grow.

For example, let’s take understanding what makes a great designer. Pretend there is a company with 100 designers. If you’ve only ever managed 5 of them, then the best designer in your experience is the best one of those five. If I ask you, “What are the qualities of a great designer?” you’d probably pattern match and list off some of the things that person does well.

Now let’s say there is another manager at that company who manages the other 95.

Between you two, who do you think, statically speaking, will have managed the best and worst designers in the company? Who do you think will have a more developed and nuanced perspective of what a good designer looks like?

This applies to a ton of different management situations: managing underperformers. Onboarding new people. Hiring in senior talent. Having a product launch flop. Managing periods of low morale. Having people on your team suddenly quit.

The first time any of the above happens on your watch, it’s always new and hard, no matter how many books you’ve read on the topic. But the fifth or tenth time or 20th time it happens, you’re no longer freaked out. You realize that you’ll be fine. You’ll get through it, because you always have. You become like a rock, solid in the face of changing winds.

The thing is, it’s hard to snap your fingers and say, “Cool, I need to get more experience firing people. Let me just practice that a bunch in the next month.” The circumstances need to be such that you get a chance to actually do it. At the same time, an inexperienced manager can do a lot more damage than an inexperienced individual contributor, so opportunities for new challenges or more reports don’t always materialize just because you want them.

When I interview managers today, I get excited about people who walk through the door having managed a wide range of teams for many years. You can tell very quickly that what they bring to the room is the kind of confidence and stability that says they’ve weathered a lot — times of scarcity and times of plenty — and they’re not going to be thrown off by a few storm clouds ahead.