Unintuitive Things I’ve Learned about Management (Part 2)

This is a continuation of Part 1, please start by reading that first.

5. Aligning on why is more important than aligning on how.

I used to spend a lot of time pondering questions like How do you make sure the right things are happening without coming across as a micromanager? and How do you make sure people are getting enough feedback on their work? and What’s the best way for designers, PMs, and engineers to work together? While these remain interesting questions, I realize now that an inherent assumption I was making was that the answer to great results lies in the tactical how, or in what each person could accomplish in their day-to-today. So I’d pore a ton of energy into working through those details with the people on my team— given this specific Problem X, let’s all discuss the best ways to make progress on X.

What I’m starting to gain a greater appreciation for is that the best results are achieved not by talking about the how, but by talking about the why.

Assuming you’re surrounded by smart, capable people, I find that there are two things that tend to get in the way of progress as teams scale: lack of motivation, or confusion about what really matters. (If there are not smart, capable people on your team, that is a separate issue which should be addressed first as discussed in #3.)

Confusion about what really matters (and in some cases, lack of motivation) occurs when there is not clarity of purpose. For example, if you get assigned a task to make a particular action 20% more efficient, would you be motivated to get up every morning and pour your energy and passion into that task? If something went wrong, would you be willing to skip a dinner with friends, heat up some instant ramen, stay up late and figure it out? I wouldn’t. I don’t really get motivated by numbers, charts, or the abstract concept of optimizing efficiency.

But if you told me, Hey, if you make this action 20% more efficient, the 50 million people who use this service will spend 5 seconds less staring at a loading screen as they wait for their information to load, I’m suddenly a lot more motivated. Doubly so if I myself have experienced the irritation of what it’s like to wait that additional 5 seconds.

In a similar vein, at many places moving quickly is highly valued and applauded. To encode that value, teams will set aggressive deadlines for launching a feature. But if not everyone understands why moving quickly is important, an aggressive deadline simply seems arbitrary. Why should I work overtime on a Saturday in order to get my code checked in so we can release next Tuesday? Will the sky fall if we slip a week or two? Does it really matter? This kind of sentiment over time breeds resentment and dissolves motivation.

Worse, what if you end up at a place where it’s possible to ship something by the aggressive deadline set, but that something won’t be any good? Should you go ahead and ship? Any reasonable CEO would say, Of course not. If we don’t have confidence anybody’s going to want to use this thing, it’s absolutely useless for us to ship it. But if people on the team don’t understand that the greater purpose is to create valuable products, they may over-anchor on the ship by the deadline goal and make suboptimal decisions for the company as a whole.

Rome wasn’t built in a day, or as a result of doing a single task. Great results are the byproduct of many people making individual decisions that collectively result in an organization moving in the right direction. You will never be able to fully control the how. People must be trusted to improvise when the situation on the ground changes. But you can control the vision. You can get people to understand why they’re here, and what it will look and feel like if we succeed.

When you spend time talking about the why, once is not enough. Twice isn’t either.

Repeat yourself until you wonder if people are annoyed by you sounding like a broken record (hint: they aren’t. In my experience you can feel like you’ve said something ten times before most people hear it for the first time). Connect every project, every task to the why, until you start to hear the why evangelized by others around you.

If everyone on the team understands what is important, then the right things will happen. Bricks will be properly laid. Roads will quickly emerge. And over time, the picture of that fine shining city that everyone held in their heads will rise gloriously from the dirt.

6. Sometimes, a great person will not work out on a great team, and that is okay.

When I first started managing, I operated with what you might consider a blanket optimism. Ever a believer in the inherent goodness of people, I reasoned that if two smart, well-intentioned individuals couldn’t agree, then surely it must be the result of some misunderstanding. My job, therefore, was to resolve such misunderstandings! After all, here I was equipped with my managerial superpowers: lenses that helped me appreciate both sides of the story, a pretty deep well of patience, and — as we have already established —extreme tolerance for spending my days talking with people.

So when people on my team would bring up their dissatisfaction about something, I’d launch into a campaign to try and help them see the other side. I’d rationalize with them about how it wasn’t as bad as they were saying, and how surely they were looking at it from the worst possible angle. I’d then go and seek out the other side to do the same — explain the dissatisfaction, try and broker a peace treaty that would make everyone happy, all the while feeling of course there is a productive way out of this.

I didn’t always succeed. At one point, after spending 40 minutes trying to convince him to change his mind, a good friend and colleague said to me in exasperation that I was being hopelessly naive. The situation wasn’t resolvable, he told me. This particular relationship just wasn’t going to work. Someone had to be moved off the project. He was right.

Over the years, I also experienced losing talented, good people from my team, people whom I’d gladly work with again. Each time, I took the departure quite hard, as a mark of personal failure. I couldn’t reconcile how someone talented and good could not work out at a place that I similarly felt was so talented and good. It was like Lego pieces not fitting together, like peas and carrots refusing to cooperate. Surely I had done something wrong!

These days, my perspective is a little different. Certainly I’m not perfect, and I’ve made mistakes that have contributed to a team member’s decision to leave. But what I now also understand is that an individual’s values and her environment’s values play a huge role in whether that particular relationship will be fruitful.

Call it what you want — fit, chemistry, harmony — but the thing a person cares about most must also be something their team (and company) cares about.

Otherwise, when push comes to shove and hard decisions get made, that person is going to feel like her preferences are constantly getting trampled upon.

If the fit just isn’t right on a particular team, sometimes a move to a new team within the same company solves the issue — new teammates and manager plus a different problem to noodle on can often turn a crash-and-burn situation into something awesomely productive. If that doesn’t work, then perhaps the fit is with the company as a whole, in which case parting ways may be the best outcome for everyone.

A good analogy is dating. You can totally imagine meeting a person who is a catch by all accounts — kind, fiscally responsible, empathetic, interesting, in possession of a winning smile— but with whom you’d struggle to be in a relationship. Maybe they’re a champion sky-diver and you have a fear of heights. Maybe they want a van full of kids and you just don’t see grubby hands and sticky faces in your future. Maybe they’re seeking to grow roots and your eyes are still dreamy with wanderlust. Totally cool. Maybe you’ll invite them to a future party and introduce them to a friend.

These days, I spend a lot of time trying to understand what potential candidates value, as well as being very transparent about what I and my company value. If what I’m saying gets them nodding along like it’s music to their ears, then they’re going to love this job. If not, that’s fine too. Even if they are super-duper talented, it’s better for them and me to not try and sell a round peg into a square hole. Each of us ought to be doing the thing we really and truly want to do, in an environment that cares about what we care about. Life’s too short to live otherwise.

7. You never regret moving a struggling person too soon. You only regret doing it too late.

When I first started managing people, I considered my role above all to be a champion for my team. It was my job to support them, defend them, and listen to them. If someone was going through a tough time — struggling through a project, getting critical feedback from peers, having trouble working with others— I’d think to myself, If I don’t step up and show some empathy here, who else will? Nobody. As their manager, I am the last line of defense. And everybody deserves a second chance.

Thus, when someone on my team started to exhibit problems, I’d double my involvement with them. I’d spend more time in 1:1s, give them feedback more frequently, and get more involved in their projects. I’d stand up for them in front of their peers and ask for understanding and time so that the person would have enough time to respond to the feedback and change their behavior.

Unfortunately, 80% of the time, that effort ultimately proved futile.

It turns out, there are three main reasons why someone is not working out on a team: they are unaware their behavior is an issue, they don’t have the right skills, or their values aren’t meshing with the values of their environment (see #6 above).

Only an issue with awareness can be addressed in a reasonable amount of time. If someone is lacking the necessary skills for their role, it’s hard to expect a quick turnaround, no matter how much feedback you give. And if what motivates a person fundamentally doesn’t jive with the values of the team, then a bunch of pep talks might help relieve short-term symptoms, but they don’t provide a cure.

Usually, what would end up happening is that I’d pour a ton of time and energy into trying to help a struggling person, and eventually wake up to discover that 50% of my entire week had been spent on that person. I’d be stressed out, my energy sapped. People whom I’d ask for advice would remark how this wasn’t a good use of my time — you should be spending most of your time on your best people, they’d tell me. Still, I thought this process was how it had to be. I thought that this amount of sacrifice was what it meant to be a caring manager.

The turning point for me was realizing that standing up blindly for someone was detrimental for them, too, and also taxing to the greater team. People know when they aren’t trusted, and the person I’d be trying to help would also end up feeling stressed out and demoralized because I’d be deep in their business and giving them critical feedback on everything they did. Meanwhile, the broader team would impatiently wait for me to take more decisive action, and every week that I dragged my feet was another week they had to put up with someone they weren’t thrilled to work with, which also affected their happiness.

At the end of the day, the kindest and most caring thing you can do for somebody who is struggling is to be honest with them, set clear expectations on what it would take for them to thrive on the team, and move them quickly off the team if you don’t feel they can thrive. The question to ask yourself is, If this person left today and I hired somebody else to replace them, would I feel confident that the team would be better off? It’s my experience that most managers don’t make the move soon enough and in fact do it far too late.

8. Your team should respect you. But you don’t need them to agree with everything you say or do.

One of my earliest mistakes as an new manager was thinking that in order to be respected and well-liked, I needed to get everyone’s stamp of approval on the things I did. After all, what better way to demonstrate that you are listening to and valuing someone’s opinion than inviting them to be a part of the decision-making process? Plus, I didn’t want things to feel hierarchical, like I was walking around flashing the I’m the boss card all the time. I wanted my team to feel comfortable with me, like they could trust me. I wanted them to like the fact that I was their manager. Making a bunch of decisions they didn’t agree with felt like the fastest way to fall into the cliche of the out-of-touch manager who is the constant source of backroom complaints and eye-rolls.

This meant I went to great lengths to ensure that every person on my team met potential new hires, and if anybody voted No Hire, I’d end up passing. Or, if an important task came up and the person I’d asked to do it politely told me, “I’d rather not,” I’d look for an alternative. Or, if I felt somebody on the team would make a great lead or manager, but another individual on the team didn’t like that person, I’d think, Well, I’m not setting the team up for success unless everyone agrees this is a good idea. (On the flip side, if someone on my team said, “Hey, I’d love to start interviewing/get an intern this summer/work on X project,” I’d be so eager to help them achieve their goal that my default response was usually “Of course I’ll support that!”)

It seems fairly obvious in retrospect that these actions made me a bit of a pushover. The burning desire to be well-liked made me tone down my critical feedback, not push folks beyond their comfort zone even when it would have been good for them, support people in whatever they said they wanted even when it wasn’t in the best interest of the team (for example, just because someone wants an intern or wants to work on X project doesn’t mean they are best suited for it), and otherwise not make hard calls that people disagreed with, even when it was the most efficient and effective thing.

If I’m to be honest, a lot of what I considered support and consideration for the people on my team actually came from a place of fear and uncertainty. I was afraid of creating conflict. I was uncertain of my own calls when other people disagreed. These symptoms can be hard to see yourself but tend to be fairly obvious to a third-party observer. They see that you are indecisive, that you struggle to make decisions without looping other people in and parroting their viewpoints. Or they see that while you are well-liked by your team, you aren’t necessarily objective in seeing their weaknesses or correcting their bad behavior. (It’s a bit of the my own children can do no wrong syndrome that annoying parents exhibit.)

Of course it’s better to get perspectives from others before diving blindly into decisions. Of course you should aim to be someone your team trusts. But in your role as a manager, you often have more information than they do. Your perspective of what is important for the organization may be more complete. And you are being asked to do a different job than your reports. I can’t think of a great leader who hasn’t made what at the time were bold decisions others disagreed with, sometimes vehemently. Listening to people is not the same as acquiescing to them. Your primary job is not to represent your team but to get the best results from them.

How can you earn respect, then? The following are traits that I see great managers embody: understanding the job their team does and continually honing their critical ability to recognize what mediocre, bad, or superb work looks like; being self-aware of their strengths and weaknesses and helping their team in ways that play to their strengths; understanding team members’ goals and giving them the coaching, training and opportunity to reach those goals; being transparent about what they believe and why, and doing those things rather than simply talking about them; setting clear expectations with team members and giving them feedback often; asking for feedback and acting upon that; dreaming big and inspiring others with a clear vision; being someone their team considers a genuinely good, caring person.

These things are easier said than done. On paper, they seem unremarkable, even cliche. The art of management is that most of the time, in the moment, it can be entirely unclear whether you’re doing the right thing. Balancing what’s best in the short-term versus long-term, figuring out which conflicting pieces of feedbacks to act upon, choosing the least bad path in an unexpectedly challenging scenario, knowing which battles to fight and which to concede— these aren’t answers you can find in a book. A group of smart people can give you wildly different opinions on what you should do. Ultimately, you need to have faith in yourself and do what resonates with you. And when you reflect back on those outcomes, you need to recognize and learn from your mistakes.

This collection represents a reckoning of what I have learned about management, and a reflection on some of my own lessons and mistakes thus far. If you are on a similar journey, or are simply curious about what management entails, I hope you’ll find something useful in this perspective.


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