Meet Them Where They Are

A few years after a senior engineer on my team left, they sent me an email. They were in business school by then, taking a leadership course, and the assignment was to interview a leader who had influenced their career. They had two or three anecdotes from their time on the team that they still remembered clearly, and they wanted to ask me why I did what I did in those moments. It would take no more than fifteen minutes. It had been a while since I heard from them and I was eager to catch up (and flattered that they had chosen me), so I said yes.

They shared with me that they were leaving #

I regularly have skip-level 1:1s with my team in order to make sure that they have an avenue for raising any feedback and discussing their career directly. This engineer was senior, close to staff, and had a great trajectory in front of them. They told me they were thinking about leaving to get an MBA. They wanted to start a company someday, and they’d decided the fastest way to learn how to do that was to go and learn how to do that.

There’s a version of that conversation where the manager starts negotiating. What if we found you a bigger scope? Have you talked to the product side? Are you sure? I absolutely understand the instinct. Losing them was going to be disruptive to the team, but I’d already learned that the question they were asking me wasn’t “should I stay?” It was “will you help?” So, I wrote them a recommendation and a while later they got into Haas at Berkeley.¹ The team absorbed the loss, others stepped up and filled the gaps. It was the right call, but it also wasn’t a hard one to make.

What a team of ten teaches you #

When you manage a handful of people, you can hold everyone’s goals in your head. You know what each person wants next, roughly when they’ll be ready for it, and the plan for the broader team. Somewhere past ten people that stops being true - and it stops abruptly.² That was the point where I learned the thing I’d end up repeating to every manager who reported to me (or I mentored) afterwards. Everyone on the team has different goals and needs, your job is to meet all of them at the same time.

Take any team of ten or more and look honestly at who’s on it. There’s someone who wants to be the tech lead and is going to be - your job is to get out of the way and give them the reps. There’s someone who wants that job too and isn’t ready yet - your job there is the harder one, which is to tell them they need more work and guide them towards closing the gaps. There’s someone for whom this is a job (a good one, done well) and who is going home to focus on the things that they are actually passionate about. There also may be someone whose next step isn’t on your team at all.

I’ve helped people transition to different teams internally, to another company externally, and to different career paths altogether (product managers, technical program managers, managers back to IC). The important lesson to internalize is: your job is to help them achieve their goal, not your aspirations for them. You can give advice, but at the end of the day the decision rests with them.

The mistake new managers often make is treating that list of engineer archetypes on a team as a problem to fix. It isn’t. Not everyone wants to be the star player, and a team where everyone is trying to be the star is a bad team. This is where the sports analogies come in, and I use a lot of them. A team roster is the clearest picture I know of a group of people at different points in their careers, all pulling in the same direction. The star who leads the team. The role player who is genuinely content doing the dirty work on defense and setting screens. The rookie who wants minutes before they’ve earned them. The veteran who knows they have two good seasons left. The coach doesn’t get the most out of that group by pushing everyone to be the star. They get it by knowing exactly what each of them can do right now, putting them in a position to do it, and being honest with them about what comes next. Sometimes what comes next is a trade to a team where they’re a starter.

Not everyone wants to be the star player, and a team where everyone is trying to be the star is a bad team.

Your job as the “coach” of your team is to build complementary groupings and create a “whole is greater than the sum of its parts” impact. Maximizing the talent on a team means maximizing each person’s talent on their terms - at the point in their life where they actually are, not at the point where it would be most convenient for you to have them.

Our interview ran over #

What started as a fifteen minute session stretched to thirty minutes. They recorded it and asked their questions - I answered them thoughtfully, but also in a reflective way where I got the opportunity to untangle the reasons for things I did on instinct years ago.

The thing that stood out to me wasn’t the memories themselves, it was how much of what I’d tried to impart to the team had stuck. Things I genuinely believe - but don’t sit and think about because they’ve become reflexes - were replayed back to me. They brought up the sports analogies unprompted, and said they see the parallels now in a way they didn’t at the time.

I wrote them a week later that the conversation had been illuminating for me too because it helped me crystallize why I feel a certain way and track down the motivations for the things I do on instinct. That wasn’t just a polite follow up to a sincere outreach from a former team member, I truly did learn about myself from our discussion. I was fortunate in that you don’t normally get to go back and ask people (or hear) what landed for them - here I was able to do it years later, after the fact.

Isn’t your job to push people? #

One objection that others may lodge is that a leader’s job is to push the team out of their comfort zone. Meeting people where they are sounds like a nice way of saying you let people coast, but I don’t find that to be true in practice.

Comfort isn’t the same thing as contentment. Your job as the leader of the team is to know the difference, and when to give people the opportunity to push and grow themselves. An engineer who says this is just a job might mean exactly that - or they might be saying it because nobody has ever asked what else they’d want or given them a chance at aiming for more. It’s your job to ask the question, understand the team’s goals, and apply some growth pressure, but you also need to take people at their word when they tell you that they are happy where they are. You need to have a balance on the team and it’s okay (even preferable) that not everyone is at the same spot at the same time.

Your push should be focused on the person who wants the next career step (whether they are ready for it now or not). You also need to be honest with yourself, if that next step isn’t on your team, you should help them achieve that ambition wherever it may be.

Support even when it’s difficult #

I’ve said to every team I’ve led that my job is to make sure that our team is doing its best work, focused on projects that matter for the business, and ensuring that we get the proper recognition for that effort. What is unspoken, but hopefully recognized through action, is that it’s also my job to make sure that everyone in their career is growing towards what is next for them. This is easy when that growth is filling in the next senior role on your own team, harder when it involves leaving for another team (or company). A team where people know you’ll back their next move, even when it means leaving for another role or opportunity, is a team people stay on, enjoy their time with, and tell others about.

I knew that helping this engineer land their new path at business school was the right move at the time, but having them come back and interview reinforced it to me. I’m sure they’re going to build something great when they do start their company.