Dynamic Steering

I went sailing recently and reflected upon management while doing so. I've had the privilege of working under great managers, good managers and terrible managers and the line between great and good is quite nuanced.

I asked myself while sailing, "What kind of manager do I want to be? And why?".

Let's explore that.

In sailing, if you ease the sail too much it starts to luff, which just means that the sail starts to flap uselessly, disallowing you to reach optimal velocity. Conversely, if you trim the sail too much, you waste power by pushing the boat sideways instead of forward.

There's a precise spot, just a hand's-width wide, where the sail stops flapping and starts pulling, and if you can find it, the boat surges. The whole craft of trimming is finding that edge and staying near it as the wind shifts.

Most management writing eventually arrives at some version of "find the balance between autonomy and oversight." This is correct and useless. Nobody disagrees with it but it also tells you nothing. It's like saying do the right thing at the right time.. Duh... but what is the right thing and when is the right time?

In other words, how do you find the balance between autonomy and oversight?

There’s no fixed answer. But I think there’s a useful way to think about it.

What sailing teaches is which side new sailors get wrong. They over-trim. Tight feels safe. Tight feels like you're sailing the boat instead of the boat sailing you. The same instinct shows up in managers, new ones and a lot of not-so-new ones.

What does luffing look like on a team? Status meetings where nothing gets decided, only reported. A senior engineer asking permission for a call well inside their wheelhouse. Reviews that sit for a week because everyone is waiting to see who else weighs in first. Tickets parked in "ready for review" because nobody wants to be the name attached to a yes.

And what does over-trim look like? People doing the work with the air gone out of it. Risk-aversion as the baseline mood. The same person making every non-trivial decision. It's a team based on fear, based on the absence of trust, which in turn hinders creativity, innovation and efficiency.

It requires emotional intelligence and the ability to assess what a team needs in order to find the optimal trim. It's really about people. Managers are as much - if not more - motivators as they are tacticians.

A team that's luffing under one manager will be over-trimmed under another. A team that just shipped something hard wants more rope than a team in the middle of an incident. The point of the metaphor isn't a setting. It's the discipline of constant small adjustments.

The incentive structure rewards the appearance of control. Over-trimming is the rational response to that pressure. Right up until the team stops surfacing problems early. Stops proposing alternatives. Stops admitting uncertainty. They're sailing the boat you told them to sail, and if it hits a rock you'll find out at the same time they do. The grip that was supposed to prevent failure is what produced it.

In my experience, the keyword is: trust.

Real trust is the kind that shows up in behavior, not on a slide. It looks like letting someone make a call you'd have made differently, then debriefing without scoreboard-keeping. It looks like protecting people from blame for honest mistakes while being direct about lazy ones. It looks like being available without being present. And it looks like disagreement: out loud, in the room, on the record. You can't polish something without friction, especially not ideas. Trust isn't agreement and nobody pays a private cost for losing the argument. Once the idea is found everyone commits and the engineers have to be afforded the freedom to develop and collaborate in peace.

The managers I'd follow somewhere else all did roughly the same thing. They let me try things. They let me get partway down the wrong road before nudging the tiller. They were specific about what mattered and quiet about what didn't. When I made an actual mistake, not a learning-mistake, they said so plainly and we moved on. None of them ever asked me for a status update they could have read in a ticket.

That's the trim. You can feel when a team has it. The boat just moves.