The Best One-on-Ones Were Walks

What a big company taught me about the one-on-one — rolling notes, walks at headquarters, and what I worry we lose in a remote-and-agent world.

I learned to do the one-on-one properly late — ten years into my career, after I moved to the US and joined Google. Before that I’d worked like a mercenary: long on individual skill, short on doing anything with anyone. The best one-on-ones, it turned out, weren’t really meetings at all. They were walks. Here are some memories around them.

Not “versus”

First, it is not “one vs. one.” In my early, shaky-English days I kept reaching for versus, and it took real effort to stop. Said out loud it’s almost casual — one-on-one, or just a one-on-one. The closest thing I’d known at earlier companies, or further back in school, was the myeondam — a formal sit-down with a superior, usually one you’d been summoned to, and in my memory rarely a good one. So the adjustment came with some dread.

A one-on-one is a catch-all for a meeting with any number of purposes. It happens mostly between a manager and a report, who tend to have a lot to talk about, but anyone can request one when there’s something worth saying face to face. A one-on-one appearing on your calendar out of nowhere still makes you flinch — and, to be fair, the ones scheduled suddenly usually were bad news.

I’m not sure how much of this was formal training, or how much was specific to the one place I worked. But here are a few things I came to like.

What worked well

A request by chat or email always got an answer — and when it came the other way, I worked to always give one. When I was the one asking, because something was off, fitting myself to the other person’s time zone — and having that land outside my own working hours — didn’t bother me. Senior or very busy people had a dedicated AA, an administrative assistant, who helped enormously; in the good years, a one-on-one could even be the reason for a business trip.

Get Chaesang Jung’s stories in your inbox

Among all those meetings, I gave the recurring ones the highest priority. I tried to talk with direct reports weekly, and with skip-level reports every four to six weeks. Awkward as it is at first, if the relationship is one that needs trust, a shorter interval is better. I didn’t really learn this until I became a manager myself — until then my own manager sat high enough up that I never got the regular version — and I picked it up instead through mentoring from another manager.

Recurring meetings were better with a rolling note. For one-off meetings with a clear purpose, I’d leave a note to refer back to — with the side benefit that my English wall got a little lower each time. I kept the recipient list as tight as possible, so the personal things, the quiet complaints about someone, stayed between two people. Building the note ahead of time and pinging it before the meeting helped a lot when I had to pull my thoughts together in the cracks of a day.

On content, I tried to talk about things that didn’t already come up elsewhere — not what the weekly or the project meeting had covered, but, say, sitting down with a direct report once a month on their career path. Or, when someone needed personal help, each of us going off to look into it like homework and trading updates the next time.

Video calls have their advantages, but I wanted more physical presence than they gave. At Google’s US headquarters, where the surroundings opened out wide, I often spent the hour on a walk. Walking in California weather was genuinely refreshing, and I still remember a manager hand-brewing coffee for me on the way back in. In Korea, dense and urban, there were limits — but the point, I think, was in the care of building a shared memory at all.

The one-on-one ahead

What actually gets said in a manager-and-report one-on-one I’ll save for another post. In a remote-first world the romance of it has thinned, no question. In the US, where there’s almost no equivalent of the Korean hoesik — the after-hours team dinner that anchors so much of work life back home — nothing beat a short walk together. And yet whether the one-on-one is even needed seems to differ sharply between Korean and American companies. I suspect that’s because managing itself is received differently in Korea.

Then there’s the agent world now arriving. What will we expect from a one-on-one there? With an agent in the chair instead of a person, does it collapse into something one-directional — efficiency, corrections? The worry runs ahead of me. And then, every so often, I catch myself short: maybe I’d already become the out-of-touch boss talking only one way, long before any agent showed up.

Part of Lessons from the Company — first-person notes from inside engineering organizations, from my years at Google and after. See the full series →

Adapted from my Korean essay on Brunch: brunch.co.kr/@chaesang/164