I’ve been running 1:1s for years and I still get them wrong. The version of “wrong” has changed. Early on, my 1:1s were status meetings with the lights off. Manager asks what you’re working on. Engineer recites their pile. Manager says “anything blocking you?”. Engineer says no, even when they mean yes. Forty-five minutes evaporate.
That isn’t a 1:1. It’s a standup with a longer time slot.
I figured out it was wrong because of one engineer. Smart, quiet, on a team I’d inherited. We’d had eight or nine “great” 1:1s in a row. He left to go work somewhere else and on his way out told me, in different words, that he didn’t think I knew anything about him. He was right. I knew what he was working on, what his blockers were, what he’d shipped that quarter. I didn’t know what he wanted out of his career, what he was sick of, what his last manager had broken in him that I was busy perpetuating. Everything I knew about him was project-shaped.
That cost me an engineer, and it cost me about three months of figuring out how to run these meetings differently.
The frame
This is your meeting. You set the agenda. If you want to talk through a tricky design problem, talk it through. If you want to vent about a teammate, vent. If you want to plan the next two years of your career, plan. If you want to talk about your kid’s soccer team, fine. I have a notes doc I never make you open.
I do bring things. Three or four every week. Coaching I want to give, feedback I owe, context you’d want, a decision I want your read on. Mine goes after yours. If we run out of time and I never got to my list, that’s okay. My list keeps. Yours might not.
One question that does most of the work
I used to have a list. Three questions, same every week, the kind of thing that lands in a leadership newsletter. They worked, mostly. They also made me predictable, which made the answers predictable.
Now I mostly ask one thing and let it breathe:
“What’s draining you right now?”
The honest answer is rarely the project. It’s a person, a process, or something they don’t want to admit they’re avoiding. Half the time the first answer is “nothing, I’m good,” and then five minutes later something real comes out because the question planted a seed. Naming the drain doesn’t fix it. It just lets us start.
If they bring me energy instead, fine. I roll with it. The point of the question is to give them permission to say something they probably haven’t said out loud yet.
What I stopped doing
I’d love to write you a clean bullet list of antipatterns. The truth is messier, and most of them are mistakes I made before I learned to stop.
I used to ask for a status update at the top of every 1:1. I told myself I was “checking in.” I was filling silence. Now if I’m asking what they shipped, it’s because I genuinely don’t know, which means I’m not paying attention to the team. JIRA exists. Standups exist. The 1:1 isn’t where that goes.
I used to ambush. The “by the way, we’re concerned about your output” drop, slipped into a 1:1 because I didn’t have the spine to schedule it as its own meeting. Every time I did it, I blew up trust for a quarter. Performance feedback gets its own slot, its own framing, its own heads-up. Not a sneak attack between “how was your weekend” and “what’s on your mind?”.
I used to solve for them. They’d bring me a problem and I’d hand them the answer thirty seconds later because it felt helpful and made me feel useful. It made them dependent. “What would you do?” is the better question, even when I already know what I’d do. Especially then.
Cadence
Weekly, 30 minutes, on the calendar. Not “ad-hoc when we both have time.” Ad-hoc never happens. Ad-hoc is what people say when they don’t actually want the meeting.
I cancel mine more than I’d like. Sprint demo collides, customer call drops in, an outage at 2am. I always reschedule. I never delete. The person sees that a 1:1 with me is a slot that survives the rest of the calendar. That matters more than they’ll ever tell me.
Skip one, fine. Skip two in a row, that’s a signal you’re sending whether you mean to or not. Skip three and you’ve made the problem for yourself.
The unsexy part
Nobody puts this on a leadership thread because it doesn’t tweet well. The actual work of 1:1s is being there, in this meeting, every week, for years. Not the clever question. Not the great coaching moment that lives rent-free in their head five years later, though those happen and you’ll remember them. The week-after-week of showing up, paying attention, and remembering the things they told you last month so you can ask about them this month.
Most of it is just that. Show up. Pay attention. Remember.
The engineer who left taught me one more thing on his way out, without meaning to. He’d told me about his daughter’s blights in passing about six weeks earlier, and I never asked about it again. Not because I didn’t care. Because I forgot, and he noticed.
I write things down now.