1:1 Questions

The best 1:1s have three jobs. Surface things that would not come up in a standup. Build a working relationship that holds when things get hard. And catch small problems before they become big ones. A well-chosen question does all three at once, which is why the question matters more than the template.

Most 1:1s fail for the same reason: they turn into status updates. The manager asks what the report is working on, the report recites the sprint board, thirty minutes disappears, and the actual conversation, the one about how they're doing, what they're stuck on, where they want to be in a year, never happens. The job of a question is to pull the meeting out of that groove.

How long should a 1:1 be?

Thirty minutes, weekly, is the right default for most manager-report relationships. Biweekly is long enough that small issues harden into big ones. Shorter than thirty minutes and you run out of space for anything that takes a moment to get to. Longer than thirty minutes and you run out of things to say, or worse, you fill the time with status.

Who owns the agenda?

The report. Their time, their agenda. The manager's job in the meeting is to ask one layer deeper and to notice what is not being said. A shared doc the report fills in before each 1:1, even with just three bullet points, changes the meeting completely. It moves the work of preparing from the manager to the person the meeting is actually for.

How do I stop 1:1s turning into status updates?

Move status to async. A Slack thread, a shared doc, a five-line update once a week. Whatever it is, it happens outside the 1:1. That frees the meeting for the conversations that only work in real time: career, feedback, wellbeing, team dynamics, and anything that needs listening more than response. If a 1:1 can be replaced by a doc, it was never a 1:1.

What about the first 1:1 with a new report?

Rapport first, work second. Ask how they like to be managed, what their last manager got right and wrong, what they want to be working on a year from now, and what you can do in the first month to make them effective. Skip the status update. There is nothing to report on yet and plenty of time for that later.

How often should I ask for upward feedback?

Lightly, every other 1:1. Fully, once a quarter. Asking once performs the ask rather than using it. Asking every time turns the meeting into a survey. Vary the framing so the question does not become routine: “What should I stop doing?”, “Where am I in your way?”, “If you could change one thing about how I manage you, what would it be?”

What is a skip-level 1:1?

A skip-level is a 1:1 between you and your manager's manager, or between you and one of your reports' reports. The point is signal, not tactics. You are looking for what the layer between you is filtering out. Keep the questions broad, ask about patterns, and never make the meeting about the person in the middle unless they already know.