Seven One-to-One Questions That Go Deeper Than "How's It Going?"

The easiest one-to-one to run is a status update. It’s also the least useful: you can get status from the board. The point of the time is the stuff that never makes it onto a ticket.

Here are seven questions I come back to:

1. What’s taking more energy than it should right now? Gets at friction (process, tooling, people) without asking anyone to complain.
2. If you could change one thing about how the team works, what would it be? Small enough to answer honestly, specific enough to act on.
3. What did you do recently that you’re proud of, that I might not have noticed? Managers miss a lot. This fixes some of it.
4. What would you like to be doing more of in six months? Career conversations work better as a direction than a job title.
5. Is there anything you’re waiting on me for? A useful check on whether I’m the bottleneck.
6. How are you, really, on a scale of one to five? A number is easier to give than a feeling, and it’s easy to follow up on.
7. What should I be asking you that I’m not? Hands them the agenda.

You don’t need all seven every week. Pick one or two, then mostly listen.

I’ve put a few hundred of these into EngMan, a free iOS app of swipeable coaching cards for one-to-ones, refinement, wellbeing, performance and more. If you prefer paper, the One-to-One & Coaching Toolkit has templates for running and recording them, plus GROW-model coaching prompts.

Written by: thechelsuk
Published: 18 October 2026, with 254 words, 1 reply.
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