Great questions to ask in coaching conversations, 1-1's and other curious contexts

A growing list of curious questions, often referenced in training workshops on topics like coaching, leadership and having effective 1-1s. They're gathered from a range of sources, and are yours to scan and try out in all kinds of conversations. And if you've your own to add, please do share them in the form at the bottom of this resource.
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"What's the one thing" — A prefix for actionable feedback

What’s the one thing I can do to make our 1-1’s more effective?

What's the one thing I can do to improve the delivery of my presentation at the next all hands?

What's the one thing you think I'm still not spending enough time focussing on?

Chris Voss's Six 'Calibrated Questions'

In his popular book on negotiation — Never Split the Difference — former FBI hostage negotiator Chris Voss introduces the idea of the 'calibrated question'. Questions designed to get someone else thinking about solutions. Here are six of his favourites:

What about this is important to you?

How can I help to make this better for you?

How would you like me to proceed?

How can we solve this problem?

What are we trying to achieve here?

How am I supposed to do that?

Questions to assess motivation

When do you feel you are at your best? What conditions create it?

Which part of your work is most energising? Least energising? What do you wish you could do less of? More of?

What area under your responsibility are you most satisfied with? Least satisfied with?

What would you say your biggest strength is? What % of time do you get to use it? How can we increase that?

Who on the team do you wish you could work with more? And less?

Questions to develop long-term goals

What skills do you want to develop? And how would you apply them?

What is the area that, if you made an improvement, would give you the greatest return?

Who in the company would you be excited to learn more from?

What parts of the business would you like to be more involved in or learn about? What interests you about that?

Questions to develop strategic thinking

How do you go about prioritising your work?

What are the biggest time wasters / savers for you each week? What could you do now to save time later?

When you get stuck on something, what is your process for getting unstuck?

What’s a recent situation you wish you handled differently? What would you change? What can you learn from it?

What do you see as your top 3 priorities this quarter?

What is one thing we’d be silly not to do to improve our product?

Are there any meetings or discussions you feel you should be a part of that you’re not?

And are you included in any you don’t want to be a part of?

Questions about a manager’s role

What could I do, as your manager, to make your work easier or support you better?

How do you feel about the amount of feedback you are getting?

What are two things that I can do differently or improve?

What was one thing that your last manager did that you like that I don’t do?

What’s one thing we, as a team, could do to improve our meetings / ways of collaborating?

What’s an inexpensive thing we could do to improve our work environment?

How useful was this 1-1, on a scale from 1-10?

What question do you wish I would ask? What question are you hoping I don’t ask?

The Coaching Habit ‒ 7 Questions to Ask

In his popular book The Coaching Habit, Michael Bungay Stanier works through seven questions, and the invitation for managers to make them an everyday habit. Here they are:

What's on your mind?

And what else?

What's the real challenge here for you?

What do you want?

How can I help?

If you're saying yes to this, what are you saying no to?

What was most useful for you?