30 Awesome Coaching Questions to Nail Your Next One-to-One

5 min readNov 1, 2019
Photo cred: Volodymyr Hryshchenko on Unsplash

If you’ve read our previous blog about getting the most from your one-to-ones, you’ll know that they’re one of our favourite topics!

Done well, they’ll drive performance amongst your team. On the other hand, when they’re not done well you can almost guarantee that engagement, trust and performance will go downhill.

I’m often presented with two main challenges when it comes to managing one-to-ones:

The art to unpicking both of these challenges is through coaching….

What is coaching?

Great question! Coaching helps an individual to bridge the gap between where they are now, to where they would like to be — without you telling them how to do it. It also creates a level playing field for a one to one performance conversation, regardless of organisational constructs like level, seniority and years of experience.

It’s important to reframe performance “management” with performance “enablement” and as a manager who is also a great coach, you are more likely to be effective in doing that — enabling self-driven performance.

As a coach (and no you don’t need to be qualified to don the coaching hat that is part of your ‘kit’ as a manager), you use questions to raise an individual’s awareness, explore all the contributing factors, unearth potential limiting beliefs/assumptions, and help them come up with the answers themselves.

Isn’t it quicker to give someone the answer?

Yes, potentially, and only if you are confident that you know the right answer. Coaching takes time and it happens at a pace set by the individual, so it requires patience and the ability to truly listen. No-one said coaching is an easy skill to acquire.

But (and it’s a big but!) we know two things:

  • Most people don’t like being told what to do;
  • People only remember 20% of what they hear (this improves, and can go up to 70% if they also speak, and write!)

In other words: when you give someone the answer, whilst it may make that specific conversation faster, you’re unlikely to see any sustained change in performance or embedded change in behaviour.

Ok, give me some coaching questions!

Here are 30 coaching-style questions to help you get the most from your one-to-ones. The questions are not in any particular order, so think of these as pick ‘n mix as opposed to a step-by-step process.

HINT: If you feel that there is more you can coach the person to reflect upon, and you that you think they could benefit from digging a bit deeper, feel free to follow-up any of these questions with a positive affirmation, and a further question, ie: “OK great/thanks for sharing that with me… what else?”

Questions to help someone identify what they want from their one-to-one

  1. What do you want to get from our time together today? / What’s the most important change in how you’re feeling that you’d like to achieve today?
  2. How can we make today a great use of your time? What would be helpful?
  3. What area(s) would you like to develop between now and our next session?
  4. Talk me through what your development goals are between now and ___? How do you feel about them? Why do you feel that way?
  5. What is the biggest challenge you’re facing at the moment? How much of this is within your control?

Questions to help someone create a meaningful goal

  1. What specifically do you want to achieve? Why do you want to achieve this?
  2. When do you want to have achieved that by?
  3. How will you know when you’ve achieved it?
  4. Who are you reliant on or what resources do you need to achieve it?
  5. What actions do you need to take to achieve the goal?

Questions to help someone open up (perhaps they’re agreeing but not contributing)

  1. What was your key takeaway from our last session?
  2. Tell me about…
  3. What do you think about __?
  4. What risks / impact do you think we need to consider before we do __?
  5. How would it impact ___ if we did ___?

Questions to help someone reflect deeper about something

  1. How did __ make you feel?
  2. Why do you think you felt that way?
  3. How has that approach served you?
  4. What else do you need to consider?
  5. Why do you think you approached __ that way?

Questions to challenge someone (as in stretch their thinking!)

  1. What’s stopping you from doing this now?
  2. Why do you think you’re avoiding __?
  3. How might you adapt your approach to get __?
  4. What else do you need to consider?
  5. How might you reframe that?

Other great conversation starters

  1. Would it be OK to give you some feedback?
  2. Would it be OK to offer a suggestion?
  3. How did that land with you? (Great after giving feedback, a suggestion or playing something back to someone).
  4. How’re you going to make it happen? (Great when you want to inspire action!).
  5. What advice would __ give you?

The following aren’t questions, but here are three handy tips you can use:

  • Give someone time to think by asking a question and saying nothing! Avoid the temptation to save someone. A great acronym to remind yourself of is W.A.I.T — Why Am I Talking!?
  • Always aim to ask an open question (who, what, where, why, how) unless you want to clarify or get a one word answer.
  • Offer to playback information that someone has shared so the individual can reflect on it . Use “what I’m hearing is” or “what I’ve understood, is” so that you are playing-back not only what you’ve heard, but simultaneously the perception that it’s left you with; this is a useful coaching exercise in itself as it provides a safe space for reflecting on how the individual is articulating their feelings and how they are explaining their position.

There you have it; 30 questions (and three tips!) to help you nail your next one-to-one. If there’s one thing to remember when coaching it’s this:

Avoid offering solutions. Remove your Manager hat and place your coaching hat firmly on your head.

Written by one of Unleashed’s expert coaches, Ally Jones. If you want more tips + tricks to help you master management, sign up to Unleashed Thinking, our monthly newsletter.




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