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The Coaching Habit: 7 great questions to ask in workshops, 1:1 meetings (and AI chats)

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The seven questions in The Coaching Habit

Michael Bungay Stanier’s book The Coaching Habit introduces seven powerful questions that can change the quality of a conversation – in workshops, in 1:1 meetings, and even in the way you work with AI.

The Coaching Habit encourages us to ask a question and then get comfortable with silence, allowing time for people to respond rather than rushing in with advice.

 “The change of behaviour at the heart of what this book is about is this: a little more asking people questions and a little less telling people what to do.”

Question 1 – What’s on your mind?

This is a question to ask when you’re exchanging small talk with someone but sense that they have something more important to discuss.

That’s because it’s a question that says “Let’s talk about the thing that matters most”.

I must admit I haven’t yet been able to say it quite like this, so my current version is “how has your week/month been?” so people can choose what they want to talk about.

Question 2 – And what else?

This question helps people to access their own wisdom, insights, self-awareness, and more possibilities.

It helps you to avoid leaping in and providing your two cents’ worth about someone else’s issue – instead giving them the space and time to uncover and create new possibilities. 

Question 3 – What’s the real challenge here for you?

This question helps people to slow down and think more deeply.

It can help you to choose the most important thing to focus on, when you have a lot of things on your mind.

It is also a valuable way to bring a conversation back to what you can do, rather than focusing on what other people are doing.

Question 4 – What do you want?

This question “helps people to more courageously imagine what better (and much better) really looks like.”

It’s a deceptively simple question but is really hard to answer. But if you can, it will help you to see where you want to get to. And once you know that, “the journey often becomes clearer”.

Question 5 – How can I help?

The benefits of this question are two-fold:

  1. It helps your colleague or client to make a direct and clear request.

  2. It stops you from thinking you know how best to help and leaping into action.


However, it’s important to realise that once you receive the answer to this question, you have a choice about your response. You don’t have to say yes.

Alternatives are:

  • No
  • I can’t do that … but I could do …
  • Let me think about that (to give yourself time).

    Question 6 – If you’re saying yes to this, what are you saying no to?

    “A Yes is nothing without the No that gives it boundaries and form,” says the author.

    “It’s all too easy to shove another Yes into the bag of our overcommitted lives, hoping that in a Harry Potter magical sort of way it will somehow all be accommodated.”

    The author recommends we stop the rush to action and towards the “Cliffs of Overwhelm”, and ask, “What will you say No to, to make this Yes rock-solid and real?”

    He also refers to Michael Porter’s definition of strategy – “The essence of strategy is choosing what not to do.”

    Question 7 – What was most useful to you?

    This is a good question to ask at the end of a workshop or a presentation.

    Reflecting on what we have learned, and coming up with an answer to this question, helps us to retain knowledge much better than if we read or hear something and then move on.

    That’s because:

    “People don’t really learn when you tell them something.

    They don’t even really learn when they do something.

    They start learning, start creating new neural pathways, only when they have a chance to recall and reflect on what just happened.”

    A related question that you can ask at the beginning or a regular one-on-one meeting is “What have you learned since we last met?”

    Want to try using these questions?

     Here’s a link to access my printable version of the questions.

    The same 7 questions can help you work with AI

    Like many people, I’m still experimenting and learning where AI genuinely helps my work – and where it can pull me into more ideas, options and feedback on my drafts than I actually need.

    One way we can enhance how we use AI is to focus on asking great questions – both of ourselves and of AI, including the seven discussed above.

    Question 1 – What’s on your mind?

    I use AI to capture first thoughts (before I lose them!) related to books I’ve just finished and projects I’m working on.

    I use versions of this question in my AI reflection tools, including Conversations about Books, for reflecting on a book I’ve just read, or in my AI Journal, where I get AI to ask me good questions about how I’m using AI in my work.

    The follow-up questions in these ‘conversations’ bring out insights that I wouldn’t arrive at on my own.

    Question 2 – And what else?

    The beauty of an AI assistant is that it doesn’t get offended if I don’t like its answers! That means I can be much more demanding with my responses and follow-up requests than I would feel comfortable being if a human was helping me.

    For example, my community engagement planning tools (including the Engagement Style Adviser) are designed to help me think outside my preferred ways of relating, so that I can engage more effectively with diverse audiences, in ways that work well for them. However, some of the suggestions I get are not realistic for me so I say no way, I’m not doing that, and what else can you suggest?

    Question 3 – What’s the real challenge here for you?

    Finding the balance between under-using AI where it could help us, and over-using it in situations where it’s not valuable, is an ongoing challenge.

    We’re all in the same boat – figuring out where it makes sense for our work and where it doesn’t, while struggling to set aside time to keep up with all the possible applications for us. This is made more difficult by the continuous rollout of new AI capabilities!

    However, asking ‘what’s the real challenge here’ at the beginning of a new task or project is a great way to reflect on what tasks you avoid doing or don’t do very well, and allowing yourself time to figure out how AI can help you with those things.

    For example, I enjoy creating images to support my written content, but I’m rubbish at graphic design. I rely heavily on the ‘Ask Canva’ AI assistant in Canva.com to help me enhance my draft designs.

    Question 4 – What do you want?

    Building on Question 3, quiet thinking on the question of what aspect of your work you would like or need help with is an excellent antidote to the ‘buzz’ of working with AI, especially if you can step away from your computer while reflecting on this question.

    Question 5 – How can I help?

    Following up on Question 4, once you figure out what your objective is, you can explain this to AI and ask for suggestions on prompts you could use to achieve this goal.

    I also ask AI for clear step-by-step instructions for technical tasks like setting up this LinkedIn newsletter and updating my website.

    Question 6 – If you are saying yes to this, what are you saying no to?

    I sometimes struggle with AI generating too much information, and too many ideas for me. This is particularly the case when working ‘on’ my business – deciding what content to create or what new services to offer.

    The best antidote to this is to know when to stop asking AI for suggestions!

    One thing I do to avoid being distracted by all the possibilities is to handwrite three pages of just anything, first thing in the morning. This practice comes from ‘The Artist’s Way’ by Julia Cameron.

    It helps me to clarify what I really want to do, and to express that in my own voice. It’s also a great way to catch new ideas and scribble first drafts.

    I am also becoming clearer on what I want to use AI for, and what I don’t. Some of the things I don’t use it for are writing my LinkedIn posts, newsletters and blogs.

    I experimented with using AI to write my first drafts last year, but I didn’t like the results as much as when I wrote them myself. (However, I do get help with headlines, as I am terrible at coming up with these!)

    Question 7 – What was most useful to you? 

    This is a great question to ask yourself after you have used AI to help you with a task. Ideally, make a note of it in an AI journal, so that you can progressively make better decisions about when and how to use AI.

    Would it help to think this through together?

    The questions in this article are similar to the ones I use when helping clients clarify the scope and purpose of a project, or how AI might support their work.

    I help councils and community-focused organisations develop clear strategic planning documents. I also offer AI coaching and practical AI courses for people who want to use AI thoughtfully.

    If you’d like help with a document, or with working out where AI could genuinely be useful in your work, you’re very welcome to get in touch.

    Here’s how you can get in touch:

    Phone:           021 215 4698

    Email:             debra.bradley@writingforcouncils.co.nz

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