Questioning Skills

by Steve Roche

Powerful questions

The human brain is naturally organised to go in search of an answer when you pose it a question. The direction that search will take will depend very much on how the question is asked (appropriately or not), when it is asked (getting the timing right), and the type of question.

New directions

The most powerful questions cause people to search in a new direction – towards a new insight, action or commitment. They are delivered with timing and rapport, honouring the person and where they are at this point.


I understand this is a big decision for you and naturally you feel some anxiety about it... I’m wondering how you will feel when the decision is made and you are ready to move forward once more?

Note that the question above is the more powerful because it includes embedded commands (the decision is made; you are ready).

Discover powerful questions by listening to discover the real issue, and learn what is underneath what is being said. Stretch yourself with your questions and you invite others to do the same.

The most powerful questions are sometimes the simplest:

  • What’s next?
  • How will you do that?

and above all,

  • What do you want?

If you get stuck, try asking:

  • What’s the perfect question for me to ask you right now?

Notice the powerful questions that work for you:

  • What do they have in common?
  • How is curiosity central to them?

Chaining questions

Specific interactions typically move from open to closed questioning, and broad to narrow focus. For example, a business coaching session may include this range of questions:

  • What do you want to talk about?
  • What’s the real issue here?
  • What’s stopping you?
  • What resources do you need?
  • What specific actions will you take?

The ability to ask chaining questions is a key skill for middle managers. This means being able to do both ‘skimming’ and ‘diving’ and knowing when to switch. This skill is closely related to information chunk size, in other words to whether the desired type of answer relates to the big picture, the detailed minutiae or anywhere in between. The successful manager needs to be able to operate across the whole range, switching from broad brush to detail and back, as appropriate. Technical managers often restrict themselves by neglecting the big picture.

Incisive questions

An incisive question can be defined as one that removes a limiting assumption from your thinking so that you can think afresh. It does this by replacing the limiting assumption with a freeing one. For example, you want to talk to your boss, but tell me you can’t do it.

I ask: What might you be assuming that is stopping you?

You say: I’m afraid he’ll simply laugh at me and think I’m stupid.

After more thought, you realise that you too are assuming that you are stupid. The assumption sits there, holding you back, limiting your thinking and thus your life. A colleague might say:

So what if he laughs? You aren’t stupid; go and talk to him!

You say OK, but still you put it off... Just telling you to do it won’t work. But a question will, because unlike a statement that requires you to obey, a question requires you to think.

Having asked the question to accurately identify the limiting assumption, the next question replaces it with exactly the right freeing one.

The key to formulating this question is listening with precision in order to formulate a question that achieves the goal of the session.

If you knew that you were intelligent [freeing assumption], how would you talk to your boss?

Incisive questions that have made a difference to people’s lives and organisations:

  • If you were not to hold back in your life, what would you be doing?
  • If you knew you were vital to this organisation’s success, how would you approach your work?
  • If you were to become chief executive, what problem would you solve first, and how would you do it?
  • If things could be exactly right for you in this situation, how would they have had to change?
  • If you knew something wonderful was going to happen today, how would you feel?

Note that the first part of each question asserts a positive assumption; the second part directs the thinker’s attention back to their issue or goal.

Challenging yourself

You can easily learn to use incisive questioning to identify your own assumptions and create your own questions to remove them.

1. If you want to take action but are stuck, ask yourself: ‘What am I assuming here that is stopping me?’

Listen to the answer, which might be: I am assuming that I don’t deserve success here.

Then remove it: If I knew that I do deserve success here, what would I do right now?

2. If you want to feel better, ask yourself: What am I assuming that is making me feel depressed?

Note the answer: I am assuming that I have no choice here – that I am powerless.

Then remove it: If I knew that I do have a choice here and am powerful in this situation, how would I feel?

3. If your team has run out of good ideas, ask yourselves: ‘What might we be assuming here that is limiting our thinking on this issue?’

Remember the answer, which could be: We are assuming that only the top people can think about this well enough.

Then remove it: If we knew that we can think about this as well as anybody, what would our ideas be now?