Questioning and Challenging

Questioning and challenging

Computers are useless. They can only give you answers.

Pablo Picasso

Do you want to know what the ultimate key skill in coaching is?

It is the ability to ask powerful questions. The ability to challenge, provoke insight and honour your coachee through questioning is critical if you want to become a coach who is really helping your people.

Effective questioning

It’s remarkable how a good question can allow a person to have a completely new take on the problem or issue under discussion. Good questions empower people. In the context of coaching they enable the other person to really think about the issue, resolve it themselves and take responsibility.

If you look up ‘question’ in a dictionary you will find that it is ‘the stating or investigation of a problem, discussion of some doubtful point’. The root of ‘question’ is ‘quest’ – ‘any inquiry or investigation made in order to discover some fact’.

When asked for their perceptions about performance in a given situation, people can often be a little brief with their response. This is sometimes due to a poor-quality question. You might, for example, ask ‘Did you feel that went well?’ This is a closed question and is likely to elicit a yes/no response or, at best, a brief answer.

To raise more awareness and encourage a deeper response, you can ask more open questions, such as these.

  • How did it go?
  • What specifically do you think went well?
  • What’s the next step?

Open questions encourage:

  • More detailed, longer answers
  • More awareness
  • Fewer influenced answers.

(An influenced answer is one that is prompted or influenced by the way the question is phrased.)


Dig deeper when the person gives a fairly general answer. This will provoke awareness.

In coaching, your questions can cause the other person to search in a direction they may not have thought of before. A powerful question can:

  • Provoke a new insight
  • Move the person to action
  • Elicit a commitment.

Often, the simplest questions can be the most powerful, for example:

  • What’s next?
  • What do you really want?
  • How will you do that?
  • What is the issue?
  • What’s stopping you?

From broad to specific

Often, questions can start broad and then get more specific. The detail itself will help to keep the interest of the person, for example:

  • As you think of next year, what do you want to achieve?’ (broad, open question)
  • What are the critical elements for you?
  • How, specifically, will you implement that change?
  • As you think about making that change, what are the possible barriers that you might need to overcome? (specific, open question)

Go for the question that will allow the person to make the biggest shift in their current perception of the situation.

Open questions

We should focus on open questions. Unfortunately, many people have a tendency to ask more closed questions, which do not generally encourage the other person to think differently or more specifically about an issue. Open questions often start with the words:

  • What?
  • How?
  • When?
  • Where?

A broader open question might start with ‘Tell me about … ’.

Beware of ‘why’

Be careful about ‘why’ questions. These can often send the other person searching for reasons why a situation is as it is. It can take them into justifications and excuses, and provoke a defensive response. In your coaching, you are looking to move forward rather than backwards. While it is often useful to look at past performance to gain awareness, your focus must be on what can be learned from it rather than justifying why it happened. So ‘what’ is often a useful substitute for ‘why’.

The only time ‘why’ is really useful, is when you are asking someone why something they did went well. This leads them into reinforcing excellence within themselves. It reinforces good behaviour.

Powerful questions

Sometimes you have to ask questions to gather information, and sometimes you will ask yes/no (closed) questions, perhaps for clarification or commitment. These types of questions do not tend to be powerful. Information gathering is often used in a coaching interaction, but it is rarely going to lead the coachee into a new insight or awareness. In the same way, a yes/no question shuts off curiosity more than it stimulates it.

So, a powerful question stimulates curiosity within the other person. And, of course, human beings are innately curious about themselves and how they make up their world. Follow the interest and the train of thought of the other person, not of your own. If you lead the direction of the questions you will undermine the responsibility of the other person.


Keep a mental or written log of the number of open questions you ask in a day or a meeting (or ask someone else to do it). You may be surprised at how low the number is. Simply putting your attention on this is likely to change the number of open questions you ask – another benefit of coaching!

The coach must be fully attentive once a question is asked. If not, then trust can be diminished, and there will be less chance of asking the next best question (see Active listening).

So, if you want to become a real coaching champion, ask questions that allow the coachee to have a new take on the issue (raising awareness) and to decide for themselves what action is required (assuming responsibility).

Powerful coaching questions

Here is a list of questions that you might find useful, based on the GROW model (Goal, Reality, Options, Will).

Goal questions

  • What is the aim of this discussion?
  • What do you want to get out of the next x minutes/rest of the day?
  • What do you want to achieve long term?
  • What are your key goals for this year?
  • In an ideal world, what would be your next move in the organisation?
  • How much personal control do you have over your goal?
  • What is a short-term goal or milestone along the way?
  • When do you want to achieve it by?
  • If you did achieve x, what would that do for you?
  • Is the goal positive/challenging/realistic?
  • Can you visualise your goal? Describe what it will feel like when you achieve it.
  • How will you measure the success of the goal?

Reality questions

  • What is happening right now (or when/where/how often/how much)?
  • How would you describe the current situation?
  • Who is involved?
  • What is your perception of the situation?
  • What evidence do you have that this is true?
  • How do you know?
  • How have you reacted to this situation?
  • How do you feel about it?
  • What is the effect on others?
  • What have you done about this so far?
  • What results did that produce?
  • What are the major constraints to finding a way forward?
  • What is really going on?
  • What do you do now that makes a positive contribution to your performance?
  • What do you do that you believe makes a negative contribution, detracts from your performance or that you could do better?
  • What were you thinking when you did x?

Options questions

  • What options do you have?
  • What else could you do?
  • What other ideas can you come up with?
  • What if you had the time/resources?
  • Would you like my suggestions?
  • What are the benefits and costs of each suggestion?
  • What is the next step?

Will questions

  • With reference to the options you have identified, …?
  • Which option appears most attractive to you?
  • What are you going to do?
  • Will this address your goal?
  • When are you going to do it?
  • What could arise to inhibit this action?
  • How will you meet these issues/potential problems?
  • Who needs to know about this action?
  • What support will you need from me/others?
  • How will you get this support?
  • What will be your first step?
  • What needs to happen to make this a reality?
  • Rate on a scale of 1 to 10 your willingness to take this agreed action.
  • If it less than a rate of 7, what would it take to move it from 7 to 9?

Some more powerful questions

  • As you think of next year, what do you want to achieve?
  • What are the critical elements for you?
  • How many new customers do you want?
  • In what part of your territory is there most opportunity for new clients?
  • What would you do if you were in my position as sales manager?
  • How are you already contributing to your success?
  • What single aspect of what you do, if improved, could make the biggest difference to improving your performance?
  • What are your key job roles?
  • What skills or knowledge are you developing right now?
  • What else can you do to help the organisation meet its objectives?
  • What do you have to contribute that is unique?
  • What do you want from your job?
  • What do you do when you’re really up against it?
  • What do you enjoy about selling?
  • What can I say to you when you are most stuck that will help you return to action?


We all go through life with assumptions and beliefs that have a significant impact on our performance for good or bad. A key skill in effective coaching is to be able to challenge those assumptions and beliefs that hold someone back. A lot of coaching stems not from fact but from assumption. We may hear someone say ‘I could never do that’ or ‘I can’t see myself doing that’. These are limiting assumptions or beliefs – not the truth, just an assumption of it.

We all have a museum of old beliefs – a receptacle for those things that we used to believe but don’t any more. It may have been, for example, that we used to feel incapable of presenting, but now we know that we are good presenters.

It is easy to let people live with their own limitations, but you can challenge them. A lot of these things that limit people begin to crumble, or at least get shaken up, in the face of objectivity and contrary evidence.

In challenging assumptions, the following steps are useful.

  1. First notice limiting assumptions and beliefs in people’s language (including body language that does not seem to match positive words). Whenever you hear the words ‘can’t’, ‘never’ or ‘won’t’, it is likely that a limiting assumption will follow.
  2. Challenge these assumptions through your questions, looking for the exceptions: ‘When has there been a time when this was not true for you?’ or ‘When have you done this before and got a different result?’
  3. Often, getting very specific on the data can bring different ‘realities’ to light. Probe for detail and objectivity.
  4. Help the other person begin to look at the situation more objectively – encourage them to reflect on the facts next time they do the task. Maybe they can do this through keeping a log or a record or you can ask them some coaching questions.

There is more on questioning in the Questioning Skills topic.