Advanced questioning skills

Developmental mentoring / coaching is about helping someone with the quality of their thinking about issues important to them. Powerful questions are what prompt this kind of thinking. Observations of effective mentors / coaches reveal that they:

• Ask relatively fewer questions than less experienced mentors / coaches (so they interrupt the mentee / coachee’s thinking less), but with greater impact from those they do ask. A rough estimate is that inexperienced mentors /coaches ask twice as many questions per hour as do experienced ones.
• Ask questions from different perspectives, to help shift the mentee / coachee’s thinking
• Balance toughness with being gently supportive
• Ask primarily open questions, but know when and how to use closed questions when appropriate
• Are very clear about why they are asking a particular question
• Have a large store of powerful questions, which they have previously used or encountered, to draw upon.

How many questions?

Ideally, the source of good questions should be the mentee / coachee themselves, with the mentor / coach supporting them in the reflections that stimulate different thinking. In practice, the mentor / coach is able to draw on their own experience and insights to offer questions that the mentee / coachee hasn’t or wouldn’t have thought of. As a general rule, the more attention you pay to finding a really good question, the less attentive you are to the mentee / coachee and what they are saying. You can help the mentee / coachee most by relaxing into the mentoring / coaching conversation. If ideas for questions occur to you, try to “park” them while you listen. Only when the conversation reaches a natural pause, do you need to concentrate on formulating the next question. If this means there is a brief period of silence, that’s not a problem – it provides extra thinking time for both of you!

Questioning from different perspectives

When someone is stuck in their thinking (or their emotions), it usually takes a shift in perspective for them to find new solutions. Observation of effective mentors / coaches tells us that they rarely spend more than four or five questions exploring an issue from the same perspective.

Stepping in is where we help someone else explores their own thinking and feelings about an issue from either a rational or emotional perspective. Stepping out involves asking them to take someone else’s perspective. For example, a mentee / coachee might come to a session in some distress, perhaps having had an argument with a more senior colleague. They may have a mixture of emotions, including anger, resentment, some shame or guilt at having lost their temper, and so on. Before they can focus on finding a solution to this problem, they will need to adopt a more rational perspective. So the mentor / coach starts with questions from the perspective the mentee / coachee is already in – for example, What’s the dominant emotion you are feeling right now? How often do you get angry like this?

As the mentee / coachee feels listened to and begins to calm down, the mentor / coach has two choices. S/he can shift to questions that are still from the mentee / coachee’s own perspective (stepping in, rational), such as Do you sense a pattern of events here? How important is it for you to have a good working relationship with this person? Or s/he can move into looking at the other person’s feelings (stepping out, emotional), asking questions, such as How do you think she is feeling right now? From either of these perspectives, it is a relatively easy step to move into stepping out, rational, where mentor and mentee / coach and coachee can discuss practical ways to rebuild the damaged relationship.

A mentee / coachee may bring an issue from any of these perspectives. Helping them to find good solutions depends on using questions to guide them gently from one perspective to another, until they are able to see a different and better way forward. It doesn’t matter if you visit all four perspectives several times in the same conversation, or only some of them – what’s important is that the mentee / coachee finds a more productive way to look at their issue.

Being tough v being supportive

Mentors / coaches use four main types of question, for different purposes::

• Challenging questions are particularly used to help people unfreeze existing assumptions, values and beliefs, which may be self-limiting or prevent them taking alternative perspectives
• Probing questions are aimed at opening horizons and creating insights, by building on the new perspectives
• Testing questions are aimed at drawing ideas together, setting boundaries and creating self-confidence (for example, that different outcomes are achievable)
• Confirming questions help people to focus on their inner values and beliefs and explore their motivation to bring about change

Mentors / coaches can use all four

Some authorities suggest that mentors / coaches avoid using Why questions, because they can appear confrontational. Yet the 5 whys technique is one of the most useful available to a mentor / coach. When someone answers a why question you can drill down into their reasoning by asking why again. And again until they have reached the foundations of their thinking and emotions. Used appropriately and sparingly, why can be very effective in signalling to someone that they are not being logical or honest with themselves.

Open v closed questions

Closed questions are ones that lead to a yes/ no answer. For example, Did you consult with colleagues about this? An open question on the same topic would be Who did you consult with? Open questions create space, where the mentee / coachee can do their thinking out loud.

Like why questions, closed questions can be valuable, if they are used selectively and for particular impact. So, for example, when a mentee / coachee repeatedly brought to her mentor / coach the same issue about whether to take a career change opportunity, he broke the impasse by asking: So what you really want is for me to give you permission to do this? Similarly, a powerful question to a person faced with difficult issues of work-life balance: Do you have the courage to be happier than your mother?

Why are you asking this question?

Effective mentors / coaches constantly question their own questioning. Useful questions to bear in mind include:

• For whose benefit are you asking this question? (How sure are you that it’s for the mentee / coachee’s benefit and not just to satisfy your own curiosity or show how knowledgeable you are?)
• How will this question advance the mentee / coachee’s thinking?
• When will asking this question have the greatest impact? (Like a good cheese, powerful questions often become stronger by being allowed to mature!)

Building a portfolio of powerful questions

You will encounter powerful questions in all sorts of places. During mentoring / coaching sessions, in books, at management meetings, even watching films. If you keep a record of these, you will be surprised at how many you gather over a year – and at how readily they come to mind when you need them.

How do you know it’s a powerful question?

Powerful questions come in all shapes and sizes, with the only common factor being that they have a significant impact on the mentee / coachee. (Sometimes that impact may not be immediate – it’s quite common for mentees / coachees to say You know that question you asked me about XYZ a year ago? Well something happened to me last week that brought home just how relevant it was… )

Recent research into powerful questions indicates that have all or most of the following characteristics: They are:

• Personal: while they may have general application, they have a particular significance to the mentee / coachee or to the current issues they face and they can immediately sense its relevance
• Resonant: the mentee / coachee’s reaction is not just intellectual, but at an emotional level, too. The question connects with their feelings and values
• Acute & Incisive: They strike right to the heart of the issue
• Reverberant: They can’t be answered fully in one go. It’s common for the mentee / coachee to report that they have been thinking about a question frequently – sometimes several times a day – to refine their thinking about it
• Innocent: Genuinely powerful questions have no other agenda than helping the mentee / coachee’s thinking. They are not about what the mentor / coach would like to know, nor about putting the mentor / coach’s point of view. They are, in essence, the ultimate naïve questions
• Explicit: They use relatively few words and very simple sentence construction.

Some common mistakes in asking questions

• “Queggestions” – questions that suggest the “right” answer tend to prevent people from working things out for themselves and can steer them towards solutions that might be right for you, but not for them. For example:
  • Wouldn’t it be a good idea if…
  • Have you thought of…
  • Why don’t you…
• Multiple questions – mixing several questions into one. For example:
  • What do you feel about working part-time, or maybe doing a job-share, or a condensed week? (A better question might be What other working patterns have you considered?)
• Not allowing the mentee /coachee time to reflect on the question. Sometimes inexperienced mentors /coaches ask a really powerful question, then spoil the effect by jumping in with another question too quickly.

© David Clutterbuck, 2014