Posted on: 01/11/2021

Asking insightful questions, a core mentoring practice

By Dr Kay Guccione, Head of Researcher Development at the University of Glasgow, and FLF+ Network Mentoring Specialist.

This blog is part of a series written for our FLF+ Network Leadership Mentors, and is provided open access so that it can be used by anyone who is interested in improving how they ask coaching questions. I draw my examples in this post from across the different mentoring programmes I’ve worked on, but you will recognise that these ideas also apply to personal tutoring, doctoral and masters supervision too, as well as to line management.


I have been enjoying working with a range of different new mentors, on various schemes, in recent weeks. Part of their orientation to mentoring practice is introducing them to a facilitative coaching style and, as I wrote about in my earlier blog post, a ‘repertoire beyond advice’. This enables them to work with a diverse range of mentees, with a range of career backgrounds and development goals. It also allows them to bring a depth to their practice beyond a superficial advisory role.

New mentors who are trying on the coaching style and trying to avoid giving advice as a default option, often ask me what coaching questions they should ask their mentees. I could define ‘a good question’ in many ways from ‘non-incendiary’, to natural sounding, to incisive, to transformational, but what I understand these novice mentors to mean is ‘what is a helpful coaching question?’. Meaning, what could they ask, that will help their mentee to reflect and learn?

Coaching and mentoring disciplines stem from a learner-centred educational philosophy which aims to develop learner autonomy and independence by putting responsibility for the learning path and decisions, into the mentee’s hands. What this looks like in practice is the mentor sitting back and allowing the mentee to drive the conversation, supporting them to reflect deeply, to think creatively and ultimately to choose their own way forward. It won’t surprise you then that my answer is that a good question to ask is the question that works for that person, at that time. However, all irritating hedging aside, I offer some general guidance below on constructing great coaching questions, with examples.

Setting the ground rules.  It’s still worth beginning by setting some focus for the coaching conversation, for example asking “How do you want to use the time together?”“What are you hoping this conversation will bring?” or “What specifically do you need from me today?”  Even brief ad hoc coaching conversations can have an impact, but this only happens if both parties are clear about the purpose the discussion.

Start at the beginning and take it from there.  For some mentees a simple “How are you?”  or ”How have you been getting along?” will set them off on a long and reflective retelling of recent experiences. It’s OK to keep them talking. Don’t feel that you have to interrupt with a question to be more ‘coach like’. Listen, and take in what they are saying, and ask clarifying questions as needed.

Keep questions ‘open’.  An open question is one that invites your mentee or coachee to give a considered answer, recount an event, or think out loud, in some way processing their experiences and making sense of them. It’s usually a question which doesn’t have a simple answer but requires some contemplation and evaluation of the matters at hand. As such, open questions spark reflection, and help them bring implicit thoughts or thought processes out into the open. Often, what mentees need is for you as the mentor to open the conversation, and they’ll talk it all out.

Keep the conversation flowing.  For others, perhaps mentees who are more skilled at mastering their own thoughts internally, more naturally reserved, or those who are more nervous or who are feeling a bit upset, “How are you?” will elicit the short response of “Fine.” and you will have to think again about how to open up the conversation. My own favourite choice in this situation is a question along the lines of “What have you enjoyed in your work recently?” or ”What have you had on your plate the last couple of weeks?”. You can keep the conversation rolling by using a drawing, mapping or other visual approach and this is particularly effective if stress or frustration make it difficult for your partner to convey their feelings in words. Coaching side-by-side, for example working together at a whiteboard, or going for a walk together or separately whilst chatting on the phone, can also reduce feelings of confrontation or embarrassment for your mentee, and allow them to talk more freely. Make sure your mentee knows you are not asking them a question for which they need to produce the ‘right answer’ this can help them to overcome a fear of saying the wrong thing, and so be willing to speculate out loud.

Let silence be.  All mentors have to practice feeling comfortable with allowing silence to be a regular part of the conversation. Silence between you may sometimes signal that it’s your turn to move the discussion forward (as in the example above). But often it will indicate that your mentee has had an idea, is thinking about a new insight, or is considering how best to phrase what they want to say. You can help them best in this case by waiting, or by using ”Keep going”, ”Go on”, or ”Say more about that’,  to encourage them to stay with the thought and follow it to its conclusion. It can take time to marshal a web of ideas in one’s head into a linear sentence. Don’t butt in on that thought process.

Beyond the conversation: supporting action and accountability.  I consider it an essential component of my own mentoring practice, to ask mentees at the end of the dialogue: ”What action(s) are you committing to, before our next session?” This helps translate ideas into reality and makes action more likely. This is because it gives your mentee impetus to identify the time and resources to complete the task they have set for themselves, and the deadline by which they want to have taken action. Further accountability can be encouraged by enquiring about the consequences of inaction, for example “What will happen if you don’t do this task?” and from a mentoring partnership perspective “What do you want me to say to you next time we meet if you don’t do this task?”

Questions for mentors to field test

Below is a list of generally applicable, or adaptable, questions for your consideration and tailoring. This is a menu of questions from which you can select those that appeal to you, rather than a structured process model. Feel free to try them out, and to adjust the language to suit your style.

  • What exciting things have you been doing since our last meeting?
  • What have you been able to make progress on since our last meeting?
  • What’s working well for you?
  • Are there any unknowns you have right now that are blocking you?
  • What’s on your to do list that you’re avoiding?
  • What would make it easier to tackle that thing?
  • What’s the first thing you’re going to do towards [objective] after this meeting?
  • When do you need to do it by?
  • Who could support you to succeed with this?
  • What does achieving [objective] mean for your progress?
  • What are your hopes for how [objective] will turn out?
  • What could arise to prevent [objective] from happening?
  • What’s the most important thing you need to get done at this point?
  • What’s on the horizon that you know you need to think about now?
  • What is pulling your attention, is that something you need to do right now?
  • What fun things have you done this month?
  • What do you find enjoyable about this work?
  • What’s prevented you from taking action on [objective]?
  • What would make it more likely you will take action on [objective]?
  • What [time/people/support] resources do you have that you’re not making best use of?
  • What are you doing that’s stopping you from being at your best?
  • What might you try instead? What else? And what else?
  • What can you do today that gets you one step closer to that [idea/aim/objective]?

The important thing about developing coaching questions as part of your mentoring repertoire, is to reflect on the approach you take, and the type of responses that your questions elicit from your mentee or coachee. Notice the effect you have on your partner’s thinking, and combine this with their feedback, to really understand what makes for an effective question.

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