The Power of Probing Questions 

Why is it important to know and to understand our Mentees? As a mentor, we could easily dish out general advice until something sticks for the person we hope to help… but how are we any different than a self-help book or a well-being guru on television? A mentor is much more effective than other methods because mentors take time and effort to truly understand a person. Knowing the mentee’s background, culture, context, beliefs, and goals is essential when mentoring someone. We can create a full picture of our mentees with patience, probing questions, keen observation and empathy. This allows us to help them connect dots from their past to their present, to fill in blind spots and to help them grow and move forward towards a brighter future. 

Asking questions is generally the first step in beginning to understand a person. From a new client who is a blank slate before you to a mentee you have been working with for a decade, there are always questions to ask that will elicit something new, something honest and something meaningful to your discussions. But what signifies a good question? How do we know what to ask, when, and why it matters? 

When asking questions, a mentor is a bit like a detective. Like any detective, you need to understand what you are trying to discover and why it matters. Your role is to find what isn’t immediately obvious and to bring what is hidden to light. Any mentee will have both observable influences in their life and hidden influences (for more on observable and hidden influences look to our ‘further reading’ at the bottom of the page).  They might not even be aware of their hidden influences. As a mentor, you can help bring them to light.

For example, you are speaking with a client who claims to be great at dealing with conflict. As their mentor, you wonder if this is true, so you ask, ‘Was the conflict resolved?’ ‘Was everyone satisfied with the results?’ or ‘Are you adept at handling conflict, or are you just not afraid of entering into it?’ This may prompt deeper questions about past trauma or context, like, ‘How did your parents or other influential figures in your life choose to handle conflict?’ With these questions to colour in the story, you can see the full picture and use the truth to engage the mentee and tread deeper waters. 

I recently worked with a client struggling with his relationship with his boss. He was complaining that the boss was micromanaging and too opinionated. I asked if his boss reminded him of anyone else, and it clicked… he said his mother loved to get involved in every area of his life and share her opinions whether he asked for them or not. Part of his issue with his boss was that he was projecting some built-up resentment towards his mother onto this new authority figure. Arriving at this realisation gave us both clarity; I could add this information to the picture I was painting of my client in my head, and my client could mentally separate his boss from past trauma. 

Questions for my next session:

• What do I really want to know? 
• What is my mentee not saying? 
• If my mentee is not being forthcoming, are they aware of it? 
• What would my mentee want me to ask? 
• What do I know about my mentee’s history, worldview, culture or personality that may help me know what to ask? 
• Am I making any assumptions that I shouldn’t? 

Questions to ask my own mentor: 

• How am I at asking probing questions?
• What am I uncovering about my clients? 
• What context about my clients should I be considering?

Further Reading: 

In the past, we have looked at the Seven-Eyed Model of Supervision developed by Peter Hawkins. Each “eye” describes a perception a supervisor needs to consider; the final perception focuses on the wider-context of the supervisee and how this influences them. If you want to read more about observable and hidden influences, read our past blog on the topic: 

Where are you at with your competencies as a mentor? Reflect on that and reach out on contact us if that would be helpful.