When you ask better questions, you get better answers, and that’s the key to unlocking meaningful growth, in any relationship.
In mentoring, it doesn’t matter whether you are the mentor or the mentee, asking thoughtful, well-crafted questions helps to create an environment of curiosity, trust, and openness.
It allows both parties to dig beneath the surface, explore new perspectives, and develop a deeper understanding of the issues at hand. Below, I have listed some of the most powerful questions you can ask in a mentoring relationship to spark productive dialogue which in turn leads to meaningful progress.
Let me know if you have any powerful questions in your mentoring toolkit that you would be willing to share, together we can create a powerful reference document.
The “Defining Objectives” stage
- What would be a good outcome for you?
- What do you see as your biggest challenge?
- How would you like things to be different?
- What’s going well at the moment and how can you build on it?
- What would success look like? How will you know when you have it?
- What would be a sign that things were improving?
Elaborating and Clarifying
- Tell me more about . . . (not technically a question, but you get where I’m coming from!)
- Is there anything else? (I’m a fan of the more direct “What else?” — keep repeating this question until you get to the nub of the challenge)
- What makes this an issue for you?
- How would you like things to be different?
- So, do you mean . . . ?
Probing and challenging perspectives
- What makes you believe that?
- What do you think this is happening?
- How might you be contributing to the problem?
- What might others think about that?
- Could that be viewed another way?
- How do you know they felt that way?
- It seems to me that . . .
Getting to action
- What might be the first step for you?
- What’s stopping you?
- What would happen if you did nothing?
- What’s the worst that could happen?
- When will you do this?
Mentoring relationships thrive on meaningful exchanges, and asking the right questions is a vital part of that process.
By focusing on questions that promote reflection, growth, and learning, both mentors and mentees can deepen their connection and maximise the value of their time together.
As you navigate your mentoring journey, remember that the goal is not to find all the answers immediately, but to engage in a process of discovery that ultimately leads to personal and professional transformation.
After all, the best outcomes often arise from the questions we never stop asking.
