50 Questions to Ask a Mentor – That Get Results!
Nicola Cronin
7 minutes
December 8, 2023

There’s a lot to be gained from finding a mentor. From increased confidence to better communication skills, it’s no wonder mentees are promoted x5 more often than those without. 

So, how do you make the most of the experience? Well, as with any learning that’s based on relationship building, it comes down to the questions that you’re asking your mentor

In order to make the most out of mentoring, it’s important to think about what questions you’re asking and why. That’s where we’re here to help!

In this article, we break down how to prepare for mentoring, what a good question looks like, and provide 50 example questions for you to use in your next mentoring session (maybe not all at once!).

Whether your relationship is new and you want to build rapport, or is losing steam after a number of years – we’ve got the questions to ask your mentor that will help you get on track!

How do I prepare for mentoring? 

First, let’s look more broadly at how to prepare for a mentoring session. Mentoring is a truly valuable experience. Luckily, the main thing you need to bring is yourself and an open mind. (Cheesy, we know.) 

If you want to really make a good impression, it helps to prepare before your session. This means thinking about the questions to ask a mentor as well as some other actions to help you get organised. 

Here are the top 3 things we recommend preparing for your mentoring sessions: 

1. Set an agenda 

An agenda for mentoring should outline the topics you want to cover and break down the structure of the sessions. Including your overarching goal in the agenda and any action points agreed upon in sessions, is a great way to stay organised. 

Share this with your mentor beforehand so they have a chance to add their notes and think about what they want to discuss too. 

2. Review your notes 

It’s easy to forget what was discussed in your last session, particularly if you’re meeting monthly. Take time to review your notes before your session. Keeping your conversation fresh in your mind means you’ll be able to get stuck in faster. 

It’s also an important way to make sure any outstanding actions have been taken in between sessions. We all know that life can get in the way! Add a reminder to your calendar to check in on what you need to do ready for your next session. 

3. Check-in with yourself 

Have you had a bad week? Maybe you’re feeling more tired than usual. It’s important to take a moment to self-reflect when working with a mentor.

We all have ebbs and flows. But we need to be mindful of what energy we are bringing into a session. Mentoring should be motivating and energising. Taking a minute to centre yourself and get in the right mindset for your session will help you make the most of the time. 

📖 Find out more about getting ready for mentoring in our guide 📖

Decorative image: a ginger man gives a thumbs up to his mentor on video chatWhat are good questions to ask a mentor? 

Next, it’s important to think about what makes a good question. We all know how to ask questions, but what about asking the right questions? 

In order to discover what questions are right for you, it’s important to consider the type of question you’re asking. Different question types will glean different information. 

Here we break down the different types of questions in more detail: 

1. Open questions 🙌

These tend to be based on who, what, when, where or why and open up the conversation. By this, we mean that they have a range of answers that go way beyond a simple yes or no.

These are your best bet for getting a conversation going and will make up most of the questions you ask in a mentoring relationship. 

Example: “Where do you see yourself in a year’s time?” 

2. Closed questions 🚪

As opposed to open questions, closed questions only need a yes or no answer. While they don’t get a conversation flowing, they are really useful for fact-finding and clarifying answers. 

It’s also good to remember that you can follow up a yes or no with more information. Sometimes explaining your answer can start the conversation, so don’t be afraid to elaborate! 

Example: “Are you Jarrod, my mentor?” “Yes, nice to meet you!”  

3. Hypothetical questions 🧐

Hypothetical questions are used to explore a scenario outside of the current reality. This question type is useful for expanding the conversation through wishful or imaginative thinking. 

They can be used to gain insight into how someone feels or what they want, without being limited by what is currently possible. 

Example: “If you could change one thing in your current role what would it be?” 

4. Feeling questions 👏

A feeling question is an open question that asks the responder to share something about their emotions on a topic. They help the conversation to go deeper and understand what the emotional drive or reaction is to a topic. 

Example: “How do you feel about your promotion?” 

5. Clarifying questions 🤝

These questions can be open or closed, the aim is to avoid confusion and take the fuzziness out of vague or broad statements. By asking someone to restate what they are saying in a different way, you can make sure you understand their meaning before moving on. 

Example: “Was this in the same meeting?” or “What specifically do you mean by X?” 

6. Extension questions 💪

This is when you ask additional questions that add to a previous question or the answer provided. They’re useful for developing critical thinking skills by focussing on a certain topic in more detail.

They’re also useful for showing listening. In mentoring, you want to build trust and show you are genuinely listening and responding thoughtfully – not just asking questions to keep the conversation going. 

Example: “What are the implications of…” or “With hindsight what have you learned” 

7. Learning questions 🧠

You can use learning questions to prompt thinking about past experiences. By reflecting on the past and drawing useful conclusions, you can aid learning and growth.

Example: “What could you do differently next time?” or “Have you been through something similar to this before?”

8. Challenge questions 🏆

A challenge question asks someone to question how they have come to a particular belief or opinion. It’s important when using challenge questions to keep your non-verbal cues relaxed and curious and to think about your tone of voice. 

This question type is great for mentors that want to challenge mentees’ limiting beliefs and encourage curiosity. 

Example: “What has led you to that conclusion?” or “Do you think that other people would see it that way?”

What are good topics to talk about with a mentor? 

There are so many things that you can talk about with your mentor! Many people seek mentoring to help them achieve a specific goal such as building a skill or confidence. 

In any case, the topics you can talk about with a mentor are broad. Here are some examples that we see coming up time and again on Guider’s mentoring platform: 

  • Communication
  • Public speaking
  • Networking
  • Negotiation
  • Confidence building
  • Career direction 
  • Work/life balance 
  • Leadership 
  • Relationship building 
  • Time management 

You can use these topics to steer your conversation and help you set mentoring goals.

📖 Find out more about setting goals in our guide 📖

50 great questions to ask a mentor 

These example questions will help you to get the right information faster and can form an integral part of your preparation for mentoring. 

Here we give you question examples broken down into sections:

Icebreaker questions to ask a mentor

  • What motivated you to become a mentor? 
  • Have you been a mentor before? 
  • Tell me about your career path. How did you get into X role? 
  • What would you say has been your greatest achievement? 
  • Did your career turn out as you’d hoped? 
  • What’s the biggest lesson you’ve learned in your current role? 
  • What challenges have you overcome in your career? 
  • What are some common misconceptions in our industry?

Questions to build rapport 

  • What skills have been the most rewarding to develop? 
  • Would you recommend X training? Why? 
  • How did you develop your engaging public speaking skills? 
  • What do you most enjoy about your role? 
  • Can you think of a time when you did something wrong? What did you learn from it? 
  • Have you ever felt imposter syndrome? If yes, how did you overcome it? 
  • What common mistakes have you seen people make in my role? 
  • What are some of the biggest challenges faced in our industry today?

Questions for developing skills

  • How can I become a better negotiator?
  • What resources would you recommend to support my learning here? 
  • I want to improve my public speaking skills, can you help me work on my presentation? 
  • Can we role-play interview skills? 
  • What skills do you find most important as a senior leader? 
  • I’ve been asked to assemble a team strategy, how do you tackle creating strategies from scratch? 
  • What are some stress management tips that work for you?
  • How can I develop my time management skills? 
  • What advice do you have for building a successful team? 
  • How can I improve my decision-making skills under pressure?
  • What are some strategies for effective delegation? 
  • How can I build a stronger personal brand on social media? 
  • What are the skills you anticipate becoming more important in the future in our industry? 

Questions on managing relationships 

  • What are some techniques you could recommend for motivating my team? 
  • How do I let my manager know I don’t need to be micromanaged? 
  • How can I give feedback to my boss on a project? 
  • Who do I need to get on board with this decision and how? 
  • How can I build relationships with other teams across the business? 
  • What are some strategies for dealing with difficult co-workers? 
  • How can I build a stronger network in my industry?

Feedback questions 

  • Do you have feedback for me on my presentation? 
  • What do you perceive as my greatest strength? 
  • How am I perceived in the business?
  • Is there something I should be doing more of? 
  • How did I handle this situation? What could I have done better? 
  • Am I presenting myself well to senior leadership? 
  • I work hard to be strategic in my decision-making, is that coming across? 
  • How can I stay motivated when faced with setbacks? 
  • I need to deliver difficult feedback in my managee’s appraisal, how would you go about it? 

Questions for following up 

  • Can you send me that resource we talked about? 
  • How do you stay up to date with industry trends? 
  • I really enjoyed our conversation today, can we schedule another session?
  • Next time, can we talk more about X? I’d love to hear your thoughts. 

There are, of course, a million other questions that you can ask in mentoring. Here are just 50 to get you started. And remember to write questions down as you go along and bring them to the next session. 

As your relationship grows, you’ll be able to go deeper and learn from one another. Questions form an important part of this so make sure you stay prepared! 

Do you have burning questions for us? Get in touch

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