What to Ask Your Mentor During Mentoring Sessions?

Everyone needs guidance at some point in their career to develop further. Having a mentor doesn’t mean they need help. It simply means they want to learn from someone who has been there and done that.

If you are currently looking for a mentor, you must understand that it does not matter how you find a mentor. What is important is how you utilize the relationship. And the best way to do so is by asking the right questions to your mentor.

Below are the types of questions, along with examples that you can ask your mentor. Implement these questions in your mentoring sessions to keep them interesting and beneficial.

1. Stories

Everybody loves to talk about themselves and their personal stories. That’s why storytelling is the best way to break the ice between you and your mentor. Besides, you will get many insights from your mentor’s past experiences.

Ask specific questions that address your concern. For example:

• Tell me about a major setback you experienced in your career. How did you recover from it?

• What’s that one most important career lesson you’ve learned over the years?

• Tell me about a time when you had a difficult boss. How did you handle the situation?

• Were you always a wonderful speaker or you had to learn it?

• How did you master the art of risk-taking?

2. Questions About Failure 

Failure is the best teacher. And it must have taught your mentor some big lessons before he could taste success. With advice from him – who has fallen into the traps you’re afraid of – you can surely avoid some mistakes.

Here are few questions you can ask:

• Do you remember making a blunder that could cost you your career? What lesson did you learn from it?

• What’s your strategy to overcome failure?

• Do you have any tips on how to boost my confidence?

• How do you determine which weaknesses can be overcome?

• How do I know if a risk is too big of a risk? 

3. Questions About Success

Just like you can learn from your mentor’s failure, you have a lot to learn from their success too. When you know their keys to success, you will have a better understanding of what works. You can better prepare yourself for pursuing your career goals.

Consider asking these questions:

• What decision contributed the most to your success?

• Where did you get this kind of confidence from? What is your suggestion for me?

• What should I be focused on right now?

• Is there any particular strategy you would like to discuss to be successful in my field?

• Where should I be networking in order to be successful in my field?

4. Questions About Skill-Building

In every phase of your career, you will require to develop specific skills that suit your job role. For example, at the initial stage, technical skills are enough to get the job done. But as you grow, and become a leader, leadership skills like communication, negotiation, and management become crucial, and you need to work on developing those skills.

So if you are working towards any particular skills, asking your mentor for advice will help you polish those skills.

You can use these question to ask your mentor:

• What would help me to deal with difficult conversations?

• How can I become better at managing people?

• What do you do to deal with nervousness when public speaking?

• How can I become a skilled negotiator?

• What other skills do I need to move ahead in my career?

5. Self-Awareness Questions

Self-awareness is one of the most important things that will help you grow. You must see yourself the way others see you. If you like it, you can take steps to strengthen that positive perception. If you don’t like it, you know where your weaknesses are, and you can work on improving yourself.

Ask your mentor these questions so that they give you detailed feedback on how your actions are impacting the way others perceive you:

• Where do you see my strength?

• What’s that one thing you want to change in me right now?

• Where do you feel I fall short?

• Am I prioritizing the right things?

• Where do you see my blind spots, and what should I do to improve myself?

With these questions, you will never sit with your mentor, wondering what to say next. So prepare yourself for your executive mentoring meetings by making a list of 2-3 questions you want to ask in each session. Don’t ask too many questions in one session; you will end up forgetting most of the lessons you learned. Also, note down the vital points that your mentor shares in every session.

Also read:

Top 3 Resources for Mentoring that Your Organization Needs

5 Step Guide to Find a Mentor at Work

5 Reasons Why You Need a Mentor