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Strategic Questions To Ask Mentors Over Text And In Person

Have you been thinking about some strategic questions to ask mentors to help you on your journey to success?

While you may be new to the idea, you’re not alone— at “Youths 4 Success,” we are elated to provide the best piece of advice and tips for every aspiring entrepreneur.

In this post, I will give you the best and proven strategic questions you can use to ask your mentor to keep the mentoring session going.

Finding a mentor willing to support you through your journey is vital for success. And we all know that questions are an excellent way to get into someone.

Imagine you sent an email or approached someone you admire in your industry and boldly asked that person to mentor you.

And the person agreed to be your mentor. But after a few months of mentoring sessions, you aren’t connected to the mentorship as you used to be. You feel like the conversation with your mentor has become repetitive.

You have asked that one question repeatedly during the mentoring sessions.

And if you feel like writing off your relationship with your mentor, think about how you started. Don’t be in a hurry to withdraw from the mentorship so soon.

This post will help you energize the relationship with your mentor by using one of these strategist questions to ask mentors.

Start asking one of these questions at your next meeting to keep the session exciting and valuable for you and your mentor.

The 4 Phases Of Questions To Ask Mentors

Questions To Ask Mentors

I have grouped these sets of questions to ask mentors into four. And these are the ultimate angles to look at if you’re looking for better-valuable time in your mentorship sessions.

  • The History
  • Situations
  • Self-awareness
  • Skill-building

I will take you through these groups of strategic questions to ask a mentor very soon. If you understand this very well, your relationship with him/her or any successful person in your industry will never be boring.

It will give you the blueprint of how they started their journey and how you can compare that to your life at the moment.

Strategic Questions To Ask A Mentor For The First Time

Below are the best questions to ask mentors for the first time. You can also use this approach to energize the relationship with your mentor.

Start With Their History/Story

Be natural and ask questions that will help you discover your mentor’s career journey.

Your goal is to be a good listener. So you have to ask questions that will let them start the conversation about their career, which is around your objectives.

Remember, everybody loves to talk about themselves! So you can ask something like, “How did you get to where you are today?” or “How did you land your current role?”

You could also ask more detailed questions about your career pursuits and concerns. These could include:

1. Was there a time you felt like you had made a mistake and felt like you had failed? How did you bounce back?

2. What do you wish you had known before taking your first management role?

3. What’s the most important leadership lesson you have learned, and how has it proven invaluable?

4. Which leadership skills were the most difficult to develop?

5. Was there ever a role you applied for and landed but weren’t 100% qualified to do? How did you proceed?

6. Did you envision your career as it is today, five years ago?

7. Can you tell me about a time when you had a difficult boss? How did you handle the situation?

8. How did you learn to embrace risk-taking?

9. How did you develop the skill of speaking so engagingly in front of groups?

Situations Questions To Ask Mentors

Now, at this point, you have already broken the ice and are feeling energized during the session.

It is time to get more granular in your request and bring a specific problem you are currently facing onboard. Be precise about what you need your mentor to help navigate.

Here are examples of some situations type of questions to consider:

1. My boss said I need to be more strategic. What does that mean?

2. I tried to delegate a task last week, and it did not go well. Can we work through what to do differently next time?

3.  I’m considering a career transition. What are some other business areas that might be a good fit for me?

4. I have two very different career path options available to me. Can you weigh in to help me make a final decision?

5. How can I stay connected to key influencers who do not work in the same office or geographical area?

6. How can I let my boss know that I don’t need to be micromanaged?

7. My performance review is coming up. What type of preparation do you most appreciate seeing from your employees?

Self-awareness Questions To Ask Mentors

To properly understand the meaning of self-awareness, let’s read what Psychologists Shelley Duval and Robert Wicklund said:

“Self-awareness is the ability to focus on yourself and how your actions, thoughts, or emotions do or don’t align with your internal standards. If you’re highly self-aware, you can objectively evaluate yourself, manage your emotions, align your behavior with your values, and understand correctly how others perceive you.”

If you don’t believe in yourself as a leader or an entrepreneur, how could you possibly lead a group of people or have a good relationship with your customers? One of the best rewards you can give yourself is the gift of self-awareness.

Learning how to believe in yourself starts with thinking positively and vocalizing positive statements to yourself to build your self-esteem.” –Brian Tracy

With that being said, if you don’t like what you perceive about yourself, you can substitute it with more positive ones that support, encourage, and pushes you towards your career and leadership goals.

One of the questions that many people go wrong when having a session with their mentors is, “How do you think others perceive me?” You see, this type of question will be unclear to your mentor.

You have to be straightforward with your question so your mentor can assist you by “holding up the mirror” and delivering precise feedback on how your actions and communication impact how others see you.

You can ask questions like:

1. What do you see as some of my blind spots, and how can I improve?

2. How could I have communicated my idea more clearly?

3. Where do you see my strengths?

4. Could you offer feedback on ways to improve my executive presence?

Skill-building Questions To Ask Mentors

Suppose there is a skill you’re currently working to enhance, such as public speaking, long-term strategic planning, marketing strategist, or copywriting.

In that case, you can use the following types of questions to ask mentors for advice and resources to help you enhance that skill:

1. What practices can you recommend for dealing with nervousness when speaking to groups?

2. Can you recommend a book or resource for dealing with difficult conversations?

3. How can I become better at managing people who do not report to me?

4. What is a suitable methodology or tool for project management and tracking team commitments?

5. Can we role-play asking for a raise and a promotion?

More Questions To Ask Mentors

1. What’s the best advice you can give to help plan a career rather than work to keep a job?

2. How do you encourage innovative ideas?

3. How would you describe your style?

4. Do you have a mentor? How have they influenced you?

5. What do you do to challenge your underlying beliefs and assumptions constantly?

6. Would you do anything differently if given the opportunity?

7. How and where do you find inspiration?

8. How do you keep your feelings separate from your decision-making?

9. How do you balance your work and home life?

10. Do you have any books that you would suggest I read?

Tips For A Successful Mentoring Session

1. Prepare and ask relevant questions.

2. Be respectful of your mentor’s time and experience.

3. Ask if you can follow up and exchange contact information.

4. Afterward, ask yourself what you learned from the meeting and how you can apply your new knowledge.

5. Thank your mentor for their advice with an email or personalized note.


With these four groups of questions to ask mentors, you’ll never sit through another mentoring conversation wondering what to ask your mentor.

You can also give this list to those you mentor, nurturing them to use it to maximize the value of your time together. Asking the right questions can help lead you to more insightful conversations with your mentor.

Your conversation might not always go where you think it will, but asking these strategic questions will help you understand what your mentor is looking for and get more out of your mentorship.

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