What questions to ask a mentor about the art of management and leadership.

Here are the sample questions: What is the most important thing about being a good leader? How would you describe your leadership style? What behaviors does a good business leader demonstrate? What makes your team members want to follow you? What should I pay special attention to to become an authentic and effective leader? How do you best choose your team members? What criteria to follow? I have this situation in the team... How can I best deal with it? How can I help employees feel comfortable and safe in the workplace? How to build trust? How can I create an environment where employees feel comfortable talking about their workplace challenges? What specific steps can I take to build team engagement? What's the best way to encourage team members to collaborate? How do you communicate difficult news to people? How to set good business goals? What is the key to an objective assessment of the employee's work? How to make it accepted by him with understanding? What is the best way to provide constructive feedback to individual team members? Are there differences in the approach to people from different generations? What? How to learn how to best deal with people from the selected national culture? How to create a good team consisting of representatives of different nationalities? How does hybrid or remote working affect leadership? Do adults need to be motivated? What role does the leader's focus on their professional development play in motivating team members? What's the best way to negotiate a salary increase? How do you deal with a toxic employee? How to decide to dismiss an employee and how best to implement it? What challenges should I anticipate when taking on a new role? How can I best prepare myself for a new, larger professional role? What are the signs that I'm micromanaging too much? How do I know when the right time is to step back and let others take responsibility? How do I know when micromanagement is necessary? How can I manage the team flexibly without hampering the innovative spirit of those involved? How to take care of yourself wisely to be full of energy and commitment as a leader?

What questions to ask when meeting senior executives.

Here are examples of good questions to ask senior executives: What gives you the greatest satisfaction in your job? What makes you smile when you get up in the morning for work? What is your typical day or week at work like? What was one of the most valuable professional pieces of advice you've heard during your professional career? Who inspires you and why? If you had an unlimited choice, from all over the world (living or dead), who would you like to have dinner with and why? What do you think is the biggest challenge facing business leaders today? What do you think about the new trend X? What kind of job would you be unsuited to and why?

A list of essential questions to ask your mentor in your next meeting

Q: How does a mentorship relationship work?

A successful mentoring relationship is built on curiosity, openness, and continuous learning, ensuring both mentors and mentees benefit from the experience.

Q: How to ask your mentor questions about career goals, career development, or career transition?

Here are the questions you may ask your mentor: How to decide what career path will be the best for me? Why are clear career goals important for overall career success? How to set them properly? Were there any turning points in your career? If so, what were they, and how did they shape your career aspirations? Can you share the key steps in your career that led to your current position? What was the most significant dilemma you faced throughout your career, and how did it contribute to your growth? What guidance and advice can you offer to someone looking to transition careers?

Ryszard Skarbek
Sep 22, 2024
15 min read

Updated: Oct 28

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A mentor can be an extremely valuable source of knowledge and support for both business leaders and specialists. Using mentoring at the right time can easily open new doors to achieving your dream goal and create completely new development opportunities, both professionally and personally.

How does a mentorship relationship work?

A successful mentoring relationship is built on curiosity, openness, and continuous learning, ensuring both mentors and mentees benefit from the experience.

To make the best use of the mentor's support, it is worth knowing what goal we want to achieve. It is also worth knowing what questions to ask our mentor to get the most out of mentoring, which is a very effective method of personal development.

Depending on what you look for in a relationship with your mentor, the questions asked can be different. And how good the answer is depends on how thoughtful the question is.

Working with a mentor may be beneficial for your private life. Mentorship extends beyond professional development; it can provide valuable insights into personal relationships, decision-making, and life balance. A mentor can offer guidance on navigating challenges, whether they involve family dynamics, friendships, or self-improvement.

Finding the right mentor will help you identify patterns in your own behavior and suggest strategies for personal growth. They can encourage you to pursue hobbies, develop new skills, or set goals that enhance your overall well-being. Additionally, having someone to confide in can boost your confidence and provide a sense of accountability.

Moreover, a mentor can introduce you to new perspectives and networks, enriching your social circles and exposing you to diverse ideas and lifestyles. As you learn from their successes and struggles, you may find inspiration to make positive changes in your own life, fostering a deeper understanding of yourself and your aspirations.

Ultimately, the support and wisdom gained from a mentor can make yoy feel happier, helping you to cultivate stronger relationships, enhance your emotional intelligence, and achieve a greater sense of purpose. Whether you are seeking advice on navigating life's complexities or striving for personal enrichment, the influence of a mentor can be profoundly impactful.

We do not always have a chance to work with a selected mentor permanently. However, we can take advantage of opportunities and ad hoc meetings with a person we consider an experienced and trustworthy individual. Don't hesitate to take advantage of this situation, and don't be afraid to ask for advice. Such development support can be referred to as situational mentoring.

In many companies, we deal with visits from senior management. They usually end with a large meeting of all employees of a given location. This opportunity can also be used to ask an interesting question. And benefit not only from the answer obtained but also, if you wish, to shine against the background of the whole team. The bosses of your location will certainly notice that.

Different questions to ask your mentor.

It doesn't matter if you are a business leader at any level of management, a project leader, or an independent specialist or expert in a given field. You can always learn something from other people. Engaging in a mentoring relationship can provide invaluable insights that contribute to your career development.

Maybe you're wondering how to take your career to the next level. Or are you facing difficult business problems? Or you are struggling with a difficult co-worker or client, or you suffer from conflicts and difficulties in interpersonal communication. Engaging with the right mentor can provide you with the career advice you need to navigate these challenges.

Or maybe you want to be a better leader? Do you admire a person and would like to know how they reached their current status, and how they worked on themselves? This is where asking the right questions during your mentor meeting can greatly enhance your career journey.

You may also be concerned about company policy or fear making mistakes that could negatively impact your reputation and future career. Seeking career guidance from mentors can help you overcome these obstacles. And finding a mentor will definitely accelerate your career growth.

These are just examples of topics that you can discuss in your relationship. A full list would be long and would depend on your company's organizational culture and level of trust.

In the lists below, you will find information on various types of questions that can be asked of a mentor, depending on what goal you want to achieve as a mentee in a life mentoring, workplace mentoring, structured mentoring program, permanent mentorship relationship, situational mentoring (ad-hoc situations), or team meetings with senior management at work.

How to prepare for the first meeting with your mentor?

Preparing for your first or subsequent encounters with a mentor is essential to ensure a productive and meaningful conversation.

Research your mentor's background and expertise to tailor your thoughtful questions effectively.

Consider drafting a few questions that align with your career goals or personal needs. Questions like these are great for showing your mentor how serious you are about your development.

To break the ice, start your first mentor meeting with friendly, personal questions that help you get to know your mentor. These questions are a great way to establish rapport and ease into deeper conversations later on.

Continue by reflecting on your mentoring goals and what you hope to achieve through this mentorship. Make a list of specific topics you would like to discuss, including your career aspirations, challenges you are facing, and areas where you need guidance.

Additionally, remember that your mentor will appreciate the time to prepare and will be more receptive to questions that lead to deeper insights. Be open to feedback and ready to share your experiences, as this allows for a more engaging dialogue.

Using reliable mentoring software can enhance your experience by providing structure to your sessions, allowing you to track progress, schedule meetings, and document key takeaways.

Lastly, arrive on time and maintain a positive attitude, as this sets the tone for every mentoring session.

Depending on your situation and needs, here are examples of the best questions to ask a mentor.

Important questions to ask on the art of expanding a mentee's self-awareness. Personal development.

Asking your mentor questions about their self-awareness journey can be an incredibly revealing experience. Many successful business leaders have had to dive deeply into their minds to reach the place they are today. By learning from their mistakes, how they accepted or overcame their weaknesses, how they worked on themselves, and how they discovered their individual, unique style, you can gain access to invaluable knowledge that you will not get during any training.

Here are examples of questions related to the journey in expanding self-awareness:

What have been your greatest successes and failures?
What have you learned from these experiences?
How did you discover your strengths and weaknesses?
In your professional development, have you focused on strengthening your strengths or on improving your weaknesses? Why?
Have you always taken constructive feedback?
How did you resolve the dilemma between people's perceptions and their expectations, and being yourself?
How did you choose what you need most for your development at a given stage?
Did you use any specific techniques or rituals to get to know yourself better and expand your self-awareness?
Have you ever had a mentor or a coach? If so, what have you learned most about yourself from this collaboration?
How do you identify and remove blind spots in the area of your self-awareness?
How did you learn to listen so well?
How did you learn to ask good questions?
What was the most important lesson you learned about yourself on your journey of expanding your self-awareness?

To expand your self-awareness, you can also utilize the self-coaching method (i.e., the art of asking questions yourself). On our blog, you will find a series of articles on self-coaching. You can use this method to solve problems, deal with demanding situations, make decisions, analyze your thought process, identify your blind spots, or eliminate cognitive biases.

Self-coaching in practice

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Key questions to ask about the mentor's experience. Workplace mentoring.

We all love talking about ourselves, particularly when we meet someone curious about our experiences.

Good questions for mentors are about their personal experiences. You can request your mentor to describe a specific situation and explain how they handled it.

Here is the list of questions to ask:

What are you most proud of about your professional experience?
Who has influenced your professional development the most? For what reason?
What helped you push your limits and find out how much potential you have?
What was the funniest situation in your professional life that you witnessed or caused?
How did you do with public speaking? How did you prepare for them?
How did you work with someone you didn't like?
What are your most valuable experiences related to multiculturalism and working in an international environment? (if applicable)
What would you do differently if the situation happened again?
If you could write a letter to yourself 10 or 20 years younger than yourself, what would the letter primarily contain? What advice would you like to give yourself?

How to ask your mentor questions about career goals, career development, or career transition?

You may ask a mentor about career advancement. The path to career success may be tricky, and career progress may seem confusing. Learning about your mentor's career journey will inspire you or equip you with specific tips. A strong mentor can provide valuable career insights, helping professionals navigate challenges, refine skills, and make informed decisions. First, decide for yourself whether you are looking for career guidance in your current role or a roadmap for long-term career success.

Here are key questions to ask a mentor about growth and career:

How to decide what career path will be the best for me?
Why are clear career goals important for overall career success? How to set them properly?
Were there any turning points in your career? If so, what were they, and how did they shape your career aspirations?
Can you share the key steps in your career that led to your current position?
What was the most significant dilemma you faced throughout your career, and how did it contribute to your growth?
What guidance and advice can you offer to someone looking to transition careers?

The right questions to mentor for competency and skill development.

Skill-based questions can help you identify areas where you need to improve or find the best solutions to achieve your goals. Your mentor may have faced the same challenges throughout their career. Asking how they overcome possible obstacles with specific skills, or asking how the mentor perceives your current level of skills, can provide you with valuable information.

Below are the right questions to ask. They are part of the skill development question type:

What specific skills should I develop to achieve my goals?
In what order should you develop individual skills? Is there any important relationship between them?
How to choose methods of developing selected skills? Is participation in training always a good solution?
Which of my current skills are good enough that further polishing won't be worth the effort?
What is your opinion on the importance of soft skills and technical skills? What is the main success factor in today's business environment?
What skills have you found most useful in achieving your goals?
How have your needs for specific skill development changed as your career progressed?
What skills have proven universal at every stage of your career?
What is the most important thing about learning new skills?

Questions for the mentor about the art of management and leadership.

When you are a leader, manager, or director, a good mentor can help enhance your leadership qualities and develop management skills, as well as support you in creating your unique, authentic style of effective leadership.

Importantly, when you, as a leader, ask a mentor about the role and responsibilities related to project management, a good mentor can help you match your style to the needs of the project and the project team you manage.

By working with a good mentor, you can also learn a situational leadership style. Extensive information on Ken Blanchard's situational leadership model can be found on our subpage. It explains, among others, the four stages of employee readiness and the rules for choosing the right leadership style depending on the diagnosed situation:

Situational Leadership Style - Ken Blanchard's Model

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One of the most important assets of an authentic and effective leader is understanding when to micromanage and when to delegate responsibility to team members. Therefore, do not hesitate to ask the mentor about micromanagement. Thorough control is often necessary in the early stages of a project, building a new team, and in all those situations where the team faces great uncertainty and the situation changes frequently.

Below you will find questions related to leadership and management:

What is the most important thing about being a good leader?
How would you describe your leadership style?
What behaviors does a good business leader demonstrate?
What makes your team members want to follow you?
What should I pay special attention to to become an authentic and effective leader?
How do you best choose your team members? What criteria to follow?
I have this situation in the team... How can I best deal with it?
How can I help employees feel comfortable and safe in the workplace?
How to build trust? How to make my team members trust each other?
How can I create an environment where employees feel comfortable talking about their workplace challenges?
What specific steps can I take to build team engagement?
What's the best way to encourage team members to collaborate?
How do you communicate difficult news to people?
How to set good business goals?
What is the key to an objective assessment of the employee's work? How to make it accepted by him with understanding?
What is the best way to provide constructive feedback to individual team members?
Are there differences in the approach to people from different generations? What?
How to learn how to best deal with people from the selected national culture?
How to create a good team consisting of representatives of different nationalities?
How does hybrid or remote working affect leadership?
Do adults need to be motivated?
What role does the leader's focus on their professional development play in motivating team members?
What's the best way to negotiate a salary increase?
How do you deal with a toxic employee?
How to decide to dismiss an employee and how best to implement it?
What challenges should I anticipate when taking on a new role?
How can I best prepare myself for a new, larger professional role?
What are the signs that I'm micromanaging too much?
How do I know when the right time is to step back and let others take responsibility?
How do I know when micromanagement is necessary?
How can I manage the team flexibly without hampering the innovative spirit of those involved?
How to take care of yourself wisely to be full of energy and commitment as a leader?

Questions to mentor that develop your interpersonal communication.

Approx. 80% of all business problems stem from poor communication. Therefore, as a leader, do not hesitate to ask a mentor for advice on how to develop good interpersonal communication. Both between you and your team, as well as between you and your boss, your main stakeholders, and your team members. In this way, you will avoid awkward misunderstandings, conflicts, or arguments that negatively affect you and your team.

One of the underestimated aspects of interpersonal communication is the influence of national culture. If you work in an international or multicultural environment, becoming aware of how the culture of a particular nation or language affects communication between people can be fundamental.

More information on the influence of national culture on relations between people can be found in a comprehensive study entitled "Cultural Types - Lewis Model":

Cultural Types - The Lewis Model

Here are examples of questions for the mentor in the field of interpersonal communication:

What is the key to effective interpersonal communication?
What does "listen to hear, not to respond" mean?
How can I learn to listen well to others?
What are "I" and "you" messages? Could you show me a specific example?
Why are open questions better than closed questions? Does this rule always apply?
Could we practice asking open-ended questions?
What is the importance of non-verbal communication in interpersonal communication? Could you show me specific examples?
How would you rate my communication skills? What should I pay attention to?
What's the best way to ask for constructive feedback?
What is the best approach to encouraging honest and open communication among my team members?
What are the barriers to interpersonal communication resulting from cultural differences? (if applicable)
How to learn to recognize upcoming conflicts in the team?
How much and when should the leader be involved in solving conflicts in the team?
What's the best way to give clear instructions to my team members to reduce the need for micromanagement later on?
How to ensure I am well-understood by my team members?
Is it better to use email or direct conversation to communicate with my team, key clients, and key stakeholders?
Do individual departments of our company have any preferences regarding the way of communication?
What are good written communication practices?
What is the key to a good business presentation?
Is storytelling just a fad or a good tool to be used in specific situations? In which?
What's the best way to design a presentation for senior management? What do these senior leaders pay special attention to?
How do you deal with a difficult boss?
How to recognize the communication style my boss prefers?
How do I set healthy boundaries in my relationship with my boss?
How to give constructive feedback to your boss?
How to learn company diplomacy and deal with company politics?
How to recognize when to be soft in written communication and when to be assertive or to specify your expectations clearly?
How is assertiveness different from arrogance or aggressiveness?
Can my level of proficiency in English (or another language) affect how I am perceived by foreigners (if applicable)

Questions to ask a mentor in ad hoc situations.

Situational mentoring may happen in various situations. You can run into a person you respect in the office kitchen or relaxation room, or you can meet them in the company canteen for lunch or during a business dinner in a restaurant. If you work in a very tall office building, you can also find yourself in an elevator with such a person. There should be just the two of you to cherish the openness and honesty in the conversation.

It may also happen that there is a person in your company whom you trust and who you value as more experienced. Such a mentor does not have to be from your department. And you don't have to belong to his department for the mentor to be willing to spend a moment with you and give you a valuable answer. Smart bosses or mentor bosses don't divide people in this way and are genuinely interested in the development of other people, regardless of their affiliation.

In that case (and in the case of your company's open-door culture), you can drop into the boss-mentor's room and ask for a few minutes of time and advice on solving the problem you're facing. Please note that everyone, including you, once asked for advice, is ready to offer it.

What all these situations have in common is the limited amount of time you have. So, you need to be concise, specific, authentic, and determined.

Below you will find a list of sample questions for the Mentor, which belong to the type of situational questions:

I greatly value your experience in X and have long wanted to ask your opinion on Y. This meeting is an unexpected opportunity for me, and I would like to take advantage of it. Could you share your opinion with me?
Many people have advised me to turn to you for advice, mostly because of your experience and openness to others. Now I've plucked up the courage to ask you for 5 minutes of your time and advice on a problem I'm facing.
I recall your presentation X (or your words/behavior) that made an impression on me (please, refer to a real and specific situation). I now have a unique opportunity to ask you directly for your advice.
I am happy about this unexpected meeting. Would you like to advise me on one thing? I value your viewpoint, and I would be grateful for your opinion.

Tips on how to ask questions when meeting senior executives.

At the beginning of this column, we mentioned that we can treat the visit of senior management as an opportunity. If you feel comfortable asking questions in a public forum, and there is a senior management representative whom you sincerely admire, I encourage you to take advantage of this opportunity.

This can apply to meetings in online videoconference mode (where you can submit a question via chat or anonymously), as well as team meetings held in a large conference room or another capacious auditorium. The latter form of meeting is, of course, the biggest challenge, because you have to get up, show yourself to everyone, and ask a question in public, often using a microphone.

It's worth doing it at least once in your life to experience it yourself, see that "the wolf is not so scary," and thanks to this experience, you can also learn something new about yourself.

The difficulty of such meetings and such questions lies mainly in the fear of making a fool of ourselves. That we will be ridiculed by others (especially those who are afraid to take such a step themselves). We also enter into a dialogue with someone we usually perceive as smarter or more important than us. And that takes courage.

So the question should be smart enough on the one hand, neutral on the other, but true enough on the third. Otherwise, participants will sense falsehood or a desire to promote themselves.

Therefore, I encourage you to make your curiosity the key criterion for asking a question in such a situation. If you are genuinely curious about the person or topic you want to ask about, the opportunity will be used to your advantage.

Here are some examples of questions you can ask in a meeting with senior management:

What gives you the greatest satisfaction in your job?
What makes you smile when you get up in the morning for work? (asked with a smile)
What is your typical day or week at work like?
What was one of the most valuable professional pieces of advice you've heard during your professional career?
Who inspires you and why?
If you had an unlimited choice, from all over the world (living or dead), who would you like to have dinner with and why?
What do you think is the biggest challenge facing business leaders today?
What do you think about the new trend X?
What kind of job would you be unsuited to and why? (That's a half-joking, half-serious question.)