50+ Mentorship Program Questions for Mentors and Mentees

Sam Cook


An image of a computer screen with a blank list for mentorship program questions.

Whenever the term “asking questions” comes up, I’ll be honest: Emmanual and Philip Hudon’s viral song “Askin’ All Them Questions” still lives rent-free in my head in those moments. It doesn’t even matter what the context is. So when we talk about mentorship program questions, I can’t help but let that song run its course until I regain mental control. Mentorship is about as impactful as viral songs like that, and asking a ton of questions during a mentorship program is pretty much essential to make sure that the relationship and the insights gained from it live rent-free in both the mentee and mentor’s heads long after the relationship has ended.

The right questions can guide a mentoring relationship and ensure that both mentors and mentees get as much out of that relationship as possible.

During my days as a high school teacher (and to date myself here, one who was teaching when the aforementioned viral song became popular), I’ve witnessed firsthand how asking the right questions can completely change how someone receives, retains, and utilizes information. Especially in a classroom built around a Socratic style, questions are a teacher’s primary tool. They’re used to review content, check comprehension, stimulate critical thinking, and even control classroom dynamics. The art of questioning is about seeking answers and fostering a more profound understanding and critical thinking.

In the context of mentorship, the dynamics are similar. Just as in education, where the right questions can stimulate higher-order thinking and encourage students to take cognitive risks, in mentorship, well-framed questions can push mentees to explore uncharted territories, reflect on their experiences, and arrive at insights they might not have reached individually.

Great questions won’t fix an ineffective mentor-mentee match. Book a demo to learn how MentorcliQ helps create successful mentoring relationships even before the mentoring relationship begins.

What Are the “Right” Mentoring Questions to Ask?

Generally speaking, there aren’t “right” or “wrong” questions to ask in a mentoring relationship, although some are certainly out of bounds. Every mentoring relationship is different, so the type of questions you ask could very much be impacted by different factors, such as:

As a standard form of practice, questions serve as the bridge between curiosity and knowledge. They can uncover hidden challenges, clarify doubts, and pave the way for new insights. Assuming the mentoring relationship is focused, the issue is not so much whether the question is correct, but whether it’s:

  • Appropriate for the context
  • Worded or phrased properly to avoid confusion and vagueness
  • Designed in a way that elicits a thoughtful and actionable response

Similarly, in mentorship, questions are not just tools for information exchange; they are instruments of transformation. They help mentees understand expectations, set clear goals, track progress, and reflect on the journey.

For example, a mentor might ask, “Where do you see yourself in five years?” to gauge a mentee’s ambition and to help them visualize and plan for their future. A mentee might ask a mentor, “What challenges did you face in your career, and how did you overcome them?” to glean wisdom from their mentor’s experiences.

The right questions can foster a deeper connection between the mentor and mentee. They can unearth shared experiences, values, and aspirations, building trust. This trust is paramount, as it ensures that both parties can be candid, open, and vulnerable, leading to a mentorship experience that is truly enriching and mutually beneficial.

You may be letting the question-asking be organic, but prepare your questions ahead of time as part of your pre-mentoring prep. In this Mentoring Masterminds video, we share some tips on how to prepare for your first mentoring session.

6 Types of Mentorship Program Questions

Now that we understand the conceptual DNA of asking the right questions, we can be even more intentional and mindful with the type of questions we ask in mentoring relationships.

The beauty of questions lies in their versatility and adaptability to various situations and objectives. It’s essential to:

  • Be specific and straightforward to avoid ambiguity
  • Ensure the question is relevant to the mentorship goals
  • Frame questions that encourage reflection and deep thinking

Mentors and mentees can employ common types of questions throughout their relationship.

Managerial questions

These are operational questions that ensure the smooth functioning of the mentorship process. They address the logistics and mechanics of the relationship.

For instance, “How often should we meet?” (which falls under mentoring frequency, a topic we’ve covered in more detail) or “What platform should we use for our sessions?” These questions set the groundwork and create a structure for the mentorship journey.

Rhetorical questions

Rhetorical questions are used to emphasize or make one think about a particular topic, and are not necessarily designed to elicit a response. That said, I’ve found from experience that both the individual asking rhetorical questions and the individual receiving them tend to want a response of some kind and not an awkward silence.

For example, if a mentor asks, “Isn’t it crucial to set clear goals from the outset?” the answer is pretty much already assumed. That makes it a rhetorical question. And yet, it’s something that can be discussed from a philosophical standpoint. And that’s really what rhetorical questions are designed to do. You’re not answering the question so much as considering the wisdom of or concept inherent in the question.

Closed questions

These questions have specific answers and are often used to confirm understanding or gather factual information. They’re straightforward and leave little room for interpretation. An example might be, “Do you have prior experience in this field?” or “Did you complete the task we discussed?”

Closed questions are often better understood as “yes” or “no” questions. E.g., “No, I don’t have prior experience,” or “Yes, I completed the tasks we discussed.”

These questions are often necessary to keep the conversation going. But they can also be the starting point for deeper questions on why. For example, “Why don’t you have prior experience?” is an excellent, deeper-level follow-up question that is far more open-ended and can result in extracting some hurdles or difficulties a mentee may have experienced in the past that have hampered growth.

Open questions

Open-ended questions are some of the most difficult yet most important questions to ask in a mentoring program. These are broad and, when executed properly, can lead to extensive discussions. They’re designed to elicit more than just a yes or no response.

That follow-up question in the previous section I mentioned, “Why don’t you have prior experience?”, would fall within this category. Consequently, this is one of the best ways to generate open-ended questions: Make them a follow-up or response to a closed question.

Open questions are great for understanding feelings, opinions, and experiences. They provide a platform for the person on the receiving end to share, reflect, and delve deeper into their thoughts. “How did that experience shape your perspective?” or “What challenges do you foresee in your current role?” are examples.

Reflective questions

These questions prompt people to look back on their experiences and analyze them. They’re instrumental in fostering self-awareness and growth. Examples include, “How do you feel about the decision you made?” or “What would you do differently if faced with a similar situation, and would you choose it again?”

Drawn mage of two men talking in a mentoring relationship. One is asking a mentorship question, shown as a question mark in a comment bubble.

And I know what you’re thinking. “How do reflective questions and open-ended questions differ?” The simple answer is that they’re not different. Reflective questions are a subset of open-ended questions. They’re specifically designed to encourage the respondent to think critically about their own experiences, choices, and decisions. These questions often mirror the respondent’s previous statements and offer them back for examination.

Since I like a good extended metaphor, if you ask a mentee, “Why don’t you have prior experience?” and she says, “I always felt that type of work was beyond my capability, so I never tried to pursue projects or work in that area,” you can ask some follow-up questions that will get her to reflect on that statement. Questions like:

  • “What makes you feel this type of work is beyond your capability?”
  • “What would it take for you to feel capable in this area?”
  • “How do you think this belief has shaped your career choices so far?”

Hopefully, you get the idea here. I realize I’ve spent a larger amount of time on this point than some of the others, but reflective questions are incredibly important in a mentoring relationship. Mentoring is incredibly introspective. Although the end goal of a mentoring relationship is growth, in most cases, mentees have hit roadblocks, snags, or personal challenges that have impeded growth. That means looking back to understand how to move forward.

Forward-looking questions

Aimed at forward-thinking, these questions encourage those being asked to envision their future, set goals, and plan their trajectory. “Where do you see yourself in the next five years?” or “What key skills would you like to acquire to advance in your career?” are typical futuristic questions.

These questions are also a natural progression from reflective questions. Once someone has looked back to better understand themselves, their issues, their roadblocks, or anything else that’s brought them to where they are today, they can begin planning how to create the future selves they want to see.

Much of this can feel like advice for running counseling sessions. Mentoring and counseling are often conflated because they can feel similar at times. The two practices share many common elements in engagement style and practices, although the end goal differs.

5 Stages of Mentoring Relationships and Questions to Ask

As the relationship evolves, the nature and depth of mentor/mentee questions change, reflecting the dynamic nature of the bond between both parties.

Each stage of the mentorship process demands a unique set of questions tailored to address the specific needs and objectives of that phase. Not only does asking the right questions ensure both parties remain aligned in their goals, but it also deepens the trust and rapport between them.

Stage 1: Rapport building

Rapport building is the foundational stage of the mentoring relationship. It’s not just about introductions but delving deeper to establish genuine trust and better understand each other.

During this phase, both the mentor and mentee invest time in sharing their backgrounds, experiences, aspirations, and even apprehensions. They explore commonalities and differences, which can be invaluable in shaping their career journey ahead. Open communication is encouraged, ensuring that both parties feel comfortable and valued.

This stage sets the tone for the entire mentorship, making it crucial to foster an environment of mutual respect, empathy, and active listening.

10 questions for rapport building in mentorship

Questions to ask your mentee

  1. What motivated you to seek out a mentorship?
  2. How would you describe your ideal mentorship experience?
  3. What are some of your personal and professional aspirations?
  4. How do you handle feedback or criticism?
  5. What are some things you’d like me to know about you that can help in this mentorship?

Questions to ask your mentor

  1. What experiences led you to become a mentor?
  2. How do you envision our mentor-mentee relationship?
  3. What do you expect from me as a mentee?
  4. Can you share a pivotal moment in your career?
  5. How do you handle setbacks or challenges in your profession?

Stage 2: Setting direction

Once a solid rapport is established, the mentor and mentee collaboratively chart the roadmap for their relationship.

This involves defining clear objectives, setting measurable goals, and discussing the strategies to achieve them. It’s a phase of alignment where expectations are clarified, and a shared vision is crafted. An effective mentor provides guidance, drawing from their experience, while the mentee brings forth their aspirations and areas they wish to develop.

Together, they create a blueprint for success, ensuring the mentorship remains purposeful and goal-oriented.

10 questions for setting direction in mentorship

Questions to ask your mentee

  1. What specific goals would you like to achieve through this mentorship?
  2. How can I best support you in reaching these goals?
  3. What are your strengths and areas you’d like to develop?
  4. How do you plan to track your progress?
  5. Are there any immediate challenges you’d like to address?

Questions to ask your mentor

  1. How did you set goals and achieve them in your career?
  2. What resources or strategies do you recommend for goal setting?
  3. How can I ensure I’m making the most of this mentorship?
  4. What challenges did you face when pursuing your goals, and how did you overcome them?
  5. How often should we review and possibly adjust my goals?

Stage 3: Progression

With a clear direction set, the mentorship enters an active learning, growth, and development phase.

The mentor provides guidance, resources, and constructive feedback while the mentee takes steps toward achieving the set goals. Regular check-ins are essential to monitor progress, address challenges, and celebrate milestones.

This stage is dynamic, often characterized by moments of discovery, learning curves, and breakthroughs. It’s a testament to the collaborative effort, where both mentor and mentee are actively invested in realizing the objectives they’ve set out to achieve.

10 questions for progression in mentorship

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Questions to ask your mentee

  1. How do you feel about the progress you’ve made so far?
  2. What obstacles are you currently facing, and how can I assist?
  3. Are there any new skills or knowledge areas you’d like to explore?
  4. How has your perspective or approach changed since we began?
  5. What additional resources or support might benefit you at this stage?

Questions to ask your mentor

  1. Based on your observations, where do you see my strengths and areas for improvement?
  2. How did you maintain motivation and momentum in your career?
  3. Are there additional strategies or tools you’d recommend for this stage of my development?
  4. How do you handle plateaus or periods of slow progress in your career?
  5. Can you share a time when you had to pivot or adjust your approach?

Stage 4: Winding down

As the mentorship journey nears its end, reflection becomes paramount.

Both parties take a step back to assess the journey, the highs and lows, the lessons learned, the strengths and weaknesses, and the growth experienced. It’s a time of acknowledgment, where the mentor and mentee appreciate each other’s contributions and the value of their relationship. They discuss the successes, areas of improvement, and even uncharted territories that might be explored in the future.

This stage is about consolidation, ensuring the insights gained are internalized and the foundation is laid for future endeavors.

10 questions for winding down the mentoring relationship

Questions to ask your mentee

  1. What have been your key takeaways from this mentorship?
  2. Is there anything you wish we had covered or discussed more?
  3. How do you feel about the goals we set and the progress made?
  4. What will be your next steps after our formal mentorship ends?
  5. How can we ensure a smooth transition as our formal sessions conclude?

Questions to ask your mentor

  1. What advice do you have for me as we conclude our sessions?
  2. How can I continue to apply what I’ve learned from our time together?
  3. Is there a way I can give back or contribute to others based on my mentorship journey?
  4. How did you handle transitions in your professional relationships?
  5. Can we discuss a plan for staying in touch or seeking advice in the future?

Stage 5: Moving on

The end of the formal mentorship program doesn’t signify the end of the relationship. Instead, it marks a transition.

The mentor and mentee might continue their association in a less structured manner, with the mentee now better equipped to navigate their path. They discuss future aspirations, potential challenges, and strategies for continued growth. The mentor might provide recommendations for further resources or mentor networks.

This stage is about empowerment, ensuring the mentee is poised for success, with the mentorship experience serving as a guiding light.

10 questions for moving on from the mentoring relationship

Questions to ask your mentee

  1. How do you feel about embarking on this next phase of your journey?
  2. What strategies will you employ to continue your growth?
  3. Do you see yourself becoming a mentor in the future?
  4. How will you integrate the lessons from our mentorship into your ongoing professional development?
  5. What are your aspirations for the next year?

Questions to ask your mentor

  1. As I move forward, what pitfalls should I be aware of?
  2. How do you handle new challenges or opportunities that arise in your career?
  3. Do you have recommendations for resources or networks I should explore next?
  4. How do you continue to seek growth and learning in your own career?
  5. Is there any final advice or wisdom you’d like to share as I embark on this next stage?

Tips for asking questions during a mentoring session

Questions are the lifeblood of a mentoring program. Having a framework and some example questions will help you get started, but as noted earlier, every mentoring relationship is different. It’s important to adjust the questions you ask in a mentoring program to fit the unique relationships and situations you encounter.

Ask a variety of questions

Diverse questions cater to different cognitive levels and elicit a range of responses. By mixing factual queries with those that probe deeper, you can gauge understanding while also encouraging critical thinking. This variety keeps the conversation dynamic so that the mentee is challenged and engaged. Whether it’s a simple check-in question or a complex hypothetical scenario, a mix ensures a comprehensive exploration of the topic at hand.

Ensure clarity in your questions

Clear and concise questions are key to avoiding misunderstandings. Ambiguous or overly complex questions can lead to confusion, potentially derailing the conversation. By being precise in your phrasing and ensuring that your intent is clear, you cultivate an environment where the mentee feels confident in their understanding and response. Clarity paves the way for productive discussions and meaningful insights.

Use open questions

Open-ended questions are powerful tools in the mentorship toolkit. They stimulate higher-order thinking, pushing the mentee to reflect, analyze, and evaluate. Instead of seeking a straightforward answer, open questions encourage deeper insights, allowing the mentee to explore their thoughts and feelings.

Be patient

Patience is a virtue, especially in a mentoring session. After posing a question, it’s essential to give the mentee or mentor ample time to think and formulate their response. This pause, though it might seem prolonged, can be the difference between a surface-level answer and a profound reflection. By being patient, you signal that you value their thoughts and are genuinely interested in their perspective.

Be receptive to feedback

No questioning technique is perfect, and there’s always room for improvement. Being open to feedback about your questions or approach is crucial. Whether the feedback comes directly from the mentee or is something you observe during the session, being willing to adapt and refine your technique ensures that your questions remain effective and relevant. A growth mindset in this area enhances the quality of the mentorship experience.

Ask and you shall receive

The mentorship journey is a dance of mutual respect, trust, and continuous learning.

By asking the right questions, mentors and mentees can ensure they’re in sync, making the most of this invaluable relationship. As the saying goes, “The quality of your life is determined by the quality of your questions.” In mentorship, this couldn’t be truer. Whether you’re seeking guidance or offering it, remember that every question is a step toward growth, understanding, and lasting connections.

The Most Important Mentoring Question for HR Leaders and Program Admins

These questions focus on what mentees and mentors should be asking each other during a relationship. But there’s one important question mentors should ask long before those partners meet: Is this match going to work?

If you’re not 100% sure that your matches are effective, all the questions in the world aren’t going to help. Mentoring works best when the mentor and mentee are well-matched across a number of criteria, including personality. If you’re matching by hand, chances are high that your mentoring pairs will have less-than-stellar feedback in the end.

All successful mentoring relationships start with the match. Book a demo to learn how MentorcliQ creates matches that lead to 95% satisfaction from mentors and mentees.

Sam Cook