Mentorship

Strategic questions to ask your mentor that unlock growth

Move beyond breaking the ice and ask your mentor the strategic questions that lead to growth. In this article, we curate 8 different types of strategic questions to ask your mentor during your next meeting.

Ryan Carruthers

October 11, 2022

Mentors help you navigate your career by guiding and advising you. An individual like this can be a great resource for learning about how to improve, identifying your strengths, and setting career goals and strategies.

To get the most out of your mentors, you need to ask strategic questions and get advice from them. It strengthens the mentor-mentee relationship, skips the guesswork, and can help you develop actionable strategies that can take you far in both your personal and professional lives.

In this article, we list many strategic questions to ask a mentor that unlocks growth. Let’s dive in.

The principles behind having a strategic conversation

If you want to ask strategic questions, you first need to understand the principles and thought processes behind the strategic conversation. 

Here are the 10 ways mentors or mentees can have better conversations from Celeste Headlee, an American radio journalist who outlined each in her Ted Talk.

1. Don’t multitask (be all in or all out, not in between).

If you’re focused on other things besides having a focused conversation, you’ll not build a meaningful connection. Avoid multitasking and be in the moment both physically and mentally while having these conversations.

2. Enter every conversation expecting to learn something.

Genuine and productive conversations between mentors and mentees hold enormous value. Enter every conversation with the spirit and expectation of learning something new every single time.

3. Start questions with who, what, when, where, why, and how.

Questions that start with the 5 ‘W’s’ and 1 ‘H’ are open-ended. They enable you to dig deep and extract the most relevant insights. Ditch long questions. Make sure that your questions are clear, short, and concise. Try to keep them free of bias and make them engaging.

4.  Go with the flow

You need to go with the flow when having a strategic conversation. Be an observer; recognize and control the direction of the conversation. Listen actively and be sincere. Try to grow and roll with it, and most importantly, have some fun.

5.  If you don’t know, admit it

You don't always know everything—which is natural. So if you don’t know something, admit it. Be transparent and honest about what you know and what you don’t. As a mentor, this can be hard as you’re supposed to help them. But a good mentor knows where they’re most useful and where they should point them to someone else.

6.  Don’t equate your experience with theirs

We all have different experiences. Although it can seem empathetic to say “I know how you feel,” avoid it. Instead, seek to understand their experience. Repeat back what you hear. Say, “what I’m hearing you say is…” This will get them to further elaborate, giving you a deeper understanding. This is much stronger than saying you’ve been there and then changing the subject to be about something you’ve experienced.

7.  Try not to repeat yourself

It is easy to lose track of the topic at hand when your mind wanders during a conversation. Therefore, you may feel disconnected and repeating what you have already discussed may seem like the only thing to do. Avoid doing this by staying focused and engaged during a conversation.

8.  Stay out of the weeds; forget dates, names, etc. they aren’t important

You may find it useful or interesting to provide every detail but this eventually bores the listener and the conversation take a toll downward.

9.  Listen. “We don’t listen to understand; we listen to reply”

We communicate so much electronically that listening can sometimes seem like a lost art. If you’re not listening to the other person that means that you’re not engaging in the conversation. Listen carefully, to reply, ask questions and add comments. 

10. Be brief

You lose other people’s attention when you talk for too long. A focused and precise conversation is always more impactful and fruitful.

Strategic mentoring questions go beyond icebreakers

Before we unpack the strategic questions you need to understand the psychology and the purpose behind them. 

Strategic questions aren’t simple icebreakers. They go beyond that. Why? Because in order to ask them you need to build a solid relationship first. Relationship building between mentors and mentees is challenging. It is often difficult to connect deeply with each other at certain levels in social situations where polite small talk is the norm instead of heart-to-heart discussions.

The science behind strategic mentoring conversations

The key to overcoming these barriers is to engage in reciprocal self-disclosure, which involves revealing increasingly personal information about yourself to another person, as they do the same for you. According to research, sharing personal details with a stranger for just 45 minutes can dramatically increase feelings of closeness. But this openness requires maintaining a delicate balance between both parties.

This is where the following strategic questions to ask a mentor help you to stay at the same pace. 

These strategic mentoring questions are curated from a study that revealed if you ask your partner these questions, you’re guaranteed to grow closer to them and drive value out of your conversations. 

Although the study was primarily about questions potential romantic partners should ask, the underlying principles can aid professional relationships as well. These well-researched questions help the other party as well to understand, validate and care - in a way that enhances the overall closeness and professional bond.

What are strategic questions to ask your mentor or mentee?

These strategic questions have a purpose: to understand your past, plan your future, or learn a lesson from them. 

So use these strategic questions next time when you’re having a productive conversation with your mentor.

Questions to understand your mentor's past and what shaped them

Your mentor used to be where you are today. They’ve been in the trenches and have invaluable life lessons that you need can learn from. In light of that, ask these questions:

  • What were some mistakes you made during your early career and what did you learn?
  • Why did you decide to be a mentor?
  • Who has mentored you? And what impact has that had on you?
  • What professional accomplishment are you most proud of?

Questions to understand your mentor’s strengths and how they can help you

Mentoring is an opportunity for you to improve your existing skills and develop new ones. Your mentor can teach you specific technical skills or invaluable softskills. Try to identify the strengths of your mentor by asking these questions. Moreover, If you'd like to improve on a specific ability, you can ask for resources and tips.

  • Which skills do you consider your strongest?
  • What strategies did you use when pursuing your career goals?
  • What decision gave you the most success in your career?
  • What would you help me with if I wanted to accomplish what you have one day? 

Questions to start identifying your career potential

Your career goals can be achieved with the help of a mentor. You can work with your mentor on developing your career goals based on your potential and creating a plan to achieve them. The following questions will help you to identify your career potential with the help of your mentor.

  • How do you determine which priorities are important to you?
  • How do you know if you should change careers?
  • What key elements should I include to achieve my career goals?
  • Are there any other areas in this field where I could find success if I change my career?

Challenging questions to bring out your mentor’s devil’s advocate

It’s beneficial to coax your mentor into calling you out. Ask your mentor the below questions to encourage them to point out blind spots they see. 

  • How do I know the goals I’ve shared with you are achievable?
  • How can I be confident your advice is applicable to my unique situation?
  • What good advice have you received throughout your career that had unintended negative consequences?
  • What potential risks do you see in my development plans? 

Questions to help you navigate challenging situations

Having access to a professional with experience in handling challenging situations is helpful. This allows you to learn how to navigate situations professionally and what steps to take. Ask the following questions if you want to handle a challenging situation as your mentor does

  • How should you handle disagreements with a manager?
  • What should you do when you don't have much experience with the project you're working on?
  • Do you have any strategies to resolve conflicts with your coworkers?
  • What steps should I take to correct a mistake at work?

Questions that increase your self-awareness

Self-awareness builds self-confidence and brings clarity. Clarity allows us to see things from different perspectives. A mentor can help you with this and make better decisions by leveraging the power of self-awareness. Ask the following questions from your mentor that increase your self-awareness.

  • Does it matter what other employees think about me at work?
  • What should worry me the most about my future?
  • Do you have any book recommendations for increasing self-awareness?
  • Is there anything you do that helps you to be more productive?

Questions to boost creative thinking

Nowadays, creative thinking is one of the most sought-after skills for life and work.  Unique and original ideas make you stand out. 

Asking questions to boost your creative thinking is one of the best ways to understand the patterns and processes involved behind the scenes to come up with original and creative solutions. Ask these questions from your mentor to boost your creative thinking.

  • What are the most important things to consider when trying to solve a problem?
  • How do you know what is a good idea and what isn't?
  • What are the biggest challenges to boosting creative thinking?
  • What practices should I follow to think outside the box?
  • What do you think are the most important books, articles, or podcasts to consume?

Questions to build a growth mindset

Everyone has a fire in the belly to achieve big things, but it takes the right practices to activate it. Asking questions to build a growth mindset is one of the great practices that encourages you to grow every day. Asking the growth mindset questions makes you feel that you’re not stagnant and just need the right direction to thrive. Your mentor can help you build a growth mindset if you ask them the following questions.

  • Is there any daily routine that you feel greatly contributes to your constant growth and success?
  • How do you review your work for errors and flaws?
  • What drives you every day to be the best version of yourself?
  • How do I keep growing even when life gets busy?

Explore all phases of your mentoring relationship

The road to career success is full of twists, turns, and bumps. It becomes a whole lot easier when you know that you have access to an expert guide at any time to help you. 

Now you can leverage that power as you know the strategic questions to ask a mentor that unlocks growth.  But remember that this is just the beginning of their mentoring journey. 

The next step is to learn about the other phases of a mentoring relationship.

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5 Mentoring session agenda templates that help mentees have better, more structure mentoring sessions.

These 5 mentoring session agenda templates include 10 discussion questions each. Mentors and mentees can use these as a launching off point to have insightful and revealing conversations that lead to growth.