Mentorship Jumpstart Questions

What do we talk about?

We get this question a lot. And we get it. Starting a new relationship can be challenging, nerve-wracking, or even scary sometimes. But the success stories we hear from the mentors and mentees every day prove to us that it's worth it. So we've created a collection of questions to spark new and important conversations within your pairing. They may not all apply to your mentorship; that's okay! Pick and choose the ones that work best. These questions as designed to guide you through the full cycle of your relationship, so feel free to bookmark this page and come back to it as your mentorship grows.

Setup: use these questions to set the terms, logistics, and expectations of your mentorship
Stories: use these questions to ground your relationship in trust, familiarity, and an understanding of each other
Situations: use these questions as examples of scenarios your mentor might be able to help you through
Skill-Building: use these questions to develop skills, behaviors, and abilities to move you toward your goals.
Self-Awareness: use these questions to evaluate the progress and/or success of your mentorship.

Have questions you think we should add? Let us know here!

Setup

Use these questions to set the terms, logistics, and expectations of your mentorship.

Have you had a mentor/mentee before? What did you like/dislike about the experience?
When are you "available" to chat? Are there times of the day or week when you're not available?
How often would you like to check in with one another?
What platforms are you comfortable communicating on? Are there platforms where you'd prefer not to be reached?
What is the best platform for me to reach you on/with?
What can I do to make this a positive experience for you?
What goals do you have for our time together?
What parts of this experience are you nervous, anxious, or unsure about?
What values are important to you? (Ex: family, community, justice, honesty)
What interests do you have outside the classroom? How are you nurturing them? How would you like to be nurturing them?
What is (or was) your major/area of study? How'd you select it?
Are there any challenges to learning that you'd like us to address through our time together?
Is there any support I can provide you that you aren't getting on campus?
What campus resources do you want to learn more about or use more?
What areas of your life do you want to work on, and how can our time together help with that

Stories

Use these questions to ground your relationship in trust, familiarity, and an understanding of each other.

What TV/movie/book/play character is most like you, and why?
How do you handle feedback? How do you feel about your reaction/response to it?
What's a skill you'd like to learn, and how can I help you learn it?
If you could curate a museum gallery, what would you put in it?
Where do you ultimately want to end up in your career (role, title, income, etc.)?
If you could learn any new professional skill (it doesn’t have to be related to your current role or industry), what would it be?
Was there a time you messed up and felt like you’d failed? How did you bounce back?
What accomplishment are you most proud of? What about you do you feel helped you achieve it?
What individuals in your life have contributed to your personal growth? How did they do it?
What’s the most important leadership lesson you’ve learned and how has it proven invaluable?
What is something you enjoy doing, but are not very good at? Why do you still enjoy doing it?
What is something you do not enjoy doing, but are very good at? Why do you not enjoy it?
What is your process for turning a bad day into a good day?
Which leadership skills were (or have been) the most difficult to develop?
What's a skill you're proud to have developed, and how did you learn it?
Mentees can ask: What’s something you’d like to change about your current role/industry?
Mentees can ask: How do you make yourself happy in your current role/industry?
Mentees can ask: What are your current goals as a leader?

Situations

Mentees: Use these questions as examples of scenarios your mentor might be able to help you through.

How do you continue to grow and develop as a leader?
What was the worst conflict you had to resolve?
What was the biggest leadership risk you took?
What was your proudest moment as a leader?
What leaders do you look up to for inspiration?
Do you have any leadership decisions that you regret, or wish you could do over?
How do you keep your team motivated?
How can I explore new interests while I balance schoolwork with work?
Did you experience some major setbacks in your career path? How did you bounce back?
How do I reach out to someone whose work I admire, but who I don't know?
How can I stay connected to key influencers who do not work nearby?
How can I make connections in my field of interest if I'm bound to this area for work/family/etc.?
Adult/graduate students can ask: How should I explain myself and my circumstances when I know I'm in consideration among younger/newer candidates for a role?
How can I combine my interests or passions with work?
I'm considering a change in my major or area of study. What are some areas of business that might be a good fit for me?
I met someone at an event, and I'd like to get to know them better/shadow them at work/learn more from them. How do I get started?
How can I find ways to incorporate my passions or interests into my (school) career?
I have two very different career paths available to me. Can you weigh in to help me make a final decision?
When have your emotions clouded your judgment? What did you learn from the experience?

Skill-Building

Use these questions to develop skills, behaviors, and abilities to move you toward your goals.

What skill(s) have always come really naturally to you?
What skill(s) are you most proud to have improved in/with?
What skill(s) do you wish came more easily to you?
Are there any skills you'd like to work on with me during our time together?
What habits have you developed that help you be successful?
What habits or patterns have held you back from success?
I have an interview coming up. What are some interview questions and other things that I need to know about to nail it?
What practices can you recommend for dealing with nervousness when speaking to groups?
What good habits will help me focus on my career?
Do you have any tips on how to improve my resumé for my job search?
How should I talk about my on-campus experiences on my resumé, or in interviews?
How is our shared industry of interest likely to change in the next 5 years? In the next 10?
Who should I connect with to improve my career prospects?
What new skills do I need to move ahead?
How do I effectively manage my time and prioritize accordingly?
Can you recommend a book or resource for dealing with difficult conversations?
Graduate students can ask: What can I do if I want to take my graduate experience into the corporate world? How should I talk about my experiences?
What skills should I be developing if I want to start my own business?

Self-Awareness

Use these questions to evaluate the progress and/or success of your mentorship.

What strengths about you do you think your friends would name, if they were asked? How about your professors?
What areas of improvement about you do you think your friends would name, if they were asked? How about your professors?
What have you learned from this mentorship experience?
How often do you check-in with yourself about your thoughts, feelings, and actions?
Do you have any feedback on how we can improve our mentoring rapport?
What makes me unique compared to other people you’ve worked with?
What do you observe when I interact with other people?
What changes will you make based on this mentorship experience?
Where do you see my strengths?
What new strengths or developments are you excited to take to the workplace?
What beliefs or goals did this mentorship help solidify for you?
What do you see as some of my points of improvement? How can I work on these?
Does my communication style support the messages I intend to deliver?
How often do you ask for feedback to learn more about yourself?
How could I communicate my ideas more clearly?
Am I progressing in the right direction?
What would you like to see me do every week/month/term to show that I’m improving throughout this mentorship?