Ambitious people can be notoriously independent, but most figures who’ve made it to the top couldn’t possibly have achieved their goals alone. Instead, political leaders, monarchs and even company CEOs have relied on teams of mentors and experts to guide them for centuries.

Historically speaking, just because advice comes from a confidant doesn’t mean it will be good, but that’s why it’s so important to go over some good questions to ask a mentor when you think you’ve found your match. Like with therapy, your first connection might not be the perfect fit, but that doesn’t mean the right mentor isn’t out there waiting to guide you to new heights.

Good Questions To Ask A Mentor That Might Help Outside The Workplace

Most people seek out mentorship in hopes of securing their dream job, but the experts you connect with can have valuable insight that can transform your personal life too.

Make it a priority to ask questions about them in the vetting process, such as why they decided to pursue mentorship, how you can get in touch with them and if you’ll be using any metrics and routines to track your improvement along the way. Once you’ve made sure you’re aligned there, move on to understanding their interests, passions and how they find a healthy work/life balance.

Good Questions to Ask a Mentor pictured: women laughing at laptop
(Photo by Surface/Unsplash)
  • Why did you decide to be a mentor?
  • What’s your preferred method of communication?
  • What can I do every week to track my improvement throughout our mentorship?
  • What personal values are most important to you? How do you stay committed to them?
  • What’s a goal you’re currently working towards?
  • What does freedom look like to you?
  • Can you tell me about an experience with imposter syndrome and how you conquered it?
  • How do you manage a healthy work/life balance?
  • What habits do you find boost your productivity?
  • Can you recommend a book or resource for dealing with [insert topic here]?
  • What do you see as my weaknesses? How can I transition them into strengths?
  • How do I effectively manage my time and prioritize?
  • What inspires you?
  • What’s going on in your life outside of work?

Good Questions To Ask A Mentor For Career Development

For someone looking to elevate to a new position or start a different career path entirely, good mentorship can be invaluable. Once you’ve established a trusting relationship with your mentor, keep yourself open to honest answers so you can use the feedback to improve. Good questions to ask a mentor include tips on asking for a raise, getting feedback on your resumé and how to know when it’s time to walk away from a position.

Good Questions to Ask a Mentor pictured: women in the workplace
(Photo by Christina @ wocintechchat.com/Unsplash)
  • How can I incorporate meaning into my career?
  • Did you carefully plan your career, or let things unfold naturally?
  • What necessary skills should I develop for rapid growth in my career?
  • What do you most enjoy about entrepreneurship? What is hardest about it?
  • Can you share a time when you felt like a failure but managed to bounce back?
  • How can I let my boss know that I don’t need to be micromanaged?
  • I have a performance review coming up. How can I most thoughtfully prepare for it?
  • How can I become a more clear communicator?
  • My salary isn’t aligned with what my peers make. How do I ask for more?
  • Can we role-play asking for a raise/promotion?
  • What tips do you have for online networking?
  • I’m in the market for a new job. Can you provide feedback on my resumé?
  • Who should I connect with to improve my career prospects?
  • How do you predict [insert industry here] will change in the next 5-10 years?
  • How do you continue to grow and develop as a leader?
  • What was your most memorable moment as a leader?
  • How do you know when it’s time to change careers?