What Should I Ask My Mentor?

You’ve got the meeting on the calendar. You’ve got coffee (or Zoom) in hand. Now… what do you say?

Great mentorship doesn’t come from small talk, it comes from honest, thoughtful questions. Whether you’re wrestling with your current job, growing in your career, or just trying to figure out what’s next, asking the right questions opens the door to wisdom, clarity, and deeper connection.

Here’s a curated list of questions you can draw from, not all at once, but as they fit your season and situation.

Questions for Direction + Discernment

• What helped you figure out what you’re called to do?
  
  
• Have you ever felt unsure about your path? What did you do?
  
  
• What signs helped you know you were in the right place? Or the wrong one?
  
  
• How do you balance ambition with surrender to God’s will?
  
  
• What would you say to someone who’s feeling “behind” in life?
  
  

Questions About Career + Leadership

• What was your first leadership opportunity, and how did it go?
  
  
• How do you deal with self-doubt or imposter syndrome?
  
  
• What’s a professional mistake you’ve made, and what did it teach you?
  
  
• What advice would you give someone starting out in your field?
  
  
• How do you handle failure, feedback, or criticism?
  
  

Questions About Faith in the Workplace

• How do you stay grounded in your faith at work?
  
  
• Have you ever felt pressure to compromise your values in your career?
  
  
• What spiritual practices help you stay connected to God in busy seasons?
  
  
• How do you navigate work environments that feel “less than life-giving”?
  
  
• Who inspires you to be both faithful and excellent?
  
  

Questions for Life + Character

• What does “success” mean to you now, versus 10 years ago?
  
  
• What are the habits or routines that keep you anchored?
  
  
• How do you approach rest and Sabbath in your schedule?
  
  
• What friendships or mentors have shaped your life?
  
  
• What virtue do you struggle with the most, and how do you work on it?
  
  

Faith-Based Reflection Questions

• What Scripture or prayer has been most formative for you?
  
  
• How do you bring prayer into big decisions?
  
  
• Has God ever surprised you in your career or relationships?
  
  
• What’s a season of waiting you went through, and what did you learn?
  
  
• How has mentorship played a role in your spiritual journey?
  
  

 Pro Tips:

• Don’t feel like you have to ask everything. Pick 2–3 questions that genuinely matter to you right now.
  
  
• Listen more than you speak, but don’t be afraid to share your story too.
  
  
• Follow up! If something they say sticks with you, bring it up next time.

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