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Conversation Starters and Questions
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Establishing a relationship with someone new can be challenging at times.  Even when you know someone well, there can still be awkward silences during a conversation.  We want to help you move through those challenges!  Below are some conversation starters and questions that you may want to keep handy to use during those moments.



  • Who is the person, living or dead, you would most want to meet and why?
  • What is the most daredevil thing you've ever done and how was that experience?
  • You are marooned on an island.  What 5 things would you have brought with you if you knew there was a chance that you might be stranded?
  • If you could fix one global issue, what would it be and why?  It cannot be water related!
  • If you had a time machine that would work only once, what point in the future or history would you visit?
  • If you had to give up one of your senses (hearing, seeing, feeling, smelling, tasting) which would you give up and why?
  • What is the one gift you have received that you will never forget and why?
  • If you are at a friend's or relative's house for dinner and you find a dead insect in your salad, what would you do?


Mentoring general: 

  • Where do you envision yourself professionally in 10 years?
  • What has been your greatest learning experience?
  • What one professional accomplishment are you most proud of?
  • What one professional blunder have you learned the most from and what did you learn?


For mentors to  ask mentees: 

  • What makes you you?
  • What values drive your actions?
  • What is your strongest attribute?
  • What unique skills and competencies do you possess?
  • What life experiences have influenced you the most?
  • What is most challenging for this task, skill or goal?
  • Tell me about the obstacles you are facing with this task, skill or goal.
  • What is the consequence of not growing in this skill?
  • What effect could your performance improvement have on your work team?
  • Tell me about a time you were in a similar situation.  What was the result?
  • What transferrable skills or experiences do you have?
  • Who do you know that does this really well?


For mentees to ask mentors: 

  • Have you had mentors/mentees in the past? What did you learn?
  • Who inspired you?
  • What professional challenges have you faced and how did you overcome them?
  • What lessons have you learned from your successes and failures?
  • What do you do to encourage your own growth and development?
  • Have you achieved work-life balance? If so, how did you achieve it?
  • Tell me about the path that has led you to where you are today.
  • Ask about a professional current event or issue of interest to you.
  • How has the industry changed over the past 3-5 years?
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