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Skills Development

21 Questions for Inspiring Great Conversations

  • 12/07/2022
  • Frances Campbell
  • 2 mins read

Guider has one simple mission: we want to power a billion inspirational conversations. To do that, we work hard to create mentoring software that facilitates quality matches and makes mentoring accessible for all.

But how do you turn your conversations from good to inspiring?

We’ve all been there, sometimes it takes a little bit of prompting to get a great conversation flowing. That’s why we’ve put together 21 questions to help you have inspirational mentoring conversations. These questions are designed for both mentor and mentee to get you to break the ice and get straight to the good stuff.

While we can’t join every mentoring session and start conversations for you (that would be weird for us too), we can provide conversation starters to take along to your next session.

Questions for mentors and mentees

  1. What made you join the program?
  2. What do you want to gain from this experience?
  3. How often do you prefer to meet?
  4. What’s the best way to communicate?
  5. What do you most want to learn about?
  6. How do you prefer to give and receive feedback? 
  7. Is this your first time as a mentor/mentee?

Questions for mentees to ask their mentor

  1. How did you get into the industry?
  2. What made you want to become a mentor?
  1. What do you see as your greatest achievement to date?
  2. What skills do you rate most highly in your current role?
  3. Do you have a mentor yourself?
  4. What piece of advice do you wish you had when you were at my stage?
  5. What obstacles have you overcome to get where you are today?

Questions for mentors to ask mentees

  1. What do you want to get out of this experience?
  2. What are the biggest challenges you’re facing?
  3. What is in your power to change?
  4. What’s your biggest goal for the next year?
  5. When do you feel time flows most at work?
  6. How do you like to receive feedback?
  7. Who in your team supports you the most?

These questions are just a start – make sure you keep note of any further questions you have and bring them along to your next session.