Tips & Tools
Tips & Tools

Conversation Thought Prompters to Unlock Potential in Mentoring Relationships

Through our mentoring roundtables across Canada we’ve generated a list of questions that you can ask to help kick start conversations with your mentee.

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Regardless of what stage your mentoring relationship is at this list of questions and thought prompters can help you to generate conversation with your mentee.

Browse each stage of the mentoring relationship for questions that pertain to:

  • Personal and Professional Development
  • Business Development
  • The Mentoring Relationship

You can always download the full list as a PDF by clicking the “Download Tool” button at the top of the page. And don’t forget to take our crash course that delves into unlocking the potential even more.

Starting the Relationship

Personal and Professional Development
  • What is your definition of success?
  • What do you value?
  • How do you learn best?
  • What is your communication style?
  • How do you deal with setbacks?
  • Why are you starting this business?
  • What’s in it for you?
  • How do you hope to grow through starting a business?
  • How does your business future align with your personal/life goals?
  • What keeps you up at night?
  • What are your coping mechanisms for dealing with stress?
Business Development
  • What is your vision for your business?
  • What is the key benefit of your product/service offering?
  • What is the legal structure of your business?
  • What are your expectations for your business?
  • Which milestones do you have planned?
  • What is your 30-second elevator pitch?
  • When do you expect to be self-sustaining?
  • What is your current cash flow?
  • Do you have any strategic partners or collaborators?
  • What are your back-up plans?
Mentoring Relationship
  • What are your expectations for the mentoring relationship?
  • What type of support (i.e. sales & marketing, accounting, networking, business review of current activities) could I offer that would be most valuable to you in the next three months? In the next 6 months? In the next year?
  • Think of someone with whom you have worked extremely well. What factors contributed to this successful working relationship?

Early in the Relationship

Personal and Professional Development
  • How well and regularly are you sleeping, eating and exercising?
  • Describe your current support system.
  • How frequently do you get away from your business?
  • What professional development opportunities have you engaged in recently?
  • On a scale from 1 to 10, rate your current stress level.
Business Development
  • What recent successes have you had?
  • What challenges are you experiencing?
  • Could you benefit from a referral to someone in my network?
  • What is your current cash flow?
  • How have you progressed on action items you established at our last meeting?
Mentoring Relationship
  • From 1 to 10, 1 being little value/5 being tons of value, rate the value of this mentoring meeting.
  • What else can I do to support you as your mentor?
  • In reassessing your goals, are there any that are no longer relevant? Are there any new goals?

Relationship Mid-point

Personal and Professional Development
  • What challenges have you had?
  • How much time are you spending on tasks versus pro-active activities?
  • How can you be more efficient in accomplishing tasks?
  • How have your family relationships been impacted by your business?
  • List some of your personal and professional successes since the start of our mentoring
Business Development
  • What is your 12-month financial review telling you?
  • What are your human resources challenges?
  • What trends are you noticing in your industry?
  • How can we turn current barriers into opportunities?
  • What is your exit plan?
Mentoring Relationship
  • What else can I do to support you?
  • Which contacts or resources I have connected you with have been most valuable?
  • What has been working well in our mentoring relationship?
  • What can be improved upon?

Closing out the Relationship

Personal and Professional Development
  • What have you learned about yourself through the experience of launching your own business?
  • In which areas have you gained greater confidence and competency?
  • In which areas do you feel you would like to further develop?
  • How do you plan to be supported moving forward?
Business Development
  • How has your product/service offering evolved over time?
  • Having gone through this experience, how might you approach things differently going forward?
  • Where do you see your business in the next 2 years? 5 years?
  • What are your succession plans?
Mentoring Relationship
  • How would you rate our mentoring experience on a scale of 1 to 10 (1 being awful/10 being awesome)?
  • What, if anything, could I have done to create greater value in this mentoring relationship?
  • Does your reality now match your expectations from the beginning of the mentoring relationship?
  • Our Futurpreneur mentoring relationship is coming to a close. Would you like to stay connected? If so, how would you like to move forward?
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