Planning First Session

Planning Your First Mentoring Session

The following questions and suggestions may help to frame your initial meeting between mentor and mentee. Use them as a starting point to begin the mentoring conversation.

Setting the Scene

  • Explore contexts and issues that the mentee would like to discuss.
  • Set out the overall plan for this first session, its timing, and what you would like to discuss.
  • Decide on questions to guide the discussion.

Discuss Expectations for the Mentoring Relationship

  • What do we understand about this mentoring relationship?
  • What are the expectations that we each have?
  • What are we prepared to do and to talk about?


  • As Mentor, how will you commit to this relationship?
  • As Mentee, how will you commit to this relationship?
  • Use the Mentoring Agreement to frame your commitment.


  • What resources provided by DS4Y will be useful to us?
  • What other resources might be useful?

Time Management

  • What time can we devote to developing this relationship? When is the best time for us both?
  • How frequently should we meet?
  • What time constraints do either of us have to manage?

Physical or Virtual Meeting Place

  • Are we able to meet face-to-face? If so, where?
  • Is there technology that we might like to use to connect for mentoring sessions? Telephone? Online?

Adapted with permission from the ArtsBuildOntario Arts Facilities Mentoring Network Orientation Binder 2017-18.