• OLI Mentor Application 2026–2027

    Empower Indigenous Youth to Aim High & Rise to the Next Level

  • Outside Looking In (OLI) is seeking volunteer mentors from diverse careers and backgrounds to support Indigenous youth in our programs. Mentorship with OLI is a two-way learning experience, providing both mentors and mentees with fresh insights, mutual growth, and shared inspiration.

    For 2026–2027, mentors may support high school students (Grades 10–12) in the Future Leaders Program and/or emerging professionals (18+) in the Indigenous Professional Studies Certificate Program.

    Only one application is required. OLI staff will confirm placements based on your availability, interests, background, and program needs. 

    Mentor Onboarding Timeline – Fall 2026

    • September–October: Mentor Applications Open
    • October 18: Priority Application Date – please apply by this date for the best chance at your preferred orientation session date.
    • October–November: Attend one mandatory virtual orientation session. You'll select your preferred date(s) later in this application; Zoom links and details will be shared closer to the date.
    • After Orientation: Submit all required documentation:
      • OLI Confidentiality Agreement and OLI Media Consent Form (feel free to click and review at your convenience; we'll send you a secure link to sign once you've completed orientation!)
      • Valid Criminal Background Check (available through OLI if needed)
    • November–December: Placements are confirmed and mentors connected with mentees on a rolling basis, wrapping up by December. Placements are determined by a combination of your availability, interests, and OLI’s programming needs to ensure each mentee is matched with a mentor.

    Mentorship Opportunities & Commitments

    1) Future Leaders Mentorship

    • Mentoring high school students (Grades 10–12)
    • Approximately 1.5–2 virtual hours per month from December 2026 to June 2027.
      • Monthly group sessions are typically scheduled for Wednesday evenings (1.5 hours between 6–8pm ET).
      • Communication between mentors and mentees may be facilitated between sessions as needed.
    • Optional: Potential in-person opportunities during OLI’s 20th Annual Camp & Showcase happening this year in Winnipeg (First two weeks of May 2027; exact dates TBD).

    2) Indigenous Professional Studies Mentorship

    • Mentoring emerging Indigenous professionals (18+)
    • All mentors and mentees are invited to attend a Virtual Meet & Greet scheduled for December 8, 2026 (7–8:30pm ET).
    • 4 virtual 1:1 sessions with your mentee. Scheduled flexibly between November 2026 and March 2027.

    3) Guest Speaking Opportunities (open to all mentors)

    • Share your education and career journey with program participants.

    If you have any questions about mentoring with OLI, please don't hesitate to reach out: 

    • Fabi at fspiessruef@olishow.com (Future Leaders Program)
    • Alan at alan.faigal@olishow.com (Professional Studies Program)

  • Personal Information

  • Are you applying through a workplace volunteer program with OLI?*
  • Are you a returning mentor with OLI?*
  • How many years have you been a mentor with OLI?
  • Format: (000) 000-0000.
  • Format: (000) 000-0000.
  • What is the best way for OLI staff to contact you? (Please check all that apply)*
  • What time zone are you in?*
  • Do you wish to self-identify as an Indigenous person in Canada such as First Nation, Métis or Inuit? (optional)
  • Do you have experience in any of the following career streams? Please check all that apply:

  • Mentorship Onboarding

    OLI will host a series of virtual mentor orientation sessions for all new and returning mentors. You only need to attend ONE session.
  • Please select your preferred date(s), and we'll send a calendar hold for each so you can confirm which one works best.*
  • Please select your preferred date(s), and we'll send a calendar hold for each so you can confirm which one works best.*

  • Criminal Background Check

    OLI requires a valid and clear criminal background check for all volunteers working directly with youth.
  • Do you have a valid criminal background check that was completed within the last year?*
  • What date was your background check issued?*
     - -
    2 digit month, 2 digit day, 4 digit year
  • Should we send the CERTN link to the same email you provided above?*

  • Mentor Availability

    OLI staff will confirm mentorship placements by considering your availability, interests, and background, alongside program needs, to ensure every participant is matched with a mentor.
  • Which OLI program(s) are you interested in mentoring with?*
  • How would you like to get involved?*
  • How would you like to get involved?

  • Future Leaders – Mentorship Schedule

    • Mentoring high school students (Grades 10–12)
    • Mentors and mentees will participate in 6 facilitated mentorship sessions (December 2026–June 2027), representing approximately 10 hours of volunteer commitment per mentor. The tentative schedule includes:
      • Wed Dec 9: Holiday Meet & Greet 
      • Wed Jan 27: Personal Management & Essential Skills (1:1 pairings launch)
      • Wed Feb 24: Career & Postsecondary Exploration 
      • Wed Mar 31: Job Seeking & Workplace Readiness
      • Wed Apr 28: Career & Community Experiences
      • Wed Jun 9: Closing Reflections & Celebration
    • Communication between mentors and mentees may be facilitated between sessions as needed.
  • Are you able to attend the virtual mentorship sessions listed below (December 2026–June 2027)? Each session runs 1.5 hours, between 6–8 PM ET.*
    Rows
  • OPTIONAL: For those located in the Greater Winnipeg Area, would you be interested in potential in-person opportunities during OLI's 20th Annual Camp & Showcase happening this year in Winnipeg? (First two weeks of May 2027; exact dates TBD)

  • Indigenous Professional Studies – Mentorship Schedule

    • Mentoring emerging Indigenous professionals (18+)
    • All mentors and mentees are invited to attend a Virtual Meet & Greet scheduled for December 8, 2026 (7–8:30pm ET).
    • 4 virtual 1:1 sessions with your mentee. Scheduled flexibly between November 2026 and March 2027.
  • Would you be available to attend the Virtual Meet & Greet on Tuesday, December 8, 2026, 7:00–8:30pm ET? (Details TBC)*
  • Can you commit to 4 virtual 1:1 sessions with your mentee, scheduled flexibly between November 2026 and March 2027? Each session is a maximum of 1 hour.*

  • Mentor Goals

  • Guest Speaker Opportunities (Optional)

    Open to all applicants, including those not able to mentor this year. Share your education and career journey with our participants.
  • Are you at all interested in possible guest speaker opportunities related to your career/industry?

  • Guest Speaker Interest

  • Please indicate which program(s) you may be interested in offering a Guest Talk:

  • Future Leaders – Guest Speaker Availability

    Guest talks take place on select Wednesday evenings, between 6–8 PM ET, separate from scheduled mentorship sessions.
  • What could you speak on or facilitate a workshop about? (Check all that apply)
  • What kind of talk are you interested in offering? (optional)

  • Indigenous Professional Studies – Guest Speaker Availability

    Guest talks take place Tuesday evenings, roughly 7–8:30 PM ET (exact time depends on speaker availability), primarily January–February 2027. November–December 2026 talks are possible pending availability and scheduling.
  • What could you speak on? (please check all that apply):
  • What kind of talk are you interested in offering? (optional)

  • Before You Submit

    If you have any follow-up questions, please feel free to add here and we can address them during our upcoming mentor orientation sessions.
  • Should be Empty: