OLI Mentor Application 2025

OLI Mentor Application 2025–2026

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 2025–2026, mentors may support high school students (Grades 10–12) in the Future Leaders Program or OLI alumni and emerging professionals (18+) in the Professional Studies Certificate Program.

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

Mentor Onboarding Timeline – Fall 2025
- October 30: Mentor Application Deadline
- November: Attend one mandatory virtual orientation session (required for both new and returning mentors). Tentative options include:
  - Tues Nov 4 (6–8 PM EST)
  - Mon Nov 10 (6–8 PM EST)
  - Mon Nov 17 (6–8 PM EST)
  - Tues Nov 25 (6–8 PM EST)
    
    Zoom links and details will be shared with confirmed applicants closer to the date.
- Submit all required documentation:
  - Mentor Confidentiality Agreement & Media Consent Forms
  - Valid Criminal Background Check (available through OLI if needed)
- December–January: Receive confirmation of mentorship program placement, 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) High School Student Mentorship
- Mentoring high school students (Grades 10–12) enrolled in OLI’s Future Leaders Program.
- Approximately 2–3 virtual hours per month (December–June).
  - Monthly group sessions are tentatively scheduled for the last Wednesday of each month, 6–8 PM EST.
  - Additional 1:1 check-ins with mentees may be scheduled as needed.
- Potential in-person opportunities in Toronto during Camp & Showcase (First two weeks of May 2026; exact dates TBD).
2) Professional Studies Certificate Program Mentorship
- Mentoring OLI Alumni and other emerging Indigenous professionals (18+) enrolled in OLI’s Professional Studies Certificate Program.
- 4 virtual 1:1 sessions with your mentee, and potentially in-person March–May 2026.
3) Guest Speaking Opportunities (open to all mentors)
- Share your education and career journey with youth and alumni/emerging professionals.
If you have any questions about mentoring with OLI, please don't hesitate to reach out:
- Fabi at fspiessruef@olishow.com (Future Leaders High School)
- Alan at alan.faigal@olishow.com (Alumni Certificate Program)
Personal Information
Legal Name*

First NameLast Name
Preferred Name (if applicable)

First NameLast Name
Pronouns (optional)
Email (where OLI staff can contact you)*
example@example.com
Primary Phone Number*
Please enter a valid phone number.
Alternative Phone Number (if applicable)
Please enter a valid phone number.
What is the best way for OLI staff to contact you? (Please check all that apply)*

EmailText Primary NumberCall Primary NumberOther
Mailing Address*

Street Address

Street Address Line 2

CityState / Province

Postal / Zip Code
Do you wish to self-identify as an Indigenous person in Canada such as First Nation, Métis or Inuit? (optional)

IndigenousFirst Nation (Status, Non-status)MétisInuit
What is your occupation(s)?*
Who is your current employer?*
Do you have experience in any of the following career streams? Please check all that apply:

Trades & TechnologyClimate & Environmental LeadershipPublic Service (health care, justice, policing, firefighting, military etc.)The ArtsFinance & EntrepreneurshipOther
Are you a returning volunteer mentor?*

YesNoI've volunteered with OLI in the past but this is my first time mentoring
If you responded yes, how many years have you been a mentor with OLI?

1 year2 years3 years4 years5+ years
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?*

YesNoUnsure
If YES: What date was it issued? (YYYY-MM-DD)?*
If NO or UNSURE: Please confirm your email address where we can send a secure link to complete your check online. Please note you will receive the email directly from our screening platform, CERTN.*
Mentorship Interest
OLI's 2025–2026 mentorship opportunities include:

High School Mentorship
- Mentorship with Indigenous high school students (Grades 10–12) enrolled in OLI’s Future Leaders Program.
- Approximately 2–3 virtual hours per month (December–June).
  - Monthly group sessions are tentatively scheduled for the last Wednesday of each month, 6–8 PM EST.
  - Additional 1:1 check-ins with mentees may be scheduled as needed.
- Potential in-person opportunities in Toronto during Camp & Showcase (first two weeks of May; exact dates TBD).
Professional Studies Certificate Program Mentorship
- Mentorship with OLI program alumni and Indigenous young adults (18+) enrolled in OLI’s Professional Studies Certificate Program.
- 4 virtual 1:1 sessions with your mentee, and possibly in-person between March–May 2026.
Which OLI program(s) are you interested in mentoring with?*

Future Leaders High School ProgramProfessional Studies Certificate ProgramBoth
Why are you interested in mentoring with OLI?
What are you hoping to achieve as a mentor, and what are you hoping to learn?
What skills/knowledge do you hope to share as a mentor? Please feel free to share any relevant experiences (work, volunteering, cultural or community involvement etc.)
How can OLI staff best support your mentoring experience?
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.
High School Program (Dec–June 2026): Would you be available to contribute approximately 2–3 virtual hours per month, with virtual sessions tentatively scheduled for the last Wednesday of each month (6–8 PM EST)?*

YesNoUnsure at this time
High School Program: Would you be available to attend our in-person Meet the Mentor Day in the Greater Toronto Area (tentatively scheduled for Sunday, May 3, 2026; location TBD).*

YesNoUnsure at this time
Alumni Certificate Program: 4 virtual 1:1 sessions with your mentee between March–May 2026.*

YesNoUnsure at this time
Volunteer to assist with OLI's Annual Dance Camp & Showcase in Toronto (First two weeks May 2026 - details to come!)*

YesNoUnsure at this time
Guest Speaker Interest

Are you at all interested in possible guest speaker opportunities related to your career/industry?
If so, what do you feel like you could speak on (please check all that apply):

Trades & TechnologyClimate & Environmental LeadershipPublic Service (health care, justice, policing, firefighting, military, etc.)The ArtsEntrepreneurshipFinancial Literacy/AcumenCareer Beginnings and/or Changing CareerEducation and Career PathwaysNetworking & Public SpeakingCommunication & LeadershipWellness and Self-CareIndigenous Community and/or CultureOther
Questions
Is there anything else you’d like to share about your interest in mentoring with Outside Looking In?
If you have any follow-up questions, please feel free to add here and we can address them during our mandatory orientation sessions scheduled in November.
Thank you for your time and interest in mentoring with OLI – we’ll be in touch within the next two weeks!

If you have any questions about mentoring with OLI, please don't hesitate to reach out to Fabi (fspiessruef@olishow.com) and Alan (alan.faigal@olishow.com).
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OLI Mentor Application 2025–2026

Personal Information

OLI requires a valid and clear criminal background check for all volunteers working directly with youth.

Mentorship Interest

Mentor Availability

Guest Speaker Interest

Questions

Thank you for your time and interest in mentoring with OLI – we’ll be in touch within the next two weeks!