Toolkit on Effective Mentoring for Youth
Facing Barriers to Success

Best practices and resources to build, strengthen, evaluate and sustain effective mentoring programs for youth considered at high-risk of under education, unemployment, homelessness, criminalization, and other negative outcomes.

Matching & Initiating the Relationship

“I feel like it doesn’t matter if they have similarities or not with you too much as long as you connect with them.” (Covenant House Youth Consultation)

StandardMentor-Mentee Match

Match mentors and mentees, and initiate the mentoring relationship using strategies likely to increase the odds that mentoring relationships will endure and be effective.1


  • Consider the characteristics of the mentor and mentee (e.g., interests; proximity; availability; age; gender; race; ethnicity; personality; expressed preferences of mentor, mentee, and parent or guardian; goals; strengths; previous experiences) when making matches.
  • Arrange and document an initial meeting between the mentor and mentee as well as, when relevant, with the parent or guardian. A program staff member should be on site and/or present during these meetings.
  • Bring all concerned parties together in person to sign a commitment agreement consenting to the program’s rules and requirements (e.g., frequency, intensity and duration of match meetings; roles of each person involved in the mentoring relationship; frequency of contact with program), and risk management policies. It is particularly important for everyone involved in the mentoring relationship to have clear expectations from the beginning.1

“Don’t try to get personal too quick […] Cause like we can talk about one thing and if it jumps to something else and it goes that route that’s whatever. But, let me be the one leading it there.” (Covenant House Youth Consultation)

Other Findings

Matching mentors and mentees based on similarities such as age, gender, race, and ethnicity, and mutual interests is frequently recommended. However, research comparing cross-race and same-race matches has found few, if any, differences in the development of relationship quality or in positive outcomes, suggesting that matching on race may not be a critical dimension of a successful mentoring relationship, in general. Similarly, there is currently no strong evidence that gender impacts match satisfaction. Some evidence shows that female-identified mentors are more receptive to long-term mentoring relationships and value intimacy and connection, whereas male-identified mentors seem to prefer more activity-based mentoring where the active part of the relationship can develop more quickly. The Mentoring Centre suggests that for youth deemed high-risk and very high-risk, matching according to ethnic and gender identity should be strongly considered.

Although the research is not yet conclusive, matching based on common interests should take precedence over matching based on race and/or gender alone. Most importantly, programs should take into consideration the individual personal interests, needs and preferences of the participants and their families.2, 3

That said, be cognizant and attentive to difficulties that may arise in mentoring across race and gender. Research shows that cross-race and cross-gender relationships can have difficulty forming, developing, and maturing. Negative stereotypes, difficulty with identification and role modeling, skepticism about intimacy, public scrutiny, peer teasing or resentment, and “protective hesitation” (fear of misunderstandings, confrontations, and disagreements) can impact the match in unfavourable ways.4

Research has shown some promising preliminary support for allowing mentees to choose their mentor. To assist in the process of matching mentors and mentees, some mentoring programs host a group event where prospective mentors and mentees can meet and interact with one another in an organized fashion, and then provide feedback to the mentoring program regarding their preferences for matching. Hosting a “Meet-n-Greet” consisting of a series of activities can help demonstrate preferences and connections. Ensure that participants only see it as a fun gathering to get to know each other to avoid feelings of pressure or disappointment. After the Meet-n-Greet, ask the mentees and mentors to name 2-3 people they felt they connected with and try to make matches accordingly. If you can’t match a mentee with a mentor they’ve named, consider matching them with a mentor that named them – helping them feel ‘chosen’ and promoting positive self-perception beliefs.4

Giving mentees and mentors some “voice and choice” in matching is based on the idea that this practice will be associated with greater engagement in the program.

In the case of cross-age peer matching, mentees should be matched with a mentor who is at least three years older than the mentee.

Consider providing an opportunity for the parent(s) or guardian(s) to provide feedback about the mentor selected by the program, prior to the initiation meeting.

If the mentor will be picking up the mentee at the mentee’s home for match meetings, an initial match meeting should occur at the home of the mentee with the program staff member present.

Prepare the mentor, mentee and family member for the initial meeting after the match determination has been made (e.g., provide background information about prospective mentee/mentor; remind participants of confidentiality; discuss potential opportunities and challenges associated with mentoring).

Programs must find a balance between sharing information with mentors that will be important to the success of the match and allowing mentees to share their story. Programs may have their own philosophy on how to go about this process. Some argue that where possible, mentors should be provided with information on the mentee’s history to better understand their specific experiences.7 Programs may choose to provide mentors with an information package on their mentee that includes information on their family background and any behavioural issues.

Mentors are asked to sign a confidentiality agreement prior to receiving any information.

Other programs allow the mentee to control when and how they will share their information. Staff meet to discuss explicit safety concerns or information that needs to be shared with the mentor. Otherwise, the mentee regulates the sharing of information.8

Consider using a trial period for a match, and/or monitor the relationship regularly to determine whether the match is as good as originally hoped.2, 5

Finally, mentors with prior experience should be oriented towards youth with higher needs or more troubled circumstances.1, 6

Key Tools & Resources

Big Brothers Big Sisters of Canada (2009). Meet-n-Greet: A Mentor-Mentee Matching Approach. Available at:

Building Relationships: A Guide for New Mentors:

Matching Policy/Procedure:

Going the Distance:

Refer to Mentoring Immigrant and Refugee Youth for pros and cons of same gender/race/ethnic mentor matching (MENTOR, 2007, pp. 43-44):

  1. MENTOR. (2015). Elements of effective practice for mentoring, 4th ed. Retrieved from
  2. DuBois, D.L., & Karcher, M.J. (Eds.). (2014). Handbook of youth mentoring (2nd Ed). Thousand Oaks, CA: Sage Publications.
  3. Liang, B., Bogat, G. A., & Duffy, N. (2014). Gender in mentoring relationships. In D. L. DuBois & M. J. Karcher (Eds.), Handbook of Youth Mentoring (pp. 159-175). Thousand Oaks, CA: SAGE Publications, Inc.
  4. Thomas, David A. (2001) The Truth about Mentoring Minorities: Race Matters. Harvard Business Review, April 2001, 99-107.
  5. Pryce, J., Kelly, M. S., Guidone, S. R. (2014). Mentor and youth matching. In D. L. DuBois & M. J. Karcher (Eds.), Handbook of Youth Mentoring (pp. 427-438). Thousand Oaks, CA: SAGE Publications, Inc.
  6. Big Brothers Big Sisters of Canada (2009). Meet-n-greet: A mentor-mentee matching    approach. Retrieved from
  7. Britner, P.A., Randall, K.G. & Ahrens, K.R. (2013). Youth in Foster Care. In D.L. DuBois & M.J. Karcher (Eds.), Handbook of Youth Mentoring (2 ed., pp. 341-354). Thousand Oaks, California: Sage Publications, Inc.
  8. Swettberg, C. (2013). Mentoring youth in the foster care system: From research to practice.  [Presentation]. Retrieved from
Funding provided by the Ontario Ministry of Children and Youth Services