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Congratulations! You've made your way to "Overcoming Common Challenges," the sixth module in the six-part online mentor training series brought to you by TCAM—The Center for the Advancement of Mentoring.

This module explores common challenges that can occur in mentoring relationships and provides strategies for addressing the challenges. Each section of the module addresses different types of challenges, such as those related to education and jobs, personal problems, teachable moments, and family situations.

Within these sections, scenarios are broken out by mentee age group. You can navigate to the scenario that applies to your mentee's age group—or you can choose to read all the scenarios.

Start Here

Use active listening and follow the six problem-solving steps when you and your mentee face challenges.

Your mentoring relationship will be filled with activities, adventure, and excitement. Inevitably, however, you and your mentee will face challenges, both together and individually. You can resolve most challenges with your mentee by listening actively and using the following six problem-solving steps:

  1. Help your mentee clarify the problem (by asking open-ended questions, paraphrasing, etc.) to identify exactly what's going on.
  2. Help your mentee articulate how he feels about the problem by reflecting.
  3. Help your mentee brainstorm possible approaches to solving the problem.
  4. Help your mentee think through the pros and cons of each approach.
  5. Help your mentee choose an approach and execute it, as appropriate.
  6. Follow up with your mentee to find out how it went.

For each challenge presented in this module, think about how you would apply active listening and the problem-solving steps.

Please refer to Module 5: "Communicating with Your Mentee" for more information on communication skills.

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Remember your role as a mentor.

When you’re feeling overwhelmed and unsure about what to do, think about what your role as a mentor includes—and what it doesn’t include.

Your role is to be a support, guide, adult friend, role model, listener, and coach.

Your role is not to be any of the following:

  • A savior. Mentors can coach, guide, and support—but they can’t “save” a child. Your mentee’s life experiences are what they are. You cannot fix them. What you can do is help your mentee develop the skills to navigate life’s challenges, make good choices, and solve problems.
  • A parent. No matter what you think of your mentee’s parent or caregiver, you cannot replace this person—nor should you. Never take sides against the parent, contradict the parent, or try to come between the parent and your mentee.
  • A lawyer. In some mentoring programs, mentors are explicitly encouraged to advocate for and broker resources for their mentees. In other programs, however, the mentor’s role is limited to coaching the mentee to solve problems and advocate for herself. Your point of contact for your mentee is your mentoring program coordinator. Please defer to your mentoring program’s guidelines related to advocacy.
  • A banker. It is inappropriate to spend more than modest amounts of money on your mentee. Spending money can set an expectation that you will regularly pay your mentee’s way and provide gifts. Instead, the foundation of your relationship should be purely relational. Look for free or very inexpensive activities to do together.
  • A social worker. You are not responsible for counseling your mentee, providing resources, or coordinating services. Even if you happen to be a social worker or mental health professional, remember that the role of case worker is very different from the role of mentor.
  • An employer. As a mentor, your role is to help your mentee to develop life skills. Focusing your relationship on hiring your mentee or connecting her to a job through friends or colleagues brings unnecessary complications to the mentoring relationship.

Note: Remember that you are a mandated reporter and that you are obligated to inform the mentoring program coordinator if you are aware, or if you suspect, that your mentee is being neglected or abused. Please refer to your program's policies related to this issue.

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This module will walk you through common mentoring challenges.

This module will help you understand some potential mentoring challenges and prepare you to respond appropriately if they arise. You do not need to work through this entire module; rather, you can navigate to the sections and scenarios that are most relevant for your mentoring relationship. Use this outline to help you navigate to the section that addresses the issues you would like to learn about.

For each challenge scenario, you'll read about what is happening, why it might be happening, and how you and your mentee can work together to appropriately address it. The challenges you encounter and how you respond to them will vary depending on your mentee's age, so the examples in this module are divided into three age groups: middle childhood (ages 7–10), early adolescence (ages 11–13), and adolescence (ages 14–18). You should select the scenarios that best apply to you and your mentee.

  • Section 1: Education, Jobs, and Life Skills This section addresses challenges your mentee might encounter in school or in his job search.
    • Scenario 1: Middle childhood (ages 7-10): Trouble in school
    • Scenario 2: Early adolescence (ages 11-13): Talking back
    • Scenario 3: Adolescence (ages 14-18): Job search frustration
    • Interactivity: You find out that your mentee has been cutting class.
  • Section 2: Personal Problem-Solving This section explores challenges such as what to do when your mentee asks you for money, how to respond if you're concerned your mentee may be involved in a gang, and what to do if your mentee's boyfriend appears to be controlling her actions.
    • Scenario 1: Middle childhood (ages 7-10): Money to go to the movies
    • Scenario 2: Early adolescence (ages 11-13): Concern about gang involvement
    • Scenario 3: Adolescence (ages 14-18): Controlling boyfriend
    • Interactivity: Your mentee is considering smoking pot.
  • Section 3: Teachable Moments In mentoring relationships, a teachable moment is an unplanned opportunity that arises for a mentor to share important insights with a mentee.
    • Scenario 1: Middle childhood (ages 7-10): Littering
    • Scenario 2: Early adolescence (ages 11-13): Cruelty to a homeless person
    • Scenario 3: Adolescence (ages 14-18): Showing up late
    • Interactivity: Your mentee is about to post online a negative status message about his employer.
  • Section 4: Family Challenges This section addresses family-related challenges, including those involving parental decisions or requirements that your mentee does not agree with.
    • Scenario 1: Middle childhood (ages 7-10): Cell phone
    • Scenario 2: Early adolescence (ages 11-13): Babysitting for siblings
    • Scenario 3: College
    • Interactivity: Your mentee is bullying someone—and her parents are encouraging it.

By the end of this module, you will be able to do the following:

  • Identify common challenges that occur in mentoring relationships
  • Identify an effective course of action for responding to each challenge

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To navigate through this module, use the menu in the left-hand column.
TCAM Partners


The Center for the Advancement of Mentoring Partners

TCAM is a project of Education Development Center, Inc. (EDC), in collaboration with Dare Mighty Things, Inc. (DMT); Dr. Roger Jarjoura of Indiana University and founder of Aftercare for the Incarcerated Through Mentoring; and Dennis Talbert, President of Empower Outreach, a faith-based mentoring program for high-risk youth. TCAM is funded by the Office of Juvenile Justice and Delinquency Prevention (OJJDP).


Office of Juvenile Justice and Delinquency Prevention (OJJDP) Logo


The Office of Juvenile Justice and Delinquency Prevention (OJJDP) supports states, local communities, and tribal jurisdictions in their efforts to develop and implement effective programs for juveniles. OJJDP of the U.S. Department of Justice strives to strengthen the juvenile justice system's efforts to protect public safety, hold offenders accountable, and provide services that address the needs of youth and their families. OJJDP plays a vital, leadership role in the field of youth mentoring in the United States.


Education Development Center (EDC) Logo


Education Development Center, Inc. (EDC). EDC is an international, non-profit organization dedicated to enhancing learning and promoting health. EDC works to reduce barriers and disparities with an emphasis on the most vulnerable populations, especially those living in poverty. EDC builds the capacity of practitioners to reduce juvenile delinquency through strategies such as mentoring system-involved youth; restorative justice; dropout prevention; and prevention/early intervention for youth violence, gang involvement, and alcohol and other drug use.


Dare Mighty Things (DMT) Logo


Dare Mighty Things, Inc. (DMT) is a management consulting firm specializing in the development of large-scale programs that impact vulnerable populations. DMT works with national, state, and local organizations to develop large-scale, outcome-based social initiatives for at-risk and high-risk populations.

User Guide


In each section of this lesson, you will be presented with three tiers of information. The following descriptions will help you navigate this self-guided experience.


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TCAM Online Training Series for Mentors and Mentoring Program Staff Terms and Conditions for Use


The TCAM Online Training Series for Mentors and Mentoring Program Staff was developed by TCAM—The Center for the Advancement of Mentoring. It is designed to be used free of charge by youth mentoring programs funded by the Office of Juvenile Justice and Delinquency Prevention (OJJDP) of the U.S. Department of Justice and by other mentoring providers and individuals.


The TCAM Online Training Series for Mentors and Mentoring Program Staff includes six online training modules for mentors, which are intended to be used in combination with in-person mentor training provided by mentoring programs, as well as two online modules for mentoring program staff about designing and delivering in-person mentor training. The content of the training series is informed by mentoring research and best practice, the expertise of the TCAM Leadership Team, and TCAM’s experience providing technical assistance to OJJDP mentoring grantees. Each module is designed to be completed in approximately 30 minutes, and individuals may opt to complete one or more of the eight modules.


Technical Requirements
Viewing and Downloading PDFs

Some of the materials in this training series are posted in PDF format. PDF, which stands for Portable Document Format, is a popular format for distributing documents on the Internet. To view and print PDF documents, you need the free Acrobat Reader software. If you do not have Acrobat Reader installed on your computer, go to the Adobe website and follow the directions to download and install the software.


Multimedia Software

The training series contains some links to multimedia resources. To be able to experience the full multimedia effects, you may need the following free software download:


Enabling Javascript

To use the training series, JavaScript must be enabled in your computer’s browser. For Internet Explorer, go to Tools > Internet Options and select the “Security” tab; click “Custom Level” near the bottom; scroll down to “Scripting” and make sure “Enable” is selected under “Active scripting." For Firefox, go to Tools > Options > Content > Enable JavaScript (checked). For Safari, go to Preferences > Click Security > Check Enable JavaScript. Close the window and click Reload.


Link Check

All of the links in this training series are checked regularly; however, the Web is an ever-changing medium, and you may find that some of the links don’t work. If you find a broken link, please report it.  Note that if you find a broken within a reading or resource on another website, only the owners of that website can repair the link.


Course Accessibility

This training series contains accessibility features to accommodate the needs of individuals with disabilities. The developers of the training series aim to achieve W3C WAI Priority 2 level. If you have difficulty using any aspect of this training series, please contact the Technical Facilitator at or 617-618-2334.


Contact Information

This training series was created by The Center for the Advancement of Mentoring, operated by Education Development Center, Inc. (EDC), in the performance of Grant No. 2009-JU-FX-K001 awarded by the Office of Juvenile Justice and Delinquency Prevention, Office of Justice Programs, U.S. Department of Justice.


For content-related questions about the training series:

TCAM Project Director (; 617-618-2346)


For technical questions about the training series:

Technical Facilitator  (; 617-618-2334)