Developing a Relationship with Your Mentee

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Overview: Start Here

Congratulations! You’ve made your way to "Developing a Relationship with Your Mentee," the fourth module of the six-part online mentor training series brought to you by TCAM—The Center for the Advancement of Mentoring.


While every mentoring relationship progresses at its own pace, many experience common stages, including forming first impressions, making a connection, navigating through challenges, growing the relationship, and celebrating the relationship before coming to closure. By developing a basic understanding of these common stages of mentoring relationships, you will be better equipped to work with your mentee.


This module also reviews some common challenges that may arise, and helps you determine when to seek additional support from your mentoring program coordinator.


At the end of this module, you will have a good understanding of the common stages of a mentoring relationship, the perspectives of mentees and mentors during each stage, how to navigate through predictable obstacles, and the role of mentoring program staff in supporting you and your mentee.

A mentoring relationship typically progresses in stages.

While mentoring relationships are fluid and progress at their own unique pace, most typically move through the following stages:

  1. Forming first impressions
  2. Making a connection
  3. Navigating through challenges
  4. Growing the relationship
  5. Celebrating the relationship and coming to closure

Note that these stages don’t always occur in this exact order, and some stages can occur more than once.

Mentors need to have realistic goals for the relationship.

Many mentors enter the mentoring relationship with high hopes for the positive impact they believe they can have on a young person’s life. These initial feelings of excitement can quickly transform into disappointment if the mentee doesn’t respond with enthusiasm. Throughout the mentoring relationship, it's important to be patient and not become discouraged if your impact on your mentee isn't as obvious as you had hoped. As the relationship progresses, you may find that you will need to adjust your expectations.

Lay the foundation and set a positive tone at the beginning.

Early in the relationship, you and your mentee will need to build a base of trust and respect on which the relationship can grow.

Your mentoring program can provide support and helpful resources.

Remember that while the beginning a mentoring relationship may feel awkward or confusing, you don’t have to deal with it alone. Reach out to the staff of your mentoring program and experienced mentors for help when you need it.

Some mentoring programs establish specific goals or milestones for the mentor-mentee pairs. Be aware of your program’s parameters, goals, and policy requirements. The orientation/training that you receive from the program will inform you about these requirements.

This module will help you better understand the stages of the mentoring relationship and how you can work to overcome issues and challenges that may arise.

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

  • Identify the common stages of a mentoring relationship
  • Understand the perspective of the mentee and the mentor during each stage
  • Identify ways to navigate through predictable challenges
  • Understand the supportive role that your mentoring program staff plays

Section One: Forming First Impressions

When you and your mentee meet for the first time, you will inevitably form first impressions of each other that may or may not be accurate. A youth who has been through one or more traumatic experiences is likely to need more time to get comfortable and feel that she can trust you. This has little to do with your ability to relate to your mentee, but is a result of your mentee’s having been abandoned or seriously disappointed by significant adults in her life. Your mentee's background and culture will also shape her behavior and worldview. As you get to know your mentee over time, encourage her to share about her life experience, background, and culture.

Mentors and mentees often approach the relationship with expectations.

At the beginning of a match, you and your mentee may have preconceived notions of what the relationship will be like. While these expectations aren’t necessarily right or wrong, it’s important to understand that a mentoring relationship can be successful even when it looks or feels different from what you anticipated. Be aware of your vision and expectations for the match, as well as your biases and stereotypes. You’ll need to recognize and manage your assumptions, approaching the relationship with an open mind. Your mentoring program’s training will also help you understand and manage your own assumptions of what to expect from your mentee and from the relationship.

Realistic expectations help provide a stable foundation for a mentoring relationship. When initial expectations are too high or are unrealistic, tension can occur. If you keep your expectations realistic, it is likely to help you and your mentee to bond.

It is also important to be clear about your role as a mentor. A mentor is a friend, a role model, a person to talk to, and another adult who is proud of the child. Mentors should not aim to be a mentor to the young person’s family, a social worker, a doctor, or a “savior.”

Program staff typically help parents and caregivers to be realistic about the role of the mentor during this initial phase of the relationship. Speak with mentoring program staff if at any time you are concerned about the expectations that you, your mentee, or his parents/caregivers have about the relationship.

For more information, see Module 1: "What Is a Mentor?"

Mentees’ expectations may be based on their past experiences with adults.

You probably don’t yet know much about your mentee’s experiences with significant adults or how these experiences have shaped his ability to have a trusting relationship with an adult. The key is to respect the newness of the relationship and let it develop naturally. Being overeager for closeness is not a good way to begin a mentoring relationship.

Your mentoring program coordinator may facilitate your first meeting with your mentee or may provide materials that describe how to lay the groundwork for the relationship. The coordinator will also share the program’s rules and expectations for mentors, mentees, and parents/caregivers. In case your program does not provide a mentor/mentee contract, use this sample contract for mentors as a guide for talking with your mentee about expectations for the mentoring relationship and for creating an agreement that you and your mentee can commit to. (The sample contract also offers templates for a mentee and parent mentoring agreement.)

Youth who have experienced trauma may resist a relationship at first.

Youth with a traumatic past (including those in foster care, those involved in gangs or at risk for gang involvement, and adjudicated youth) may have good reason to be very cautious about trusting and beginning to bond with an adult mentor. Try not to take this personally. They are simply relying on behaviors that have protected them from harm in unsafe situations.

Your patience and commitment will give your mentee time and a reason to begin to trust you and develop a relationship with you. Be patient with yourself as well. Trust doesn't develop overnight. Your mentoring program's staff should be able to provide suggestions for how to navigate this potentially sensitive stage of the relationship. For more information about working with young people who have had challenging life experiences, review Module 2: "Understanding Your Mentee's Background."

During this early stage, you and your mentee are getting to know each other, establishing norms, and beginning to bond. Especially during this early stage of the mentoring relationship, you should focus on being reliable and a good listener, willing to learn about your mentee and her experiences. For more information, visit Module 5: "Communicating with Your Mentee" and Module 6: "Overcoming Common Challenges". Additionally, click the link to download “Identifying Common Experiences and Interests.” This worksheet can help you and your mentee discover the things you have in common and it might help to generate ideas for activities to do together.

Section Two: Making the Connection

The next stage of the relationship is "Making the Connection." In this stage, you and your mentee begin to really feel connected. You understand each other fairly well, and your relationship now feels less fragile and more comfortable. You see more and more signs that your mentee trusts you and is willing to confide in you.


During this stage, you may begin to see changes in your mentee’s behavior that may be a result of your relationship with him. Perhaps your mentee is showing increased enthusiasm about getting together with you, or maybe he has developed a new interest, based on activities you’ve engaged in together. You may even note that he is increasingly able to develop healthy relationships with peers and adults.


It is critical to deepen your mentee’s evolving trust in you. You can do this by remaining committed to the relationship, respecting established boundaries, keeping your word, and honoring plans you’ve made with your mentee. To deepen the connection, you should also find ways to recognize and celebrate your mentee for his interests, skills, hard work, and other achievements that you have had the privilege to witness.

A connected relationship opens up new possibilities.

At this point, your mentee sees you as a reliable adult friend and trusts you. As a trusted figure, you now have an enhanced ability to be a positive influence in his life. With this trusting relationship established, you can help your mentee to set meaningful, positive goals and seek out new interests and activities.

This is a good time to ask your mentee if he wants to brainstorm new goals for the mentoring relationship. There are a variety of goal-setting activities that can accommodate his personality and skills. For example, you can help him to start using a journal or blog to record his thoughts about the future, or you can support him in creating a poster or other work of art that captures his goals for the future.

  • Be a creative coach. Once your mentee has set one or more new goals, focus on supporting him to reach them.
  • Reflect and celebrate. Now that you understand your mentee on a deeper level, make an effort to acknowledge and praise the positive ways in which he’s developing. For example, you could say: “It took a lot of courage to ask your teacher for help when you realized that you were falling behind. Great job!” Or, “I saw how you held back and let Janet take the lead the other day. It was generous of you to share the limelight and support your friend.” You can also turn your acknowledgement into an open-ended question such as: “I noticed you stepped aside and let Janet take the lead. How did that feel? What made you decide to do that?”

Connect on the major – and minor – issues.

Most of your conversations with your mentee will be about everyday topics such as school, crushes, pastimes, etc. Your ease with this part of the relationship lays the groundwork for you to support your mentee when more critical issues are at stake. By confiding in you and discussing personal information with you - even when it’s negative - your mentee is demonstrating that she trusts you and has confidence in your ability and willingness to be there for her.

Section Three: Navigating Challenges

The next phase of the mentoring relationship is "Navigating Challenges and Growing." Like all relationships, mentoring relationships evolve and change—and, like all relationships, its progression can be complicated and surprising. We’ll review a few of the kind of challenges that emerge even in the best of mentoring relationships and suggest strategies for managing these challenges.

A deeper connection can also uncover new challenges.

When you and your mentee are comfortable and connected, and things seem to be going well, it is common for challenges to arise. For example, your mentee may:

  • confide in you about something that puts her or someone else at risk of harm
  • skip several planned activities or distance herself from you
  • do something that seems to jeopardize her future

While there is much more information about handling challenges in Module 6: "Overcoming Common Challenges," the following are some suggestions for approaching difficult situations.

1. Stay within the boundaries of your role as a mentor.

It is often more appropriate that other adults in your mentee’s life help her to handle significant challenges. Focus on being the best mentor you can be within the limits of your relationship. Make sure you know whom to contact at your mentoring program if you need support or if something arises with your mentee that you’re not sure how to handle. For example, your mentoring program coordinator can provide an objective perspective and can connect your mentee to appropriate resources and services. It is also important to remember that, in most cases, your mentee’s parents and/or caregivers are deeply invested in her well-being. Work to keep lines of communication open with your mentee’s parent/caregiver, and seek his or her permission and guidance as appropriate.

2. Don’t take it personally.

Remember that if your mentee behaves poorly or puts herself or others at risk, it is not an indication of the youth’s feelings toward you, nor is it a sign that she has a character or personality flaw. Acting out is normal behavior to be expected of children and adolescents.

3. Prioritize the safety of your mentee.

As an adult friend - not a peer - you have an obligation to report to mentoring program staff if you learn about something that puts your mentee at risk. Even if you are a trained social worker or human services professional, in this relationship you are a mentor, not a case worker. Although your mentee may be angry at you for sharing this information, explain that you must put her safety first, no matter what.

4. Model commitment and consistency.

Even with solid agreements and contracts in place, your mentee may not show up for mentoring activities or live up to commitments. While this can be frustrating, remember that reliability and consistency are critical behaviors to model for your mentee.

5. Look for teachable moments - and note the positive.

The mentoring relationship provides many opportunities for your mentee to discuss and practice life skills. For example, if your mentee consistently misses or shows up late for mentoring activities, it’s likely that there are other situations where he doesn’t show up when he should. Ask him open-ended questions about his schedule and his communication with you. Support your mentee as he develops this and other life skills. Look for the good in your mentee and be sure to verbalize what you observe.

6. Seek support from program staff.

Some mentees, particularly those from challenging backgrounds, may fear success or be concerned that they will be criticized by former friends for “selling out.” As a result, some youth may relapse and have violent outbursts, become withdrawn, hang out with peers who exert a negative influence, or engage in petty crime. Turn to mentoring program staff for support to help you address these challenges. For more information about specific populations of youth, see Module 2: "Understanding Your Mentee's Background."

7. Communicate openly with your mentee’s parent/caregiver and mentoring program staff.

Talking with your mentee’s parent/caregiver about the challenge that has emerged may help you to better understand the situation. A lack of communication can leave you and the parent feeling frustrated; and it is not helpful for your mentee to observe tension between you and her parent/caregiver.

8. Listen actively.

Active listening takes practice, but it can be a very effective way to respond and communicate in almost any situation. Visit Module 5: "Communicating with Your Mentee" for guidance about how to be an active listener.

Your focus during this stage is on remaining committed while navigating challenges, remembering that your mentee’s life experiences may have shaped her behavior. Please see Module 2: "Understanding Your Mentee's Background" and Module 6: "Overcoming Common Challenges" for additional information on how specific risk factors can impact youth and how to manage challenging scenarios, respectively.

Section Four: Celebrating and Closing

The final stage of the mentoring relationship is closure. During this time, you and your mentee may become closer or may experience increased distance. You may find that you and your mentee feel proud of the relationship and want to spend time together frequently, or, conversely, you both may be ready to move on. Just as a relationship takes time to grow, it also takes time to wind down. The keys to navigating the end of a mentoring relationship are communicating openly and creating an agreement about future contact.

Define the end and prepare for what’s next.

You and your mentee have invested time and energy in developing this relationship. You’ve had some ups and downs, but you’ve also seen tangible evidence of your mentee’s positive growth and development. Now the mentoring program is coming to a close, or you or your mentee is moving away, or your mentee no longer wants a mentor. Whatever the circumstance, your final act as a mentor is to communicate how much you value your mentee by participating in a formal closure meeting.

Celebrate the mentoring relationship and work out a plan for the future.

Set aside time to meet with your mentee so that you can both reflect on his growth and the success of the mentoring relationship. Make sure you and your mentee have time to reflect aloud (and perhaps in writing) about the ways in which he has changed and grown since you first met. You can also reminisce about the fun times you’ve shared. Be ready to listen to his fears about moving ahead, and be prepared to share your own. You may want to consider having a final special outing with him.

If your program allows and you and your mentee both desire, you may want to explore continuing the relationship beyond the formal completion date recognized by the mentoring program. You’ll need to work out how you’ll stay in touch, how often you’ll be in contact, and other such details.

Stick with the program!

You may find that once this mentoring relationship comes to a close, you’re still interested in being a mentor. Let your mentoring program coordinator know and get ready to embark again on the exciting journey of mentoring a young person to reach his or her full potential.

Summary: Summary

Congratulations! You have completed the "Developing a Relationship with Your Mentee" module developed by TCAM. Now that you’ve completed this module, you should have a better understanding of the stages of the mentoring relationship, the perspectives of mentees and mentors at each stage, strategies for addressing challenges that arise, and the role of mentoring program staff in supporting you and your mentee.


Remember that when mentoring a young person, you will have to work to build trust—and this takes time. Your ability to adjust your expectations and demonstrate patience with your mentee is critical. Your mentoring program’s staff can offer you essential support, helping you understand the meaning behind your mentee’s actions and giving you effective strategies for relating to her. You should turn to your program’s match support whenever you encounter a problem in the relationship that you’re not sure how to solve.

Check out these additional resources on mentoring relationships:

  • Mentoring for Meaningful Results by Kristie Probst provides asset-building tips, tools, and activities for youth, adults, and caregivers entering and involved in a mentoring relationship. The book was created with input from MENTOR/National Mentoring Partnership and Big Brothers Big Sisters of the Greater Twin Cities.
  • The Good Teen: Rescuing Adolescence from the Myths of the Storm and Stress Years by Richard M. Lerner, Ph.D., is based on an eight-year study of 4,000 teens from 25 states. The book explores the myth of the “troubled teen” and presents the characteristics of adolescent behavior that are proven to fuel positive development.
  • The Search Institute is an independent, nonprofit, nonsectarian organization committed to helping create healthy communities for every young person. It offers information on mentoring and many downloadable resources that you can distribute for free.
  • “Common Stages and Sources of Support for the Mentoring Relationship" is a downloadable handout from TCAM with strategies to help mentors navigate each stage of the mentoring relationship and understand where to go for support.