A mentor needs a checklist, perhaps a job description, of the tasks you need to perform, and a bit of a roadmap for the experiences you will have.  I do my mentoring work in a nearby prison for youth who have been convicted of sex crimes.  They are often lonely, needy young men, who also have amazing resilience and fortitude.

This list is a good starting point on the art of mentoring, and learning about who you are, what you value in life, and how your experiences shaped your life.

• Be a good role model.  Ultimately, it is not what you say, but how you act.

• First, do no harm.  This is the corollary to the Golden Rule.  You do this work to help others, and to nurture young souls.  “If you aren’t part of the solution, you are part of the problem.”
• Be on time.  Be accountable and professional.  Just showing up in your mentee’s life is enormous, and, often, a new experience for them.  If you are going to be late, or need to reschedule, contact them promptly, and apologize.  They have had a lifetime of people not showing up in their lives.
• Be clean and presentable.  Your visit is important to them, and by you taking care of yourself, and being prepared, you model healthy behavior and good social skills.  One of my young men scrupulously examines my choice of shirts and is sensitive to my breath.  You are a role model in this work, and you will be examined and tested.
• Coffee and food are good ice breakers, and provide a social atmosphere.  You are also teaching your mentee how to socialize, and chat over a cup or a snack.  Giving the coffee and the food is also an act that models care and compassion.  The prison I visit has a canteen, and the menu choices, ordering, paying, and being served our selection has offered countless lessons in real life living and accountability.
• Don’t pry.  If they have a story they want to share, or a bit of their history, they will let you know and they will tell you.  A lot of people have asked them questions about this stuff, as part of their job, and you may come across as yet another social worker gleaning information and pumping them for details about stuff they probably don’t like talking about.  If you create an atmosphere of trust, and genuine positive mutual regard, you will hear stories.  Your challenge then becomes to be able to listen without overtly dropping your jaw when they share some astonishing anecdote of what they have survived.
• Share some things about your life, your adolescence, your hobbies, a funny story you heard, some pleasant event that has occurred in your life.  Be a teller of nice stories, stories that don’t expect a response, or talking about their own lives.  But, in doing this, you are modeling social skills and developing trust.  Once there is trust, you will hear their stories, and their dreams.  You are growing men here, which is complicated business.
• Confidentiality.  Don’t gossip about your mentee, or their lives, and respect their privacy.  They probably don’t have much privacy in their lives, and this time with you will develop into a time where they can truly be themselves, let their hair down and confide in you.  Confidentiality and trust are intertwined.  You are developing a healthy relationship, and you are modeling that.  There is gossip in prison, too, so be professional at all times when you are visiting.
• Don’t preach your own version of religion and spirituality.  They’ve had a lot of that, and you aren’t there as a minister or proselyte.  You will get questions about your spirituality, and I’ve tried to answer those inquiries with a lot of “I” statements, and a sense of continuing inquiry and journey.  This area can be a rich source of good conversations.
• Be open about your obligations as a mandatory reporter of abuse.  Most mentors have a legal obligation to report child abuse and elder abuse.  Let your mentee know of your obligations.  I think it is a good idea to spend a few minutes early on about your legal duties, coupled with what you think mentoring is and what you are there for.  Your mentee is curious about that, as well, and they also have ideas of what they expect from you.  This is a continuing conversation.  We have all grown from that conversation.
• Be open to challenges and opportunities for real change.  One of my mentees disclosed to me an incident of being a victim of sexual abuse. I reported this to staff, and the next day, I sat with my young man as he told his story to a supportive team of staff members.  After four years of institutionalization, and countless treatment and counseling sessions, he was finally able to share this burden.  My role was to be non-judgmental, supportive, and to facilitate counseling for him.  He told me later he couldn’t have gone through that without me at his side.  And, that report speeded up his emotional growth and his successful completion of sex offender treatment.
•   I suggest you also have a moral obligation to report suicidal ideations, depression, and other significant emotions, thinking, and plans you hear from your mentee.  Make these reports openly, compassionately, and with a commitment to be emotionally supportive with your young mentee as professional staff deals with this information.
• Be seen as a resource, and an advocate for your mentee’s best interests.  Yes, sometimes, you need to be the messenger of a “not nice” incident or state of mind.  So be it.  There’s a bit of parenting in the job of mentor, and parents need to speak loving truth.  I strive to be open and up front with what I am doing and what I value.
• You will have a continuing dialogue with staff members and your mentee about your mentee’s life and their well being.  Make this a fruitful time, and be supportive of the work that needs to be done.
• Be mindful that some things that need to be done or said can only be done by a volunteer, someone who isn’t bound by a lot of rules and procedures.  For example, staff can’t bring gifts for one youth.  You can.
• Be sensitive to their health and their emotional state.  If they are tired, drained, or worried about something, let them know you care and that you are aware of their condition.  Be supportive, and helpful.  Normalize their worries, and show compassion.
• Model good problem solving skills.  Tell stories of how you have experienced difficult situations and crises.  Explain how you worked through it, and talk about the resources you have had for such events.  If I tell about a mistake I’ve made, that message becomes even more meaningful and productive.  You are modeling your humanity, not your divinity.
• Model respect.  Be courteous, kind, and compassionate, not only to your mentee, but to the staff members and other people around you when you visit.  Remember, it is not what you say, but how you act that is the most effective message you deliver.
• Be upbeat.  No matter what kind of day you’ve had, or what you are worried about, be positive, cheerful, and supportive.  You do this to give them healthy energy, and to model healthy, positive living.  You can use your own experience that day to be the basis for your message, and how you deal with it.
• Invite your mentee to offer their suggestions on how you should handle a problem.  Engage them in healthy decision making and empathic behavior.  You are partners in this endeavor we call mentoring.  Learn from each other.  When they are teaching you, they also learn the lesson.  You are creating an atmosphere of learning, and mutual positive regard.
• Plan some fun activities.  A birthday, a holiday, or some major event in the institution are opportunities to plan something positive, uplifting, and supportive.  Then, show up for those events.  Be on time, and behave appropriately.  Such behavior is often a new event in their lives.  Several of my young men had never, ever had a birthday party or presents.  Throwing a simple birthday party for them turned into the highlight of their year and gladdened my heart beyond measure.
• Mail them something regularly.  A birthday card, a Christmas card, a postcard from some place you’ve visited, a copy of an interesting article you read in the paper, or a funny cartoon from the comics section, or an article about one of their favorite musicians, all of these things brighten their day.  Sometimes, writing two sentences on a note card and sending it to them does immeasurably good work.
• Find an appropriate book for them.  Suggest some good reading.  You might consider reading the book together at some of your meetings, which helps you assess their reading and comprehension skills, and makes your meetings meaningful and productive.  I sometimes donate appropriate books to the institution, so that all the youth can benefit from some positive and useful materials (Scrabble dictionary, math tutoring educational materials, appropriate young adult novels, Native  American cultural materials, etc.)  We all have books on our shelves that are gathering dust, and a donation is not  only good for your tax returns, but also good for your heart.
• Be  involved in their education and counseling work.  Attend the periodic staffings on your mentee, and ask some questions.  You will often notice things, or hear concerns that your mentee doesn’t express to staff.  When appropriate, bring those up.  One of my young men couldn’t see well and needed to have an eye exam.  No one else noticed this, but I did, and he now wears glasses and can do much better in school. You also establish a dialogue with staff and you show them you can be a resource for them to use in helping your mentee.
• Look for ways to bring more of the community into the institution.  Last year, my wife and I arranged for a friend and his band partner to put on a concert in the institution.  Everyone had a grand time, and the youth got to ask questions, and enjoy a professional rock and roll performance.  Master gardeners and volunteers from the local Celebrate Recovery and AA organizations now come regularly, and others offer a variety of educational and cultural activities, as well as mentoring.
• Respect their family time.  Such time is often sporadic or even non-existent.  Be flexible, and expect some emotional fall out, both before and after such events.  You are part of the support system, and your mentee will naturally compare your relationship and your behavior on your visits, with their family experiences.  Soft pedal the differences, and don’t sit in judgement about their family.  Your mentee is well aware of the differences, and needs to not have to justify or explain what they see and what they feel.  And, some day, you will hear what they think.  This is a good space to practice your quiet cheerleading, unconditional personal regard skills.  The day one of my guys graduated from high school, I stepped back, and didn’t spend much time with him.  He knew I was there, and he needed to spend time with his family.  He knew I supported him, and that was enough.  I still got to see him graduate, and he had the space to navigate through family waters.
• Practice self care.  Take a break once in a while.  Have a “safe place” you can process the stories you hear and the emotions you experience.  You will hear some tough stories, and experiences that deeply touch your heart.  On the way home, there is a “crying spot” for me.  Sometimes, I stop there for a few minutes, and I often take some deep breaths, and cry, letting the sadness, the loneliness, and the “matter of fact” tone of one of my guy’s stories whirl around in my head, and find a place to go.  Yes, I carry around those stories, but I also need to process them and deal with the sadness, and the tragedy of young lives.  I have a big heart, and broad shoulders, but I also have my limits, and I need to respect my limits.
• Surround yourself with supportive friends and activities, so that you are emotionally healthy and balanced, and can bring that goodness with you on your visits.
• Tell your stories of your own growth and experiences to others, so that these young lives can be a part of your community.