How To Have A Transformative Mentoring Conversation With An Urban Teenager

Can a conversation really make a difference?  Michael Freeman writes about the power that one conversation can have on the trajectory of a young person’s life. What if you and a conversation could be the bridge for a young person to strive towards success?


We, at Elevate Your G.A.M.E., believe in the power of transformative mentoring conversations.  We believe that one powerful mentoring conversation can change a young person’s life and their future. And we are seeing it happen.

Let me tell you about how one mentoring conversation changed a young man at Compton High School. I had a mentoring conversation with Dennis when he was a ninth-grader. His mentor was not there that day and so I filled in. He was playing on the freshmen basketball team, and he shared with me that he was failing his English course. So I asked him why, and he explained: “Look, if I make the winning shot in a game, everybody is going to be all over me, but if I get A’s in my classes, nobody is going to say anything.”  As a result, he was pouring his energy into basketball and not into his school work.  

During the course of that conversation, I found out that he was failing all of his vocabulary tests because he would never study the words.  So I challenged him to study for the upcoming test. I told Dennis that I would call him on Thursday night to give him a phone test. He aced the phone test and then he aced the real test that Friday. This changed his academic life. This young man is now a college graduate. He graduated from California State University Los Angeles with a degree in Business Management, and he now owns a business.


A lot of people would like to have these kinds of transformative mentoring conversations, but many of them get stuck in one of three places:

1. They don’t know what to talk about.

2. They know what to talk about, but they don’t know how to start the conversation.

3. They don’t know how to keep the conversation for it to make an impact.


Thankfully, Elevate Your G.A.M.E. has a mentoring conversation tool that solves all three of the above problems.  We have two apps that contain this mentoring conversation tool. The version with Bible verses is called “Go Mentor Church.”  The version without the Bible verses—for secular environments like public schools—is called “Go Mentor Youth.” To get the apps, simply search for them on your app store or click on the following link. To access the website versions, click on the following links.


Every mentoring session starts with a video that operates as a conversation starter. After the video plays, the app automatically brings the conversation questions onto the screen. If using the tool remotely, ask your mentee to download the app and then direct them to the mentoring session you have selected. Ask them to watch the video. Then after the video, use the questions to initiate the conversation. After the conversation, click on the “Go to Survey” button. Click on UYWI in the list of Youth Programs—at the beginning of the list—then fill out the quick survey.


1. Don’t ask “Yes/No” questions.  Ask “Why/How” questions: “Yes/No” questions will not take you very far into a conversation. You want your mentee to talk with you in sentences and in paragraphs, not with one-word answers. “Why/How” questions will lead your youth into talking longer and deeper on a certain subject, and will encourage them to share their deeper thoughts and opinions.

2. Ask follow-up questions to get them to explain further and to get them into a deeper conversation with you: This requires careful and active listening.

3. Ask questions in a relaxed conversational way: If you are using scripted questions, you can rephrase them in a way that fits how you normally talk.

4. Give them positive affirmations during the conversation: Say things like, “You’re on the right track with that.”

5. Share your answers to the questions too: This gives you an opportunity to share nuggets of wisdom without “preaching” because it is within the context of the conversation. Also, it makes it a conversation and not an interview.

6. Be vulnerable, transparent, and share some of your struggles: This will help them open up more about their struggles. However, make sure that you share appropriately. Some of your personal life may not be appropriate for you to share.

7. Be careful not to talk too much. Otherwise, it will become a lecture and not a conversation:  If you are doing 80% of the talking, then something is wrong. Seek to get them talking at least 50% – 70% of the conversation time—his is what the questions are for.

8. Remember key things they tell you in the conversation: When you talk to them again, mention some of what you remember. For instance, you might say, “You told me that your grandmother was sick, how is she doing now? I have been praying for her.” This will build your relationship with them.


If you need a tool to start these mentoring conversations, check out the Go Mentor Youth app from Elevate Your G.A.M.E and teach your youth how to use it to have transformative mentoring conversations with their peers and siblings.


Michael Freeman grew up in Compton, California. After graduating from Compton High School, he attended Georgia Tech in Atlanta, Georgia. Upon returning back to the Los Angeles area in 1978, Michael joined World Impact (an urban missions organization). He worked in urban ministry with World Impact for twenty-three years. Between 1988 and 1997, he served as director of World Impact’s ministry in Chester, an urban community in the Philadelphia area. He and his wife, Glynette, (with a team of missionaries) planted Refuge in Christ Church in McCaffery Village, a housing project in Chester. They, also, established Frederick Douglas Christian School—a Christian elementary school for urban children.  

After returning back to Los Angeles, in 1997, Michael worked with the Watts ministry of World Impact, developing partnerships with churches to train and coach them in ministering to urban residents through The Nehemiah Team Project. In 2002, he resigned from World Impact and became the co-founder and executive director of Elevate Your G.A.M.E., which conducts mentoring programs at urban high schools.  Michael is, also, the author of a book entitled, “Seven Days in the Hood.” He and his wife have raised two children, Isaiah and Eboni.

1 Comment

  1. Jenny Dickson on July 20, 2020 at 5:44 pm

    I love Elevate your GAME. They have made an impact in Long Beach and I use their resources to have conversations with teens. Thank you, Michael Freeman and team!

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