Start with the answer you did not write for him.
A parent wants better grades. A mentor wants more discipline. A young man wants a job so he can help at home. All three may be reasonable concerns, but they are not the same goal. If the first meeting ends with a plan only the adults wanted, the program has an agreement on paper and a different situation in the room.
Ask the young man what he would like help with. Then listen long enough to understand the answer. That does not mean accepting every decision without challenge. It means knowing what he thinks the problem is before explaining what you think he should do.
Find the shared problem.
The school concern and the work concern may meet in an ordinary scheduling problem. A young man working late needs a realistic place for schoolwork. A family worried about missed classes may need clearer information about the actual conflict. Sometimes people disagree about the goal. Sometimes they have never put the same facts on the table.
A useful mentor can ask: what is fixed, what can change, and what information are we missing? The answer should lead to a next action. Map the week. Ask an adviser a question. Review a job schedule. Make the issue concrete enough to investigate.
An agreement should be recognizable.
A direction such as 'be more responsible' leaves too much room for interpretation. A commitment such as 'bring the work schedule and assignment deadlines to Thursday's conversation' can be understood by everyone involved. It also gives the next meeting something to review.
The young man should be able to explain the agreement in his own words. If he cannot, slow down. A plan is not clearer because an adult used more confident language. Check the task, the timeframe, the support, and the reason it matters.
Keep responsibility in the right place.
The mentor is responsible for the support he promised. The participant is responsible for the action he agreed to take. A parent or partner may have a separate role. Put those responsibilities in plain language rather than letting one person quietly carry the whole plan.
At the review, ask what happened. If the task was completed, look at the evidence. If it was not, understand the interruption before adding another promise. A young man learns more from participating in that process than from having every decision made around him.
Use A Better First Conversation and the 90-Day Legacy Plan to begin. They are tools for an honest discussion, not a script that can replace one.