Mon–Fri 9:00 AM – 5:00 PM 4522 S Ashland Ave, Chicago, IL 60609
Southside Mentors Collective Chicago, IL · Since 2011

Mentoring

How to be a good mentor in the first three months

By Devon Marsh, Program Director · March 2026 · Six minute read

Every new mentor asks some version of the same question on their first Saturday: what am I supposed to say? Here is the answer we give, and the reasoning behind it.

New mentors at a Saturday training session New mentor training, Saturday morning

The first thing to know is that you are not going to fix anything in three months, and trying to will cost you the relationship you are actually there to build. A fourteen-year-old can smell a project from across the room.

Month one: be boring and reliable

Turn up on the same night. Sit in the same place. Ask the same unremarkable questions about the week. What you are demonstrating in the first month is not wisdom, it is predictability — and for a lot of our students that is the rarer commodity.

Do not open with the hard stuff. Do not ask about home. Ask about the game, the class they hate, the sneakers, the group chat. Let them decide what to hand you and when.

Month two: notice things out loud

By the second month you know enough to say specific things. “You said that test was Thursday — how did it go?” is worth more than any speech about potential. Specificity is how a young person learns that you were listening the whole time.

The whole job in the first season is proving that you are the kind of adult who remembers.

What to do when something serious comes up

It will, eventually, and the answer is always the same: you do not handle it alone. Tell the program director the same night. You are one part of a system that includes a family, a school and our staff, and nobody expects you to be a social worker.

Month three: let it be ordinary

Somewhere around month three the visits stop feeling like an appointment and start feeling like a habit. That is the goal. The advice, the college conversation, the hard talk about a suspension — all of that lands later, and only because you were still there when it came up.

If you are three months in and it still feels awkward, that is normal, and it is worth saying so at your check-in. Half the mentors in this building felt exactly the same way in November and are unrecognisable by spring.

Devon Marsh, Program Director

Devon Marsh

Program Director

Came through the homework lab as a sophomore in the early years, went to UIC, and came back to run mentor training and every match in the building.

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Three months from now

You could be the one who remembers.

Matches open in September and January. Screening starts two months before, which means the useful thing to do today is send the form.