Last night I found myself toting five mentees all over the city Pittsburgh (they are all originally from Homewood or East Hills, but now they live in Homewood, Homestead, Point Breeze, and the North Side). We spent most of our time in Oakland eating at the "O" and then in the South Side where we finally ended up watching a movie. When I first picked them all up, all they were talking about was girls. That's been pretty much all they talk about lately (not out of the ordinary for 16 year old kids), but with yesterday being the first day of school I thought I'd try to get them to open up about some other topics. No luck. So about ten minutes into the car ride to our first destination I made a deal with them... that there was no possible way any of them could make it through the entire mentoring time together with out talking about girls. I won't specify what I wagered with them, but let's just say it was enough incentive to gain their interest. We actually ended up shaking on it, and my master plan went into full effect. For about three minutes, nobody said anything in the car. When we arrived at our destination, we all got out of the car and within two minutes one of the boys messed up (lots of college girls walking around Oakland these days). He begged me for a second chance, so we agreed that all of the boys would get a second chance at double or nothing if they messed up... but only one more chance. We all actually ended up having a great evening of mentoring time together, just as I hoped would happen if I could somehow figure out how to get their attention. One by one, each one of the boys used up their first chance. By the end up the evening, all except for one mentee made it and I had to pay up (the last five minutes of his drive home were brutal with all of us trying to get him to mess up). We all enjoyed a great time of mentoring together.
As I reflect on our time together, several themes emerge. First, mentoring stretches me, and I learn new things, every single time that I do it. Second, mentoring is a ton of fun! My mentees always crack me up with their antics, and it keeps me on my toes. Third, mentoring requires a lot of creativity. Each new stage of development for mentees requires a new game plan from the mentor. Finally, a lot of good conversation can happen when we create the right kind of environment. As adults in the mentoring relationship, it's our job to ask the right questions and be thinking about the broader outcomes of the match so that our mentees receive the kind of support that they need in their development. That's what mentoring is all about at the end of the day.
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