First Person: Bringing Mentors and Mentees Together

By the time the leaves were starting to pile up on the ground in early November, I had already exchanged four emails with my mentee. We’d talked about our favorite music, applying for internships, and our experiences with high school sports. All in all, I was beginning to get a good mental picture of Ivan and his personality, interests, and dreams.

But we still hadn’t met face-to-face!

And so, on an unnaturally warm late-autumn evening, I took the 4 train up to the Bronx to visit my mentee’s school. Trudging past the beat-up lockers and into the cafeteria that smelled of chicken nuggets and teen sweat, I was transported to my own high school experience a decade earlier. But my nostalgic reverie was broken by the amazing scene unfolding: Like a middle school dance, the mentors and mentees were sitting on opposite sides of the cafeteria, anxiously looking for their match. And then, smack-dab in the center of this awkward scene, mentors and mentees would come together, introduced by the iMentor coordinator, joyously connecting like old pals.

As I waited my turn, I scanned the crowd of students, mostly young men, bookbags and jackets piled high on the lunch tables. “Where is he?,” I wondered, old high school anxieties coming back to me. After all, it wouldn’t be cool at all to sit by myself in the cafeteria, would it…

At long last, there he was! And before I knew it, Ivan and I were sitting down, mentor and mentee together for the first time. We were given a series of exercises to go through, talking about academics, college, and career goals. But mostly, we just immersed ourselves in the things we’d already been discussing online: Did you see the game last night? Are you nervous about your upcoming interview? What does your family want you to do when you grow up?

At the end of two-hour conversations, all of the pairs came together for a group picture:

And then, we each headed out into the night, exhausted but thrilled to be connected in-person!

Takeaways

• Bring your pairs together early. As mentioned above, Ivan and I had emailed for a while before meeting for the first time. These emails were helpful but I noticed a significantly higher level of detail and communication in the emails that followed our initial meeting. You’re just more inclined to invest in a relationship once you’ve met someone in the flesh.
• Make the meeting mandatory. Even though the schedules and lives of professionals and teenagers are hard to reconcile, make it clear that attendance is required. This way, you won’t have participants skip out, presuming that writing an email is sufficient.
• Host the meeting in a strategic space. Although the mentees traveled to Manhattan for subsequent events, the first meeting was intentionally held in their school. Not only did this ensure high mentee attendance, but it made them feel comfortable (even if they were nervous about meeting a new adult), gave them some expertise (which can be a rare feeling when it seems like your mentor is the one with all the answers), and helped the mentors get a sense of what the mentees’ daily experience was like.
• Provide a mix of structured and unstructured activities. It was great to have some academic/career-focused activities to work on when our conversation naturally ebbed. But it was also nice to have the opportunity to just connect with Ivan, person-to-person. As a result, I left that night with a better sense of my mentee as a human being, as well as of his goals in life.

First Person: Connecting Mentors and Mentees

No sooner had I been matched with my mentee than we were able to start emailing. In fact, at the same time that I logged-in to my email account to read about the details of our match, I was presented with the following writing prompt:

As a result, I was able to email my mentee right away, using the prompt to share details about my life and interests. And within 24 hours, I had received a response back with his own answers to those same questions. While the message wouldn’t have earned an A+ in a grammar class, it was packed with interesting information about my mentee’s background, his hobbies, and his dreams. It also allowed me to ask lots of follow-up questions (What colleges are you interested in? What position do you play on your football team?). And so, within a day of our initial match, we were off to the races!

Takeaways

• Transition quickly from match to connection. The opportunity to email my mentee as soon as we were matched leveraged my initial excitement into a great first message, which led to a terrific response from my mentee.
• Provide structure for communication. As excited as I was to connect with my mentee after we were matched, I still wasn’t sure how to break the ice. However, having an explicit assignment (answering 10 questions about myself) provided a comfortable way to initiate the communication and get things rolling.
• Get mentors and mentees on the same timetable. Though I was pumped to get started, if I had not heard back from my mentee within the first week, I might have lost a great deal of my enthusiasm. Thus, synchronizing our schedules and expectations led to that incredible moment when your first communication is responded to right away. It was even better than my initial “You’ve Got Mail!” on AOL!
• Encourage genuine dialogue. When writing prompts are used to stimulate conversations, you occasionally get that phenomenon where both parties respond to the prompt – but not to each other. The prompt I was given, on the other hand, explicitly told me to dig deep into what my mentee wrote, asking questions and noting similarities/differences. These initial questions opened up shared interests (Bills vs. Cowboys trash talking, for one!) that we still talk about to this day.

First Person: Matching Mentors

After my mentor training, I was so pumped to get matched with my mentee. In fact, I hounded iMentor’s program coordinators endlessly, asking in that backseat/long road trip way, “Am I matched yet? Am I matched yet?” And yet, the days and weeks passed and still no sign. I began to curse the mentoring gods: “Why me? Am I that unmatchable?”

And then, like a lightning bolt out of the blue, a new message in my inbox: You have been matched with a mentee! Faster than a kid coming down the stairs on Christmas morning, I tore into that email, eyes devouring random details left and right: Ivan. Economics. Movies. Even hours later, the factoids about my mentee and his interests floated in the swamp of my mind, disconnected and my thirst for information unquenched.

However, once I finally met Ivan a few weeks later, the picture quickly came into focus. Here was someone who, though from a very different background than myself, was like an old friend. We moved from one topic in common to another, two hours flying by in the blink of an eye. And despite my initial jitters and apprehension (“What will we talk about? Is he going to hate me???”), we ended up hitting it off!

Takeaways

• Don’t let too much time elapse between mentor training and matching. Your mentors will be excited to get started after training and you want to capture that momentum! Plus, you don’t want anyone to have too much time to get cold feet and pull out, after you’ve worked so hard to recruit them.
• Make it clear to your mentors how you plan to match them. In addition to giving them a sense of the timeline, let them know which criteria you’ll use to pair them with a mentee. This way, they’ll know what to expect when they finally are matched.
• Match across multiple variables. I’m confident that Ivan and I have stayed connected because we’ve had multiple things in common. While one critical commonality can certainly fuel some relationships (e.g., a doctor mentoring a young person who desperately wants to go to med school), having a panoply of shared interests has kept our relationship vibrant, even when we temporarily exhaust one topic.
• Communicate the details of the match. Even though I still hungered for more info, getting an email with some background about my mentee at least broke the ice in our relationship. For instance, the very first time I met Ivan, I asked him about his favorite football team, knowing that this was something he valued from the email I received. And 45 minutes later (as well as ten months later), we were still talking about it!