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Five Keep-it-Real Lessons From the Frontlines of Mentoring

Mentorship truly is a wonderful real life example of the motto, "You don't have to change the whole world, start with one person."


I'm GOOD's first Fellow, and I'm on a yearlong mission to discover the best practices in entrepreneurship education, and figure out how they are (or aren't) empowering middle and high school-aged girls. Follow and engage with me on my journey of learning and doing.

January is National Mentorship month, and the statistics on mentoring speak for themselves. Youth who are mentored are 46 percent less likely to use illegal drugs, 27 percent less likely to use alcohol, and a full 52 percent less likely to skip school. I recently spent six months mentoring six sophomores in East Oakland with BUILD, a nonprofit that provides hands-on entrepreneurship training and college preparation to high school students. As you might guess, along the way I learned some real life lessons on how to be a good mentor.

"Just be real" was the main advice from Jessica, a senior BUILD student on how to be an excellent mentor. Jessica shared that advice during the initial mentor training, which had students describe why mentors are such a key part the BUILD experience. When asked what her mentor did right, Jessica emphasized how her mentor was really there for her—not just to support her business idea and team, but to individually coach her through personal challenges.


Mentors were described as this unique mix of teacher, coach, and friend. The BUILD staff conveyed to my cohort of new mentors that we needed to be at the axis of authority and love. Use your authority to push students in the right direction but show them that you care by truly being there for them.

I'm a former teacher, so I figured that my experience with a roomful of 40 third graders, would translate into me understanding this axis pretty well. I thought I had this mentor role nailed. Well, I was wrong. Piloting the roving mentor program for BUILD, I was asked to provide support to three to four teams of sophomores who were in the process of getting ready to pitch their business ideas. To get it right is much harder than it looks—here are a few of the lessons I picked up over the past six months.

1. Ask, don't tell: As a teacher, your authority role is established. As a mentor you are walking on a fine line--you ask instead of telling. I pushed my students in the right direction by asking lots of questions: "How else can you tweak your idea? What other materials do you think might be more cost effective?" Asking the right questions shows that you are actually listening, and is often much more powerful than the best advice that you can dole out.

2. Collaborate vs. Dictate: As a teacher you assign the work, as a parent you set the rules, but as a mentor you dive into the work alongside the students. In September, I was an active part of my student's production line. I felt amazing to be a proactive collaborator—a part of the team—and able to connect with students on a personal one-on-one level.

3. Consistency is key: Being a mentor is an incredible position to be in. You get an insight into the life of your mentee that no one else has privy too. You become a respected confidante just by being there and listening. For students whose lives may be a revolving door of adults it's important to maintain that consistency and commitment. It takes time and perseverance to be become both a trusted confidante and professional coach.

4. Be Real: I stuck with Jessica’s advice of "be real." That means saying upfront—hey I'm not exactly like you / I don't come from the same community or have the same challenges. Or even more simply—I'm not a teenager and have forgotten what it's like! Acknowledge your differences, but most importantly let your mentees be themselves. One of the best compliments I received from a student was "You just let us be us…ya know?" Don't kill their uniqueness, their individuality, but bring it out in the most encouraging and positive way possible.

5. Be Selfish: The "my" is important—my students, my mentees. That's the beauty of mentorship: you can be selfish. You can hone in on your group of students and truly be there for them, professionally and personally. In just a few months I became so attached to my team of six rockstars teen-preneurs! From helping them figure out the best logo for their business card, to coaching them on how to pitch to their VC, to taking them out for a victory dinner after a successful sale—Tuesday's in East Oakland easily became my favorite day of the week.

The experience also made me reflect on the first sixth months of the GOOD Fellowship. I've been incredibly lucky to connect with women entrepreneurs from around the world. Each of them broke down their own struggles and learnings. And a recurring theme was the value of having the right kind of mentor and support network. Entrepreneurship is always seen as a solitary role but it doesn’t have to be. Having the right co-founder, mentor, and support network can do wonders.

Here are my questions for you, GOOD Community: Who have been your best mentors? Are you a mentor, and what do you do to connect with your mentee? What do you think girls need in a mentor?

Mentorship truly is a wonderful real life example of the motto, "You don't have to change the whole world, start with one person." Even if you only have a half hour of time each week or an hour once a month– find a girl. A student. A youth that you can be "real" with, and provide that spark of inspiration.

Want to mentor a student from a low income community? Click here to say you'll do it, and if you're in the Bay Area, Boston, or Washington, D.C., mentor with BUILD.




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