mentorsI just finished reading Sheryl Sandberg’s Lean In, and the “Are You My Mentor?” chapter really stood out for me. It highlighted an issue I’ve grappled with for years: how awkward and ineffective a formal mentorship can be.

There’s already plenty of advice for young people on how to be good mentees. But as someone who has been both a mentor and a mentee, I want to provide some solid tips to mentors instead, so they can guide their mentees in a more meaningful way:

  1. Don’t say you’re open to mentoring young entrepreneurs unless you have time. While I believe that most mentoring should happen organically, if you do volunteer to be an advisor or a mentor for a formal program, make the time. Leaving young entrepreneurs hanging is the equivalent of having an amazing date and never calling again: not a good look. If you’re excited about a young entrepreneur, email them back (even if it’s just to say you’re busy and will follow-up in a month).
  2. Don’t call yourself a mentor on the first date. I recently had a man I’d never met before introduce me to a woman (who I had also never met) by saying: “We really loved your pitch. I wanted to introduce you to my colleague. I think she would make a really great mentor for you.” The woman then concurred and said, “I’d really love to be your mentor.” It felt like someone was proposing marriage on the first date. It was tough to respond because I didn’t know anything about the woman, I didn’t know why she thought she’d be a good mentor, and I had no idea how she defined mentoring. If you want to be someone’s mentor, be cool. Don’t come out of the gates asking for a mentorship relationship. Let the relationship evolve.
  3. Do set boundaries. I participated as a mentor in a formal mentoring program for high school girls. My mentee and I became really close, and I was able to guide her through a lot of tough decisions about school, applying to college, working and so on. However, towards the end of the year, she started asking about things like drinking and boyfriends. While I was comfortable with certain things, there were other things that were not appropriate to discuss. As a mentor, you need to set the limits on what you will and won’t advise about. Your relationship with your mentee will hopefully be a very close one, but make sure that you’re comfortable with all of the topics you’re discussing.
  4. Don’t eliminate all personal issues. I know a lot of mentors want to focus only on “work and career” issues, but (especially for women) career often intersects with our personal lives, so it can be helpful for your mentee to talk about certain personal issues. One of my “mentors” (really, I just see her as a friend who gives great advice) recently listened as I vented about a stressful situation. As a result, she noticed a pattern in my behavior that crossed from my career into my personal life: I was too trusting. Now it’s something I’m working on. As a mentor, don’t shy away from talking about certain personal issues; they can actually illuminate patterns that hold your mentee back in her career.
  5. Do introduce, invite, and observe. A lot of mentoring sessions happen one-on-one, either over coffee, lunch, or on the phone/Skype. While those are great for hashing out problems, observing your mentee is also valuable. I make it a point to invite my mentees to events I’m attending or make introductions for them. Observing your mentees in action allows you to give even better feedback. Are they nervous about walking up to people they don’t know? Are they too overbearing when talking in groups? My ability to help my mentees is much greater when I can observe them in a variety of settings.
  6. Don’t be afraid to mentor someone older than you. We traditionally think of mentors as people who are older than us, but that couldn’t be farther from the truth. Not only have I been mentored by someone younger than me, but I’ve also mentored someone older than me. Age does NOT matter when it comes to mentoring — don’t shy away from a mentorship opportunity because the age dynamic might be weird. Besides, there are plenty of kick-ass startup founders out there who are starting big companies right out of school. They can certainly teach a bunch of oldsters some new, successful tricks!
  7. Do have a mentor yourself. Even if you’ve IPOed your company, there are still things that you probably want to accomplish, whether they are personal or career-oriented. Always be learning — you’ll need to learn from different people at different points in your life. And who knows, you might just learn a thing or two from your mentee, too!

Jessica Brondo is the Founder & CEO of, and the Founder & Chairperson of The Edge in College Prep, two ed tech companies focused on test prep and college admissions based in New York.