How to Find (and Keep) a Mentor in 10 Not-So-Easy Steps

Most people misunderstand mentoring. I certainly did. I never knew what it meant, until someone actually invested in me and he taught me how mentoring really worked.

Most people misunderstand mentoring — I certainly did. For the longest time, I said I wanted a mentor but didn't understand what that even meant. That is, until someone pulled me aside, invested in me, and taught me what a mentor really was.

I see a lot of young people approaching mentoring the wrong way.

They ask a leader they admire to mentor them, forcing the person into an awkward position in which she feels bad for saying "no" or obligated to say "yes." But this is not how mentoring works.

Common misconceptions of mentoring

I have a passion to see that change. There is a lot of misunderstanding about how mentoring works, including how to begin a relationship with a mentor. Here are some of them:

• Mentoring is about me.

• I need to wait for a mentor to find me.

• Being mentored is more passive than active.

• I need to ask someone to mentor me up-front.

Face it: Everything you know about mentoring may be wrong. It's time to start seeking out a mentor the right way. In finding a mentor, there are 10 important steps I've found that usually work:

1. Find someone you want to be like

Don't just find someone who has a job you want or a platform that you covet.

Find someone that is like you, someone with a similar set of strengths and skills you want to emulate. Otherwise, you'll just end up frustrated.

Spend some time finding the right person. In fact, have several candidates before committing to a single mentor.

2. Study the person

Follow his blog. Get to know people who know him.

If you don't know the person well, see if he is really like his public persona projects.

Make sure you understand his strengths and weaknesses. Set your expectations realistically.

3. Make the "ask"

Don't ask for the person to "be your mentor" right off the bat. That's a big ask. Far too big for the first meeting.

Rather, ask for an initial meeting — something informal, over coffee maybe. Keep it less than an hour.

Come with questions that you're prepared to ask, but let the conversation flow relationally. (Note: the formality really depends on the potential mentor's communication style — something you should be aware of before the initial meeting.)

When in doubt about when to make the ask, just go for it. (That's what I do, and it usually works.)

4. Evaluate the fruit

After meeting, do you want to spend more time with this person?

Did she begin the meeting by encouraging you or telling you what to do? Did she ask questions, or wait to provide answers?

Did you leave the meeting feeling better about yourself? Was a connection made? If not, feel free to let the relationship go and seek out someone else, instead. You don't have time to waste on a self-centered tyrant.

If it went well, then immediately put together a follow-up plan.

5. Follow up after the meeting

This is not like dating. It's okay to appear overly ambitious. You want this person to know that you're serious.

It's appropriate to follow up immediately, thanking your prospective mentor for her time.

A good way to do this is via email or other form of passive communication, so that you don't appear overbearing or waste the person's time.

This is also a good time to mention that you'd like to do it again. If she reciprocates, offer to get something on the calendar. (You may need to suggest a time.)

Make sure that it feels relaxed and not contrived. You're still vetting each other at this point.

6. Let the relationship evolve organically

We sometimes place too high of expectations on mentoring. We want to give it a name, because it gives us a sense of status and importance. But really it's just a relationship.

Mentoring is organic. It's healthy to let it grow like any other relationship — over time and based on mutual respect and trust.

Don't force it. That will kill a potential mentoring relationship faster than anything. Give it time; it needs to grow.

7. Don't check out when you feel challenged

I was recently speaking with a friend who's mentored a number of young men over the years. He said the saddest part about what he does is that a lot of guys check out whenever he challenges them.

It will happen. You'll get to a point where your mentor will feel comfortable enough to call you out. And what you do next is crucial to your growth.

Remember: this is what you signed up for. Don't wimp out when it gets tough; this is where the really good stuff happens.

8. Press into relationship

Don't wait for the mentor to initiate. Learn how to manage up. Persevere. Ask for more of your mentor without demanding it.

This doesn't bother him (at least, it shouldn't). It honors him. It shouldn't be a big deal to ask this person to coffee or lunch, outside of your normal meeting time.

If a mentor can't be a friend, then he's probably not a mentor. Finding ways to solidify the bond you've created will only strengthen the relationship.

9. Ask your mentor for feedback

Feedback can be hard, but it's good. As your relationship with your mentor progresses, this will be the #1 way you grow. It will be a highlight for the both of you.

While asking for feedback may initially feel weird, eventually it will become almost second-nature. You will find yourself thirsting for those words you used to fear.

Similarly, a good mentor will treat these times with great care and sensitivity.

10. Commit to the process

You can't be mentored in a summer. That's an internship. Mentoring takes real time and real work.

In order for it to be a real mentorship, you have to commit to the relationship. Come hell or high water, you're going to make it work.

Then, you will begin to understand what it means to be a student, a disciple, a protege.

Do you have a mentor? How did you find him or her? Share your mentoring experience in the comments.