You’ll find that experts in most fields recommend getting a mentor. Whether it’s in the business world (including here on Bplans), the arts, academia—you name it, and a thought leader in the space will refer to the benefits of seeking a mentor.

But then what? If you approach a distinguished person that you can learn from and ask for guidance, and they accept, what you should do next?

Listen to Peter and Jonathan talk with Caroline Cummings about finding a mentor on the third episode of The Bcast, Bplan’s official podcast (at 12:44):
Click here to subscribe to The Bcast on iTunes »

In this article I’ll cover how to be excellent mentee material and get the most out of your experience with a mentor.

The 5 stages of mentorship

Caroline Cummings, Palo Alto Software’s Vice President of Business Development, has been both a mentee and a mentor. Today, she actively mentors several entrepreneurs, though she has been asked to mentor many more.

The truth is, not everyone makes a “good mentee.” To find out whether or not you’re ready to work with a mentor, read on. I sat down with Caroline to discuss the desirable timeline of stages for a mentorship.

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This stage comes before you ever ask a person to be your mentor. Don’t just ask someone you admire only to realize they can’t actually teach you what you need to know.

Look inward; where are you weak, or inexperienced? Do you need connections, or an insider’s perspective on an aspect of your business? Tip number one for being a good mentee is clearly identifying your needs, both to yourself and to any potential mentors.

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Once you’ve set some goals for yourself with what you’d like to get from a mentor, set about the business of researching who it is that you know (or don’t know) that fits that bill.

Here are some tips to remember about choosing who to approach:

  • Keep it realistic (Taylor Swift probably doesn’t have the time or interest). People who have been known to mentor entrepreneurs in the past (or present) are ideal as you already know it’s on their radar. Research people who are local and have done work that you admire and that is relevant to both of you (not necessarily in the same field). Consider that they’re wishing to have a beneficial experience, too.
  • Make sure that the potential mentor has either experience in your chosen field, or experience in a leadership or management position. You’ll need both, but they don’t have to come from the same person.
  • It’s advisable to have multiple mentors. “A good place to start would be to find two mentors and have them be very different,” says Caroline. Her suggestion is to start at least with one person with strong leadership skills and one person who has a successful focus in an area where you know you are weak.

You can even use sites that are basically a mentor-to-mentee Caroline uses the site MicroMentor and has found success.

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This of course is the part that’s likely to be a little nerve-wracking.

You’re a new entrepreneur, or an established one seeking guidance, and you’re going out on a limb to someone you respect. Good for you! Now how does a good mentee make the ask?

Some suggested ground rules:

1. Be clear on how much time the mentor has, and how much time you’re willing to commit. This is key, because the time you spend together is the basis for the benefits you’ll get. Caroline says that frequently when it comes to mentoring, “The biggest challenge is time. Mentees may have expectations that are too high.”

Your mentor is likely a very busy person; politely suggest a time structure that would work for you, for example, meeting every other week for an hour, and see if they are amenable.

2. When actually making the ask, be well-mannered and direct. Say why you’re interested in learning from them specifically, and of course, clarity of intention is key. Tell them what your goal is for this experience, making it obvious that you are a serious mentee candidate who respects their time.

3. Mentorship and money don’t go together. If you reach out and the answer is, “Yes, but for a price…” think carefully.

At this point, this “professional mentor” is more like a hired consultant or business coach; not necessarily what you’re looking for.

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Entering into a wishy-washy, ill-defined mentorship can be a fruitless experience.

Caroline stressed the importance of an “engagement contract”—not an actual written document, but the basic understanding between mentor and mentee that there are stated goals, a general schedule, and both parties are willing and able to show up for each other and do the work.

One of the first things Caroline does when vetting mentees is assign them the “homework” of filling out the LivePlan pitch page, so she can get a high level sense of where they’re at with their business. “I’ve fired mentees for not doing ‘homework,’” she states simply, “probably about a third of the people. You have to do the work.”

You’ll also want to determine how long the mentorship will go on for. Three months? Six months? The eventual outcome of mentorship is that it will end because the mentee has been an avid learner and has graduated to new and great prospects, so there should be a kind of phasing out period, where meetings with your mentor become gradually less frequent toward the end of your time together.

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Gratitude is so important to having a lasting, positive connection with the person who generously took the time to mentor you.

Caroline notes that doing something thoughtful like sending a handwritten card or posting a rave review of them on LinkedIn can go a long way toward sticking in someone’s memory. These are people who genuinely want to give, and showing your appreciation for that will help cement your beneficial relationship into the future.

Coaches don’t get on the field

Caroline told me that one piece of advice that has always stuck with her from her days of mentoring with big brothers big sisters is the notion that “coaches don’t get on field.”

For those of you who aren’t sports buffs (myself included), the idea is that when the coach walks onto the field, the game stops. The players look for direction, instead of acting. In the context of mentoring, this means that the ultimate goal is for the mentorship to become unnecessary.

You shouldn’t be dependent upon a mentor, and they shouldn’t be telling you what to do or doing it for you. They should be guiding and inspiring you so that you become more capable, competent, and independent in your business on your own, through the things you’ve learned from them.

Do you think you are mentee material? Why or why not? 

AvatarAngelique O'Rourke

Artistic + intellectual pursuits. Social justice. Actress. Model. Musician. Eugene // Portland.