Six Habits of Highly Effective Mentees

There’s no shortage of people hailing the benefits of mentors. There’s also ample advice on how to find mentors. Few talk about what to do once you’ve made contact with someone who wants to help you. You sit down to lunch with a potential mentor. What do you say? How do you act? How frequently do you follow up, especially if the person is busy and important?

I know many professionals who would like to be mentors but are not, mainly because once they start interacting with a potential mentee they find it’s not nearly as fulfilling as they imagined. I place the blame in many cases on the mentee and how s/he approaches those early interactions. Smart mentees realize that successful mentoring relationships don’t necessarily happen automatically; rather, they’re the result of genuine engagement and sustained effort.

Drawing upon my own experience and that of others, here are six habits of highly effective mentees.

1. It’s all about the questions you ask.

Here’s an example of a bad question: "What career should I go into?" Expect a worthless blue sky answer, or something that corresponds closely to what he does.

Here’s a better question: “I’m deciding between these two jobs, which each offer these benefits and these drawbacks. What do you think? Which factors should I consider most highly – salary, geography, etc?”

In other words, present options and then get help on how to think about the options.

Here’s a common question mentees ask that I think is problematic: “What would you do if you were me / you were in my shoes?” This is ambiguous. This either means, “What would you do in this situation?” which is asking what the mentor herself would do after considering her own situation, which is not what you really want. Or, it means, “If you were me, you had all the same strengths, weaknesses, opportunities, and threats as me, what would you do?” It’s unlikely the mentor (or anyone) knows you well enough to have a 360 degree perspective. So the question fails with either interpretation.

2. Have strong beliefs, weakly held.

This is maybe the hardest habit: How do you at once demonstrate greenness, a blank slate, and open-mindedness (ie, a genuine interest in hearing an advisor’s ideas and potentially incorporating them into your own life) while also showing potential through your existing ideas and convictions? In other words, mentors want to mentor someone they can influence, but they only want to influence people they think can be successful, and people bound for success tend to have beliefs about the world. Asking a million questions but putting forth no ideas of your own, or simply nodding hungrily at anything and everything the mentor says, puts you too far in the "green" direction. By the same token, acting like you’ve figured out the world is just as much a turn-off — who wants to help someone who thinks he doesn’t need help?

So how do you walk the line between these two extremes? Try articulating your existing stance to your mentor in an expository fashion: here is what I feel, here is why, here is my level of certainty.

3. Have a long term perspective.

Mentoring relationships are like any friendship or romance — it takes time. Lots of time. Years of time. If things are going well, don’t try to cover every topic on your mind in one meeting. Meander. Dive deep. Have a memorable conversation about just a couple things. Don’t bring a "pump-and-dump" attitude to the relationship.

4. Be open to topics not on your short-term agenda.

Say you’re trying to start a business and you meet with a start-up expert. You want to pick her brain about successful start-ups. One problem: everyone wants to ask this gal about start-ups. She’s bored of doling out the same advice. So spend some time probing her on off-the-beaten path topics. Religion? Politics? Wander on the path less trekked upon.

For example, if you’re young, everyone is going to want to give you advice about colleges and higher ed. Be open to hearing it.

In the long term, you’ll have plenty of time to cover the topic that made you interested in her in the first place.

5. Follow up by showing interest in them (at least four times a year).

To form a long term relationship you need to stay in touch. But what does "stay in touch mean"? A meeting a year? An email every month? Phone calls? It all depends on the situation.

Nothing beats an in-person interaction. So aim for those, but it can be hard to see busy people. At the least, email him four times a year.

Remember, in your communications, show interest in his life, and he’ll reciprocate and show interest in your life. Send a relevant article, or comment on a move his company recently made. Set a Google News Alert on his name.

If the mentor reads blogs, maintaining a blog is one of the best ways to stay in touch. Because it is "opt-in" — people choose to read blogs — you can get away with more frequent communications. If you email someone, he feels an obligation to read and respond. If you write a blog post, you’ve created no such obligation, and he still will probably read it in his RSS reader.

Try to be creative in your communications both in format (try postcards!) and timing (never send an update during the holiday season).

6. Don’t make the mentor do the work.

It’s not up to the mentor to figure out how to mentor you. It’s up to you to figure out what you need help on.

Need an introduction to someone? Need to figure out which of three options is best? Have a life/personal question that would be great over a cup of coffee? Take the initiative.

What should be added to this list?

For more on this check out my book My Start-Up Life. Thanks to Chris Yeh, Ramit Sethi, and Cal Newport for giving feedback on this post.

18 comments on “Six Habits of Highly Effective Mentees
  • 1) Understand your mentor. His or her background. Expertise. Experience. Interests. Strengths. Weaknesses. etc.

    2) Internalize mentor’s advice. Listen carefully to what the mentor says, take notes on it, and bring up what you did related to their advice on a subsequent meeting.

    3) Give back to your mentor. Show them Web 2.0 stuff if they don’t know about it. Share with them something interesting that you read. Give them a book.

    4) Be well read, knowledgeable, and driven. Mentors are more willing to engage someone who is interesting…

  • Forgetting a big one people, don’t ask about their personal lives unless they discuss it (even then that you have to know how far you can go before mentor becomes friend). More so if you want future advice from these individuals.

    I’m having a hard time finding a mentor in my field of study (through my professors and department) which is kinda depressing. The value of a mentor is having someone as an anchor in which you can direct your self in the safest and best possible direction. Not sure where I’m going wrong. Perhaps its the individuals I talk too?

    • Gunnar, it can definitely be frustrating to not get the right guidance when you need it the most. There is a start-up that helps students connect with role-models in their professional fields. Check them out on and it might help you! Good luck

  • Definitely choose someone who you can totally respect. That makes the most important part of being a “mentee” easier: paying attention. You really have to take whatever suggestions your mentor makes seriously just so that they know you truly value their opinions and experience.

  • Great post. I’ll just add one thing: seek out mentors while you’re still a student. I’ve noticed that people, no matter how successful they are, like to help younger people who are just starting out. They remember when they were your age and will respect you for taking the initiative to seek them out. Just make sure you listen and show them that you highly value/appreciate them taking the time to meet with you.

  • I second Jack’s comment. For reasons that I fully don’t understand, people are incredibly kind towards students, especially if they attend their alma mater.

    This is one of the main reasons that people still want to get into HBS–school loyalty is amazing.

  • I’d like to add one thing to the blog part. A lot of us older folks don’t know what an RSS feed is. But we do understand e-mail. That’s why it’s a good idea to offer e-mail subscriptions to your blog. Which, ahem, Ben, you do.

  • Ben, this is a great post – you’re right the topic is definitely not covered enough.

    I think you can also make a mentor want to play an even larger role in your life by offering to help them when opportunities arise. Are they having a big event and need a few extra hands on deck? Offer to help. It might not be very exciting or directly helpful to you, but the gesture goes a long way.

  • Gotta admit, I just asked the, “What would you do in if you were in my position?” question.

    But I feel that it was properly asked, if not please do tell me.

    I am trying to finalize an internship for approximately two weeks located away from home. I asked a few people/mentors that are all directly related to the company I am interning, where they think a 16 yr old kid should stay/live. A cheap/safe hotel? A host family? I asked for suggestions and what would they do if they were in my position. I guess a better question to ask might of been, would you let your kid do this?

  • My advice: be genuinely curious and interested, in everything!

    Hmmm… in fact, imagine the insights you might make might if your mentor were an expert in a different field, with a totally different perspective.

    Also, some people focus a lot of their efforts trying to find a mentor that is much more experienced and better connected…

    …but overlooking the value of strong long-term relationships with peers that can blossom over the years as you all become those more experienced and connected people yourselves.

    Great post, Ben!

  • Encourage them to help by asking YOU questions, and take those questions seriously. Some of the best mentors I’ve had were really just good at eliciting the responses or guidance latent in my own heart.

    Also, be thankful. Show appreciation. Let them know they made a difference, and that you’ll remember their work and their words.

    And with that, thank you, Ben. 🙂 Great post.

  • Ben — What I clearly remember from our first lunch meeting back in — whenever that was — is that your questions outwitted my responses. I came away humbled. And, over the years, that one interaction got my mind churning about this very topic. I like your conclusions. Once again, wisdom.

  • Thanks for sharing. Not very often does anyone post help for mentees.

    I recently received some advice from a mentor-type very similar to #1…

    “Ask the question you want the answer to”

    His analogy: a guy often asks a girl “do you have a boyfriend?” instead of asking “will you go out with me?”

    Question 1 might get you to the answer you want (eventually) but really doesn’t help you especially if she says yes because then you look particularly bullish or arrogant if you continue to question 2.

  • Woaw, this is excellent.

    I just contacted someone I desperately hope to mentor me and after the first few emails, I’m stuck.

    I’m a bit worried because I know A LOT about him, but I dare not revel it for fear that I might frighten him away.

    Thanks MrCasnocha

  • I actually wrote a long essay about how to establish that mentoring relationship, which basically boils down to “signal that you’re worth the investment.”

    Until you have a mentor, you can’t be a highly effective mentee, even though your numbers 5. and 6. are part of the essay.

  • Siempre me pregunto qué tan frustrados Vincent Van Gogh debe ser. Quiero decir, él pasó por la vida de un mendigo, sin que ninguno de sus pinceladas obteniendo Zapatillas Puma
    ningún interés y decidió que el mejor camino a seguir era hacer un trabajo de Tomás el incrédulo en la oreja y luego acabar con todo. Avance rápido de unos años (bueno y algunos más) y Puma Baratas
    su arte es reconocido y tiene etiquetas estúpidas precio que se le atribuye a la izquierda, derecha y centro.
    No es la primera persona a ser más famoso hombres Completa Puma
    post-humor, ya sea: Tupac Shakur, James Dean, Jeff Buckley y Kurt Cobain se han convertido en ídolo, incluso más que cuando sus corazones estaban zumbando Hombres Puma Clyde

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