Taking down my hang-ups about mentorship

Rafe Steinhauer ’07 is a Lecturer and Entrepreneurial Program Manager in Princeton University’s Keller Center. Rafe teaches two sections of ENT 200 Creativity, Innovation and Design, and manages the Tiger Challenge program.

Below is a list of the hang-ups I had about asking someone to mentor me. Mentors have been instrumental in my career and personal growth, but first I had to get over these hang-ups, all of which I have seen in Princeton students with whom I’ve worked.

The hang-ups go something like this:

• “I understand generally why having mentors might be helpful. But it’s hard for me to ask someone without being able to visualize what the relationship will look like and the value it will provide.”
• “The person I want to ask is too busy/important. Who am I to ask?”
• “I can’t think of anyone I’d want to ask.”
• “What if I meet with someone and the conversation is not that helpful?”
• “I don’t know what I’d ask them. Sure, I could use some guidance, but I need to have a little more clarity about where I’m stuck before I’d feel ready to ask someone for help.”
• “I’m fine [e.g., I don’t have the requisite humility to seek guidance about me yet].”
• “I’m in a good place; I don’t need that kind of help right now.”
• “I’m only a Sophomore; I don’t need that kind of help yet.”
• “My assigned advisors at school haven’t been that helpful; I don’t need more people to give me superficial advice.”
• “The best guidance comes from people who know me best. I’ve got all the help I need between my family and friends.”
• “We haven’t explicitly used the term ‘mentor,’ but I have people that play this sort of role for me already.”
• “I’m a mess right now. If I speak with a mentor about my life, I’m going to start crying, and I don’t want to seem like a mess in front of that person. Maybe I’ll ask when I’m in a better place.”
• “I’m just too busy right now.”
• “Having mentors feels too corporate, like networking and other things future MBAs would do. I don’t know what I want to do, but I know it’s not banking, consulting, tech, or anything too business-y.”

I was 26 and a struggling entrepreneur when my first mentor, Ted, asked me, “What do you happily skip sleep to do? I’m sure you have to stay up late a lot, but what things do you stay up late to do without noticing, and which things do you kvetch about?”

It was a really easy question to answer in that moment — anytime I was doing educator-activities (e.g., breaking down film for the Ultimate team I was coaching; writing curricula for the SAT students I was tutoring; or composing emails to coworkers explaining things related to the company), I was engaged and happy to stay up late. Anytime I had to code, or think about sales and marketing, or do anything related to company-building, I would be a grump-monster about it.

For most people, this particular question will not be life-altering. But for me, this question changed (and accelerated) the trajectory of my career. It was the right question, at the right time, asked by the right person.

Ted and I had had many conversations before this one, each of which was “merely” helpful. If you were to dissect the conversations I’ve had with all my mentors (and with my mentees), only a few have been profound; most conversations are valuable in smaller ways. It is the relationship that allows a mentor to be well-positioned to make the observation, or ask the question, that becomes a pivotal moment for you.

Here are a few quick thoughts about overcoming each hang-up above:

Hang-up: “The person I want to ask is too busy/important. Who am I to ask?”

Thought: I’ll let Ted address this hang-up. “Your presence in someone’s life is actually a gift, and helping is something people feel honored to do. Find someone you like who can challenge you. Ask them to coffee. Pay for the coffee. Be yourself. In fact, being yourself is something mentors can help you with.”

When you ask someone to mentor you, make sure you give them the space to decline and the ability to suggest the frequency with which you’ll chat. If they really are too busy, then they’ll say sorry (if this happens, don’t take it personally). More likely, they’ll say, “I’d love too, I’m really busy right now, how about we put something on the calendar for October?”

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Hang-up: “I can’t think of anyone I’d want to ask.”

Thought: Then let’s start a step back. Is there anyone who you’d like to learn more from about the work they do, or how they got to where they are, or just get to know better because they seem smart and down to earth? If you can’t think of anyone as a mentor, it might be because you haven’t gotten to know enough “adults” first, or because you are thinking of this is as super-formal or transactional, rather than as a unique type of relationship. Invite an alum, staff or faculty member to get coffee. We love that!

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Hang-up: “What if I meet with someone and the conversation is not that helpful?”

Thought: Yeah, this might happen. If the relationship feels flat, you don’t need to reach out to the person again. Also, you may frequently get conflicting advice, which creates anxiety. Much like Ted and the “skip-sleep” conversation above, the best mentors will ask you questions and give examples, leaving you to discover insights for yourself and apply them at your discretion.

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Hang-up: “I don’t know what I’d ask them. Sure, I could use some guidance, but I need to have a little more clarity about where I’m stuck before I’d feel ready to ask someone for help.”

Thought: I see this hang-up All. Of. The. Time. Frankly, it drives me crazy, especially because it was my biggest hang-up too. A great mentor will ask you the questions (like the “skip-sleep” question above), not vice-versa. Your role is to show up and open up.

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Hang-ups: “I’m fine [e.g., I don’t have the requisite humility to seek guidance about me yet].” & “I’m in a good place; I don’t need that kind of help right now.” & “I’m only a Sophomore; I don’t need that kind of help yet.”

Thought: Mentors have helped me when things were going well, when they were going poorly, and in between. Even if things are going well right now, a push and prod can only help. And building the relationship early will be useful later.

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Hang-ups: “My advisors at school haven’t been that helpful; I don’t need more people to give me superficial advice.” & “The best guidance comes from people who know me best. I’ve got all the help I need between my family and friends.”

Thought: A great mentor will get to know you better than assigned advisors typically do. But unlike friends and family, mentors’ explicit role is to help you figure out how to live the life you might want. Mentors cannot replace friends and family, but friends and family also cannot replace mentors. Friends and family frequently prescribe what they want for you, and they care about the health of their relationship with you, which can water-down their advice. Great mentors know you well enough, but they don’t need your affection or validation. This gives them the ability to provide you affirmation when they sense you need it, but it also allows them to cut through your BS and ask you tough, challenging questions when that is what you need.

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Hang-up: “We haven’t explicitly used the term ‘mentor,’ but I have people that play this sort of role for me already.”

Thought: I’ve spoken to students who have expressed this, and it’s been true. Great. I’ve also spoken to students who have expressed this, but after a little digging it became clear this was not so true; they were shielding themselves from the vulnerability it would take to ask these people for mentorship explicitly.

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Hang-up: “I’m a mess right now. If I speak with a mentor about my life, I’m going to start crying, and I don’t want to seem like a mess in front of that person. Maybe I’ll ask when I’m in a better place.”

Thought: Now sounds like a good time to ask. Bring a tissue box to your first meeting, and don’t schedule it right before a date.

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Hang-up: “I’m just too busy right now.”

Thought: Are you envious of people who seem like they get so much more done each day than you do? Maybe a mentor could help you figure out how to better manage your time? Or prioritize? Or nudge you towards greater self-care, if that’s what will help you reach your big picture goals.

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Hang-up: “Having mentors feels too corporate, like networking and other things future MBAs would do. I don’t know what I want to do, but I know it’s not banking, consulting, tech, or anything too business-y.”

Thought: Yeah, this is how I felt in college. Then I ended up getting an MBA. :)

I think I disparaged mentors and networking as “things that tools did” because I was insecure that I didn’t know who I wanted to be. I felt like networkers were people clawing for access to jobs and communities, without really knowing themselves yet. And I imagined that these relationships were purely transactional.

But mentors helped me figure out what my role in the world might be. And since I discovered an inspiring professional mission (“help equip people to co-create a world in which they and others want to live”), asking for more help (from mentors and through networking) became even easier. Mentors also helped me confidently design a life and career for me, independent of the choices and actions of others.

No matter where you are on the spectrum from “totally lost” to “a clear and specific mission,” mentors will help you move further along the path towards creating a life that feels deeply resonant with what you love, what you’re good at, and what you believe the world needs.

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Postscript #1: A template email for asking someone to be your mentor. Please edit it to fit your voice.

Dear ________,

I’ve appreciated your ___(say what you appreciate about them or why you think they’d be a good mentor for you)______. Would you be open to being a mentor of mine? I know I’d benefit from periodic conversations in which we discussed how you’ve approached creating the career and life you have, and from you pushing me towards a greater understanding of my own path and decisions.

I completely understand if you decline for any reason. If you are interested and able to mentor me, would you prefer meeting once to start? Or with a regular frequency, say quarterly, semi-annually or annually?

Gratefully,
-___(Your Name)____

Postscript #2: An opportunity to meet Ted

Ted recently founded Molly School. People, ages 18–80, work on a project in Amsterdam for a month. Ted provides general coaching (mentorship!) and sets people up with experts in Amsterdam who can provide subject-matter expertise on their projects. Participants have worked on things ranging from startups, to fine arts, to writing, to baking (bread), brewing (coffee), and brewing (beer … the finest of arts, IMO).

Spots are open for July, 2019. Reach out to Ted here if you’re interested!