Making the Most of Mentorship: How to Prepare for a Meeting with Your Mentor

When I was 25, I met Martha. She was at the peak of her career, probably in her mid 50’s, and had a strong professional reputation as an effective community leader.

She had her own practice as a business consultant—a job that seemed completely dreamy to me. She met with prominent leaders to advise them on working through organizational change.

I looked at her with stars in my eyes. I wanted to know everything about her work and how she got there.

And so I mustered up my courage and asked her for a mentorship meeting.

We met for breakfast in a great little neighborhood spot. I could tell she was busy as she came in, finishing up a phone call before she joined me at our table.

After a warm welcome, she asked me, “So, how can I help you?”

It shouldn’t have, but her question took me aback.

I made a mistake

I had done a big, brave thing by asking her out to breakfast. I knew I wanted to know all about her and I put myself out there by requesting her help.

But I hadn't thought much beyond that. I didn’t have a clear sense of how she could help—I thought that would just come clear through our conversation.

“I’m really interested in what you do,” I stammered. “I figured I’d pick your brain a bit to get some advice.”

We had a meandering conversation and a nice breakfast, but walking away from that meeting I knew I had made a big mistake.

Here was a busy, smart person who generously gave me her time. Because I didn’t have a sense of what I wanted to know, I wasn’t setting her up to be helpful. Which means I was potentially wasting her time, and potentially leaving her with a less-than-stellar impression of me.

I vowed to never make the same mistake again.

Fast forward to this week

On Monday I met with my mentors, Deb and Cathy. I'm fortunate to be part of a program called Venture Mentoring Service where experienced professionals volunteer to serve as mentors for entrepreneurs like me.

On a quarterly basis my team of mentors help me think through any questions I'm grappling with. They've helped me to make strategic decisions about Penney Leadership's direction and offerings, tailor my proposals to specific industries, and ensure that the work is sustainable for my business' #1 asset: me.

Even though I serve as a mentor myself and I know firsthand how rewarding it is, I always come away from these meetings thinking to myself: Wow, I can't believe these smart ladies willingly give their valuable time to me.

I'm incredibly grateful. And also incredibly driven to make the most of our time together. I want to ensure that they walk away from each meeting with the feeling that they've helped in meaningful ways—that our meetings are well worth their time.

Here's how I prepare to meet with my mentors

Nobody wants their “brain picked”—they want thoughtful questions that enable them to share targeted insight, experience, and resources that truly help you to move forward.

Thoughtful questions take preparation.

A week before each meeting, I set a calendar reminder to create and send an agenda. That agenda starts out as a big, messy ball of ideas jotted down on a scrap piece of paper.

Here's my process of preparing to meet with mentors—you can use it, too:

1. Make a bulleted list of wins since the last meeting, making special note of any progress made on items they advised on.

What have you accomplished since your last mentor meeting? List work products, decisions made, lessons learned, milestones reached.

2. Jot down current and upcoming projects. Calling these to mind helps to surface any challenges, opportunities, or roadblocks in the way.

What projects are on your plate right now or coming up soon?

3. Create a mind map of questions or challenges you're holding at the moment. Allow your mind to wander and go on tangents; let it be messy; get it out of your head and onto the page where you can work with it.

Start with "Questions" in the center of your page; draw lines off in different directions and brainstorm challenges, wonderings, or roadblocks you're working through.

4. Widen the view by considering four types of questions:

Developmental Questions: What questions do you have related to your own growth? How might your mentor help you consider how you're developing your skills and your career?

Operational Questions: What questions do you have about getting your projects done? How can your mentor provide clarity or perspective on your current work?

Strategic Questions: What questions do you have about trends, changes, or opportunities that are happening out there in the world? How might your mentor help you anticipate what's coming around the bend?

Whole Human Questions: What questions do you have about the interplay between work and life? What's happening in your personal world that affects how you show up professionally?

5. Distill your thoughts into an agenda. Once it's all out there, look back through what you've written and circle key words and phrases. Notice what's bubbling up to the top and use these key questions to create your agenda of discussion items.

Once I've moved through this process, I finalize my agenda and email it off to my mentors with a note that I'm looking forward to the call.

Key Takeaways:

• Asking for mentor support is a brave step, but it's only the first step—it doesn't stop there.

•  Preparation for mentor meetings is key.

•  As the mentee, I'm responsible for forming the agenda, facilitating the conversation, and following up.

•  My goal is that my mentors walk away from every meeting feeling as valued and helpful as they truly are to me.

Thoughtfully prepare for your next mentor meeting with this free, downloadable Mentor Meeting Preparation Guide.

Penney Leadership Free Resource: Mentor Meeting Preparation Guide

This guide walks you through a process to make the most out of a meeting with your mentor. You'll surface thoughtful questions that enable your mentor to share targeted insight, experience, and resources that truly help you to move forward.