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How Do I Ask Someone to Be My Mentor?

How Do I Ask Someone to Be My Mentor?

Simply put, you don't. Let it grow organically.

As a mentor, I have learned as much by providing guidance to others as I once benefited from the guidance provided to me. A mentor-mentee relationship should be a mutually beneficial partnership between two people, with implied or outlined obligations to one another.

The key to a successful mentor-mentee relationship is to be aware of your obligations and take them seriously. Most of the time you have a mentor and don't even know it yet.

This rings true with my very first business mentor, Cynthia Porter, a healthcare marketing executive and the first female in sales at HBOC, which is now McKesson. To this day, I have not taken a position in which she hasn’t advised me. 

I first met Cynthia when I responded to her job posting looking for a support person to help her with the day-to-day activities of her market research firm. At that time, I was going through a career transition as I was beginning to consider motherhood and took a drastic pay cut to “balance it all.”

When I took the position I didn’t know Cynthia would be my mentor all these years later. Today, I see a lot of early-in-their-career motivated employees seek out mentorship. In fact, I get asked all the time by these ambitious young guns about being their mentor.

Their emails often look the same:

Dear Katharine,

I’m a 20-something, trying to gain experience in marketing to become a CMO like you.

The next question usually looks something like this:

Can I pick your brain about your career and how you got to where you are today?

Will you be my mentor?


E.Y.E. (Eager Young Employee)

This method is not effective and I would like to help inform these go-getters about how mentor-mentee relationships can start and how they work. Hopefully, one day they can build successful and mutually beneficial relationships with industry pros as I have with my mentor, Cynthia, for over 15 years.

Prove Yourself

I was taking a new career path and took a step back from my previous position. I was hired as Cynthia’s administrative support. I knew that in order to get her attention I’d have to be reliable, capable and accountable. I worked extremely hard to get to know her inside and out so I could anticipate her needs and act on them even before she asked. 

Over my three years of doing this, instead of her seeing me as beneath her, she viewed me as her right-hand woman. I had gained her trust. Once that happened, she didn’t have to “manage” me, instead she could “coach” me. She also began to give me much more responsibility with each success.

Tip #1: Show the person you hope to become your mentor that you’ll put in the work for them first. With social media, now you can find out what they’re working on and what things they may need before even making contact. When you do finally connect you immediately know what to talk about and may be able to offer your expertise to help them first.

What do they need? (Social Media Skills: teach us 'older dogs' new tricks?)

How can you be of service? (What value can I provide for them?)

Let It Evolve Organically

I never asked Cynthia to be my mentor. Instead, I would ask her questions related to what obstacles I was encountering at the time. Our relationship continued to grow and over time, she put more energy into my professional development even though I never asked her to.

Tip #2: When you ask someone to “be your mentor,” it often comes with a stigma that the duty requires a lot of time and attention. When you solicit advice on one particular thing you may be struggling with start small, as it is more manageable for your hopeful mentor to provide you with guidance in a quick conversation. This allows for the relationship to develop organically and for the person that you admire to be helpful in smaller doses at first. 

Executives typically have intense schedules and for many, their day is planned out in 15-minute or 30-minute increments. Once you’ve built a foundation, the next level of support for the heavy lifting feels natural and you will most likely be able to get more time and guidance.

It’s A Two-Way Street

At the beginning, Cynthia was advising me much more than I could advise her. As I developed professionally, that began to shift and I became of value to Cynthia. I began to pay her back for taking me under her wing and helping me grow into a great marketing professional. I made introductions that were useful for her and her business. I lent my expertise related to projects she was working on. I became a legitimate sounding board for her, as much as she was for me.

Tip #3: It’s not all about you. Always look for ways that you can offer help to your “mentor.” The more invested you are in the relationship, the more invested he or she will be.

I’m working with someone I might consider as a mentee right now. We first met on Twitter while she was working and living in New York City. She took an interest in the mission of my work and even supported my brand through social media. She happened to move to Atlanta over a year later and we were able to meet in person for the first time. Now, I’m helping her in doses as she brings a new company to life.

This relationship wasn’t forced, nor did she ask me to be her mentor. It evolved organically and we’re finding ways to support each other. That’s the key! You never know where this two-way street may intersect. 


Katharine Mobley is the CMO of WeCareCard, a SaaS payments company, revolutionizing the giving and gifting marketplace. She is a data geek and a social media addict. With over 17 years’ experience in her field, she has witnessed drastic changes in marketing and advertising, specifically with the evolution of the CMO and the role of social media.

Have more questions? Follow up with the expert herself.


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Community Discussion
Natalia Truong

This is such a great article! Thank you for sharing these valuable points.

May 24, 2017

Leilani Carbonell Pedroni

Thanks for writing this article! I changed my career path relatively recently and finding a mentor is something that has been constantly on my mind. Your article provides some good steps for me to take!

May 4, 2018

Gilene Janvier

This article is very timely and much appreciated. I'm having lunch with someone that I admire and really want her to be a mentor. I will keep your nuggets of wisdom in mind tomorrow. Thanks.

May 17, 2018