How to Lean In to a Mentorship That Works


Whether you are on the road to becoming a professional blogger, content to keep your day job, or hungry to move up the ladder in corporate America, a great mentor will help you get there. Early in my career I was disappointed by the promises of mentorship by well-intentioned women who simply didn't have the wherewithal to make time to sit down and teach me. So, I learned by observation, careful listening, and a fair amount of trial and error. As a result I try to make myself available and accessible to aspiring bloggers and publicists. But I've also learned that not only is it impossible and somewhat exhausting to sit down for coffee or share the same insight over and over, but that just because I value mentorship as a reciprocal relationship, not every mentee is looking for the same give-and-take. Instead, some potential mentees are looking for me to draw them a treasure map to a mythical X marks the spot of career glory and never-ending happiness. As much as I wish I could, not only do I not have the ability to write the script, the true value of a mentor is someone who encourages you to uncover your own special gifts, and how to use them to create the kind of success that you define. And then she joyfully helps you get there.

These days, even with a book written on the subject, and career consulting sessions, one of the most common types of email I continue to get are from young women wanting my advice on how to break into the industry. What I end up doing with these emails ranges from suggesting a paid consulting session, to writing a few lines, to offering to meet for coffee,  hitting the delete button, and sometimes, offering them a position with my company. Honestly, it all depends on the tone of the email and a sixth sense if this person and I are a match.

How far we get after that first email exchange fact depends on many other factors – my own availability, our personality fit and their dependability, enthusiasm, and integrity. A few people have recently quoted a passage in Sheryl Sandberg's Lean In where she essentially says that the best way to get a good mentor is to be good at what you do. And not surprisingly, demonstrating your own skills and talents and the “what I can do for you approach,” is a much more enticing proposition than, “I want what you have, can you tell me how to get it?”

I reached out to the other IFB writers about their experiences as mentors and Ashe echoed Sandberg's point with “I don't think mentorship always means having something to take from the other person because they're in a more advantageous place than you.  It's like any relationship, which means sharing ideas and problems and reaching out to one another for help.” Cora remarked how you should never “cold-call a blogger you've never met and ask them to be your mentor. Or insinuate that her turning you down has anything to do with her not supporting women.” Ugh, indeed.

There are two women that I have mentored for more than two years and I decided to dig a bit deeper into what makes these relationships work by asking them about mentorship. Nacole Gray is a style expert and blogger, a former fashion copywriter for Guess?, and currently developing a style video series for After meeting with Nacole for coffee, I eagerly hired her to work directly with me as my social media coordinator at a digital agency and advised her on getting her blog up and running. She also considers Freelance Fashion Writer Chantal Gordon-Benoit and Fashion Stylist Mahjuba Levine as additional mentors.When I asked Nacole what has made these relationships work, she shared, “I followed up when I said I would. I also displayed my willingness to learn and to start at the bottom. You have to be humble and you have to be willing to work for what you want (whether that means working as an intern or for very low pay as you start your career). Nothing is ever handed to you, especially in this industry. I always communicate how grateful I am for their time and support.”

Martha Chavez won my heart when she made a not so easy traveling a situation a breeze with her infectious smile and zippy sedan during SXSW. I nicknamed her St. Martha and she has come to my aid a hundred times over. In return I'm hatching a plan to bring her to California and have slowly entrusted her with more job responsibility. Martha is currently the editorial assistant at PR Couture. She remarked that “having someone who's on your side and genuinely wants to help you is so refreshing and makes you want to do that much better. Also, since working together is done remotely, the times we've gotten to work together in person have been priceless!” (and sometimes result in shenanigans like the picture snapped above by the lovely Erika Astrid during Fashion PR Confidential).

What I love about Nacole and Martha is their genuine interest in being helpful. They have such enthusiasm for my work, so being around them makes me feel good! And I think I have the same effect on them (I hope!).  Nacole soaks up information and puts it to quiet, powerful use. Her intrinsic sweetness, triumphs, and ability to have you spilling your guts without even realizing it draws people to her and builds her natural allies. Martha reminds me to celebrate my success and myself, whether it's through a surprise delivery of chocolate covered strawberries to mark my new website launch, or the perfect “just because” gift. Of course I want these women on my team and of course I'm always thinking about how I can help them get to where they deserve to be.

5 Ways to Approach a Potential Mentor

  • Be generous – start off the relationship by sharing something you know they will appreciate – be it a cat video or social media campaign. A quick “Oh hey Crosby, I saw that this brand was looking for this– it reminded me of you. I'm not sure if you'd be interested or who have friends who are, but here you go!” is the way to go.
  • Instead of asking for a coffee date, offer to bring the coffee to them.
  • Ask a specific question instead of a general, “tell me what to do” cry.  Like “Hey, Ashe, I hope you're doing well– can I get your input on this brand offer that I've received? It makes me uncomfortable, but maybe it's a totally normal pitch. I'd love to hear what you think.”
  • Instead of leading with, “I know you are busy but,” lead with a genuine compliment and “I don't know how you do it all, but I am so grateful that you do.”
  • If you are looking for a traditional mentor, clearly explain what type of time commitment you are looking for. A vague, please be my mentor won't likely turn into anything, but a “Can you spare 30 minutes once a month and give me feedback on how my business/blog/career is going?” will.

If you are having trouble reaching out to someone that you admire, I recently wrote an email template script for how to start a conversation with a potential mentor, as well as several other common job-related emails that can be hard to write.

Do you have a mentor? Do you want one?

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7 Responses

  1. Meaghan

    Very interesting. While I understand that anyone considered a potential mentor is busy, it was a little disturbing to read that Crosby has deleted emails that don’t grab her attention or meet her needs. We all need a little help now and then, especially when we’re in search of some career advice. Hopefully that “how to” article for starting a mentor conversation will help!

  2. Hey Mishka

    I also want to point out that a mentor can be someone you don’t even recognize as such until it dawns on you how much you’ve learned from them. This happened to be several times. If you’re lucky, you realize it while you’re still engaged with them somehow and able to continue learning.

    The intentional seeking out of someone you admire to obtain some knowledge and guidance isn’t a ‘bad’ idea at all, but don’t forget how much wisdom might be found right in your current network!


  3. Stephanie Nwaiwu

    I would love to have a mentor, but I’m a bit shy in the reaching out category. I am also prone to not picking the right mentor, which is the main reason why I have held back from seeking one out.

    But this is great advice that I will definitely heed if the need arises.