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Managing Millennials Q&A: Why Isn’t My Mentee Reaching Out?

Originally published 19 September 2017 by Lindsey Pollak

Note to readers: This is the sixth post in my new series based on questions I frequently hear about managing millennials — those ongoing management challenges that can really make or break workplace relationships.

Each month I’ll tackle a question and provide some advice for managers and millennials (and, of course, millennial managers). I hope the advice I share is helpful for all generations.

Have a question you’ve been dying to ask? Send me an email and I will try to cover it in a future edition!

While it’s been relatively common over the years for a young professional to ask me how to best approach and benefit from a mentor, recently I’ve been receiving more questions from the mentors themselves. Specifically, they’ve been asking, “Why isn’t my millennial mentee reaching out?”

This question surprised me the first time it was asked. Why wouldn’t a junior person do everything he or she could to engage with a leader who expressed interest in being a mentor?

When I myself have been in the “mentee” position, I’ve always tried to follow the wise advice of Levo League’s Tiffany Dufu, who says:

“A good mentee runs through doors a mentor opens.”

After all, there’s no question that a strong mentor can provide an invaluable career boost, whether you’re a mentee in a formal program or you’ve made a personal contact on your own.

But the reality many mentors have been reporting is that often millennial mentees are more apt to tiptoe than jump into the relationship. And it struck me that young professionals are generally not taught how to be good mentees. Thankfully, a few of my clients have been ahead of the curve and invited me to develop “Mentee Training” to help address this issue.

Here are some suggestions from my new program to help mentees get into the groove of the mentee relationship and ways that mentors can smooth the path as well.

Advice for Millennial Mentees

We often assume that the heavy lifting is being done by the mentor, but I advocate that the mentee should set the scene for a productive relationship. Consider it a form of managing up. Here are some ways you can ease the responsibility for your mentor:

  1. Handle all the logistical elements.

Make it easy for your mentor to participate by initiating the meeting or call, sending a calendar invite and creating an agenda or sending questions so he or she can prepare for the topics you hope to cover.

2. Don’t be afraid to be persistent.

Sometimes it might seem as if mentors are too busy if they don’t respond right away, but it’s more likely they just need a little nudge. If they agreed to be a mentor, you can expect they are committed. Help make it easy for your mentor to say yes by offering several choices of times to connect and always remind them that you understand if they are in a busy period.

3. Demonstrate your enthusiasm.

Mentors want to feel that they are being heard so make sure you are actively participating in the meeting by taking notes and asking questions. Then keep your mentor apprised of how you are using the advice they’ve offered with quick follow-up updates.

4. Help them help you.

Your mentor can’t read your mind, so be specific about the career development and networking advice or connections you are seeking. If there are specific areas where your mentor excels, mention that you’d like some pointers in that skill.

5. Remember that mentoring is a mutually beneficial relationship.

No matter how senior your mentor might be, there’s undoubtedly something you know more about than they do, whether it’s creating a video presentation or communicating with millennial customers. Ask if you can help your mentor by asking the simple question, “Is there anything I can do for you?”

Advice for Mentors Managing Millennials

Think back to when you were in the mentee role yourself and what would have made it more productive for you. Here are some suggestions to get you started.

  1. Put your mentee at ease.

Your mentee is likely to be a little apprehensive about the relationship, especially if you are of different generations. Your first step should be to confirm that your discussions are confidential; you’re there to help, not spy or tattle for senior colleagues. Also be honest with your mentee — and yourself — about your availability and bandwidth for mentoring. Alert your mentee to busy times or potential scheduling conflicts so they don’t worry that you are just blowing them off.

2. Get to know your mentee on a professional and personal level.

A solid relationship will take time to build, but you both will benefit. Find out more about your mentee both professionally and personally — ask questions about their backstory and what they like to do in their free time; then share some personal details with them about yourself.

3. Diversity your mentoring activities.

Sitting around going over a list of issues week after week can get pretty stale. To inject some creativity into your meeting, offer to review a client email or sales presentation; role play a tough conversation; or go on a “field trip” together to a networking event or volunteer activity.

4.  Be generous with information.

Tell stories of what has worked — and almost more importantly, what hasn’t — in your own career. Share useful resources, whether they are books, organizations, events, apps or even your connections. Above all, recognize and congratulate your mentee when there is progress or a breakthrough.

Two Mutual Responsibilities of Mentors and Mentees

For the best possible outcome, both sides should adopt these two practices.

  1. Have thestyle conversation.”

With so many communication options today, it’s easy to make the wrong choice when trying to engage with a mentor or mentee, particularly if you are of different generations. Take the advice of Michael Watkins, who wrote about the value of specifying your communication preferences in his book The First 90 Days. If one of you leans toward email and the other prefers chat apps, openly discuss a way to bridge the gap.

2. Do “small goods” for each other.

To help nurture the relationship, both parties should make small, thoughtful gestures, such as:

  • Writing a short note of encouragement or thanks
  • Sharing a relevant article, video or podcast
  • Engaging on professional social media by “liking” or sharing the other person’s post
  • Inviting them to an outside event, meeting or other activity

I’ve been on both sides of the mentoring relationship and know firsthand that the mentor/mentee relationship can be immensely rewarding. I hope these suggestions will help you build and grow enjoyable and beneficial mentoring relationships of your own.

What has helped make your mentor/mentee relationship more successful? I’d love to hear from both sides on Twitter or in the comments below.


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