Mentors: Passing Along Wisdom

That Must Have Hurt

When I was a kid I learned a lot by trying things out to see what happened. But I learned even more by watching my younger brother. He was more adventurous than I was, and I always preferred to let him go first—especially when it came to daring bicycle tricks. Watching him pop wheelies off the curb showed me what was possible; seeing him ride up the steep hill and end up in the cactus down below taught me what wasn’t.

Ever since, I’ve been a believer in learning vicariously.

Missing the Connections

But in professional life these days, I find it much harder to learn vicariously. Modern creative work is often done in individual cubicles. People stare at their screens, wearing headphones and interacting mostly with technology. The current trend is toward working remotely, where mistakes are even more hidden. And even when we work in the same office, the environment often isn’t conducive to learning from the experience of others (except when speakers make a special point to package and present their discoveries for a conference).

This can create a major problem for large organizations, where the wisdom of older employees is not passed down to emerging leaders. It’s also a problem for solo practitioners who can feel isolated and passed by when others are learning from each other in large groups.


One way to fill the gap is through mentoring. A good mentoring relationship brings together an older, more experienced mentor with a protégé (sometimes called a mentee). Mentors pass along wisdom by sharing experiences that have shaped their lives. Protégés benefit from vicarious learning, and mentors benefit by expanding their influence and impact. A vibrant relationship is built upon trust and vulnerability. Good mentors challenge, support, and even open up doors that the protégé could never open alone.

In his book on leadership, Michael Lindsay talks about how important mentoring has been for the top tier of leaders he studied: “In fact, mentoring was a markedly consistent factor in the early lives of the leaders I interviewed. Fifty-one percent of them mentioned a specific mentor or sponsor who had aided them in their climb to the top. Having a good mentor proved more significant in predicting career success than where one went to college or how wealthy one was as a child.”
View From the Top: An Inside Look at How People in Power See and Shape the World
D. Michael Lindsay, Ph.D.

What Makes Mentoring Work

I’ve had the privilege of being mentored by several leaders and artists in my formative years, and I continue to mentor others now. Without going into great detail about each relationship, I’ve distilled some lessons from those experiences.

  1. Organic Relationship
    When I was mentored by people I already knew and respected, the relationship felt more natural. If I selected my mentor, or he selected me, it generally worked well. However, when I was part of a program where a mentor was assigned, the relationship felt synthetic or forced.
  2. Life Scope
    Mentoring is way more than just skill development—it’s about wisdom for living. When I gave my mentor access to just a part of my life, the mentoring was weak. But when I gave him access to my entire life, the mentoring could really take off. I found that often the most powerful and relevant conversations were about topics that I didn’t anticipate sharing.
  3. Working Together
    Deep discussions about life were helpful by themselves, but they were maximized by collaboration. Working with my mentor allowed me to watch him solve problems, respond to challenges, and demonstrate expertise. Debriefing what I noticed gave us fodder for more learning and accelerated development.
  4. Investment
    Mentoring works best when it’s intentional. That costs time and money. Spend it.
  5. Dynamic
    On one hand mentoring is not just hanging out; but on the other hand it’s also not merely going through some curriculum or transferring knowledge. There needs to be a good balance between having an agenda that comes from the protégé and guidance that comes from the mentor. When my mentor tapped into what I was passionate about and wanted to learn, he was able to guide me and challenge me beyond what I thought was possible. Like all good relationships, there is a dance to it.
  6. Championing
    My good mentors had this in common: they believed that I could achieve way more than I thought I could.

Finding a Mentor

Look for someone wise in your community who is worth emulating, who has a generous heart, and who wants to increase their impact in the world by influencing others. Take them to lunch, offer to pay, come prepared with questions, and let them know you are teachable.

Finding a Protégé

Look for someone around you who wants to learn, who has potential to master their craft, and who is willing to open up their life to influence. Look for willingness to be vulnerable—if the protégé wants to limit your access to just a segment of life, you could be wasting your time and influence.

Do We Need to Name It?

Mentoring doesn’t need to be too formal or structured. If you find yourself focused on whether you are doing it right, then re-focus on your values and goals.

I heard the story of a young lady who asked an older woman to be her mentor. The woman declined, saying she already had too much on her plate. So the young lady just invited her to get coffee instead, which she was happy to do. The young lady kept initiating, and several coffee get-togethers later, the woman realized she had inadvertently become a mentor anyway, even without the official title.

You don’t necessarily have to ask someone to “be your mentor” in order to learn from them. Mentoring is about the relationship, not about following an official program.

Related Roles

Here are some relationships that are similar to mentoring.

  1. Discipleship
    In Christian circles, discipleship is a very similar relationship where younger believers learn from more experienced ones. Unlike mentoring, discipleship tends to focus more on matters of faith.
  2. Internship
    Some internships have a mentoring quality to them, but are often more narrowly focused on skill development and job experience.
  3. Coaching
    Coaching is very similar to mentoring. One difference is that a professional coach is trained and certified in supporting you as you develop, whereas a mentor is usually not trained in mentoring. Also, coaching is less focused on the life experience of the coach and more focused on the progress of the client/protégé. Even if you have a mentor, you will certainly find value in hiring a coach. The result is that you tend to go farther faster.

Learning Vicariously

Mentoring is not the only way to learn. You can learn a lot by trying things out, seeing what works, and making some mistakes. But if you want to acquire skills for living quickly, nothing beats learning from the life experience of others.

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