Mentoring in the Business World and Beyond

Feb 21, 2023

I’m not sure what the legendary basketball coach John Wooden would think about this, but here is one humorous approach to mentoring younger talent. Ron Swanson = questionable mentor.

The need for effective mentoring is just as strong today as it has ever been. Here are four mentoring tips I’ve learned along the journey, and they all center around “both”:

1. Both caught and taught. 

People say that influence is better caught than taught. In my experience, it’s both caught and taught.

As for “caught,” consider this entrepreneur’s story. Without realizing it, she had several mentors in her life. She says that healthy mentoring is people who are responsive to you without being responsible for you. Accordingly, she’s a big believer in peer mentoring.

I agree with this mindset and can name a number of impactful conversations that happened with my kids in the car or key learnings for clients that were completely unscripted.

But you can also go too far in that direction and neglect structured guidance altogether. After all, most of my unscripted conversations with clients come because the client has approached me and said, “I need help in _______________,” and in the process of talking about his current need, we end up talking about other matters as well.

Several surveys over the past five years have shown that about 75 percent of Fortune 500 companies have mentoring programs in place. Employees want development in the workplace, not just friendly chats. They want structure and direction that makes growth seem not only possible but likely.

2. Both work and personal.

Traditional workplace mentoring usually goes like this: An experienced employee serves as the trusted guide, counselor, and supporter to another (usually younger) person for the purpose of the second individual’s job growth.

That same mentee might seek out a mentor for his personal life—how to be a better husband and father, for example.

Today, however, mentoring has become much more holistic and organic, especially with and for millennials. Good mentors may (and usually do) focus primarily on one area of life, but they don’t treat a person as a series of disconnected parts. It’s a holistic, caring relationship based on mutual respect that extends beyond the normal business skills and goals into values, beliefs, friendship, and even personal issues at times.

Think of Star Wars—the 1977 version. Obi-Wan Kenobi is our picture of a holistic mentor—both work and personal.

Obi-Wan teaches Luke how to use a lightsaber and how to handle his dad coming back into his life.

You just never know when you’re going to have to guide someone through father issues of an evil empire ruler who is poised to destroy the whole world with those darn magical powers.

3. Both for beginners and seasoned veterans.

Like we’ve said, traditional mentoring is “old guy mentors young guy.” Kind of like this.

I’d challenge you to reconsider that stereotype, though, and allow mentoring to go in multiple directions. You may have already done that without realizing it. For example, if you’re over 45, you’ve probably had someone under 25 coach you up (at least informally) on digital or social media.

Many companies have followed what Intel figured out years ago. An administrative assistant can meet with an executive about time management, or an executive could meet with an administrative assistant for help on identifying the true culture of the company.

So there is reverse mentoring (like your kids teaching you technology); there is peer mentoring (when equals help each other); and traditional up-and-down mentoring.

4. Both one-time and ongoing.

At any given point, I’ve got traditional coaching clients—a few Fortune 1000 executives, a few private family company CEO’s, and a few young entrepreneurs that I’m working with. We outline expectations up front for a year and re-evaluate after the year is over. In recent years, I’ve added one-day strategy sessions to my offerings and people can sign up instead for one day that’s usually high energy in front of a whiteboard.

But once someone is in my portfolio, they stay there for life. It’s not that I am on the clock or in their P & L. But there is an ongoing open relationship that never dies.

Some mentoring is in the moment for a particular season and some just rolls through life seasons.

Banyan or Banana Tree?

Let me go back to the original definition—mentoring is the intentional influencing by one person of another person. It’s intentional (that is, not accidental). It’s individual. And it’s influential.

It’s a banana tree. Not a banyan tree.

A banyan tree is a massive beauty. It spreads out its branches, drops air-roots, develops secondary trunks, and blankets the land. A full-grown banyan can cover more than an acre of land. All sorts of animals, including humans, find shelter in its shade.

But nothing grows under the dense foliage of a banyan tree. And when it dies, the ground beneath lies barren and scorched. When it’s over, it’s over.

The banana tree is the exact opposite.

Six months after a banana tree sprouts, small shoots appear. At 12 months, a second circle of shoots appears beside the first. At 18 months, the main trunk bears bananas that nourish all sorts of animals, including humans. Then the tree dies. But the offspring are fully grown, and in six months they too bear fruit and die. The cycles continue unbroken. When it’s over, it keeps going.

In other words, it’s another “both.” Good mentoring is thinking about both now and later.

Nelson Mandela said, “What counts in life is not the mere fact that we have lived. It is what difference we have made in the lives of others that will determine the significance of the life we lead.”

Mentor well. Set aside some time in the coming days and take a look at your leadership influence. Who are the “next generation” people you are investing your time, energy, and even money to influence? Then, make sure you’re planning with an eye toward who they will mentor someday!

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