Mentor speaking to mentee. Mentoring, youth mentoring.

Consider the whole person: How to improve your mentoring by thinking holistically

By Rick Woolworth, HBR 

Editor’s note: It’s easy to perceive a mentoring relationship, especially one in an academic or professional context as just that: professional. While a good mentoring relationship should lead a mentee towards their goals, the article below describes the importance of understanding the mentee in question holistically, extending the conversation beyond the goals that you’re mutually working towards. Give this article and others on mentoring a read at the HBR

Aspiring leaders need more and better mentoring than they’re getting today.

According to a recent study, the supply-demand imbalance is severe:  while more than 75% of professional men and women want to have a mentor, only 37% have one.  What’s more, most of the people currently acting as mentors aren’t having as dramatic an impact as they could because they’re too narrowly focused on career advancement.

In 2018, I spent a few hours with a Stanford University research librarian pulling up all the articles, studies and books on mentoring we could find. We found that the vast majority focus on how it is practiced in the workplace and how organization-wide programs are administered. There was remarkably little analysis or advice on how to mentor the whole person, extending beyond the career to include discussions about behavior, values, relationships, parenting, finances, and even spiritual life.

In my experience as a Wall Street executive for 35 years, as a mentor to many colleagues and friends, and now as the president of a non-profit dedicated to helping leaders establish inter-generational relationships, I’ve learned that this more holistic approach is dramatically more effective in helping people fulfill their true potential. In fact, it’s one of the beauties of mentoring and what differentiates it from coaching for skill-building or performance.

Mentoring the whole person takes more effort, more time, and more thought. Here are some practices for doing it well:

Share your stories. When I meet with a younger person for the first time, I say: “Tell me your story. Start at the beginning and take your time — 20 or 30 minutes. I may ask a few questions, and everything you say will be confidential between us. Then, when you’re finished, I’ll tell you my story if you want me to.” (They always do.) This simple exercise can transform the trajectory of a mentoring relationship because it shows that you’re truly interested in understanding your mentee and his or her journey, not just in dispensing professional advice. It gives you knowledge of the person’s past which enables you to make more probing inquiries over time. When I tell my story, I make sure to describe one or two of the difficult chapters in both my career and personal life, including my marriage. This signals that all aspects of our lives are on the table.

 Ask great questions. Effective mentors develop a storehouse of probing questions on any number of subjects. Examples include:

  • What keeps you up at night?
  • Can you see yourself being stimulated and fulfilled on your current career path for the next five years?
  • What do you do to “reboot” so that the busyness and tech overload in your life does not result in burnout?
  • Who has been most influential in your life?
  • What did you love doing in high school?
  • What would you have done differently in your life if you had the chance?
  • On a scale of 1 to 10, how would you rate your marriage/romantic relationship right now?
  • How was your relationship with your parents?
  • Were you raised in a particular faith or religious tradition?

During my second meeting with one new mentee, Kate, she told me how unhappy she was working all hours for a top consultancy. I took a step back and asked about her upbringing. Within minutes, tears were rolling down her face as she realized her obsession with career success was in large part to gain the approval of an emotionally distant father. She left our lunch with new insights into her motivations and ambitions, and is now much happier working fewer hours as a still highly regarded consultant.

Start with the end in mind. Perhaps the most important question you can ask a mentee is:  How do you personally define long-term success?A simple yet effective way to unpack this question for a mentee is to say:  “Imagine that tonight there is a party honoring you on your 80th birthday. Write down five brief things you would like family and close friends to say about you.” Once they share their list with me, I normally share my own answer to this question. If you don’t do this early on in your mentoring conversations, it is like sailing a ship without the ultimate destination in mind and you’ll find that it is possible to give a mentee good career advice that is poor life advice. For example, a seasoned lawyer advising a new associate fresh out of law school how to climb the ladder to partner, might tell him or her to work 70-80 hour weeks on a consistent basis. But the senior person hasn’t asked about relationships, kids, health, etc., which could, for the junior, be more important than career and financial success. An added benefit of spending most of your time asking questions is that it prevents you from talking too much and providing too many solutions.

Teach them how to fish. My most valuable mentor over a 25-year period was Bob Buford, a successful cable television entrepreneur in Dallas.  He was a master of insightful inquiry and sparing advice. At one stage in my career I was struggling with a difficult boss, and I was hoping Bob would tell me what to do. Instead, he asked a series of questions that enabled me to identify the real issue and come up with a course of action on my own. “You just needed to talk out your confusion,” he told me as we finished our meeting. Bob was teaching me how to fish by not providing the fish.

Unpack your mentee’s “toolkit.” A valuable area to explore is your mentee’s innate gifts, aptitudes, personality characteristics, and passions. Most younger people have limited self-awareness about how they are uniquely “wired.” Without this perspective it is easy for them to aspire to be people they are not built to be. I learned this the hard way during my 23 years at Morgan Stanley. My strong suit was developing relationships with the decision-makers of our corporate prospects and clients. As my success grew in this area, I was asked to manage a growing number of people in our group as well. I discovered over time that this was a burdensome drain on my energy, while working with clients was energizing and a welcome challenge. Once I was able to reorient my responsibilities back to my natural strengths, my career satisfaction returned. Ask your mentees to take advantage of personal assessment tools such as StrengthsFinderMyers-Briggs, the Enneagram personality assessment, and Johnson O’Connor’s aptitude tests.

Of all the ways you can spend your time, mentoring has one of the highest returns on investment. It enables you to take everything you have learned and “pay it forward,” shaping the next generation of leaders. As Harvard Business School professor Clay Christensen puts it, “The only metrics that will truly matter to my life are the individuals whom I have been able to help, one by one, to become better people.” Hall of Fame college basketball coach John Wooden once said: “Mentoring becomes your true legacy. It is the greatest inheritance you can give to others. It is why you get up every day.”

By mentoring the whole person and not limiting your conversations to career matters, you will have even greater impact and will be felt by your mentees — and everyone they influence — for years to come.


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