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Three Best Practices for Mentoring

Updated: Nov 11, 2020

The follow is a blog written by Rick Woolworth, (Yes, those Woolworth’s!) Rick left Wall Street decades ago to promote mentoring of men. It’s long, but well worth the read.

Mentoring becomes your true legacy. It is the greatest inheritance you can give to others. It is why you get up every day. – John Wooden

Most mentors are well-intentioned, but not intentional about growing their mentoring skills. Whether you are currently engaged in mentoring or intend to do so in the future, you can be a great mentor with impact that lasts decades. Three best practices can elevate your mentoring to a whole new level — sharing stories, mentoring the whole person, and integrating mentees into your network.

My views on mentoring are the product of more than 1,000 hours of mentoring conversations over the past 10 years. After a 35-year career on Wall Street, I “pro-tired” (I don’t believe in the concept of retiring) and founded a non-profit named Telemachus. Our sole mission is to mentor emerging leaders ages 25 to 40 through facilitating one-on-one mentoring relationships, conducting workshops, and hosting an annual conference.

A few great mentors shaped my character and life trajectory. Without their influence, I am certain I would not be enjoying a fulfilling “encore career” and a marriage of over 40 years. Recently, my wife (Jill) and I were Fellows for 18 months at Stanford University’s Distinguished Careers Institute where we were full-time students in class alongside undergraduate and graduate students. This experience provided opportunities to mentor students as well as a close-up view of millennial culture.

1. Share Your Stories If you want to know what’s ahead, ask the people coming back. – Chinese Proverb

Whenever I meet with a younger person for the first time, I say: Tell me your story. Start at the beginning and take your time – you have 20 or 30 minutes. I may ask a few questions, and everything you say will be confidential between us. When you’re finished, I will tell you my story, if you want. They always want to hear my story.

This simple practice can transform the trajectory of a mentoring relationship. You will move to a whole new level when you ask questions like: Tell me about your relationship with your father and your mother. What did you love doing in high school? What would you have done differently if you had the chance? It is a privilege to be given this window into another person’s journey during the first meeting. Over time, it also allows you to ask pertinent questions with knowledge about their past.

When I tell my own story, I make sure to describe one or two of the difficult chapters from my work life and marriage. By doing this I am signaling that all aspects of our lives are on the table, enabling us to get more quickly to the issues my mentee is facing. What follows are helpful approaches to use when you share stories.

Humanize yourself. One of the many benefits of sharing stories is that it levels the playing field — you are humanized. The younger person has likely placed you on a pedestal given what you have accomplished in your career and personal life. You are right-sized when you tell your story. As well, you normalize the struggles they are facing and may encounter in the future.

Be authentic. Millennials highly value authenticity and “straight talk,” while disdaining hypocrisy. It is important that you be authentic in recounting some of your past struggles and challenges. By doing this you are establishing the norms and “culture” of your future interactions; your mentees will feel more at ease sharing their issues when you set the example. An illustration of this was when I met with a female graduate student while at Stanford. After I told her about some difficulties Jill and I had earlier in our marriage, she felt comfortable enough to begin talking about her marriage and her distress that her husband had moved out the previous weekend.

Take notes. It may feel awkward at first, but nearly every time I share stories with another person I ask if I may take some handwritten notes while we talk. If I have the privilege of people sharing their journey with me, I owe it to them to remember key details, especially when they describe some of their past or current struggles. The system I developed is to copy my notes into the Contacts app on my iPhone or computer, along with the date. The next time I talk with this person, even if it is three or six months later, I have instant recall of what we discussed. I can then ask questions like Tell me about that demanding manager who was making your life miserable or How is it going in your marriage with the in-law problem you talked about last time? I assure you this will differentiate you from 99% of other mentors and is a disarming expression of how serious you are about helping your mentees with their personal and professional challenges.

Why sharing stories is essential. The importance of sharing stories came home to me 10 years ago when I met with Bill George, a top professor of leadership at Harvard Business School, former CEO of Medtronic, and bestselling author of True North. He emphasized that sharing stories is an essential practice in HBS’s Executive Education programs. Midlevel leaders from companies around the globe come to HBS for three months and are assigned to small groups. Bill noted that the critical factor determining which groups thrived was whether or not all members followed the program’s recommendation to share their personal stories for 30-45 minutes. No shared stories led to weaker group dynamics.

Sharing stories will differentiate you from the vast majority of other mentors. How many younger people have been asked this by someone older who was intently listening and able to recall what they said months later? You are signaling early on that you truly care and are there to help them on their journey.

2. Mentor the Whole Person We’re here for a reason. I believe a bit of the reason is to throw little torches out to lead people through the dark. – Whoopi Goldberg

Most mentoring today is focused on issues related to career advancement. While work is obviously an important part of a mentee’s life, there is so much more to explore as your relationship develops. Your mentees are like an iceberg — limiting your conversations to their careers is only dealing with the portion above the water line. Mentoring affords you the opportunity to get to know the whole person so you can help them flourish in all aspects of life for years to come.

Type in “mentoring” in the Books section of Amazon and you will find that most of the books have a career orientation. During our time at Stanford, I spent two hours with a research librarian in the University’s library. We discovered that the majority of the articles, studies and books on mentoring focus on how it is practiced in the workplace. As well, there is much written on administering mentoring programs in both for-profit and nonprofit organizations. In contrast, remarkably little can be found on mentoring the whole person and best practices for how this is done.

A holistic approach is one of the beauties of mentoring and differentiates it from coaching, which tends to focus on developing a particular skill or enhancing performance. Why not open the aperture of your conversations to potential topics like your mentee’s key relationships (whether single, married or in a partnership), parenting, health, finances, or spiritual life?

Here are some practices for mentoring the whole person.

Ask great questions. Effective mentors develop a storehouse of probing questions on any number of subjects. These questions are the portal to expanding the dialogue into many aspects of your mentee’s life. Examples include:

  1. Who has been most influential in your life other than your parents?

  2. What keeps you up at night?

  3. Can you see yourself being stimulated and fulfilled on your current career path for the next 5 years?

  4. On a scale of 1 to 10, how would you rate your marriage relationship right now?

  5. Were you raised in a particular religious tradition?

  6. What do you do to “reboot” so that the busyness and tech overload in your life does not result in burn-out?

Teach them how to fish. A Dallas-based businessman named Bob Buford was my most valuable mentor over a 25-year period. Bob was a master at asking insightful questions and giving concise advice. At one stage in my career I was struggling with work issues related to a difficult boss. I was hoping he would tell me what to do. Instead Bob asked a series of questions that enabled me to identify the real issue and come up with a course of action on my own. As we finished the meeting he commented, “You just needed to talk out your confusion.” Bob was teaching me how to fish by not providing the fish. Note that an added benefit of this questioning approach is that it prevents mentors from talking too much and readily providing solutions.

Start with the end in mind. Perhaps the most important question you can ask a mentee is: What is success? Long-term success? If you don’t do this early on in your mentoring conversations, it is like sailing a ship without the ultimate destination in mind.

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.

Without starting with the end in mind it is possible to give a mentee good career advice that is poor life advice. If a seasoned lawyer is advising a new associate fresh out of law school how to climb the ladder to partner, she may tell the associate to work 70-80 hour weeks on a consistent basis: Turn the lights on in the morning and off at night. Billable hours are the currency of a law firm. If this mentor fails to ask the young lawyer about his long-term life goals and about key aspects of his life such as his marriage, parenting, health, etc., the senior lawyer is implicitly making the assumption that career and financial success are this new associate’s most important objectives in life.

Unpack your mentee’s “toolkit.” A valuable area to explore is your mentee’s innate gifting, 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 mentees 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 professionals in our group alongside my client work. I discovered over time that managing a large group of people drained my energy and was a burden, 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.

Asking your mentee to take advantage of personal assessment tools such as StrengthsFinder and Myers-Briggs can provide constructive insights into their makeup. Other excellent tools are the Enneagram for personality assessment, and Johnson O’Connor for aptitude testing.

Why using a holistic approach is important. Kate was a new mentee. During our second meeting she began telling me how unhappy she was working at a top consulting firm logging 70-hour weeks and leaving no time for her personal life. I began probing her upbringing and asked about her relationship with her parents. Several minutes later 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 who had rarely affirmed her. By exploring Kate’s life beyond her work life, she left our lunch with new insights into her motivations as a high achiever. She is now much happier working fewer hours, yet still a highly regarded consultant.

3. Introduce Your Mentee To Your Network The best way a mentor can prepare another leader is to expose him or her to other great people. – John Maxwell, NY Times best-selling author on leadership

One of the greatest gifts you can provide your mentees is introducing them to your network of key relationships. This takes little time yet can have enormous impact — in some cases it can be life-changing. Your mentees will benefit from diverse perspectives on various aspects of their lives, including work, relationships, values and world view.

As individual mentors we only have our own set of experiences to draw from. In my case, I am a white male who has only worked in finance in New York, been married over 40 years (although I often punctuate that by saying I am in my fifth marriage to my first wife!), and have a Christian world view. Introducing mentees to my network allows them to develop over time a portfolio of advisors who can offer different viewpoints on subjects ranging from career choices and leadership development to sensitive personal topics like money, in laws, and sex. In addition, these other advisors often reinforce a theme or course of action that I am advocating to my mentee.

Here are some ways to open up your network to your mentees.

Connect them with trusted work colleagues and professional contacts. Whether you are actively engaged in your career or have moved to a new chapter, you are sure to have a work colleague or two for your mentee to meet. One former colleague still thanks me for introducing her to one of my mentees. She ended up hiring him and he became an integral part of her business. I connected another mentee, who was finishing her MBA and considering a job offer from a private equity firm, with a friend who was a senior woman at a leading private equity firm. She was able to advise my mentee not only on the business prospects and culture of the firm making the offer, but also on navigating the challenges for women in a male-dominant industry.

Have them meet your friends and family. Why not have your mentee meet some of your close friends? One of my mentees recently moved to Austin and it was a joy for me to connect him with two younger friends as well as one in my generation. This was especially helpful to my mentee as he was trying to establish some community in a new location. When another mentee was in the midst of a painful divorce, I had him meet a peer whose first marriage had fallen apart years earlier but who is now happily married.

If you have a spouse and children, why not invite your mentee to join you for dinner and get to know you on a more personal basis? Jill and I have had countless dinners over the years with mentees (and their spouses or partners). When our daughters lived at home, we often included mentees at family dinners. Be sure to accept any offer a mentee might make for you to meet in their home. My late mentor Bob Buford did this when he was in our area and accepted our invitation to spend the night. One of my best memories was being with him at the breakfast table with our three young daughters. These kinds of interactions can advance a mentoring relationship over time to an intergenerational friendship — the most advanced form of mentoring in my experience.

Remember that most of mentoring is “caught not taught.” We have all heard that roughly 90% of communication is non-verbal. Many mentors don’t realize that their lasting imprint on a mentee is often how they conduct their life, whether at work, home or other settings. How you serve as a role model is as important as your face-to-face meetings.

There are limitless ways this modeling of behavior can happen. I was fortunate to have a college coach who for four years was a role model and mentor. I recently asked ©Rick Woolworth, 2019 7 several of my teammates to reflect on the impact “Coach K” had on them. One responded, “He inspired me every day we were together with his demeanor and how he handled life.” An example of this influence was when our tennis team was about to play another team who had two players with reputations for making bad line calls against opponents. Coach K exhorted us to take the high road and not retaliate – “kill them with kindness.” I have quoted him many times in many contexts.

Share your content. I often email my mentees articles, videos, TED talks, book titles and links to websites that they may find helpful. Think of yourself as a curator providing your mentees with thoughtful and challenging ideas and perspectives. Whenever one mentor sent me an article or commentary he had written, I dropped everything and read it. There was always a lesson or message in what he passed on. He was a merchant of wisdom.

Handwritten notes of encouragement or advice can also have a lasting impact. At one point when I was at Morgan Stanley I was grinding on a situation with a contentious colleague. I called Bob for his counsel and a few days later I received in the mail a prescription form used by doctors. Bob wrote:

Rx for personal pain: Do something for someone else. Dr. Buford

Closing Thoughts 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. – Clay Christensen, Harvard Business School Professor, Author of How Will You Measure Your Life?

Of all the ways you spend your time, mentoring has one of the highest returns on investment. By spending just small increments, you will impact the lives of your mentees over the next 50+ years. What’s more, your time investment will have a multiplier effect because these mentees will in turn positively influence their families, friends, organizations and communities. In this way you build a long-lasting legacy.

Many people today complain about the leadership crisis in our country. Mentoring is an opportunity to do something about it. It enables us to take all we have learned and “pay it forward,” shaping the next generation of leaders.

Finally, mentoring is not only wonderfully rewarding, it is one of the few things we do where we get better with age. By utilizing the three practices presented here – sharing stories, mentoring the whole person, and introducing mentees to your network – you can become a more effective mentor and have a generative impact that will be felt for years to come.

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