How to Be a Better Mentor


A mentor’s job is to foster one-to-one relationships that challenge people to rise to higher levels of competence and responsibility. This article discusses three key characteristics of an effective mentor:


1. An effective mentor asks challenging questions that help people expand their scope of responsibilities.

2. An effective mentor is highly connected to the person being mentored.

3. An effective mentor challenges others with penetrating insights.


Most firm and organizational leaders see the value of mentoring. But mentoring is often narrowly viewed as supportive or educational rather than as a vehicle for delivering accountability and driving performance. The idea, for example, that mentoring is a way to challenge a young estate tax expert to grow into someone who brings in new clients is not well understood. Mentoring is commonly tepid and sparse, making brief appearances during reviews that are predictable if not superficial. But with practice, effective mentoring can become a strong foundation for every firm’s growth and success.


When Kevin Corcoran stepped into his role as CFO of VWR Education LLC, a scientific education products company based in Rochester, N.Y., he did not know anyone on his management team, including his own boss. He needed to be able to connect with his team quickly, and they with him, in order to become, and execute as, a strong leadership team. Fortunately for Corcoran, the senior management team had recently implemented a program to help its leaders become better mentors. The immediate goal was to improve communication and strengthen the connection among the leadership team members. Two years later, stronger mentoring has delivered much more. It has become part of a culture of accelerated professional growth where leaders challenge their top talent in regularly scheduled coaching sessions that are based on open discussions and yield tangible results.


The notion that mentoring wastes time is false. It is a productivity accelerator. Effective mentoring grows responsible employees and frees up the mentor to perform higher-order duties, such as developing new business. “I don’t have time to mentor” is usually a cover for “I don’t know how.” The leader who allows this mentality to prevail is choosing comfort over progress.


Firm leaders should determine which of their tasks bring the most value to the business and draft a “stop doing” list, which includes responsibilities that will be transferred via mentoring. The road to a stagnant firm is paved with the phrase “It’s easier if I just do it myself.”



One of the most important elements to a strong mentoring relationship is not giving people answers. Exceptional mentoring is more concerned with teaching people how to think rather than telling them what to think.


“You don’t realize how good some professionals are until you put yourself in a conversation where you’re discussing weaknesses and deficiencies. Voluntarily walking into your boss’s office to openly discuss your shortcomings seems counter- intuitive but it can lead to an incredible depth of learning and understanding,” Corcoran said.


The “answer guy,” who knows the business top to bottom, spending all day dispensing water from a well of technical expertise, is the antithesis of a mentor. No one has to do any thinking in his presence. He complains that people are too dependent on him for answers, without seeing that he keeps it that way. He suffers from the “I know” syndrome.


The best cure for the “I know” syndrome is to practice the art of “mentoring questions.” Mentoring questions make people think. For example, when asked about how to respond to a demanding e-mail from an important client, a mentor might ask, “What do you think is the best way to handle this?” The question is not rhetorical, or a pop quiz with one right answer. The mentor is genuinely interested in the other’s thinking. Such questions send an important accountability signal: You own this problem.


“I can have direct and candid conversations with my boss, and I’m not worrying about his motivation when we’re having a ‘mentoring’ conversation. He puts new challenges in front of me to consider, but he doesn’t make the decision for me. That is my responsibility. I’m also encouraged to offer new ideas to improve the business. It is all about trust,” Corcoran said.


Here are some other examples of mentoring questions:


  • “Are you interested in carrying the ball on something new?”
  • “Do you believe you have a sufficient grasp of the regulatory environment in this situation?”
  • “How would you evaluate your options?”
  • “Is there a better way to do this that we haven’t considered?”



Technique: Question Counting

In your next one-on-one with a direct report, try keeping a “question vs. answer tally” on a pad during the conversation. Two out of every three sentences a true mentor utters are questions. Many who try this are surprised by how few questions they ask.




Great mentors have a person-to-person connection with those they are helping to develop. They let people inside their heads, sharing their visions and passions but also their strategic concerns and dilemmas. Those around them feel “in touch” with the person behind the suit. They tell stories about their own professional development, making it clear that growth is expected.


When Corcoran’s organization started delivering more vigorous mentoring/ coaching to the next level of staff members, he allowed himself to be coached by one of his direct reports in front of his entire finance team. It was not rehearsed. The direct report “went down a path of asking some pointed questions about a position that I had taken. I put myself out there in front of a lot of people who work for me. It was a very powerful teaching and learning experience. It would be very difficult for me to subscribe to mentoring if I’m not willing to do it myself,” Corcoran said. “After that experience, mentoring became an important part of our team’s operating culture.”


Effective mentors are on a mission to know more about their people. They make the most of time spent traveling or lunching together by asking questions like “What are your most challenging business relationships?” and “What projects are you most excited about?” They foster innovation by asking “What skills do you have to offer our firm that we aren’t currently tapping?” Thinking out loud with a mentor allows strategic thinking to emerge.


A mentor’s job is not to “fix” frustrations and concerns, but it is absolutely his or her job to find out about them. “From a coaching view, you are more curiosity-driven; you’re going to encourage the coachee to think for themselves instead of follow. The conversation should be about the person who is being mentored and encouraging them to think imaginatively and creatively about other possibilities or about their role in a situation or problem,” Corcoran said.


Strong mentors are free of the illusion that they must have all the answers. They know that self-confidence grows when people overcome obstacles themselves, not from extra support. Mentors expect discipline, but foster an atmosphere of adventure and creativity.



When a connection is established, the door to challenge automatically opens. But many leaders hesitate to walk through. Great mentors keep people on their toes. A junior partner at one of my client’s firm was frustrated when he approached a founding partner about the problem of being stuck in the weeds. “The new generation hasn’t stepped up,” he complained. The founding partner responded with a clever question: “Do you think of yourself as a victim here?” The junior partner was stopped in his tracks, and it got him thinking. “How good are you at building a strong team?” the founding partner calmly but pointedly asked. She had the gumption to shake up the junior partner’s thinking. Mentors act that way. They develop penetrating insights about the professional blind spots of those they want to develop, and then challenge people to face them. Along with technical and business skills, they pay attention to people skills. Whether a talented team member is hesitant or arrogant, clumsy-with-ambition or talented-but-lazy, true mentors skillfully put what they see on the table.


Great mentors “go for it” when it comes to giving people all the insight they have in the service of professional growth. The question: “Do you want to know what I think about you?” is not out of bounds. Subordinates are wondering anyway, and they will make up the answers if they are not hearing them directly. True mentors are blessed with the opportunity to evaluate how various team members respond to this level of challenge. The most mature rise up to meet it; the least mature can’t handle it.


“We face challenges every day in the accounting profession. Mentoring provides a path to personal growth, professional development and self-discovery that helps us face those challenges. With mentoring, we are prepared to confidently tackle the difficult issues that come our way,” Corcoran said.



The value of challenging insights is enhanced by humility. One great mentor was known to say, “I’m not the sharpest guy when it comes to client relations, but here is what I see when I watch you operate.” He would then add, “Is there anything in what I’m saying that could help you, or do you think I’m off track?” If a mentor has shared his or her own flaws, and efforts to mature as a professional, penetrating feedback is less likely to be taken personally. What is more likely is that the mentor’s value will increase exponentially. A top performer in one of my client firms, who is receiving great mentoring, said, “When I get approached by other firms, I think to myself, ‘This kind of relationship is hard to replace.’ ”



The biggest hurdle is making mentoring a priority. For a simple test of your mentoring, look at yourself. Do you have a challenging mentor? Do you meet regularly with your mentor to discuss growth, not projects? What would it take to make that happen? The best way to learn to be a better mentor is to have one yourself. If you have a boss, ask him or her for more-challenging mentoring. If your boss can’t deliver it, find someone who can. If you are a firm leader, consider hiring a professional who can “mentor the mentors,” holding them accountable for starting a cascade of better mentoring throughout the firm.



Who Should Mentor?

Mentoring is most fully leveraged when the mentor is the boss. In firms without clear lines of reporting, it remains ideal for the mentor to have a direct influence on compensation and advancement. This allows mentoring to become a forum for generating tangible deliverables that are tied to compensation. This is more important than other factors worth considering, such as shared career tracks, interest in mentoring, and personality traits. A skilled mentor can offer value to any willing employee.




  The purpose of mentoring is to grow responsible team members, freeing leaders to perform higher-order tasks.


  Effective mentoring drives performance by strengthening accountability.


  A strong mentor avoids perpetually giving answers; instead he or she asks “mentoring questions” that challenge people to own tasks, and expand their capacity.


  An effective mentor has a person-to-person connection, telling stories of his or her own professional development and getting to know his or her team members’ goals and challenges.


  A strong mentor should be skillfully challenging. The growth of the person being mentored is a higher priority than his or her personal comfort. The mentor should “go for it” by sharing penetrating insights.


Erik Thompson ( is a licensed psychologist and founder of Thompson Leadership Development Inc., in Burlington, Vt.


To comment on this article or to suggest an idea for another article, contact Loanna Overcash, senior editor, at or 919-402-4462.





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