Why mentoring CEOs matters

No school or training program can fully prepare a CEO for the day-to-day challenges at altitude. No matter how learned or experienced, a chief executive will have times when they need someone to listen as they work through a problem or opportunity.

This is among the types of support CEO mentors Jim Walsh and Cheryl McDuffie James provide, working with company leaders in peer advisory groups and one-to-one sessions. Although both are evangelical about the advantages of mentoring CEOs, they underscore that the relationship is truly a two-way street — with the mentor benefitting at least as much as the leader they guide.

Here’s what these two former executives, now CEO mentors, had to say about the value mentoring brings to everyone involved.

1. Perpetual growth

A CEO may be at the top of the corporate ladder, but that doesn’t mean there’s no room left to grow. It can be difficult, however, to find an insightful mentor who has both the executive-level background necessary to understand where a leader is coming from, along with the coaching skill required to bring out their best.

McDuffie James offers both of these critical attributes. Although she spent much of her career working with global companies, today she focuses most of her mentoring attention on owners of midsize businesses. She finds that, with her background, she’s able to share a wider perspective than most of her clients have previously enjoyed.

“I’m able to give them some best practices and experiences they aren’t usually exposed to that are working for organizations much larger than them,” she says. ”They can use some of those same ideas within their companies, and it helps them to stretch and grow.”

Such exchanges allow a CEO mentor to pass on hard-earned knowledge. For the mentee, the interactions can be a reminder to stay curious, because as McDuffie James says, “There’s always something, whether it be a big or small nugget, that they can continue to learn — month after month, year after year.”

2. Holding up a mirror

One of the most common outgrowths of mentoring is self-awareness. Like all humans, executives sometimes get in their own way and may need help from a mentor to recognize when a problem they’re encountering actually comes from within. This realization delivers a powerful impact, explains Walsh.

“When you create self-awareness, you put someone in a place of choice. And when you put someone in a place of choice, they have control. And when you give them control, they have freedom.”

A more self-aware CEO is a wiser, more effective one. Often, all it takes to prompt a breakthrough is to hold up a mirror to the executive. “Members already know the answers to their problems,” McDuffie James remarks. “It’s just a matter of asking the right questions.”

Walsh holds the same view of mentorship. To him, it’s not about telling mentees what to do. It’s about holding them accountable for the actions they’ve chosen to take — especially when the next step goes against the grain.

More than once, for example, Walsh has guided CEOs who knew they needed to let someone go but kept putting it off because the move was highly uncomfortable. Walsh responds to such concerns by encouraging executives to be honest, respectful, and caring.

Confronting the difficulty head-on, and with their values and humanity top-of-mind is, Walsh says, “a freeing experience. And once they feel that, they no longer avoid uncomfortable situations.”

3. Mutual reward

A CEO in a mentoring relationship gains an ally, someone to help and support them without an ulterior motive. “I’m there to truly invest in them and help them with their own goals and growth,” McDuffie James shares.

How does that experience reflect back on the CEO mentor? She says that earning such a high level of trust is incredibly rewarding.

“A lot of my members don’t have someone that they can talk to. They’re used to listening to everybody else’s problems and dreams,” she says. “To be that for them is a very sacred relationship, and it’s one that I really, really value.”

Mentors are privy to CEOs’ innermost thoughts and enjoy a front-row seat to their professional and personal development. One of the biggest wins in McDuffie James’s coaching career was helping a Vistage member whose personal life was suffering because of the extreme demands his company placed on him. She helped this executive establish work-life boundaries so he could spend more time with family and experience greater joy outside the job.

For Walsh, the mentoring role is also about delivering a positive impact. By “influencing the influencer,” as he puts it, his work reaches far beyond one person. “That’s what really drives me,” he says.

McDuffie James concurs. “I can see in real time that I’m changing lives and that I’m part of other people’s lives being changed by the mentee. I see their employees and their families all reaping the benefits.”

4. The personal touch

Some of the rewards of mentoring CEOs are available to those serving as consultants or advisors, but McDuffie James and Walsh point out a key difference — the personal element. Conversations between CEOs and their mentors stretch beyond profit margins and personnel problems to delve into doubts, insecurities, and fundamental life struggles.

“I was drawn to mentoring because I get to practice the human touch,” Walsh reflects. He strives to cultivate a safe space by listening respectfully, speaking truthfully, and taking the time to celebrate wins before moving on to the next issue.

McDuffie James concurs that the rewards of mentoring come through in interpersonal connections. “The relationship that I build individually with each client helps me have a deeper understanding of who they are and what they care about,” she says.

Then there’s the unparalleled opportunity to leave a legacy. “I had a mentor, and they brought out the best in me,” Walsh says. “They helped me through some of the toughest times in my life. So for me, it’s about paying it forward.”

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