When I knew I was ready to be an executive coach

For many former CEOs and business owners, an encore career is the result of a sudden, life-changing realization.

One day you’re enjoying the C-suite. The next, you feel in your bones that you’re ready to move on — whether you crave more time with family or are yearning for a challenge.

Former executives Matt Doherty, Ken Mandelbaum and Dick Singer experienced such epiphanies. For each of them, a moment of startling clarity led to the exciting world of executive coaching.

If you have considered becoming a mentor or coach, are searching for an opportunity to help others or are looking for inspiration for a new direction, their insights will be invaluable. So read on!

The a-ha moment

Matt Doherty started as an elite athlete, playing NCAA basketball alongside a young phenom and future NBA legend named Michael Jordan. During Doherty’s tenure at the University of North Carolina, then-Head Coach Dean Smith led Doherty and his Tar Heels teammates through March Madness to a National Championship victory.

Decades later, when his own high-pressure career as head basketball coach at the University of Notre Dame and his alma mater, UNC, came to an end, Doherty couldn’t help but reflect on what those days and what it meant for his “leadership journey.” He was struck by the lasting impact so many of his coaches, including Smith, had had on his life. And he realized that coaching executives would empower him to take those lessons even further.

“That’s why I got into coaching,” says Doherty. “I want to make an impact.”

Ken Mandelbaum’s path was a little different. He was busy running family-owned retail, real estate, and financial services companies when he had a chance to become a seminar leader for a personal development enterprise. For a lifelong learner with a passion for education and training, the experience was transformative.

It came to him in a blink, Mandelbaum says. “My passion and my gifts were in coaching and business development—helping other companies grow.” He felt deep down that he was meant to encourage people to “see what’s possible for themselves beyond the constraints of what they were brought up to believe.”

For Dick Singer, the transition came following a successful career as a broadcasting executive. He still remembers the day in early 2003 when someone asked him if he’d ever heard of Vistage. He hadn’t, but then he researched the organization and was immediately taken with the mission. He launched his first peer advisory group for CEOs within months.

With the benefit of hindsight, Singer recognizes that coaching was a natural fit. “All the years that I was in the broadcasting industry, the thing I enjoyed doing more than anything else was mentoring people.”

A leap of faith — and determination

Swapping broadcasting, athletics, or real estate for executive coaching isn’t just a career change. It’s also a life change.

Heading in an entirely new direction can be intimidating, but Doherty, Mandelbaum, and Singer all attest that enthusiasm for coaching — along with a healthy dose of grit — can enable a late-stage job-changer to overcome nearly any obstacle.

“I didn’t have any trepidation,” says Mandelbaum. “I was absolutely clear. I could do it.” As it turns out, starting his first Vistage group was more difficult than he initially imagined but tapping “shared determination” with his clients, Mandelbaum soon adapted.

Singer also went to the well of commitment. Early on, a friend questioned what would happen if he failed. “Failure is not an option here,” he remembers saying. “If you go into something thinking ‘what if,’ then ‘what if’ is going to happen.”

Fortunately for Doherty, the initial stages of peer advisory group leadership leveraged skills he’d already built and enjoyed. “I like recruiting,” he says. “I like to sell. I like the challenge. And I like to bring a team together, then make them play as one.”

Reaping the rewards

Coming from such diverse backgrounds, what do these three executive coaches think about their choice of encore career now?

“I like the independence of it,” says Doherty. “I control my own destiny.” He describes a month-long trip to the Hamptons made possible by the flexible schedule that CEO coaching allows.

Asked the same question, Singer talks about the personal growth he’s experienced thanks to his current role. “It helped me to really pay attention, not just to what people were saying but to what they were feeling,” he shares. Even better, “It’s kept me young and relevant.”

For Mandelbaum, coaching was the ticket to his best self. “I set out to have an extraordinary life and to be someone who I’m proud of,” he says. Doherty concurs. “I was looking for a purpose. I was looking for fulfillment. And I found it.”

Paying it forward

The best part for each of these coaches is the opportunity they have to learn from and help others. As Mandelbaum explains, “You reach into people’s hearts and souls when you do really great work with them.”

Singer is buoyed by the coaching process itself. He enjoys diving deep into Vistage members’ issues, and the group sessions he facilitates evoke what he describes as “psychic satisfaction.”

In particular, he recalls working with a client who was declaring bankruptcy. Because Singer’s own life had changed directions, sometimes in ways beyond his control, he could provide perspective. “I could really empathize with what he was going through,” Singer explains. “I said, look, you’re going through a tunnel here, but you’re going to come out the other side. You’ll survive and learn from this.”

Mandelbaum has also been called on to help clients through difficult transitions. He’s recently been guiding a physician who felt he had lost his sense of purpose. As a coach, Mandelbaum helped him explore possibilities outside his profession, encouraging the client to ask, “What could be my natural self-expression beyond practicing medicine?”

The decisive moment

Eruptions of clarity like the ones Mandelbaum, Doherty, and Singer experienced are a gift, but the life transformations they’ve since enjoyed didn’t come free. To fully realize the vision took years of hard work, self-reflection, and a willingness to learn some things and let go of others. But all of them agree, they wouldn’t turn back if they could.

When your “a-ha” moment comes, here’s hoping you grab on tight.

Related Resources

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