Personal Development

How do you measure success as an executive coach?

Success as an Executive Coach

For former CEOs and business owners, an encore career as an executive coach offers a new level of fulfillment and satisfaction.

While coaching can be challenging, many Chairs have experienced impactful moments that confirm, beyond a doubt, that they’re in the right place.

We spoke with three current Chairs Ken Mandelbaum, Matt Doherty, and Dick Singer on what success means to them. They offered stories about the tangible ways they’ve helped their clients improve their businesses and their lives, and how this new career has provided opportunities for them to learn and grow.


Beyond business

Executive coaches help their clients with specific business concerns. However, The most memorable experiences often come when helping with issues beyond the office.

Ken Mandelbaum, a former retail and real estate executive, says he has helped more than one client with their marriages.

“People that I’ve worked with have told me I’ve saved their marriage,” he says. “Those are the kinds of things that make the work I do as enriching as it is.”

Another profound moment occurred when one of Mandelbaum’s clients, who was adopted as a child, shared that he was thinking about contacting his birth mother. Mandelbaum and his group helped him work through his fears surrounding the situation.

When the client finally did reach out to his mother, “She said, ‘Every single day for the last 35 years, I’ve hoped for this call.’ A whole new world opened up for both of them.”

Matt Doherty is a former men’s college basketball coach who led teams at the University of Notre Dame and the University of North Carolina. Over the years, he’s helped clients navigate through the rough patches of working with family.

Doherty says he has “a good number of people that are running family-owned businesses. So, they’re taking over for a father, or they may be handing [the company] off to a son or daughter.”

When struggles arise in these situations, Doherty tells them, “‘I’ve been there. I can help you with this. I’ll tell you the landmines I stepped on.’ I have lived through many of the experiences my members have dealt with.”

It takes a village

Dick Singer, a former radio broadcasting executive, recalls that one of his most significant moments occurred early in his coaching career. He was scheduled to attend a retreat with his peer advisory group at a ski resort near Pittsburgh.

The day before the retreat, Hurricane Ivan hit the city, causing widespread flooding. Singer knew that he still wanted to be there, even if only one other person showed up. So he and his wife made the long, treacherous trek through the flooded streets.

Most of the group members made it as well. The next morning, one member came to Singer and said he had to leave because he had learned his office was flooded.

“The whole first floor got wiped out from this hurricane. He said, ‘Some of our vehicles literally floated away.’”

Before the member left, Singer asked him to share what was happening with the group.

“Long story short,” Singer explains, “when he left that meeting, he had office space, he had computers set up, he had a place for all his employees to meet on Monday.”

The rest of the group worked together to provide space, equipment, and encouragement.

Singer thinks about this story whenever someone asks about the rewards of becoming a coach. “I tell them, you’re going to be helping business people be better business people — and better people.”

Mandelbaum has experienced a similar spirit of collaboration in his coaching groups.

“I have one member who runs a $1 million IT business. And I have other people in billion-dollar companies in the group,” he says. He describes how the IT leader recently led a group session about AI. “He just volunteered to do it, and everybody loved it!”

Mandelbaum believes that having a mix of different skill sets, backgrounds, and company sizes means each person has something unique to contribute to the success of the group. And they love helping each other.

“I find everyone that I work with is very interested in using their life for something,” he says. “It’s not just about themselves. It’s about the impact that they can have on other people.”

Self-improvement and growth

For each of our interviewees, helping clients is one of the greatest benefits of coaching. Another advantage is the opportunity to improve themselves and their lives.

Dick Singer describes coaching as a satisfying experience. “When I go to sleep at night, I sleep well because of the rewards. I’m inspired every day.”

When Singer started his encore career, he sometimes second-guessed himself, wondering if he was providing enough value.

“Over time,” however, “you see that people are staying in the group, they’re not leaving the group, they’re anxious for their one-on-one. They’re not afraid to be vulnerable. They’re not afraid to reach out and help other members. I think that begins to alleviate those self-esteem issues.”

The longevity of his members is one way Singer measures success as a coach. He has clients who have worked with Vistage for 20 years, which makes him feel proud of the value he’s providing.

For Doherty, coaching has given him “a renewed purpose and fulfillment.”

During his basketball coaching career, Doherty experienced self-doubt. “Impostor syndrome,” he describes, “you know, am I good enough? Our worst enemy is ourselves with our negative self-talk. So we all need encouragers, and sometimes we have to encourage ourselves.”

Executive coaching has helped Doherty find this encouragement for himself and his clients.

Finding success

Helping clients work through personal relationships, building a group that supports each other, and continuing to grow in an encore career — these are the experiences that define success as an executive coach.

For Mandelbaum, Doherty, and Singer, these “fist pump” moments solidified coaching is where they are meant to be.


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About the Author: Vistage Staff

Vistage facilitates confidential peer advisory groups for CEOs and other senior leaders, focusing on solving challenges, accelerating growth and improving business performance. Over 45,000 high-caliber execu

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