The Creative Coach: Starting & Maintaining Executive Peer Groups

Episode #1051: In this episode of the Arete Coach Podcast, Severin Sorensen interviews Cindy Hesterman, a Vistage Chair and recipient of the 2004 Vistage Robert Nourse Chair of the Year Award and 2013 Red Scott Award. Severin and Cindy discuss how one question led Cindy to a legacy of executive coaching, the power of curiosity, financial literacy, and managing peer groups. Continue reading for a discussion on creating powerful peer groups and coaching with creativity.



About Cindy Hesterman

Cindy Hesterman is a Vistage Chair and recipient of the 2004 Vistage Robert Nourse Chair of the Year Award and the 2013 Red Scott Award. She has been an executive coach for 19 years with Vistage Florida and currently works with CEOs and other top executives in the Tampa, Florida area.


Cindy facilitates three Vistage groups and has approximately 50 one-to-one executive coaching sessions each month. Prior to executive coaching, Cindy was a CPA and held executive positions such as CFO and VP of Finance and Accounting. During her time in the finance and accounting industry, she was involved in over 35 M&A transactions.


Today, Cindy is a certified Predictive Index Practitioner and has served as a trainer for new Vistage Chairs in Florida, Michigan, and New Mexico. Cindy’s passion for helping executives achieve their best, and her heart for serving others, are key to what have made her the impactful executive coach that she is today.


Key highlights

The question that lead to a legacy

Timestamp 02:33

Before entering the executive coaching industry, Cindy was a highly successful Chief Financial Officer. The company she was working with had enrolled her in TEC (now called Vistage), and eventually merged with a larger business. When the merge happened, they requested that Cindy move from Tampa, Florida to Cambridge, Massachusetts. Cindy was torn on what to do and brought the decision to her peer group. Two peer group members posed the question of whether Cindy would consider becoming a Vistage/TEC Chair and start leading peer groups. Cindy initially decided to continue her work in the financial executive industry, but decided to change course after having her first child. Since that decision, Cindy has been coaching and impacting the lives of others through her position with Vistage.

Starting the first Vistage group

Timestamp 08:18

When Cindy first started coaching and was recruiting members for her Vistage group, she and the President of Vistage Florida held a happy hour event to encourage local business leaders to join Vistage. At this event, Cindy invited several potential group members but her efforts were sidetracked by an individual who arrived at the event intoxicated. Her potential group members mistakenly saw this individual as a representation of what the values of Vistage are. Because of this, her potential members chose not to be involved with Vistage. From this, she learned that it is important to only invite those individuals who can represent Vistage well. After this event, she hired a coach for herself who helped her overcome imposter syndrome and self-doubt. She learned that her passion for executive coaching and Vistage can be a driving force for others to join her peer group.

Creating a culture

Timestamp 13:01

Cindy’s experience as a Vistage peer group member before her career as a Vistage Chair taught her the importance of carefully selecting peer group members. In Cindy’s peer groups, she has a vision for a “world class group” that is diverse and a place for feedback and learning. Keeping in mind this vision, her first Vistage group increased in numbers quickly. Today, Cindy is always actively networking and instead of placing new potential clients on waitlists, refers them to other coaches. This allows her to not only receive referrals but also give them. Her peer groups each have their own culture that changes based on the integration of new members and ideas.

From CFO to coach

Timestamp 17:42

Cindy’s previous experience as a CFO gives her great insight into the financial skills needed to run a successful business. In her coaching practice, she incorporates her knowledge of financial literacy through exercises and planning strategies that she encourages executives to participate in. One of these planning strategies she encourages her clients to participate in is a 13-week forward-looking cash flow projection. She will also ask CEOs and executive coaches questions about their dashboards and ratios to help them lead financially healthy businesses.

The knower and the questioner

Timestamp 25:17

Overtime, Cindy has learned “that it’s more important to ask the right question than it is to have knowledge of the business.” Early in her executive coaching career, Cindy tried to be an expert in all her coaching clients’ fields. However, she learned that it was more important to be curious about their business. Severin relates this realization to impostor syndrome. He states that “imposter syndrome drives you” to say, “I must be the knower.” However, Severin explains that skilled executive coaches realize “I’m not the knower. They’re the knower. I am the curious questioner…”

The Recession & COVID-19

Timestamp 27:58

During the Recession of 2008 and 2009, Cindy was coaching several executive leaders. She explains that during the recession, she went from 15 to 6 group members with some losing 90% of their revenue. Cindy shares that she felt guilty that her members were facing such financial losses. Looking back, she realizes that her guilt stemmed from not being able to “save” her coachees. During this time, a Vistage trainer in Florida recommended that she attend Vistage Boot Camp again. Doing this helped her “get out of that funk” and helped her realize that her coachees’ financial struggles were not her fault. She recognized that she was “responsible only for asking the right questions, not saving their business.” This mindset helped her as challenges from the COVID-19 pandemic arose. She shares that she “knew what could happen” during this time and focused on her responsibility to “help them,” “ask them the right questions,” “and help them explore what the possibilities are.”

The “phone factor”

Timestamp 39:47

When asked about a lesson she wishes she learned earlier in her coaching career, Cindy shares what she calls the “phone factor.” She explains this by stating that “if my phone rings and I see who’s calling and I cringe or I have negative emotion, then I recognize this is not someone I should be working with.” She uses this “phone factor” as a key indicator for the health of her groups and whether or not someone would be a good fit for her peer advisory groups.

Creating and maintaining groups

Timestamp 41:12


It is important to be selective when creating groups. Cindy states that “if your gut is telling you that something’s not right, or if you just have this hesitation about how they’re going to fit with you or with the group, then listen to your gut and don’t bring them in.” She also recommends that “the minute you start feeling” a peer should leave the group “do some exploration” and start “asking questions.” Severin agrees with Cindy’s perspective and shares a story of his own experience removing an individual from a group. In response Cindy shares that “if you don’t envision 10 years from now that this group is still a great dynamic, then don’t bring in that person that you think is going to disrupt it.”


When leading and maintaining these groups, peer group members will occasionally seek to hire each other or invest in each other’s companies. Because of this, both Cindy and Severin have their own unique policies for addressing these situations. One of Cindy’s policies is not allowing employees from the same company join her peer executive groups. This protects the group dynamic of learning and development that she has created within each of her groups.

Identity and destiny

Timestamp 51:54

Cindy’s why is rooted in her identity and destiny. She shares that her identity “is to be a caring and trusted leader” and that her “destiny is to lead workers and impact many others.” Because of this, her “why” or the driving force behind her coaching is the positive influence she can have on others which, in turn, creates a positive ripple effect of the influence they can have in their own circles. Her passion for helping others is greatly evidenced by her best day ever as a Vistage Chair: when she received the Red Scott Award. Before Red Scott’s passing, he was a mentor to Cindy. He decided that he wanted to create an award for servant leadership so that he could leave behind a legacy. Before his passing he named the first two recipients. One of these recipients was Cindy. Cindy also shares a quote from Red Scott titled “To Leave a Legacy.” This great award is testament to the servant heart and genuine care that Cindy has for the executives she coaches.

Curiosity and creativity

Timestamp 56:11

When asked what has made her a difference-maker in the executive coaching industry, Cindy shares that her curiosity as a coach has driven much of her success. Since she was a child, she was curious, and this carried into her adulthood. Her curiosity has also helped her as a CFO by instilling questions such as “what company could we acquire” and “what could we do differently?” Today in her coaching, she uses her curiosity to ask powerful questions such as “what could this business be that’s different?” Cindy is also very creative. She states that she is known as a “creative chair” who will “try almost anything.” Cindy loves “bringing in construction paper, crayons, and pictures, and having people do all kinds of imaginative things” during retreat sessions to bond her groups together.

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