From Start to Legacy: Reflections on Starting Executive Peer Groups & Career Learnings

Episode #1019: Creating your first Vistage peer group, confronting correlations between a client’s personal and professional life, the Five Minute Journal, and the importance of financial literacy among CEOs are just a few of the many topics discussed with Phil Holberton, an executive coach, Vistage Chair of 8 years, and instructor of organizational leadership at Brandeis University. Continue reading for inspiration from an executive coach who has faced some of life’s most challenging circumstances head on with determination and grit.



About Phil Holberton

Phil is an executive coach, Vistage Chair (of 8 years), instructor on organizational leadership at Brandeis University, and mental fitness coach. Phil’s journey to executive coaching began in his early career as the Chief Financial Officer for a number of private and public companies including Cambridge Neuroscience and General Cinema Theaters. In 1996, Phil started his coaching practice and thereafter became a Vistage Chair in 2012. Phil has served as Vice Chair of the MIT’s Enterprise Forum and is a past President of Boston’s Financial Executives Institute. Currently, Phil manages his website speakingofleadership.com and serves as a Vistage Chair.


Phil found his passion for coaching through his experience helping students with their acceptance speeches and engaging in a CEO peer group. After a peer group leader asked Phil to sub for him, Phil realized executive coaching might be a career of interest to him. Since then, Phil has maintained a thriving executive coaching career that embodies his passion to help people be the best they can be. With his experiences as an executive coach and peer group advisor, Phil offers great insight to the executive coaching profession.


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Key highlights


Phil’s journey from CFO to coaching

Timestamp 01:57


Phil Holberton began his career as a CFO. When asked how he moved from his financial career to executive coaching, Phil shares three turning points. The first was a story of his own experience helping a CEO who was in the process of getting terminated. In this story, Phil was able to help the troubled CEO address the problem at hand and create an impactful severance and retirement package. The second turning point came from an opportunity helping students with their acceptance speeches which gave Phil insight into what coaching would be, and feel, like. The final turning point was when Phil was asked to be a substitute leader of a peer group, which spurred his interest in the role of an executive coach and Vistage Chair. Since then, Phil has continued to be a lifelong learner, helping others become the best version of themselves.


Starting your first Vistage group

Timestamp 09:49


Severin and Phil reflect on the process of starting their first Vistage peer advisory groups. In Phil’s journey, he was requested to take over another chair’s peer advisory group and combine it with his newly started group. This combination did not bode well for Phil, however he learned that it wasn’t about him as a coach, but about the customs and culture of the previously coached group as a whole.


Severin, in response, reflects on the time needed to begin starting a Vistage group and quotes Conrad Prusak’s metaphor as he related starting a group to starting a fire in a blizzard. Phil and Severin compare the volume of individuals who eventually joined the group and attended luncheons versus those who did not.


Financial literacy

Timestamp 19:34


In discussing Phil’s time as an auditor, Severin asks about his findings on financial literacy among CEOs and key executives today. Phil responds by stating that while it depends on the company, most of the businesses he coaches have CEOs with little knowledge about the details of finance or financial literacy. Severin relates to Phil’s findings by sharing times he reviewed the basics of financial literacy with some peer advisory groups.


Phil comments on CEOs who are new to the financial side of running a business and states that they need additional direction at times. Both Severin and Phil explain how it is important to have a curious mind and how this helps coaches be lifelong learners which ultimately helps their clients in situations where they need additional guidance.


Covid-19 and looking forward

Timestamp 24:16


The Covid-19 pandemic empowered Phil to look at his practice and how he works with his executives. Phil states that many of the business leaders he works with cannot wait to “go back to the way” they used to do business pre-Covid. Phil believes there is no going back to the former way of working, there is only going forward. While the workplace might begin to incorporate aspects of the pre-Covid environment, it will never be completely the same. Throughout the Covid-19 pandemic, Phil has supported the need for a positive mindset in his app the “Five Minute Journal.” This app allows users to post three gratitudes, a picture, and three goals they want to accomplish. Phil states that his app has helped him get his day started with a better mindset and encourages others to do the same.


The need for a “why”

Timestamp 32:03


When asked what his “why” is, Phil shares his desire for everyone he interacts with to become the “most awesome human being and person that they are able to become.” In his experience with key executives, Phil has realized that many leaders do not have their own “why” or reason for creating a product or service. Phil states that leaders need to have an emotional appeal to what they are doing to support the pursuit of their highest potential.


A balanced perspective

Timestamp 36:24


In Phil’s executive coaching practice, he isn’t afraid to ask how his clients’ personal lives are going. By gaining insight into all aspects of a client’s life, Phil is able to understand the potential challenges they face. Phil explains the need to understand the state of his executives’ personal lives by sharing an example from his own personal life. When the home life of an executive is riddled with troubles, it is likely that their effectiveness at work is reduced. Helping his executives confront potential correlations between their personal and work lives, and guiding them to the correct resources, is vital in Phil’s executive coaching practice.


Quotes and determination

Timestamp 40:15


Phil’s favorite quote, “A journey of a thousand miles begins with one step,” comes from his experience recovering from a major seizure. After three years of personal training, three days a week, Phil has been able to complete squats with 80 lbs. Phil’s determination and grit is displayed in his recovery from the seizure. Related to this great feat of determination, Phil also shares a quote that he likes to use: “Leadership is a contact sport. Get out of the stands. You get in the game.” Phil believes that in order to be an effective leader, executives must know the ins and outs of their business and remain in a state of emotional stability to “get right in the game.”


The expanding coaching industry

Timestamp 48:10


As the coaching industry develops with no licensing requirements, Phil has noticed the importance of putting guardrails up to prevent poor coaching practices. Phil also states that many believe coaching is currently an elitist sport focused only on executive teams and senior members, and that this could likely change. Introducing executive coaching to schools and other organizations has increasingly been seen as a possibility for the executive coaching industry.


A legacy of grit

Timestamp 49:48


Phil wants his legacy to be one of great impact that can be passed on to future generations. Currently, Phil is interested in writing a book about “becoming an awesome human being” that may cover his own experiences and research. In reflecting on his legacy, he shares his experience abandoning alcohol and smoking as a medication. Phil displays a great amount of determination and grit as he shares these stories. Phil states that part of his success in breaking his addiction was to “just do it” and face the challenge head on with determination and grit.





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