Building A “Circle of Trust”: Growth-Stage CEO Peer Coaching

Years ago, as part of an HR Master’s program, I participated in my first group process experience: a three-day offsite with program peers, highlighted by an unstructured learning journey that shed light on personal biases, conflict, the need for active listening, and understanding group dynamics. As the "organized" and “controlling” type, the experience was both highly uncomfortable but also positive and formative.  

One of my peers in the program (someone who I did not know prior to the session) looked across the circle of students and stated early on that she clearly did not like me. Her opinion was based on certain expressed observations and non-verbal gestures. While I was somewhat taken aback by the commentary, at the break I went ahead and approached her and asked why she felt the way she did. As we talked, it was clear to me that we came from different backgrounds and different life experiences; and with it, very different perspectives on the way one shows up in a group setting. As a peer coaching moment, that impromptu sidebar conversation still sticks with me to this day. It generated another level of self-awareness in me, beyond what I thought I already possessed. 

In some ways, that singular experience fueled my interest in group and team facilitation which led me to take part in, and champion, many subsequent C-level executive and team development initiatives and interventions, both as a senior HR executive, and currently as an executive and team coach.  

Last year marked the start of a new group process journey in my work with middle market growth equity firm, Edison Partners, called CEOQuarterly. The first of its kind for the firm, CEOQuarterly aims at bringing together small cohorts of portfolio company CEOs on a quarterly basis. A curated community where founders and placed CEOs can engage in a trusted and confidential space for shared learning and connection, during each quarterly session participants focus on critical skills that help one to be more situationally effective; share stories and experiences across a wide range of strategic or operational topic areas; hear from experts (some who sat in their very seat); and offer peer coaching and reframed problem-solving. 

Over time, all participants grow by leveraging the trusted relationships formed during the experience.  As process designer and facilitator — along with Casey Myers, the head of Edison’s value creation arm, Edison Edge — it has proven to be a personally meaningful experience, as measured by how everyone emerges changed for the better, despite tight schedules or ever-present pressures to perform. 

The CEOQuarterlys represent the diverse range of Edison Partners’ portfolio company CEOs: from fintech to cybersecurity to state/municipal emergency services to electronics manufacturing services… just to name a few. All but one are first-time CEOs who naturally bring a healthy dose of skepticism to the experience, with a natural expectation to secure a high-value return on their time. 

Like many peer coaching experiences, such as in-company-designed C-level leadership events, bringing together interested parties for shared learning and community building can turn magical well beyond the content. During the CEOQuarterly, highly successful and often guarded leaders become quite transparent and vulnerable, which grows over time, both within and outside the process. 

In parallel to CEOQuarterly, I help lead the investment firm’s CEO Summit, held in different locations every year. This year, using a similar “small groups learn better” approach, we put three dozen CEOs and board members through a change and transition simulation experience. In groups of five to six, we focused on highly intentional leadership, including the importance of building change agility and resilience, while learning how to gain buy-in and navigate resistance through major organizational change events, like M&A or digital transformation.  

In the spirit of shared learning, here are three critical takeaways should you consider a similar process of small group executive-level interventions like CEOQuarterly: 

1. Set a tone of personal ownership. Successful C-level peer-based interventions require participant ownership around both content and process. By co-designing the experience with the peer assemblage from the outset, participants are well aware that their engagement will generate greater value in support of each other, both individually and as a group.
2. Group dynamics matter. Create group norms from the very start. Consider a cohort’s “purpose”. Create an environment where individuals can be fully authentic and honest about what they’re facing. Peer coaching that works often involves participants playing multiple roles which include sounding board, observer, mirror, reframer, challenger, and supporter. Through in-depth storytelling, participants become more open to helping one other and learn about their own strengths, weaknesses, and need for adaptive behaviors.
3. Be ready to pivot. Planned agendas can change as quickly as the respective businesses the individual participants are leading. For example, at a recent CEOQuarterly session, we had a clear idea and plan for the sequencing and nature of events. However, several CEOs conveyed they were experiencing parallel and serious business turbulence. As a result, the session turned into a coaching, reflective, and reframing exercise, guided by such timely discussion topics as:

• YTD progress against forecast and overall plan for 2024? Successes? Failures?  

• What at-once decisions need to be made before the year is over that could have a material impact on the business (i.e., strategic, talent, financial)? 

• Unforeseen or known challenges to be addressed in 2025 planning?  

• How to best leverage the capabilities of your Executive Leadership Team? 

• In what ways can you function as your best self as a CEO? In what ways can or could you do better?  

The journey of a growth-stage CEO can be a lonely and isolated one, under pressure to grow and meet investor and board expectations, even with resources provided by PE sponsors. Making the journey a collaborative and shared experience and building a true “circle of trust” among peers can be a game-changer, and can illustrate and uphold the value that a small, powerful, and trusted peer community can deliver.