Share
Facebook Facebook icon Twitter Twitter icon LinkedIn LinkedIn icon Email

Coaching Corner

Letting go to grow: How one entrepreneur reclaimed his life and business

Published 9 May 2025 in Coaching Corner • 5 min read

In our Coaching Corner series, we share real-world coaching cases that come from our work with leaders.

The challenge

Frank has enjoyed tremendous success as an entrepreneur. A few years back, he decided to sell his latest venture and retire from starting up, preferring instead to use his capital to invest in new businesses. In total, Frank has now invested in six fledgling ventures, but things have started to unravel. Discontented with the performance of some of these companies, Frank has stepped up his role from angel investing and advisory support to a more hands-on approach. In fact, acting as CEO, Frank has effectively taken over at the helm of at least four companies.

This is not a sustainable situation. Stretched beyond his energy and capacities, yet feeling unable to relinquish full control, Frank is coming into conflict with his six CEOs. The performance across the portfolio of companies is in decline and revenues are starting to fall. What’s more, Frank’s family is complaining. What was supposed to be a chance to spend more time with loved ones has instead become the busiest and most stressful period of his professional life.

Feeling torn in multiple directions and faced with the possibility of all six of his investments failing, Frank decided to seek out support from an executive coach.

Frank's coach offers him a session on the move – in a chauffeur-driven vehicle that takes in the sights and sounds of Frank’s home city

The coaching journey

Frank’s coach suggests an interesting and somewhat novel approach. Instead of meeting in an office or over lunch, he offers Frank a session on the move – in a chauffeur-driven vehicle that takes in the sights and sounds of Frank’s home city. This literal coaching journey gives Frank an opportunity to move through the different districts of the city – the iconic places of his childhood and adolescence – to spark memories and key moments that may yield key insights into the way he thinks and operates.

In their first session together, they passed several sports arenas where Frank had participated in team activities as a young man. As they pass one of these spots, the vehicle accelerates powerfully, and Frank is jolted by a memory of car racing. Questioned by his coach, an interesting and important idea begins to emerge. Frank is urged to recall his experiences both as a car racer and in team sports. Revisiting these formative episodes, a few things occur to Frank that prove helpful. First, in conversation with his coach, he remembers an experience of goalkeeping in a competitive sport as a young man. Probed further, he recalls the way that his fellow team members would rally to protect the goal whenever it (and he) came under attack. Frank’s coach invites him to consider whether the same dynamic could extend to other sports of his youth. Frank responds that in Formula One racing, while the racer is the star performer, without a dedicated and talented team, there would be no wins or successes. This is a breakthrough moment for Frank.

From here, he and his coach work together across successive sessions, exploring the importance of the team. Specifically, Frank’s coach invites him to ponder the role of teamwork in the success of the businesses he has founded over time. He is also challenged to think about the companies that he is invested in: when Frank takes over the reins of these firms, what does it mean for the incumbent CEOs who also want to be the star performers of their organizations?

Yoking this to Frank’s experience in racing, he agrees that success is unattainable if there are too many hands on the steering wheel. Meanwhile, Frank’s family has signaled that if he is not physically with them, he is failing to be part of this important team too.

Frank organizes a regular bimonthly meeting with each CEO, however, these meetings take place over dinner and Frank is purposeful in limiting his role to listening and advising.

The impact

Encouraged by his coach, Frank develops a focused plan for his leadership. Concretely, he makes time to garner feedback from the CEOs of his companies and his family, and to pinpoint those moments when he steps in and oversteers the team (and fails to be part of the team and part of the negotiation) in his habitual pursuit of protagonism. Over time, these feedback sessions yield invaluable insight into behaviors that had been subconscious; controlling behaviors that may once have yielded positive results but have over time become a form of micromanagement.

Armed with these new insights, Frank makes a bold and purposeful decision. He sells his shares in all but the two companies that represent the most promising and interesting ventures. From here, Frank organizes a regular bimonthly meeting with each CEO, however, these meetings take place over dinner and Frank is purposeful in limiting his role to listening and advising when asked to do so. He has taken the bold step of banning himself from the office.

Frank has managed to take a step back and hand over the running of both organizations to their respective CEOs and dedicated teams, and as a result, both businesses are thriving. He has embraced his role as an important and valued member of the team – not the star protagonist. This decision has not only given him a sense of liberation, but time and space to be with his family and take pleasure from the other areas of his life that he had earmarked for a fulfilling and enriching retirement.

Questions to ask yourself:

  1. Do you struggle to delegate? If so, how does it make others feel and respond?
  2. Do you value and understand the role of other people in a team, or do you prioritize protagonism?
  3. What could you do to step back where necessary and empower others to perform?

In this series, we share real-world cases that come from our work with leaders. Read on to discover the specific challenges that face each of the leaders we have coached – and the insights that have helped them navigate their multifaceted challenges to find their own solutions. How might these insights and questions apply to you?

 

Authors

Vincent Pieterse

Executive coach, leadership expert, and author specializing in leadership and organizational culture

Vincent Pieterse is an executive coach, leadership expert, and author specializing in leadership and organizational culture. With 40 years of experience spanning corporate, academic, and entrepreneurial sectors, he brings profound expertise as a coach, educator, and researcher.

Pieterse’s approach is rooted in social constructivism, viewing leadership as shaped by social interactions including thoughts, language, attitudes, behaviors, identities, and group culture.

Drawing inspiration from art and language and with a PhD in business administration, he emphasizes “naming” challenges to shift perspectives, helping leaders see obstacles differently and develop innovative solutions that integrate theory, strategy, and practice.

Related

X

Log in or register to enjoy the full experience

Explore first person business intelligence from top minds curated for a global executive audience