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Gil: The Power of Coaching in Succession Planning

Gil smiling after he got a succession planning coach.
Gil lept forward with a coach.

The moving melody of “It Is Well With My Soul” played from Gil’s iPhone. He had spent 45 years working his way up from driver’s helper to CEO. With emotion in his voice, he shared his deepest desire: “That’s all I want...for it to be well with my soul.”


Gil’s words capture a sentiment many business leaders can relate to - the quest for peace and fulfillment after pouring decades into building a successful company. But as Gil discovered, achieving that sense of soul-deep wellbeing requires more than just hard work and business savvy. It demands thoughtful planning for the future, and often, the guidance of a trusted coach to light the way.


The Succession Planning Challenge

For many entrepreneurs, succession planning is a daunting challenge. How does one begin to step back from a company that’s been the center of their life’s work? What’s the right timeline? Who will take the reins? Without a clear roadmap, the process can feel overwhelming, leading many to put it off until it’s too late.


Gil found himself wrestling with these very questions. He had spent his career growing the business, working his way up from an entry-level position to CEO. He knew he couldn’t stay at the helm forever, but the path to a successful transition seemed shrouded in uncertainty. That’s when he invited me in for an outside perspective.


Partnering with a Coach

As a coach specializing in guiding entrepreneurs through succession planning, I had the privilege of working alongside Gil on his journey. From our first meeting, it was clear that Gil had a wealth of experience and insight to draw upon. What he needed was a thought partner to help him clarify his vision and break down the daunting process into manageable steps.


Together, we began mapping out a plan, identifying key milestones and decision points along the way. We discussed Gil’s goals for the future of the company and his personal aspirations for life after the transition. Having an objective sounding board allowed Gil to think through the big picture and fine details with fresh perspective.


The Power of Visual Planning

One of the most pivotal moments in our work together came during a session in Gil’s “war room” - a conference room dominated by a massive whiteboard wall. As we began sketching out the succession planning process, the power of visual thinking quickly became apparent.


With each step and strategy mapped out vividly, the path forward took on a new level of clarity. Breaking down the complex process with the Cultivating Impact Succession Planning Method, made it feel achievable. Gil could see how each step fit together, from building his leadership team to crafting his exit timeline.


Building a Strong Leadership Team

A central pillar of Gil’s succession plan was identifying and developing the right talent to carry the company forward. Over the years, he had built a strong core team, including three C-level leaders poised to step up in his absence.


Through our coaching work, Gil honed his ability to delegate effectively and empower these future leaders. He learned to step back and let his team take on more responsibility, allowing them to grow into their roles. By investing in his people, Gil laid the foundation for a smooth eventual transition.


Creating a Long-Term Vision

With a capable leadership team in place, we turned our attention to crafting Gil’s long-term exit strategy. After careful consideration, Gil landed on a seven-year timeline for his departure. This plan gave him ample runway to groom his successors, solidify key client relationships, and gradually step back from day-to-day operations.

Having a clear timeline and milestones provided Gil with peace of mind. He could see the path ahead and felt confident in the future of the company he had worked so hard to build.


Coaching Lessons Learned

Thinking about Gil’s succession planning journey, several key lessons emerge:

1. Start early: The earlier you begin planning for the future, the smoother the eventual transition will be. Don’t wait until retirement is just around the corner.

2. Seek outside perspective: A coach or trusted advisor can provide invaluable insight and guidance, helping you see blind spots and explore new possibilities.

3. Break it down: Succession planning can feel overwhelming, but breaking the process into smaller, concrete steps makes it manageable. Focus on one step at a time.

4. Invest in your team: Your people are your greatest asset. By developing strong leaders and empowering them to step up, you ensure the company’s success long after you’re gone.

5. Communicate openly: Transparency is key throughout the succession planning process. Keep your team and stakeholders informed and engaged every step of the way.


Peace of Mind and a Lasting Legacy

As Gil’s iPhone played the final notes of “It Is Well With My Soul,” I was struck by the peace and contentment on his face. Through our work together, he had found the clarity and confidence to map out a future that aligned with his deepest values.


Gil’s story is a powerful reminder of the transformative impact of coaching in succession planning. By partnering with a trusted guide, business leaders can turn a daunting challenge into an opportunity for growth, fulfillment, and lasting impact.


If you’re a CEO or entrepreneur grappling with the question of what comes next, take a page from Gil’s playbook. Seek out a coach who can help you clarify your vision and break down the succession planning process into manageable steps. With the right support and a clear roadmap, you too can find the peace that comes from knowing your legacy is secure.


Remember, it’s never too early to start planning for the future. By taking proactive steps today, you set the stage for a tomorrow where you can say with confidence, “it is well with my soul.”


Harry T. Jones


P.S. Shortly, we will be publishing my new book. Until then, I am considering a “beta” test group at a greatly reduced cost, to coach a group of entrepreneurs through the succession planning process. This will be a six-month group built on the concepts of a peer advisory board or mastermind. 


Imagine establishing your legacy over the next twelve months with a trusted coach who has walked where you are now. In return, I will learn a lot from you!


Interested? Email me, and just put “Interested” in the reply line. No commitment. I will keep you informed.


To your legacy business!

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