16 Sept 2026
The Inner Game of Leadership: How Great CEOs Keep Growing
The skills that build a company are not always the skills required to scale one.
In this episode of The Deal Factory, Jeff Harkness sits down with his own CEO coach, Chuck Gulledge, for a candid conversation about what happens to a leader as the business grows around them.
After beginning his career as a CPA with Arthur Andersen, working in the capital markets, and spending years studying companies and their leaders, Chuck made a major career pivot at age 50 to become a certified executive coach. Thirteen years later, he works with CEOs and leadership teams across the country, helping them navigate strategy, execution, people, succession, and what he calls the “inner game” of leadership.
Jeff and Chuck break down the difference between a consultant and a true coach, why CEOs must move beyond the “Superman” phase of entrepreneurship, and how identifying constraints, finding your highest and best use, and building operating systems can transform a growing organization.
They also explore Momentum Hub, Chuck’s approach to turning strategy into execution, why AI will enhance leadership without replacing the human side of coaching, and what happens as entrepreneurs evolve from doing everything themselves to multiplying leaders.
For founders and CEOs scaling businesses in the trades and service industries, this conversation asks an important question:
Are you still the leader your next stage of growth requires?
Key Discussion Points
Chuck’s journey from CPA and capital markets executive to CEO coach
Why he left his established career at age 50 to pursue coaching
The difference between a CEO coach and a consultant
Why coachability matters more than simply hiring a coach
The loneliness that comes with leading and scaling a company
Finding your highest and best use as a CEO
Why leadership and the “inner game” become more important as companies scale
Turning strategy into execution through Momentum Hub
Why strategic plans need to become living operating systems
People, strategy, and execution as fundamental building blocks
Identifying and attacking the top constraints inside a business
Why bad meetings quietly destroy organizational productivity
“Where do we play?” versus the more important question: “Where do we not play?”
How CEOs unintentionally create cultural problems by tolerating the wrong behaviors
Why customer experience and winning can strengthen company culture
The evolution from founder “Superman” to building and multiplying leaders
Family-business succession and why the next generation has to earn leadership
Why AI can improve business systems but cannot replace human connection
Why self-doubt does not disappear when a CEO becomes successful
Why Chuck believes every CEO should have a coach
Chapters:
0:00 Intro
0:39 Intro: Meet Chuck Gulledge
2:17 How Does Someone Become a CEO Coach?
3:40 Arthur Andersen, Capital Markets & Learning Leadership
4:40 Discovering Executive Coaching
5:40 Making a Major Career Pivot at 50
7:25 Why Entrepreneurship Can Be Lonely
8:40 CEO Coach vs. Consultant
10:45 Why Leadership Is the Real Work
12:25 Finding Your Highest and Best Use
14:50 What Makes a CEO Coachable?
17:05 The Inner Game & Building Better Leaders
18:30 Momentum Hub: Turning Strategy Into Execution
21:30 Will AI Replace CEO Coaches?
25:30 The Fundamentals of Scaling Leadership
27:40 Finding and Attacking Business Constraints
28:45 How Bad Meetings Waste a Company’s Time
30:30 Strategy: Where Should You NOT Play?
31:55 What Are You Tolerating Inside Your Business?
32:35 Culture, Customers & Building a Winning Team
35:15 How CEOs Change as Companies Scale
36:25 From Superman to Multiplying Leaders
38:45 Family Business Succession & Leadership Transitions
43:10 When Should a CEO Hire a Coach?
44:00 Why Every Leader Needs Coaching
45:50 Every CEO Has a Journey
47:10 The Inner Game at the Highest Level
48:20 The Priority Paradox & CEO Accountability
49:00 How to Connect With Chuck
49:45 Closing Thoughts
