Leadership Evolution: Insights from Steve Graves on Executive Coaching and Business Stages

In a recent conversation on The Matt Waller Podcast, I had the privilege of sitting down with Stephen Graves , an executive coach with over three decades of experience working alongside CEOs, business owners, and entrepreneurs. Steve has built an impressive career, coaching leaders of global corporations and entrepreneurial ventures alike, providing profound insights on leadership, business development, and personal growth. What makes Steve’s perspective particularly intriguing is his ability to distill complex leadership concepts into actionable frameworks, applicable across industries and stages of business growth. This article unpacks some of the key themes we discussed, offering insights that are relevant to leaders in every field.

The Evolution of Executive Coaching

One of the first topics we explored was the dramatic evolution of executive coaching over the past decade. Steve recalled how, when he first entered the field, coaching was more of a niche service, far less prevalent than it is today. Over time, however, executive coaching has grown into a significant industry, with a variety of specialties and models emerging.

Steve offered a useful distinction between coaching and consulting: while consulting focuses on adding value to a company, coaching centers on the individual leader, with the impact radiating outwards to the organization. This people-centric approach has become more valuable as companies realize that the success of their organizations is closely tied to the effectiveness and well-being of their leaders.

Steve also emphasized that coaching has become accessible to a much wider range of people. “In today’s world, if you’ve had any success in business, you can almost migrate into coaching,” he remarked, pointing out that many former executives and entrepreneurs now turn to coaching as a way to give back. The democratization of coaching has created a robust, albeit crowded, field where leaders have access to a wide range of coaching models and approaches.

The Stages of Business Growth: Zero to One, One to Five, Five to 500

One of Steve’s key insights during our conversation was his classification of businesses into three distinct stages: Zero to One, One to Five, and Five to 500. This framework is not about the age or size of a business, but rather about its level of complexity and the nature of its challenges. Understanding these stages helps leaders identify the specific needs of their organizations and adjust their strategies accordingly.

1. Zero to One Stage: In this phase, businesses are focused on proving their viability. Leaders are often grappling with the basics—finding product-market fit, building initial teams, and securing early customers. The challenge here is survival and moving from an idea to a sustainable business.
2. One to Five Stage: At this stage, businesses have established themselves but need to scale. The primary concerns are operational efficiency, scaling systems and processes, and finding ways to grow without losing what made the company successful in the first place.
3. Five to 500 Stage: In this mature phase, businesses are often dealing with more sophisticated challenges, such as balancing organic growth with acquisitions, managing complex markets, and possibly navigating investor expectations. Leaders in this stage are less focused on survival and more on optimizing and sustaining long-term success.

Steve pointed out that each stage requires different leadership skills. A leader who thrives in the Zero to One phase might struggle in a more mature company, where the challenges are less about proving the business concept and more about managing a complex organization.

The Changing Role of the CEO

Steve’s insights into the role of the CEO were particularly compelling. He explained that being a great CEO is not a one-size-fits-all role. Instead, the best CEOs are those who are the right fit for their company’s stage of development and market conditions. The skills needed to take a startup from Zero to One are vastly different from those required to lead a publicly traded corporation in the Five to 500 phase.

He also touched on a common mistake in executive hiring—selecting leaders based on past success without fully considering the context in which that success occurred. A leader who thrived in one organization may not be the right fit for another, especially if the company’s culture or stage of growth differs. This misalignment can lead to failure, even for executives with stellar track records. Steve referred to this as "historical competence," noting that success in one context doesn’t necessarily translate to success in another.

The Importance of Compressed Learning

One of the trends Steve has observed in recent years is the growing pressure on leaders to compress their learning curves. With the rapid pace of change in today’s business environment, leaders don’t have the luxury of gradually developing their skills over time. Instead, they need to be proactive about identifying gaps in their knowledge and seeking out the resources and mentors to help them fill those gaps quickly.

“Because of the accessibility to information and opportunity, the window for both is so much larger,” Steve noted. The result is that leaders can achieve success faster, but the pressure to continually improve and adapt is also higher. Executive coaching plays a crucial role in helping leaders navigate this accelerated learning process, ensuring that they stay ahead of the curve.

Writing as a Leadership Tool

Toward the end of our conversation, Steve and I discussed the power of writing as a tool for clarifying and organizing thoughts. Steve shared that, for him, writing is a feedback exercise—a way to crystallize half-baked ideas and turn them into actionable strategies.

For leaders, writing can serve as a mechanism to think through complex issues, develop frameworks, and even test new ideas. As Steve said, “I’m a framework guy,” and writing forces him to bring precision to his thinking. While many leaders may not have time to write every day, even occasional writing can help sharpen their thinking and improve decision-making.

Conclusion

Steve Graves offers a wealth of knowledge for anyone interested in leadership, business development, and personal growth. His approach to executive coaching—focused on the individual, contextualized to the stage of the business, and grounded in real-world experience—offers valuable lessons for leaders at every level. Whether you’re running a startup, leading a growing company, or managing a mature enterprise, the insights Steve shared in our conversation can help you navigate the challenges of leadership with greater clarity and confidence.

If you’d like to learn more about Steve’s work or hear more episodes like this one, subscribe to The Matt Waller Podcast. Stay tuned for part two, where we’ll dive deeper into leadership strategies and explore more about the evolving role of today’s executives.