The Tail Wagging the Dog: How to Realign Your Leadership Compass

As entrepreneurs, we often start our ventures with visions of financial freedom and a life rich in personal fulfillment. Yet, many of us find ourselves trapped by the very businesses we created—falling into the common trap where the business starts running us instead of the other way around. This is a classic example of "the tail wagging the dog."

From Technician to Entrepreneur to CEO: The Evolution of Leadership

The entrepreneurial journey typically begins with promise and autonomy. The entrepreneur is the head cook and bottle washer, juggling multiple roles with agility and determination. This is the technician stage, where we’re deeply involved in the day-to-day operations, working in the business, not on it.

Michael Gerber, in his seminal book The E-Myth, explains how many entrepreneurs struggle to transition from being technicians to becoming true business owners. This is where the trap is set. As the business grows, so does the complexity of these roles. Entrepreneurs, often mired in tasks, fail to make the critical shift needed to elevate themselves to a higher level of leadership. It’s here that the reluctance to delegate and step back begins to hinder the company’s growth.

The CEO’s Role: Managing Resources and Leading People

A crucial insight is that people aren’t managed—they’re led. The role of a CEO is not as hard as many make it out to be. It’s about managing the resources—systems and processes—while leading the people. The CEO’s primary responsibility is to support the people so they can take ownership of their roles, set meaningful goals, and collaborate effectively to drive the company forward.

At the end of the day, a business is about getting, keeping, and growing customers. Successful businesses focus on getting, keeping, and growing the right customers. To achieve this, a CEO must get, keep, and grow the right people. This is why culture eats strategy for breakfast. Your role as CEO is to set the example, champion the culture that supports success, and manage resources so that each person has the support they need to do their job to the best of their ability. This creates a culture of empowerment and accountability where everyone supports one another.

Marshall Goldsmith wisely noted that hard work isn’t what moves the needle—it’s the right kind of hard work, focused on top priorities. The CEO’s role is to work on the business, not in it. This involves trusting others to handle operational aspects and ensuring that every action aligns with the company’s vision.

Evolving to a Servant Leader: Caring About the People

The true challenge emerges when the company’s needs start dictating the CEO's life, leading to a misalignment of priorities. To break free from this cycle, CEOs must evolve beyond traditional roles and embrace servant leadership. As Jim Collins describes in Good to Great, a Level 5 leader—what I call a servant leader—is someone who deeply cares about the success of their people. They understand that the company’s success is intertwined with the success of each individual on the team.

A servant leader prioritizes the well-being and growth of their employees. They model the behavior they want to see, fostering a culture where people are empowered, trusted, and motivated to take ownership of their roles. This creates organic accountability—much like the accountability found in the Marine Corps, where every Marine knows their role is crucial to the mission’s success.

In the Marines, when they hit the beach, they're faced with a binary decision: get off the beach or die trying. Accountability comes from being accountable to one another—Marines are either covering someone who is moving or they are moving. They pride themselves on their ability to improvise, adapt, and overcome, knowing that their actions are vital to the mission and to the men on their right and left. This bond, this understanding of the purpose of their actions, is what drives them forward.

The Marine leader knows they can only impact the actions of a few Marines around them. The best communication is often just one Marine to the right or one Marine to the left. Each person must own their job, knowing that everyone—from the company, the Marine Corps, to the nation—is relying on them to do their job so that the vision of victory can be realized.

Building Systems and Processes: The Foundation of a Self-Sustaining Business

Systems and processes don’t need to be perfect; they need to be reliable and repeatable. The transition from technician to entrepreneur involves creating these systems so that the business can operate independently. This allows the entrepreneur to step into the CEO role, focusing on the vision and ensuring that the right people are in place—people who believe in the vision and have the skills to execute it effectively.

The next evolution, from CEO to servant leader, is about recognizing that it’s the people, not just the systems, that drive the company forward. A servant leader knows that by putting people first and caring about their success, the company will naturally thrive.

Conclusion: Reclaiming Control and Realigning with Your Vision

The tail-wagging the dog is a metaphor for what happens when entrepreneurs fail to evolve. To stop the tail from wagging the dog, one must evolve from a technician who does the work to an entrepreneur who inspires, to a CEO who leads, and finally to a servant leader who cares deeply about the people doing the work.

As you continue to grow and mature in your leadership journey, remember that your business should serve your life, not the other way around. Build systems, trust your people, and lead with empathy and purpose. This is how you reclaim control, align your business with your personal goals, and ultimately lead a life of fulfillment and success.

Servant leaders can’t fall victim to the tail-wagging the dog because they care enough about their people to ensure they have what they need to succeed. Leadership is about vision, culture, curiosity, and empathy—knowing people want to be great and allowing them the space to achieve greatness. That’s what makes a Level 5 leader. When the tail starts wagging, it’s a sign that evolution is necessary. It’s a journey, and when people refuse to evolve, the company stops growing. But those who embrace the next step will find that every crisis is an opportunity to grow into the leader their company needs.