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Leadership Lessons from Simon Sinek and Jocko Willink: A Dream Conversation Come True

Writer: Kate MayeskiKate Mayeski

Updated: Mar 3

There are moments in life that make your heart skip a beat—like when you pass your grade-school crush in the hallway. That’s exactly how I felt when I saw that two of my biggest leadership inspirations, Simon Sinek  and Jocko Willink, had done a podcast together. I've been following these two badass leaders for over a decade, devouring their books, watching their talks, and applying their principles to my leadership approach. Their insights have shaped not only my personal growth but also how I lead and serve the teams I have the honor of working with. So, when I saw their conversation drop on YouTube, you better believe I dove right in.


Why This Conversation Matters


Upon first glance, you'd likely have some preconceived notions about these two individuals. Simon presents as the emotionally intelligent "positive Polly," and on the surface, Jocko looks more like the team lead who literally barks orders. But after the first few seconds of listening to them, you might be surprised to learn that both leaders teach universal principles. So whether you're a small business owner, CEO of a large company, running a non-profit, or a recent graduate starting their career, there's something to learn here for everyone.


Simon Sinek, the visionary thinker behind Start with Why, has spent years teaching leaders about the power of purpose, trust, and human-centered leadership. Jocko Willink, a former Navy SEAL commander and the mind behind Extreme Ownership, is all about discipline, accountability, and taking full responsibility for everything in your world. Their philosophies may seem different on the surface, but at their core, they align in powerful ways—both advocating for leadership that prioritizes people, fosters accountability, and demands self-improvement.


In this conversation, Sinek interviews Willink about leadership, discipline, and the universal principles that apply whether you're leading a Navy SEAL team, a Fortune 500 company, or a growing small business. Here are the most powerful takeaways from their discussion.


Key Leadership Insights for Business Owners and Leaders


1. Leadership Principles Are Universal


Willink emphasizes that the same leadership strategies that worked in the SEAL Teams apply in civilian life. Leadership is about people, and whether you're in a boardroom, leading a remote team, or scaling your small business, the fundamentals remain the same: trust, respect, and accountability drive success.


2. Building Relationships is Essential


Both Sinek and Willink agree that leadership is rooted in relationships. In the military, strong bonds translate to high performance and trust under extreme pressure. In business, the same principles apply—leaders who care about their people build teams that are engaged, resilient, and high-performing.


3. Humility is a Leader’s Greatest Asset


Willink makes it clear: ego is the enemy of effective leadership. When leaders let their egos take control, they stop listening, learning, and growing. The best leaders—whether on the battlefield or in the boardroom—stay humble, admit when they’re wrong, and remain open to new ideas.

Stack of books and plants, simon sinek start with why and leaders eat last, and Jocko Willink and extreme ownership

4. Extreme Ownership: The Path to Accountability


One of the most powerful lessons from Willink’s philosophy is Extreme Ownership—the idea that everything in your world is your responsibility. No excuses. No blaming others. True leaders own their actions and decisions, which creates a culture of accountability that trickles down to the entire team.


5. The Challenge of Managing Underperformance


Willink points out that a common misconception about military leadership is that you can simply fire underperformers. In reality, both the military and corporate environments require a structured approach to coaching, mentoring, and giving people opportunities to improve before making tough decisions.


6. Continuous Self-Improvement is Non-Negotiable


One thing that struck me was Willink’s commitment to constant growth. Despite his accomplishments, he still pushes himself to get better—whether in leadership, writing, or public speaking. This mindset is a reminder that great leaders never stop learning.


7. Open-Minded Leadership Wins


Willink and Sinek agree that the best leaders don’t just give orders; they listen. A true leader surrounds themselves with smart people, values their input, and fosters a culture where ideas are shared openly. When teams feel heard, they take ownership of their work and drive innovation.


8. The Brotherhood Factor: Leadership is About Human Connection


A major theme in their conversation was the depth of relationships formed in high-pressure environments, like military service. Willink reflects on how difficult it is to replicate that sense of brotherhood in civilian life. However, leaders can create strong, connected teams by fostering trust, support, and a shared mission.


What This Means for Business Leaders Everywhere


Listening to these two leadership giants discuss their philosophies reaffirmed why their work has profoundly impacted me. Whether you lean more towards Simon Sinek’s vision of purpose-driven leadership or Jocko Willink’s disciplined approach, the core message is the same: leadership is about people. It’s about trust, humility, accountability, and continuous growth.


For those of us leading teams—whether in business, non-profits, or our personal lives—this conversation is a powerful reminder that great leadership isn’t about rank or authority; it’s about service. It’s about setting the example, lifting others up, and creating an environment where people can thrive.


Funny enough, people often mistake me for a military veteran—not because of my buff muscles or that I'm a killer shot at the range (things I aspire to...), but because I tend to use short, direct responses like "Copy that," "Negative," or "Roger." While I don’t hold the honor of serving in the military, I’ve had the privilege of knowing many who have, and their discipline, communication, and leadership principles have shaped me in ways I never expected. Studying veterans like Jocko Willink and individuals who deeply respect the military, like Simon Sinek, has influenced my leadership and communication skills in the best way possible.


If you haven’t already, do yourself a favor and watch the full conversation here. Whether you’re new to these leadership philosophies or, like me, have been following Sinek and Willink for years, I guarantee you’ll walk away with insights that will change the way you lead.


If you're looking to level up your leadership, strengthen your team, and grow your business, reach out to Maverick May Solutions. Let's work together to take your leadership and organization to the next level!



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