What Below Deck Taught Me About Leadership

Your organization should probably run like a mega yacht. Let me show you why. 

Below Deck is truly terrific trash TV. It also happens to be a compelling case study in leadership. 

For the uninitiated: Below Deck (the original, set in the Caribbean) premiered in 2013. That season was weird. We don’t talk about it. Since then, Bravo has chartered Below Deck Mediterranean, Below Deck Sailing Yacht, and Below Deck Down Under. There was one season of Below Deck Adventure Yacht that never really clicked. The Below Deck universe amounts to 32 seasons and nearly 450 episodes of adventure, workplace drama, and absolute mayhem. One episode revolves around a guest furious that their cappuccino isn’t dry enough and another features a cameraman stepping in to save a deckhand’s life. 

Charter guests range from charming to insufferable, but the show is not about the guests. It’s about the yachties; the crew who live and work on boats. Life aboard a mega yacht is relentlessly hierarchical: the deckhands and steward(esses) are the frontline staff, the Bosun, Chief Stew, and Chef are middle management, and the Captain is the President & CEO. A yacht is an unusually revealing workplace. Teams assemble quickly, live and work together around the clock, serve demanding clients, and have almost no room for error. Leadership mistakes surface immediately.

So, where do the leadership strategies come into play? While the Bosun and Chef have important managerial duties, it is the Chief Stew and the Captain who set the culture. Boat culture and crew cohesion (or lack thereof) determine whether the 9-week season ends with record-breaking tips from guests or someone rage-quitting halfway through a charter.  

Leadership theory provides plenty of labels: autocratic, bureaucratic, coach, democratic, laissez-faire, pacesetter, servant, transformational, transactional, and visionary. Below Deck manages to feature nearly all of these approaches, often within a single episode. The leaders who consistently succeed don't rely on authority. They build trust, develop their staff, and create teams that perform well under pressure.

Captain Lee: Transformational Leadership

Captain Lee Rosbach is the blueprint for a Below Deck captain. A transformational leader, Captain Lee stewarded the show, ship, and yachties from 2013 - 2023. He set high expectations for his team, communicated clearly, and kept people accountable. Always outspoken, Captain Lee projected a tough exterior, but his crew knew he cared deeply about them and their careers. He focused on developing professionals who would contribute to the boat and the industry. 

Despite his catchphrase, “work hard or get fired,” Captain Lee supported his crew through mistakes and offered second chances. The transformational approach is rewarding, but also takes its toll. Captain Lee ultimately stepped away from Below Deck due to health issues, but his influence remains in the DNA of the show. 

Captain Sandy: Coaching Done Right (Eventually)

Captain Sandy Yawn's development as a leader is arguably the most interesting case to watch unfold over her 10 seasons leading the crew on Below Deck Mediterranean. As the only female Captain in the Below Deck universe, Captain Sandy consistently champions women pursuing careers on deck. Always invested in helping her crew members grow, Captain Sandy’s coaching often crossed into micromanagement. Her relentless optimism could veer into toxic positivity that prohibited her from identifying or solving underlying issues. 

Captain Sandy’s real impact is her evolution as a leader. Over the last three seasons, Captain Sandy has fundamentally altered her approach. Her forced positivity gave way to candor, she became more intentional about mentorship, and showed the crew (even those she didn’t immediately connect with) more patience and attention. It’s unusual to get the opportunity to watch a leader grow over the course of a decade, but that is exactly what makes Below Deck and Captain Sandy so compelling. 

Aesha: It’s Better To Be Loved Than Feared

If Captain Lee built Below Deck and Captain Sandy grew it, Aesha Scott represents the next generation of leaders. Over 7 combined seasons as Second Stew and Chief Stew on Below Deck Mediterranean and Below Deck Down Under, Aesha makes everyone around her better through her humor and confidence. A visionary leader, Aesha demonstrates that warmth and high standards aren’t opposites, but reinforce each other. She promotes people based on work ethic and enthusiasm, delegates confidently, and trusts her team to rise to expectations. Aesha’s leadership hinges on transparency and she expects strong communication from her team. People want to work hard for her because they don't want to let her down. Humor isn't just part of her personality; it's part of how she creates psychological safety. 

It’s easy to understand the visionary nature of Aesha’s style in comparison to the legendary Chief Stews, Kate Chastain and Hannah Ferrier. When under pressure, Kate fell into an autocratic leadership mode and Hannah became overly laissez-faire. They both got the job done to a high standard, but became known for favoritism, burnout, and a cult of personality. Aesha offers a different model. She leads by example, creates buy-in instead of compliance, and builds teams that improve because they genuinely want to impress their leader.

What Below Deck Taught Me About Leadership

Management training and leadership frameworks are useful career tools. But there is something uniquely influential about watching leadership play out in real time (against a beautiful backdrop). 

Every season of Below Deck is a journey. Not just for the guests, but for the crews who must live and work in close quarters. Each leader inherits a new team under new conditions. The cameras capture the successes, failures, recoveries, and consequences for every decision. 

You can learn a lot about accountability, delegation, motivation, and culture while watching someone forget the preference sheet, deal with entitlement, or take far too long to get the inflatable slide over the third deck of the boat. Most offices don't have anchor watches or inflatable slides. But the best captains on Below Deck understand something many leaders forget: culture beats control, trust outperforms fear, and people deliver when they know their leader wants them to succeed. 

Turns out Bravo has been consistently producing world-class leadership seminars since 2013. 

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Jennie Lamensdorf is a Cultural Strategy and Partnerships Executive based in Los Angeles. As the Principal Consultant and Advisor of Arts & Culture Partners, Jennie helps organizations employ art, creativity, and cross-sector collaboration to strengthen brands, engage communities, accelerate innovation, and build enduring public value. She believes there should be more art everywhere. Jennie is a Board Member of Artadia, NYC and Art Omi, Ghent, NY.