Leveraging diverse collaboration and learning from setbacks can propel educational leadership team to success.

Sailing through adversity: 4 Olympic-sized lessons in educational leadership


Leveraging diverse collaboration and learning from setbacks can propel educational leadership team to success

Key points:

When Lara Dallman-Weiss and Stuart McNay set sail together at the 2024 Paris Olympics, they weren’t just navigating open waters–they were challenging traditional norms in a sport historically dominated by single-gender teams. As the first U.S. mixed-gender team to compete in the 470 sailing class at the Paris Games, they embodied the transformative power of gender equality in high-performance teams.

I had the opportunity to speak with Dallman-Weiss and McNay–a two-time and five-time Olympian, respectively–about their journey, the strengths of diverse teams, and cultivating the resilience needed to overcome obstacles together. Their experiences offer powerful lessons for leaders across sectors who must navigate the uncertainty of a highly competitive context.

Diverse perspectives are powerful

Dallman-Weiss and McNay aren’t just different genders; they also come from different parts of the country and sailing backgrounds. Dallman-Weiss began her career on the lakes of her native Minnesota before honing her talents at Eckerd College in Florida. McNay, a Bostonian by birth, sailed to an All-American career at Yale University before entering Olympic competition in 2008. This diversity of experience strengthens their partnership.

“Men and women bring different strengths to the boat–physicality, timing, coordination–but the real power comes when those strengths are harnessed together,” McNay noted. “Sometimes male sailors try to solve the problem with more physicality, while female sailors solve it with better timing or coordination.”

This balance of perspectives is crucial in leadership at large. In any organization–be it a startup or a multinational corporation–the ability to blend diverse approaches is key to maximizing talent, capacity, and impact. According to a McKinsey study, companies in the top quartile for gender diversity on executive teams are 25 percent more likely to have above-average profitability. Diversity is a competitive advantage.

Just as Dallman-Weiss and McNay complement each other’s abilities on the water, creating environments where diverse voices are not only heard but actively encouraged is a game-changer in any field. Drawing from a broader range of experiences makes organizations more adaptable and more capable of withstanding challenges.

Pressure is a privilege

“I love pressure,” Dallman-Weiss offered. “That whole ‘pressure is a privilege’ mantra really rings true for me.

“I think both of my Olympic trials were some of the most stressful moments of my life,” she continued. “We had a lot to prove. And that pressure was insane. And one of the things that I always worked with my performance coach was that if not this, then something better is in store. And he just instilled in me the idea that, ‘Okay, if I don’t get there, if this doesn’t happen, it’s because something better is waiting for me.’ I took that through with me to our Olympic trials.”

The idea that pressure is not something to shy away from but to embrace is powerful for leaders in all fields. Embracing pressure as a privilege requires leaders to develop strategies to manage it effectively. Whether it’s through mental coaching, leaning on your team, or reframing the situation as an opportunity to rise to the occasion, pressure becomes a resource for strength and motivation. Viewing pressure as an opportunity rather than a burden allows leaders to inspire their teams and drive performance.

Learning from adversity: Resilience through setbacks

“Each setback has to be a learning lesson,” McNay told me. “It’s important to reframe any setback, not just for your mentality and enthusiasm, but also because setbacks often highlight your weaknesses more than successes.”

Seeing setbacks as opportunities for growth and improvement embodies the essential spirit of a world-class competitor–it lies at the heart of every Olympian. Embracing setbacks as vital parts of the process, rather than as failures, enables leaders to cultivate the mindset needed to lead with courage and optimism. It empowers leaders to elevate team members to their highest levels of performance, even in choppy waters. 

Allyship and the role of male advocates in supporting women in leadership

Women in leadership know the importance of having male allies, especially in male-dominated fields. Dallman-Weiss noted that many women in sailing struggle to gain the same level of experience as their male counterparts due to fewer opportunities and less access to resources.  Having a male advocate helped her navigate these spaces and challenges.

“I was often the only female,” she said. “I was there to race. I knew what I was doing. But there’s this level I had to prove that I even knew how to walk my way around a boat. One of my biggest lessons was to have a male that knew me and could speak up for me, especially when I was younger.”

Her experience mirrors what we see in many sectors, including education.

Women, particularly women of color, in education face additional barriers to leadership positions, whether they be biased career pipelines that funnel them away from key experiences and opportunities for growth, or a cultural bias that holds them to materially different standards than their male peers. 

In systems where bias is a daily reality, men have an interest in acting as allies, ensuring their talented female colleagues are put in positions to maximize their potential. According to a report by Credit Suisse, companies with higher percentages of women in decision-making roles generate higher returns and better average growth. By actively supporting female colleagues, male leaders not only promote fairness but also drive better outcomes for their organizations.

Navigating toward a more inclusive future

Leaders–whether at the helm of an Olympic-class sailboat or in boardrooms–who are charting a course through complexity and uncertainty can glean important lessons from Dallman-Weiss and McNay’s partnership. Their journey exemplifies how embracing gender equality, leveraging diverse collaboration, viewing pressure as a privilege, and learning from setbacks can propel any team to success.

Because leadership, like sailing, isn’t simply an exercise in navigating around stormy weather, it’s about putting to use the full range of assets on hand, drawing on diverse strengths to adjust course, cutting through the chop, and ultimately reaching the finish line stronger than when you started.

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