Behind every confident executive or visionary entrepreneur is a hard-earned lesson, something that reshaped how they lead, think, or connect with others. In candid conversations with some of hospitality’s most accomplished professionals for It’s Personal Stories, we asked a simple question: What is the greatest lesson you’ve learned in your career? The responses were honest, humbling, and deeply instructive. These are the lessons that don’t just teach, they transform, guiding leaders through complexity, uncertainty, and growth.

1. “You don’t have to be perfect to be effective.”

For Leslie Hale, President & CEO of RLJ Lodging Trust, the most impactful learning came with experience. “Early on, I thought being perfect meant being prepared and always having the answer. But I’ve learned that effectiveness comes from adaptability and authenticity.” Letting go of perfectionism allowed her to lead with greater clarity and confidence, making strong decisions even when not every detail was known. Her insight is a powerful reminder: perfection is often paralyzing, but progress is empowering.

2. “Listening is not the same as waiting to speak.”

Brian Quinn, Former Chief Development Officer of Sonesta Hotels & Resorts, shared a deceptively simple truth that changed the way he negotiates and leads. “So many of us are conditioned to talk, pitch, persuade. But I’ve learned that real value lies in truly hearing the other side.” For Quinn, listening isn’t passive, it’s a strategy. It builds trust, reveals insights, and strengthens relationships far more than any prepared script.

3. “You can’t manage what you don’t understand.”

For Lindsey Ueberroth, CEO of Preferred Hotels & Resorts, stepping into leadership meant digging into the details. “One of the best lessons I learned was to roll up my sleeves, dig into the details, and ask questions until I understood the full picture.” Curiosity became a defining part of her leadership style. Whether the topic is finance, technology, or branding, she believes leaders must be fluent in every corner of their business, not just its strategy.

4. “Trust your gut but validate it with data.”

David Eisen, VP and Editor-in-Chief of HOTELS Magazine, navigated editorial judgment and business realities with this balanced approach. “Instincts matter, especially in hospitality. But when you pair them with data, you make decisions with real power behind them.” His lesson reflects modern leadership: intuition is valuable, but evidence strengthens conviction and guides smarter risk-taking.

5. “Build your brand before you need it.”

Emily Goldfischer, Founder of Hertelier, learned early that a personal brand is an investment, not an accessory. “Your brand is what people say about you when you’re not in the room,” she explains. “You can’t wait for the crisis to build credibility, you have to start early, be consistent, and show up for others.” Her insight underscores that reputation is long-term work and a leader’s most portable asset.

6. “Empathy isn’t a soft skill - it’s a core strength.”

For Mark Hoplamazian, President & CEO of Hyatt Hotels Corporation, one of the most transformative lessons was discovering the business power of emotional intelligence. “Early in my career, I underestimated the impact of showing vulnerability and compassion. Now I see it as essential to building trust.” Empathy, he notes, bridges the gap between vision and execution and fuels the loyalty needed for teams to navigate change.

Lessons That Lead

From embracing imperfection to listening deeply, the greatest career lessons often emerge not from triumph but from challenge, reinvention, or reflection. These insights don’t live in textbooks, they come from conference rooms, late-night decisions, difficult conversations, and moments of self-doubt. While each leader’s story is unique, the wisdom they share is universal. Growth is rarely linear. The most powerful learning happens when we question, adapt, evolve, and allow ourselves to be vulnerable.