545: Will Guidara - The Remarkable Power of Giving People More Than They Expect (Unreasonable Hospitality)

Episode Summary

Executive Summary: Ryan Hawk interviews Will Guidara about the leadership and service principles behind 11 Madison Park and Unreasonable Hospitality. The conversation centers on surrounding yourself with the right people, using feedback wisely, teaching as a leadership tool, and obsessing over small details that shape experience. Guidara also shares how Miles Davis, his father, Simon Sinek, and journaling influenced his philosophy and execution.

Main Topics: Surrounding Yourself with the Right People: The episode opens with the premise that long-term success depends heavily on who you choose to be around. Hawk promotes his Learning Leader Circle, and Guidara reinforces that teams win when leaders get to know people deeply and put them in the right roles. Miles Davis as a Leadership Model: Guidara explains how a restaurant review comment about needing 'more Miles Davis' led him to study Miles Davis’s approach to music. He drew leadership principles from Miles’s words—cool, endless reinvention, and collaboration—and used them to shape the restaurant culture. Feedback, Criticism, and Clear Filters: The conversation explores how to stay open to feedback without becoming reactive or designing by committee. Guidara argues leaders should evaluate criticism carefully, keep core convictions, and decide what to change versus what to protect. Teaching, Public Speaking, and Learning: Guidara describes making teaching part of the restaurant culture so every employee learned to speak, explain, and train others. He frames public speaking as a leadership skill and says teaching is one of the best ways to learn. Care, Trust, and Right Person/Right Role Leadership: Using the story of his father’s Vietnam platoon and the soldier nicknamed Kentucky, Guidara argues that caring enough to understand people’s strengths builds trust and unlocks hidden talent. He connects this to retention, morale, and performance. Excellence in the Small Details: Guidara highlights lighting and music as examples of operational details that shape the guest experience. He emphasizes assigning ownership, coaching mistakes, and using small details as levers of excellence. Brainstorming Big Before Getting Practical: He explains that innovation should begin with ambitious, unconstrained ideas before practicality enters the process. This philosophy shaped 11 Madison Park’s strategic planning and helped generate breakthrough ideas.

Key Arguments: Long-term success depends on choosing the right people to surround yourself with and investing time to understand them. Feedback is valuable, but leaders must filter it through their own convictions rather than changing for every critic. Miles Davis influenced the restaurant’s culture because his approach embodied cool, collaboration, and endless reinvention. Leaders should put people in roles where their strengths can shine; misaligned roles often cause underperformance that looks like failure. Teaching is a powerful form of learning because it forces clarity, structure, and responsibility. Public speaking matters because leaders must be able to communicate ideas clearly and confidently to groups. Great leadership and hospitality are not complicated; they require more care, thought, and effort than most people are willing to give. Attention to details like music and lighting can materially improve the customer experience and should be actively managed. Strategic planning should include the whole team and encourage big ideas before constraints are discussed. Young leaders should choose the right mentor or boss over the most attractive company, because personal growth comes from who teaches you.

Data Points: Learning Leader Circle size: 12 people - Hawk says only 12 people are selected for each annual circle cohort. Application frequency: 1 time per year - Applications for the Learning Leader Circle open once annually. Restaurant recognition: 4 stars - 11 Madison Park received four stars from the New York Times under Guidara’s leadership. Restaurant recognition: 3 Michelin stars - 11 Madison Park earned three Michelin stars. Restaurant ranking: #1 - In 2017, 11 Madison Park was named the world’s best restaurant on the World's 50 Best Restaurants list. Annual strategic planning cadence: 1 day per year - 11 Madison Park closed for a day each year for its strategic planning meeting. Team teaching structure: 5-6 managers to 60 employees - Guidara notes that only a handful of managers were teaching a much larger dining room staff, which prompted a broader teaching model. Book ranking duration: almost a year on the bestseller list - Hawk notes Unreasonable Hospitality stayed on the bestseller list for nearly a year. Simon Sinek editing session: 60 pages cut and 2 chapters removed - Guidara recounts reading the book aloud to Sinek, who then helped trim substantial material. New executive silence rule: 6 months - Hawk mentions Cartier’s practice of not letting outside executives speak in meetings for six months. TED Talk practice example: 20 minutes - Hawk references building habits such as 20 minutes of daily gym time or daily reflection, in the context of journaling and practice.

Pivotal Quotes: "If you’re willing to surrender yourself with others who will push you, challenge you, make you think differently... this could be for you." — Ryan Hawk: Hawk pitches his Learning Leader Circle as a curated peer group for leaders. "Teach with the intention of learning and learn with the intention of teaching." — Will Gudera: Guidara shares a lesson from his father about the reciprocal relationship between teaching and learning. "Too many people approach creative brainstorming by taking what’s practical into consideration way too early in the process. Start with what you want to achieve instead of limiting yourself to what’s realistic or sustainable." — Will Gudera: Guidara explains how the team at 11 Madison Park generated breakthrough ideas by starting with ambition before constraints.

Implications: For leaders, the message is to invest in people, prioritize clarity and teaching, and protect a culture that values care and creativity. In hospitality and beyond, excellence comes from intentional detail, trust, and bold ideas refined later.