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Episode 427: Nathan Caldwell talks about Empowering Kindness, developing leaders and beating the calendar
AttractionPros Podcast
53 minutes
6 days ago
Episode 427: Nathan Caldwell talks about Empowering Kindness, developing leaders and beating the calendar
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Nathan Caldwell is the Bestselling Author, Thought Leader, and Speaker of Empowering Kindness. A lifelong performer-turned-leadership coach, Nathan’s early career on stage taught him how guest-facing energy is created (and depleted) every shift. He later guided culture and leadership through multiple corporate acquisitions, evolving his research and writing into the book Empowering Kindness and the practice behind it. Empowering Kindness supports organizations with practical, science-backed frameworks that lift performance by building trust, clarity, and courage. In this interview, Nathan talks about Empowering Kindness, developing leaders, and beating the calendar.
Empowering Kindness
“Kindness takes strength, bravery, and wisdom to execute upon.”
Nathan pushes kindness far beyond “being nice.” Drawing on research and lived experience, he frames kindness as a disciplined leadership choice: seeing others’ needs (empathy), stepping into the gap despite discomfort (bravery), and applying the right response at the right time (wisdom). He cites studies showing that environments rich in kindness elevate wellbeing and performance, arguing that people are literally built to respond to good. Leaders operationalize this by defining what kindness looks like in specific roles, training for it, and equipping teams to deliver it consistently—not hoping people will “just be kind.”
Instead of the tired “compliment sandwich,” Nathan recommends an “Oreo” culture: clearly state what “good” and “excellent” look like, and call them out often. Doing so deposits trust so that hard feedback is welcomed rather than resisted. When leaders are known for recognizing excellence, coaching moments land as invitations to rejoin that standard, not as gotchas. The outcome is a reinforcing loop of clarity → recognition → trust → growth.
Developing Leaders
“They must be great at filling people up with energy.”
Borrowing from his performer background, Nathan describes the “energy lifecycle” of guest-facing roles: guests draw energy all day; if leaders only pull, teams burn out. Great leaders replenish through coaching, recognition, and practical support. He also normalizes the loneliness of leadership and urges leaders to build peer networks, learn continuously (books, webinars, podcasts), and identify personal recharge rituals. The goal isn’t endless cheerleading; it’s deliberate energy management so people can show up strong for guests and each other.
Nathan’s prescription is both organizational and personal. Organizations should create forums and rhythms where leaders learn together and hold one another accountable. Individually, leaders must notice depletion, own recovery, and return to the floor refueled. That self-awareness is a kindness to the team: a recharged leader is capable of the courageous conversations and steady presence that growth requires.
Beating the Calendar
“You have to beat the calendar. You have to win against the calendar. Intentionality is the only way to do it.”
Seasonality and turnover can’t be excuses. Nathan warns against hoping people “pick up” experience during the busy months; that’s how issues get swept under the rug until they become trip hazards. Instead, map the precise competencies leaders need (e.g., handling difficult conversations), then schedule training, role-plays, and practice reps before peak season. Treat these as must-run plays, not nice-to-haves. When int