Quilting Culture: Kind Leadership for  Growth ft. Nathan Caldwell

Overview:

In this heartfelt episode of Live with Sondra, host Sondra Shannon, CEO of Gatemaster  Technology, welcomes Nathan Caldwell, keynote speaker and founder of Empowering  Kindness. Together, they explore how kindness in leadership transforms culture, drives growth, and fosters loyalty—especially in the attractions industry.

Insights from This Live

• Kindness is not weakness:
  True kindness in leadership is about using your strength to meet others’ needs, not about being nice or popular.
• Culture must be intentional:
  Leaders must clearly define and reinforce expectations for how team members treat one another—not just offer perks. 3. Forgiveness fuels innovation: Organizational forgiveness allows people to recover from mistakes, rebuild trust, and continue contributing meaningfully.
• Growth starts with equipping:
  Managers must shift focus from task execution to people development, offering training and opportunities to grow.
• Internal competition harms culture:
  Pitting team members against each other stifles collaboration, sharing, and ultimately, performance.

Notable Quotes

• “Kindness is an attitude towards seeing the need in others and then using your strength, your wisdom, your ability, your opportunity, the power that you have to fulfill that need.”
  – Nathan Caldwell [10:30]
  Nathan defines kindness as a proactive leadership trait, emphasizing its role in empowering others to grow.
• “The moment people are being put into your care, your entire responsibility stack just changed from the tasks to the people.”
  – Nathan Caldwell [50:43]
  Nathan stresses that management is about developing people, not just overseeing tasks.
• “If you say common sense is not so common, [while pointing at somebody who doesn’t know what to do] yet you know it…you are a terrible teacher.”
  – Nathan Caldwell [23:48]
  This bold statement challenges leaders to take responsibility for teaching and guiding their teams.
• “As soon as you pit people against one another, sharing stops. Sharing and caring stops.”
  – Nathan Caldwell [31:40]
  Nathan warns that internal competition erodes trust and collaboration within teams.
• “Kindness isn’t weakness. It’s wisdom and strategy. And it holds a great team together when the pressure is on.”
  – Sondra Shannon [55:34]
  Sondra reframes kindness as a powerful leadership tool that holds teams together under pressure.

Empowering Kindness Approach

Nathan’s Empowering Kindness method centers on equipping individuals to grow through clear expectations, training, and encouragement. His approach emphasizes building cultures where kindness is modeled and reinforced daily.

Nathan’s Preferences and Technology

Nathan values simplicity and reflection, often finding leadership clarity during quiet moments with black coffee in cool weather. His tech background informs his belief that kindness and clarity must be embedded in fast-paced environments. 

Improving Guest Experience

Nathan and Sondra agree that guest experience improves when staff feel supported and valued. Kindness in internal culture translates directly to how guests are treated, creating memorable and positive interactions.

Creating Memories and Guest-Centric Culture

The Herschend values and Dolly Parton’s example show how kindness can be embedded in every layer of a business. From frontline staff to leadership, treating others with care creates memories worth repeating.

Gatemaster’s Guests’ Appreciation and Value

Sondra shares how her team at Gatemaster Technology supports clients with grace,  especially when they’re under pressure. She reminds her staff that their kindness may be the brightest part of a client’s day.

Closing

This episode reminds us that kindness is a strategic advantage. Whether leading a team or serving guests, kindness builds trust, drives growth, and creates cultures people want to
be part of.

Connecting with the Speakers