Will Guidara

Creating Connections in Flight: A Lesson in Empathy from Delta Airlines

smgaillard Uncategorized , , , , , , , , , , , , , , ,

As many of my close friends and family know, I am a nervous flyer. Over the years, I have had to face this fear head-on, seeking the support of a therapist and using strategies, including medication, to overcome the challenges of flying. While it hasn’t been easy, I’m proud of my ongoing efforts to confront this fear.

Flying isn’t something I do often—time and expense tend to be barriers—but recently, I had the opportunity to attend the National Education Leaders Workshop in Atlanta. It was an incredible event, full of ideas on reimagining teaching and learning in the schoolhouse. To experience it, though, I had to book a flight.

Before the trip, I reviewed my strategies with my therapist and felt optimistic. For the first time in a long while, I didn’t feel that familiar pit of anxiety in my stomach as I prepared for the flight. Instead, I felt calm anticipation.

As I sat at the gate with my colleagues, I began to notice small, powerful moments unfolding around me. At one point, a pilot walked out—likely heading for a quick coffee—and spotted two young boys playing with a toy plane. He knelt down to greet them warmly, telling them how excited he was to have them on his flight. Then, he invited them and their parents to visit the cockpit before takeoff. Later, as I boarded, the gate agent greeted each passenger—including me—by name. Touched by her effort, I made sure to thank her personally, using her name from her nametag.

These intentional acts of connection helped dissolve any lingering nervousness I had about the flight. They also served as a powerful reminder of the importance of small, meaningful gestures in leadership. Witnessing those moments inspired me to think about how such intentional actions could foster trust and belonging in the schoolhouse, reaffirming my commitment to creating a culture of connection in our community. The flight itself was smooth, and I even shared a lighthearted exchange with the pilot, who joked about our shared baldness. These small yet meaningful moments reminded me of a recent book I read, Unreasonable Hospitality by Will Guidara. It’s a must-read for leaders who want to create cultures of connection and build meaningful moments within their organizations. Check out the book here.

Delta Airlines demonstrated a commitment to humanity and empathy during that flight, and it left a profound impact on me. Their intentional gestures—from personalized greetings to creating special moments for passengers—highlight the power of thoughtful actions. As a school leader, this translates to practices like ensuring every student and teacher feels personally welcomed, celebrating achievements in visible ways, and creating opportunities for connection that make each person feel valued and supported. Their thoughtful gestures weren’t just routine—they were intentional, and they made me feel seen and valued. As a school leader, this experience reinforced my belief in the power of small yet meaningful actions to create a culture of connection in the schoolhouse.

Four Action Steps for Building Connections in Your Schoolhouse

  1. Greet Students and Teachers at the Door Be present and intentional at the start of the day. A warm greeting at the door sets a positive tone and ensures that everyone—students and teachers alike—feels seen and valued.
  2. Write Handwritten Notes Take time to write notes to teachers, celebrating the amazing things you see happening in classrooms. A personal, sincere message can uplift and inspire.
  3. Make Positive Phone Calls Home Share good news with families about their children. A positive phone call can build trust and strengthen relationships with parents and guardians.
  4. Surprise Your Team with Small Acts of Kindness Bring a favorite coffee order, leave a sticky note of encouragement on a desk, or organize a quick celebration to recognize milestones. These unexpected gestures build morale and community.

Building Psychological Safety

The Delta crew had no idea I struggled with flight anxiety, but their thoughtful actions created an environment where I felt safe and at ease. Similarly, in our schools, we may not always know the struggles our students, teachers, families, and staff carry with them each day. It is our responsibility to create an atmosphere of psychological safety—a place where everyone feels supported and valued.

Each act of connection, no matter how small, sends a powerful message: “You matter. We’re glad you’re here.” When we lead with hope and belief, we create ripples of positivity that can transform our schoolhouse communities. Let’s commit to making these moments a daily practice, knowing that our words and actions have the power to uplift, inspire, and connect.

Building the Band: Cultivating Collaboration in the Schoolhouse

smgaillard Uncategorized , , , , , , , , , , , , ,

The principalship is a calling steeped in paradox. It is a role of service, yet it can often feel isolating. As leaders, we navigate the balance of vision and strategy while seeking connection and collaboration. We crave the kind of creative partnership that defined the great songwriting duos—like Lennon and McCartney, Ann and Nancy Wilson, or Stevie Nicks and Christine McVie. These partnerships thrived on synergy, mutual respect, and a shared goal of creating something timeless.

For me, The Beatles’ creative dynamic has always been a source of inspiration. I’ve long yearned to be the Lennon to someone’s McCartney or the McCartney to someone’s Lennon, building something extraordinary with a thought partner. That kind of collaboration can feel like a salve for the loneliness that sometimes accompanies leadership. But as I reflected the other day, I realized I might not be destined to be part of the duo. My role is to ensure the conditions are right for these partnerships to thrive.

This epiphany came as I watched two teachers collaborate on a shared vision for our school’s culture. They were bouncing ideas off one another, refining strategies, and creating something beautiful in the process. In that moment, I realized: they were Lennon and McCartney. My role wasn’t to join their duo but to ensure they had the space, encouragement, and support to succeed.

George Martin, reflecting on his work with Lennon and McCartney, once said: “My job was to make it easier for them to express themselves and to capture that in the best way possible.” That wisdom resonates deeply with me as a principal. Leaders must recognize that collaboration is not about claiming the spotlight but about amplifying the voices of others. It’s about creating the conditions where creativity and synergy can flourish.

Every school faculty has the potential to be a great collaborative band like The Beatles. The role of the leader is to help that band find its rhythm and create its best work. This realization brought both clarity and peace. I may not be in the band, but I can help the band I serve become something extraordinary—a group defined by its collaboration, creativity, and profound impact.

Leaders must tune into these moments and reflect on the ways we cultivate collaboration in our schools. It’s not always about being part of the duo or the band. Sometimes, the most meaningful contribution is ensuring the band can play its best.

Four Ways Leaders Can Foster a Culture of Collaboration

1. Create a Shared Vision

Collaboration thrives when everyone rallies around a common goal. Build a vision that is clear, compelling, and rooted in the needs of your school community. Like Will Guidara’s team in Unreasonable Hospitality, bring people together to align their work with a shared purpose.

2. Honor and Empower Partnerships

Seek out and celebrate the Lennon-and-McCartney-like duos in your building. Create opportunities for those partnerships to deepen, whether through shared leadership roles, co-teaching models, or collaborative projects.

3. Provide Tools and Time

Collaboration doesn’t happen by chance; it requires intentional structures. Build time into schedules for teams to meet, reflect, and create together. Provide resources—whether it’s professional learning, materials, or guidance—that remove barriers to teamwork.

4. Reflect, Celebrate, and Elevate

Regularly highlight collaborative wins, both big and small. Reflection helps us learn and grow, while celebration fuels the energy to keep creating. Whether through shout-outs in staff meetings or sharing stories in a blog post, elevate those moments where synergy shines.

The bands we serve have the potential to be like The Beatles, and with thoughtful leadership, it can become a force for something extraordinary. And at the heart of it all is the belief that collaboration is the foundation of every masterpiece.

Let’s help our schools find their rhythm, their harmony, and their shared purpose. Together, we can lead the band and inspire greatness for the kids we serve.