As we focus this first quarter on Healthy Leaders, I’m reminded that one of the most important—and often overlooked—indicators of a Healthy Leader is humility. Not the kind that downplays confidence or conviction but one that keeps a Leader grounded, open and genuinely connected to the People they serve. Healthy Leaders understand that Leadership isn’t about position or recognition. It’s about service, trust and putting others first.

Which turns my thoughts immediately to Colleen Barrett. Colleen led with a quiet strength rooted in humility. She never needed the spotlight, yet her influence was undeniable. She showed us what it looked like to lead with heart—listening first, serving Employees and staying true to the values that make Southwest special. Her example continues to shape how many of us think about Leadership today.

I’ve also been fortunate to experience that same kind of humility firsthand through a cherished mentor (and CCB protégé) who had a profound personal impact on me: former Southwest Airlines executive, the late Teresa Laraba.

Teresa demonstrated humility in a way that was both subtle and powerful. Throughout her Southwest career, including serving as Senior Vice President Customers & Culture, she led with grace, authenticity, and an unwavering commitment to People. She didn’t lead for recognition; she led because she genuinely cared about the work and, more so, about the People doing it. Teresa had a way of making you feel seen and valued simply by how she showed up every day.

I shared her story during a Southwest Leadership session a few years ago as a way to reflect on the lasting impact of humble Leadership. Her example confirmed that humility isn’t weakness, it’s strength with intention. The best Leaders don’t make it about themselves; they make it about the Team. They ask thoughtful questions; listen more than they speak; and give credit freely when things go well.

We unfortunately lost Teresa far too soon when she passed away in 2015, but her legacy lives on through the countless Leaders she influenced and the Culture she helped shape. Her example, much like Colleen’s, continues to guide how I strive to show up with humility, care and a genuine commitment to serving others.

In my experience, humility is foundational to healthy Leadership. It builds trust, creates psychological safety and invites others to bring their full selves to work. Leaders who lead this way don’t need to be a hero; they simply need to serve with authenticity and heart. That lesson—taught by Colleen Barrett and modeled by Leaders like Teresa Laraba—is one I carry with me every day.

XOXO,
Bobby