Leadership, Like Jazz: Lessons in Awareness, Adaptability, and Authenticity

In 1991, a stranger handed me a cassette tape at a South Florida district band concert. That tape, filled with iconic jazz trombone recordings, sparked a lifelong passion for jazz and set the foundation for the leadership principles I now use as an independent school leader. Like jazz, effective leadership requires acute awareness, adaptability, and authentic communication.

Today, I am proud to continue performing and teaching and have had the immense pleasure of performing and recording with iconic artists such as Aretha Franklin, Kirk Franklin, K.C. and the Sunshine Band, and Arturo Sandoval, to name a few. My current role as a leader in independent school Admission and Enrollment offers new territory for implementing the values I learned and continue to learn as a jazz scholar.???

Having enjoyed careers in both higher education and independent schools, I’ve had many opportunities to connect the dots between the lessons jazz offers to any number of applications. Several years ago, I presented a Faculty Colloquium at Illinois Wesleyan University entitled “Demonstrating The Art of Musical Communication Between Members of a Jazz Quartet.” Over time, I continue to learn that the lecture performance from years ago makes a strong case for what we can learn from the principles of jazz performance as it applies to impactful communication and meaningful collaboration in leadership settings.?

Beyond Empathy: Developing Acute Awareness Jazz musicians listen intently to each other, constantly aware of subtle rhythm, harmony, and melody shifts. This allows players to adjust in real time, ultimately creating band chemistry. The slightest feel change from a drummer, chord substitution from the pianist, or root shift from a bassist can add a whole new, unexpected palette for a soloist.??

Leaders develop acute awareness by actively listening to their team members, reading the room, and adjusting based on verbal and non-verbal cues. While the payoff isn’t spirited applause from the audience, teams with refined listening and awareness work more efficiently. My team begins every meeting with norms. Similar to a jazz quartet agreeing on specific baseline terms (key, tempo, and style), beginning a meeting with norms can set the stage for greater awareness, empathy, and healthy collaboration.??????

The Art of the Pivot Jazz is built on improvisation—musicians must be able to pivot direction at a moment’s notice. In leadership, the ability to pivot when faced with the unexpected—whether it’s a new challenge, market conditions, team departures, or team dynamics—is a critical skill.?

Recently, during my ensemble’s performance at the Jazz Education Network’s JENerations Jazz Festival, my bassist realized—just 10 minutes before the downbeat—that they had left their music back at school. Panic could have set in, but thanks to quick thinking, an iPad, a solid internet connection, and the iReal Pro app, we were able to provide enough chord changes to keep the show going. Ironically, that moment of distraction pushed the bassist to play beyond their usual boundaries. Without relying on the sheet music, they trusted their instincts and leaned on the foundation of work they’d already put in, delivering a swinging, commanding performance.?

Leaders who can pivot gracefully show adaptability and resilience, which empowers their teams to stay calm and focused, even when plans unravel.??

Finding Your True(est) Voice Just as jazz musicians like myself work to develop their unique sound, leaders must discover their authentic voice. In leadership, authenticity means communicating in a way that reflects your true values and vision, which encourages others to do the same. Despite being a trombonist, I have always connected with the sound of the tenor saxophone. I’ve spent hours transcribing the recorded solos of tenor icons such as Sonny Rollins and Hank Mobley, hoping to channel their unmistakable sounds. While the sound of my trombone will never equal the timbre of the tenor saxophone, the voice I generate is the most authentic version of me.?

Leaders who communicate with authenticity foster trust and inspire others to bring their whole selves to work, creating a more inclusive and open environment. I speak with my students daily about the importance of performing authentically. In my rehearsal space, there’s a sign that reads, “Do not Impress: Express!”—a reminder that you don’t need to bring every tool to every solo or every meeting. Learning when and where to use those tools is key to finding and using your authentic voice.

The Power of Repetition In jazz, recurring motifs create structure and familiarity, grounding the performance. Leaders, too, must repeat key messages, values, and goals to ensure alignment within the team. One of my favorite Wynton Marsalis solos is on his adaptation of Ray Noble’s Cherokee from his album “Standard Time Volume 1.” While pianist Marcus Roberts plays the melody as it was intended, Wynton begins the track with a muted solo on a repeated punchy rhythmic motif centered on the tonic pitch, Bb. This glaring repetitive theme by Marsalis momentarily shifts the listener’s attention away from the melody, providing fertile ground for potential improvisational exploration. Yet, despite this illusion of cacophony, the integrity of Noble’s beloved standard remains fully intact.??????

Through repetition, leaders reinforce important themes, helping their team stay aligned and focused on long-term goals, even navigating day-to-day challenges. However, it is sometimes the repetition of ideas that, rather than distract, adds depth to an institution’s gold standard. In the admission arena, there are some ideas that just plain work! No matter how you slice them, Open Houses offer an opportunity for prospective families to explore and get to know a new school community. While each has its unique flavor, the essence is there, and the mission is clear.?

The Turnaround In jazz, the turnaround is a musical phrase that returns the song to its beginning or transitions to something new. For leaders, a "turnaround" might be a moment of redirection, where they need to recalibrate the team’s efforts or introduce a fresh perspective. Just as jazz musicians must intuitively guide a piece back on track, leaders must navigate organizational transitions—whether shifting strategy or revitalizing morale. When Sinatra and Basie famously aligned their meteoric talents at The Sands Hotel in Las Vegas in 1966, Basie and Sinatra would always begin “Fly Me To The Moon” with the recognizable harmonic turnaround intro played by Count Basie. During his prolonged piano interlude, Sinatra would take his time, affectionately introducing the tune and claiming at the conclusion that Basie’s tempo was the right tempo for the song. Sinatra then proceeded to launch into the famous opening lyrics. In this case, Basie and Sinatra found a tempo that mutually fit their imaginations but defied previously existing norms.????

Leaders who can effectively manage turnarounds demonstrate vision, adaptability, and the ability to lead their team through change with confidence. The turnaround looks different for everyone, but it should be considered an opportunity, not a conclusion. In my first year as Associate Director of Admission, I had several learning moments that could have gone sour–but my creative, problem-solving musician persona has allowed me to adapt and lead, turning potentially challenging situations into successful ones.??

Just as every great jazz album balances structure and spontaneity, effective leadership relies on awareness, flexibility, authenticity, consistency, and the ability to navigate transitions. The best communication happens when leaders, like jazz musicians, create space for others to express themselves and adapt in real-time. In music and leadership, the harmony between preparation and improvisation allows creativity and collaboration to flourish, leading to inspired outcomes.