The Art of Organizational Leadership – Improvisation within Form

The key to thriving, especially in chaotic times, is to have adaptive leaders at every level of an organization. If we want leaders at every level of our organization, we must acknowledge that leading authentically is, at its heart, an act of self-authorship. This means that, as leaders of leaders, we can’t simply ‘make’ others into leaders. I can’t force that growth upon you. Instead, my role is to create the conditions where you can discover and embrace the most authentic, most impactful version of yourself..

On the other hand, we have a business to run!  We can’t have a bunch of snowflakes blowing around here finding themselves.  We need people to do certain things!  We have a mission, vision, purpose and values. There are legal requirements and we have to make money.  

Those truths stand in tension with one another.  How do we as an organization cultivate self-expressive leaders at every level without becoming a carnival freak show? 

More Art than Science
The answer to this question is really more art than science.  An enterprise will not have leaders at every level if we try to manage our way to that result – we can not manage our way to leadership.   If someone got to where they are by someone else telling them what to do, they are not a leader.  Managing is easier but it does not lead to excellence and durability in the long term.    

A beautiful metaphor for how to run a business with leaders at every level is improvisational jazz.  Improvisational music actually adheres to form.  It works off of a chart and there are various forms this chart will take – maybe a 32 bar AABA ballad or a 12 bar blues.  There is a time signature, chords and melody.  That is how everyone knows where to come in after a drum solo – everyone, even the caveman drummer, is soloing over the form of the song.  The rule is you can take things as far outside as you want as long as you stay tethered to the form.  

Most people have heard the original Rodgers and Hammerstein version of My Favorite Things from The Sound of Music. I would have gotten my ass kicked in 1981 if the kids from my neighborhood had found out, but true confessions: my sister and I wore the soundtrack out. We spent endless hours dancing around the living room singing along and acting out the scenes like a couple of sissies. There is 8 mm footage somewhere in a closet in my parents’ house documenting this thespian folly.

As I got older, I traded show tunes for the drums. By my late teens, I was deep into the world of improvisational jazz, which is when I first heard John Coltrane’s 1961 take on My Favorite Things. It couldn’t be further from the original. While the original is a stiff, show-tuney ¾ waltz, Coltrane’s version is revolutionary. Drummer Elvin Jones overlays a heavy 6/8 African polyrhythm on the ¾ framework, creating an intricate two-against-three feel. Harmonically, instead of the original’s fast-moving chord changes, pianist McCoy Tyner locks into a hypnotic modal vamp. Tyner’s piano solo is expansive, it’s authentic, and personally, I think it’s one of the best piano solos ever recorded. Dancing on top of the rhythm section Coltrane takes the song into an alternate reality.  They took a classic standard and created a completely novel experience, yet it remained, undeniably, the same song. You can find over 30 different versions of My Favorite Things on Spotify today—all unique, all the same song. 

Let’s apply this to business. On one hand, we are proud of individuality; on the other hand, we don’t really tolerate real individuality. If we are honest, our impulse is to homogenize it. What do you think would have happened if Atlantic Records tried to make Coltrane play it like Julie Andrews? Trane would have wrapped that soprano sax around the producer’s head. They would have killed the magic. Clearly, we can’t have an organization where everyone is simply ‘finding themselves’ in isolation, but if we want to be a company with leaders at every level, we must honor the uniqueness of every individual, while staying true to our mission, purpose, and values—our musical chart.

Ours is a covenantal relationship.  It rests on shared commitment to ideas, to issues, goals, to purpose and even some process.  Covenantal relationships induce freedom.  Once we know what our company is all about we can improvise.  But we need that framework to play music together.  

Leading Leaders
If we embrace the reality that self-expression, blazing one’s own trail, is the essence of leadership, then individual performers can be great leaders. But not all leaders are great leaders of leaders. They can inspire, they can trailblaze, they can cast a vision of the future, and in that sense, they can help unlock potential in others. However, these individual performers may not be capable or they may not operate in a context where they are called on to actively support the development of others. They can be Elvin Jones, a legend and an inspiration to many drummers, myself included, but they are not John Coltrane leading the quartet.

Let’s extend the music metaphor. Since the essence of leadership is authenticity, the role of a leader of leaders can be understood as that of a producer. It’s not your record, but you are helping the artist capture the clearest, most authentic, most impactful expression possible. The legendary producer Rick Rubin approaches it exactly this way; he views his job not as controlling the artist, but as helping them reach a destination they haven’t yet discovered. He acts as a guide, a psychologist, and a curator of taste, stripping away the noise to create a safe space for authenticity. When we approach leading this way, we are engaging with the world—and our teams—rather than trying to entrap them.

Creating a True Learning Environment 
It is impossible to teach anything that can’t be broken down into repeatable elements. Car or plane operation, onboarding an applicant—those things can be taught. With leadership, just as with art, you reinvent every time. In music, you learn and play with scales, chord structures, patterns, and rudiments. Sometimes artistic expression can mean bending or breaking a “rule.” In leadership, we learn principles, patterns, and perspectives and use those to improvise a response to new opportunities and problems. It is really quite similar.

Warren Bennis contrasted managers and leaders in his book “On Becoming a Leader.”  The distinction is vital for us to grasp. Look at how these roles diverge:  

Manager	Leader
Copy	Original
Surrender to Context	Master Context
How and When	What and Why
Control	Trust
Systems	People
Accepts Status Quo	Challenges Status Quo
Does things right	Does the right things

You see why we can’t train that list on the right?  Managers who simply accept convention may reach the top of a bureaucratic organization, but will never use their talents to the fullest. Leaders must understand the difference and a leader of leaders must help others see it. 

Here is another great chart from Bennis’ book.  This one is Learning vs. Training 

Learning	Training
Active	Passive
Ideas	Facts
Dynamic	Static
Discovery	Dogma
Risk	Rules
Exploration	Prediction

Leadership Transformation
Training preserves the status quo and makes great soldiers of us all.  True learning is experienced as a personal transformation.   A person does not gather learnings as a possession but rather becomes a new person.  

Think of the most influential musicians: they are not the most technical musicians. Eric Clapton or B.B. King are not the best technical players—they have soul, they connect with the heart because it is who they are. Their experience has transformed them, and that is what shows up on stage. John Bonham is, in the view of many, the greatest rock and roll drummer of all time because when he played, who he was was on display. Objectively, Bob Dylan and Willie Nelson are not amazing singers. They are leaders because they are authentic. They have lived life, they have seen some things, and it has made them who they are, and who they are is on display. That’s what we are going for here. We are looking to break the next Bonham of business managers, the Clapton of sales, the Dylan of service delivery.

Leaders are not made by others, but if they are fortunate they have someone empowering them in the transformation process.  To be a great leader of leaders I must embrace the fact that there is no human who will do what I say. The only power I have is the power of persuasion, inspiration and expectation.  

Ultimately, our role as leaders of leaders is to be the producer—creating the space where talent can flourish. We define the mission, provide the framework, and empower our people to improvise within it. Our organization, our world doesn’t need more managers keeping time; we need leaders who have the chops and know the chart well enough to make it their own.