John Coltrane: lessons from jazz improv for startup leaders

In a startup, entrepreneurs must be able to improvise when designing solutions to deliver competitive advantage, either as brilliant creativity or as a back-to-the-wall response to adversity. Either way, it’s the spontaneous convergence of design and execution while producing something novel. Improvised behaviours are needed because where rapid change and uncertainty combine with little time or resources, it is a coping alternative when turbulence exceeds the capacity to plan and resources. It’s the very essence of entrepreneurship.

A long-standing stream of start-up strategy thinking has recognised ‘deliberately emergent’ approaches to turbulence, by embracing new approaches and routines for adaptively achieving product-market fit. The lean startup methodology, for example, emphasises systematic customer experimentation in search of functional business models with minimal misdirected effort.

Making strategic adjustments by pivoting and retesting business models is integral to the process. Equally, agile software methodologies are based on adapting to change over following a plan, customer collaboration, and individual interactions over processes. By being adaptable and open to surprises (good and bad!), entrepreneurs use resources at hand to achieve ends that were unknowable in advance.

Some might view this as ad hoc, trial and error, or experimental,  but it’s all a bias towards action rather than a predilection for analysis.  It is the deliberate impromptu act of deviating from a routine, creating a novel product to solve a problem or exploit an opportunity, spontaneous responses to events that are both unexpected and unplanned-for.

Although startups differ in many aspects from jazz combos, lessons about improvisation may be drawn from that context.  I’ve been a clumsy, enthusiastic saxophone player for several years now, able to knock out a few recognisable Glen Miller and Simon & Garfunkel tunes and get folks’ toes tapping. They say ‘don’t play the saxophone, let it play you’ – but sometimes I just can’t get a decent sound out and it sounds like a strangled parrot.

As part of learning the sax, you have to be able to improvise, playing jamming ‘free flow’ sessions to stretch your style, and speed of thought, playing chord progressions as spontaneous practice. Alas my clumsy concrete fingers constrain my dexterity, but playing sax is fun, relaxing and energises me. My favourite saxophonist is the late American John Coltrane, also known as Trane. Coltrane pioneered the use of modes in jazz and was at the forefront of free jazz. He played with some of the greatest jazz exponents, including trumpeter Miles Davis and pianist Thelonious Monk.

Growing up in North Carolina, in the 1930s, he benefited from a musically family. His mother sang and played piano, his father played clarinet and violin. When his family moved to Philadelphia, Coltrane found himself in a cauldron of jazz and a breeding ground of the hard bop style as he began gigging with club trios and R&B combos. At the Granoff Studios, he took a course of music theory and lessons. Practicing at home, he would finger but not blow into the sax so that he could quicken his reflexes without waking his neighbours.

Coltrane's perfectionism was legendary. Borrowing exercises from pianists, he stunned fellow saxophonists by forcing his fingers to navigate arpeggios, trills, and wide leaps in melody. In 1955 his career took off. Miles Davis hired Coltrane into his quintet, gambling on a 29-year-old with a jagged style. The quintet's albums Round About Midnight and Cookin’ were landmarks, but Davis grew aggravated with Coltrane's unreliability due to his drug habits, and in 1957 Davis fired him.

The dismissal was a shock. In its aftermath, he quit drugs and alcohol. Under the mentorship of pianist Thelonious Monk, Coltrane started obsessing over harmonic variation. I would go as far as possible on one phrase until I ran out of ideas he said. His unique style was dubbed sheets of sound. With these modal forms, Coltrane found a way to combine side-slipping chromatic movement with more lyrical lines. The end result was the sound of a sax flitting, hovering, baiting the rhythm section, then colliding with it head-on in a moment of harmonic convergence. He had created his own, unique trademark style.

His greatest recording success, A Love Supreme (1964), was a blockbuster selling a million copies. It solidified Coltrane's innovator status. In one of jazz's defining moments, Coltrane conjugated a leading four-note motive through every register and key, then gravitated back to the original key to chant the four-syllable mantra, a love supreme. Coltrane went further with his experimentation. His music became even more exploratory, dropping the rhythmic pulse that had structured even his most wayward previous ventures. Coltrane began bridging out to a new generation of free jazzers, but on July 17 1967, he died of liver cancer, aged 40.

To truly know Coltrane’s work is to hear every note in context, my favourites being his chord substitution cycles known as ‘Coltrane changes’, heard on Giant Steps, considered to have the most complex and difficult chord progression of any jazz composition. His development of these altered chord progression cycles led to further experimentation with improvised melody and harmony that he continued throughout his career.

Coltrane’s left behind a considerable body of unreleased work that has been posthumously issued. He won the 1981 Grammy for Best Jazz Performance for Bye Bye Blackbirds, a live recording made in 1962, and he was given the Grammy Lifetime Achievement Award in 1992, twenty-five years after his death. Coltrane lives on, in 100 albums on iTunes.

Coltrane was a jazz innovator, he did what any startup entrepreneur does: he improvised, inventing novel responses and taking calculated risks without a scripted plan or a safety net on guaranteed outcomes. Coltrane didn't dwell on mistakes or stifle ideas – like entrepreneurs in today's hurried, harried world of startups, he made it happen. He knew that spontaneous creativity was an act of discovery and the heart of his jazz. With less than 1% of the notes on the written page, he made up the rest on the fly - no going back to correct mistakes or rethink a passage.

In his revelatory book, Yes to the Mess, jazz pianist and management student Frank Barrett shows how this improvisational ‘jazz mind-set’ and the skills that go along with it are essential for effective startup leadership. He describes how like skilled jazz players, startup leaders need to master the art of improvisation, perform and experiment simultaneously. Here are lessons startup entrepreneurs can take from Coltrane around improvisation:

Playing it safe gets you nowhere. If you don't take risks, you'll never excel. Playing it safe all the time becomes the most dangerous move of all. Rote activity doesn’t lead to the path of innovation for disruptive technology.

Learn from mistakes. It’s impossible to hit the perfect notes all the time. When you play a wrong note, you learn from it and move on. Similarly, with your startup culture, it is ok to fail because each thing that doesn’t work leads you to something else that does.

There is no such thing as a mistake in jazz – come and listen to me play! Coltrane built a constant change of pace to create new sounds. Startups should also embrace errors and accept new possibilities as they adapt, solve problems and learn.

Experimentation leads to innovation. With so much of jazz culture emphasising improvisation, I find it important to note the value of experimenting fearlessly in business, to try new things and innovate.

Jazz follows a basic chord progression with a simple beginning, middle and end. In startups, we also start with minimal structures. Iterations begin as prototypes progress and then final aesthetics, allowing us to identify what works and what doesn’t throughout the iterative phases of product innovation.

This is one of the most important lessons to keep in mind. This idea is most embraced in the fields of design thinking and user experience design, in which prototypes (or samples) are built, tested, and improved upon. A 20% thinking, 80% doing mantra gets you success.

Make it matter in live performances A favourite saying of jazz trumpet legend Miles Davis was If you’re not making a mistake, it’s a mistake. Jazz musicians assume that you can take any bad situation and make it into a good situation. It’s what you do with the notes that counts. Reach beyond your comfort zone.

Expect surprises and adversity. In jazz (and startup life) is about how you respond. If running a startup was always smooth sailing, and it followed the notes on the score, everyone would do it. The old adage applies, that ‘a smooth sea never made a skilled sailor’, so anticipate hurdles and maximise learning from them.

Jazz has its roots from being–in the-moment collaborative innovation, just like the act of starting and growing ventures. If you're not actively seeking new challenges and ways to expand your horizons, living the ups and downs, you are falling behind.

Listening to those around you is more important than what you play yourself If you're the one talking, you're not learning anything. Listen, absorb what you hear, and use the information to make a conscious choice about whatever you're facing.

In jazz, performers vary their sounds and provoke others to respond, creating new music through collaboration. Similarly, in startups, there is constant ideation and creation to disrupt, to simplify the complicated and generate new ideas. This collaboration happens best when everyone is working and listening together.

A jazz player listens in two special ways. Firstly, they ‘listen with generosity’, listening for the beauty, brilliance and ingenuity of their band mates, encouraging the expression of their virtuoso talents. Secondly, they ‘listen to the silence’ between the notes.  In business, listening rather than talking is a key skill. In your startup, listen closely so you can move as one.

There's a time to stand out as a soloist and a time to be a team. In jazz, it is common for individual performers to alternate between lead and supporting roles in a single performance. when each team member focuses on helping the team look good, the end product comes out significantly stronger Startups should employ a similar approach to develop the team and bring new thinking to the fore.

You rocked a project. However, it's more likely the case that your team rocked a project, together. Katie was on top of the customer pitch, Sue got the product demo sorted, James nailed the process map. The best startup leaders are those that make others sound and look good.

Jazz, like a startup, is about pitting your wits in the heat of the moment. Just watch the different solos and see how the other members support the soloist and you will be surprised on the amount of dynamic emotion that is created. If you’re a startup founder, grow your business by building an outstanding team of outstanding individuals.

Find your own sound: rely on minimal structure and maximum autonomy Jazz musicians prepare themselves to be spontaneous. Startups must do the same. Coltrane played jazz as smooth and cool, and as a rage; his solos never seemed to begin or end. Coltrane wasn’t methodical, but wasn't messy either. His sax playing was a conversation, a give and take, a connection and a dialogue between himself, his instrument and his audience. Coltrane knew this instinctively, he used innovation to find his own sound.

Coltrane teaches us that you have to find what’s right for you, leading to finding your own place of uniqueness. You have to find what you do best, and find what is best about you, for you.

What Coltrane and entrepreneurs share is the ability to address complexity and thrive while playing in the messy, fertile space of uncertainty, ambiguity and promise. He said, I start in the middle of a musical sentence, and move in both directions at once. His spirit of adventure, desire for improvisation and innovation captures the essence of an entrepreneur, setting out the score a startup founder’s journey of expression and discovery.

The metaphor of jazz improvisation for entrepreneurs, facing problems which are unstructured and ambiguous, is clear. Nurturing spontaneity, experimentation, the serendipity of a jazz combo doesn’t just happen, it takes preparation and practice, but improvisation is the core cultural driver.

Entrepreneurs also improvise naturally, working with scarce resources under conditions of uncertainty. With little time or even inclination for contingency planning, they are routinely called upon to ‘think on their feet’ by necessity or choice, floating hypotheses about what might work and what might not, and leaving both the hypotheses and themselves open to contradictory data and recalcitrant forces.

Improvisation is doing better than the best work you could have done, it only takes a spontaneous reaction for us to make the best use of things in hand, rather than waiting for better things to come our way.