🌀 Birth of The Cool – Miles Davis Leadership & Life Lessons

🌀 Birth of The Cool – Miles Davis Leadership & Life Lessons

🌀 Birth of The Cool – Miles Davis Leadership & Life Lessons

🌀 Birth of The Cool – Miles Davis Leadership & Life Lessons

🌀 Birth of The Cool – Miles Davis Leadership & Life Lessons

Birth of The Cool - Miles Davis Leadership & Life Lessons

Birth of The Cool — Miles Davis Leadership & Life Lessons


Legendary musician Miles Davis left a massive artistic legacy, but he is also a masterful study of long-reaching success that can serve as a stunning example for any leader today. For those who already know jazz — and for those who don’t — here are some leadership (and life) lessons to take from Miles Davis himself.

Whether you love jazz or not, you’re likely familiar with Miles Davis’ classic 1959 album “Kind of Blue.”

One of the best-selling jazz albums of all time, “Kind of Blue” represented not only a radical change of sound for Miles Davis but for jazz music as a whole. Although the album’s timeless tunes and incandescent performances could provide a lifetime of study for students of jazz, it also has much to teach us about leadership, collaboration, and creativity.

Miles Davis was an extraordinary creative leader and it’s partly because of how he led his band members, that he turned out such an innovator.

During the Kind of Blue sessions, Miles Davis found a powerful combination of transformational and facilitative leadership which he would continue to use for the rest of his life as a band leader to reinvent himself and create one breakthrough in music after another. And this is where any leader of any field will find inspiration.

The fact is that nurturing spontaneity, creativity, and experimentation is no longer an optional approach to leadership.

It’s the only one approach. The current velocity of change demands nothing less. It demands paying attention to the mental models, the cultural beliefs and values, the practices and structures that support improvisation. This can help your organization emulate what happens when jazz bands improvise.

Miles Davis brought together some of the most talented musicians in their own right to work with him in his musical exploration. How did he do it? Let’s explore the lessons of Miles Davis in the art of leading the best to be their best.

Here are seven major takeaways from the extraordinary career of Miles Davis that anyone striving for leadership should apply today. Even if you’ve never held a trumpet, Miles Davis’s life contains valuable lessons in leadership that any of us can use.

Lesson #1: Look For Raw Talent

Birth of The Cool - Miles Davis Leadership & Life Lessons - Look For Raw Talent

When the drummer Tony Williams joined one of Miles Davis’ later groups he was just 17 years old. Just as Miles Davis did with Coltrane during Kind of Blue he would continue for the rest of his life to find young raw talent. He would bring them in and support them in finding their own voice.

Miles Davis’ great combos included players with different styles and tendencies.

He hired players who would complement his playing and each other’s. He didn’t need anyone who sounded like him because he had that covered.  It is important to remember as a leader that our success is a reflection of the past while we are hiring for the future. Hiring people with complementary but different skills and areas of expertise broadens the set of problems they can solve and increases their impact on the organization.

As an established adult, Miles Davis came full circle by regularly including great young musicians in his bands.

Miles always sought out fresh sounds, new players with unique approaches to improvisation, and across all ages, demographics, or national origin. These musicians he chose blossomed into widely accepted masters of their instruments and music in general. He was unwavering in his ability to spot great talent.

There is no doubt that Mile Davis wanted to find ways to more fully realize the incredible potential of his team.

He got the best players in the world and forced them to listen to the music by not telling them what to do. Simplify the task down to its essential elements, put your smartest people on it, and force them to listen — to each other, to the interaction between the company and its customers, and to the market.

As you rise up the ladder to success, never be too busy to mentor.

This drives the industry and also your own personal legacy. Such engagement helps you always keep a leg up on the competition by associating with new blood while generating goodwill and good karma. This is especially important for a future workforce that is largely of color.

Miles Davis, as a bandleader — I mean, the boss — had an incredible ear for musical talent.

He regularly surrounded himself with amazing young players, often whose skills were not yet widely known. In time, their performances and recordings by Miles Davis’ groups would show others — and many times the sidemen themselves — what these musicians were capable of.

If you stay too narrowly focused on merits you will only get more of the same. You will be creating a team that can only reproduce the past.

We should care much more about getting people who genuinely share the values we want to promote, who can apply creative thinking and curiosity to problem-solving and most importantly can bring in fresh perspectives. Either because they are younger and represent the next generation or because they bring with them a different background than the rest of the team.

Lesson #2: Be True To Yourself

Birth of The Cool - Miles Davis Leadership & Life Lessons - Be True To Yourself

From Steve Jobs to Lady Gaga to Martin Luther King, Jr. those who are courageous enough to be transparent in their being are those we tend to watch — not cookie-cutters. Embrace yourself as you develop your career and watch what happens.

Over time, Miles Davis clearly stopped trying to play like his other trumpet idols, and found his own distinct, personal sound.

It became more melodic, more intense, focused on the middle register of the horn, and always displayed his masterful use of silence. And then for decades Miles Davis kept reinventing himself, the music, and his overall approach to jazz.

It’s not uncommon for leaders to face pressures that push against what they believe to be right.

But we must go with our gut and have the moral fortitude to carry on — to do what we believe is right. If we believe we have the right people and tools and we’re satisfied with the results, we must sometimes recognize other opinions as “noise” and block them out.

Sometimes it takes you a long time to sound like yourself.

There’s some solace in the fact that even the great Miles Davis had to spend some time trying things out before really coming into his own. I think his words will resonate with any creative who pours their soul into something, but still feels a little like they’re in someone else’s skin.

Enjoy your self at every level of your experience. And at the same time continue the search and quest to refine and improve your skills.

We can learn from everyone around us, it does not matter if they are “better” then us or not. There is always something interesting to learn from each other if we listen and look. And we can learn from almost any situation if we are open enough.

As I think about Miles Davis I find someone who was simply himself.  

There are stories of him turning his back on the audience while playing.  Definitely breaking the rules, but he was himself. He didn’t care that at every stage of his growth that there were people there complaining about his musical direction. He simply was himself.

And there is a paradox you must accept if you want to find your voice: it takes work.

This is counterintuitive because all of the great voices we admire seem as if they were always present in those creators. This is a falsehood. It took them a long time to learn how to create like themselves. Have patience. Be willing to experiment and try different things.

Lesson #3: Keep It Simple

Birth of The Cool - Miles Davis Leadership & Life Lessons - Keep It Simple

One of Herbie Hancock’s favorite Miles Davis moments came at a time when Herbie claimed he’d grown tired of playing the same music over and over. Miles Davis said to him, “Don’t play the butter notes.

With Kind of Blue, Miles Davis turned around 180 degrees and went toward simplicity.

Simplicity that empowered and freed his players to improvise and create, rather than pushing them to the limits of their technical mastery. There are probably business benefits in relying on radical simplicity to free and empower employees in a similar way.

For sure, Miles Davis didn’t like extra stuff.

He would whisper in people’s ear as they were playing the Blues in F — “don’t play the F.” He would challenge himself and his team to question every note. It’s not only about the final product, it’s also about the resources you’re consuming to build it. Miles Davis didn’t like unnecessary notes because it distracted him from playing the necessary notes.

In business, Toyota has four simple rules that provide minimal structure.

Including, “the pathway for every product and service must be simple and direct.” Aside from those rules, workers have autonomy to improve their techniques and suggest improvements. Keeping things simple is your business’s path to success.

Too much structure kills innovation. Guided autonomy is the key. Far simpler than meaningless “organizations”.

Jazz has basic fundamental structures that serve to facilitate coordination among players, but they’re loose enough to allow for freedom. A similar balance of clarity and flexibility is ideal in the workplace, giving teams guided autonomy.

Simplicity is elegant, beautiful, powerful. But it demands more energy, more time, and often more money. Simplicity is the weapon of the few.

Many in the business world are experts at making things needlessly complex. Despite this, the best leaders know how to cut through the complexity and find simple solutions. By becoming more aware of the ways that you create complexity, and experimenting with ways of countering it, over time you too can become a simplicity-minded manager.

One of the essential attributes of a modern leader is the ability to cut complexity everywhere.

Develop the ability to take large, complicated things — and information — and make them very simple. It is important to spend your time doing the things that bring you closer to your goals. Everything else that simply takes up your time needs to be shunned. Keep the things that work and get rid of the things that do. keep things simple. Cut the fluff.

Lesson #4: Give Space To Mistakes

Birth of The Cool - Miles Davis Leadership & Life Lessons - Give Space To Mistakes

In classical music, mistakes are easily identifiable and frowned upon; but in jazz, they are embraced, because errors encourage improvisation. Thelonious Monk, who was known for his creative improvisation, was always looking for the right mistakes in his music to express the beauty of uncertainty.

If someone plays an unexpected note the next note will make it right. 

At Pixar they have a principle called “Make each other look good,” which means that whenever someone says something in a meeting, instead of trying to find the flaws, everyone else will make it sound right by looking for opportunities and adding to it.

An experimental approach favors testing and learning as you go. It means presenting ideas, then observing how others pick up and build on them. 

This is leadership with a mind-set of discovery, floating hypotheses about what might work and what might not, and leaving both the hypotheses and yourself open to contradictory data and recalcitrant forces. You might run several experiments simultaneously, testing various programs and approaches to see what works and extracting lessons to fashion your next moves.

As a leader, you will want to build a culture that loves to test and encourage your colleagues to think this way.

Miles famously took a lot of criticism for constantly breaking protocol. He would play gigs with his crew and change things every night, always adjusting, never letting anyone get comfortable. His younger musicians would question him on this. Miles would say “I pay you to experiment on stage.

You might think that a lot of leaders say they are giving their team a great amount of freedom.

But they rarely give the “don’t worry I will have your back” kind of trust, which Miles Davis gave these musicians. Giving people freedom without trust feels more like a disclaimer of responsibility and produces stress and anxiety — not creativity. When you couple trust and freedom with a bold ambition, people will reward you with their courage, ingenuity and they will surprise you by going above and beyond.

Errors are an important source of learning. Instead of punishing mistakes, I encourage leaders to adopt a policy of enlightened trial and error.

On the song ‘Freddie Freeloader’ Miles Davis comes in one bar early at one point. Then, the band immediately adjusts to this unexpected entry in such a seamless way that very few people notice the subtle glitch. This is the power of collective improvisation: Everybody listens to everybody else and adjusts to what they are doing.

Making mistakes is inevitable. But there is a way to think of them differently and see their benefits.

If we can embrace the reality of mistakes, we can free ourselves to be more creative in our lives. Mistakes are part of the trial and error, experimental nature of life. The more you adopt the experimental, evolutional frame, the easier it becomes to handle mistakes. Handling mistakes well can help you relax and enjoy all aspects of life more.

Lesson #5: Unlearning is The New Learning

Birth of The Cool - Miles Davis Leadership & Life Lessons - Unlearning is The New Learning

We all have routines, habits based on what has worked for us before. But this can lead to us getting better and better at the wrong things — what I call skilled incompetence. We need to be suspicious of our own patterns and be fully present in the moment, seeing situations for what they are now and not what came before.

One of the principles jazz musicians live by is mastering the art of unlearning.

There is a temptation to play what has been played well in the past. It’s risky to make something up in front of an audience. That’s why jazz musicians have to trick themselves into unlearning their own routines and habits so they don’t automatically fall back into clichés. The enemy of jazz improvisation is routines, habits and success traps.

Holding on to stubborn, outdated beliefs and mistaken assumptions can make you obsolete in a business or industry without ever knowing why.

World is changing at the speed of thoughts. What’s holds true today does not to be necessarily hold true tomorrow. To become — and remain — a strategic, lifelong unlearner, you need to consciously challenge what’s worked in the past.

No, unlearning is not about forgetting the what you have learnt.

Unlearning is an art of letting go of old knowledge, skills, information or habits in order to make a room for new ideas and learning which might be better for success in life. You need to recognize the changing world is demanding to let go old and learn new knowledge, skills and competencies.

The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn.

There sure are some things which we need to consciously get rid of. In other words — “Unlearn”. I think our minds are way too precious to keep in a lot of garbage, we need to process and throw away the unnecessary stuff.

What you are is what you have been. What you’ll be is what you do now.

The secret to effective learning is to be willing to unlearn and try to find new methods — even if your previous approaches brought about great results. That is why unlearning and relearning usually happen together as a consecutive process.

Change is continual, and in order to stay current and not dive into the world of the obsolete, unlearning is a vital component.

Everyone has acquired knowledge that built their mountain of ideas, some still viable and others outdated. Our world is in constant flux, and the most successful persons will be the ones who unlearn, learn, relearn and evolve with it.

Lesson #6: Go Straight to The Top

Birth of The Cool - Miles Davis Leadership & Life Lessons - Go Straight to The Top

Miles Davis was able to maintain his popularity in a world where jazz music faced a declining audience and decreased demand. He had a strong work ethic and did all he could throughout his life to learn, improve, and create new ways of playing old styles, an attribute that kept him in the spotlight long after most jazz musicians had faded into the background.

When Kind of Blue was recorded, people were looking for the “next Charlie Parker.”

Miles Davis knew exactly who the best was and he wasn’t too proud or distracted to waste his time elsewhere. Charlie Parker was playing music that no one else was even thinking about at the time. So why would you train anywhere else? Find the people who are the best at what you are trying to do and to go to them. Stop wasting your time searching the noise for a perfect answer.

By the way, Miles Davis was known for his sense of fashions.

It was, indeed, part of his personal brand but it never stagnated. He was savvy enough to rock the suit-and-tie look when a more polished vibe was in fashion and was open enough to move right into the chic wrap-around glasses, fringe and other iconic cool looks of the ’70s. Similarly, he used sitars and other instruments in his work when no one else was even thinking about such combinations in jazz.

Miles Davis most likely developed his need for excellence from his family; it is rare for such a drive to develop on its own.

He certainly felt the pressure to do well in whatever career he chose with so many famous relatives in the family, and the intimidation factor doubled when he found that neither parent particularly approved of his decision to become a professional musician. Because of the way he was raised, Miles Davis always felt a drive to gain his parents approval through success, and took it hard whenever his mother or father disagreed with any of his choices.

How easy is it for high performers to recognize your excellence?

There is a tendency among many leaders not to toot their own horns about their own performance and accomplishments. While a leader may not need to sing his own praises, it is important that someone does it for him. A leader’s excellence will attract others who want to achieve the same level of competence, while increasing the leader’s credibility and ability to guide, mentor and teach.

And when it comes to tactics and strategy, think beyond status quo.

That simply means proposing a new idea that may be worth exploring — perhaps it’s already great, and is there a way it can be even better? It’s leadership’s responsibility to create a culture where challenging the status quo is encouraged. Leaders need to have a forward-thinking, growth mindset — a state of mind that doesn’t settle for an attitude of the bare minimum and instead looks to their teams for insights on how things can be improved.

Lesson #7: Cultivate Provocative Competence

Birth of The Cool - Miles Davis Leadership & Life Lessons - Cultivate Provocative Competence

One common obstacle in organizations occurs when leaders choose to address only those issues for which a solution is imaginable. Miles Davis did just the opposite. He surprised his band by stretching them beyond comfortable limits, calling unrehearsed songs and familiar songs in foreign keys so that they would have to experiment in the margins. That’s provocative competence at work.

Great leaders like Miles Davis are able to see peoples’ potential, disrupt their habits, and demand that they pay attention in new ways.

It’s important for executives to break their teams out of competency traps. Leaders should aim to introduce incremental disruption in their teams, to encourage people to jump out of their comfort zones and provoke a vulnerability that inspires learning.

How can a business foster a culture where innovation actually occurs? 

The secret lies in challenging highly developed skills with a tolerance for — no, an embrace of — ambiguity. Provocative competence builds the muscle of creativity, which in turn gives rise to innovation. New ways of doing things grow from new perspectives. Provocative competence involves introducing a small disruption to routine.

Encourage people to take a risk and do something they might not otherwise do.

Anyone seeking the unconventional, imaging the unimagined, runs the risk of colliding with the existing rules and norms of the organization. But without the capability to imagine and design radical new concepts, a company will be unable to escape decaying strategies. The response to the future’s unpredictability is to think differently. Learn to see different, learn to be different, and you will discover new horizons.

In most organizations there is a great emphasis on maintaining control. But as a leader, you will want to say yes to the mess!

At the core of value creation are individuals who cleverly question routines, attack conventional wisdom, challenge dogmas to find new opportunities, discover new insights, dare to experiment, analyze mistakes, and start over again. In this context, provocative competence is not some idealistic utopia for screwballs, but simply logical.

Improvisation thrives best in a management culture that encourages experimentation.

It’s most likely to succeed in organizations that are loose, fluid, and flexible, in which individuals can play different roles, and where team members know they can take risks. Leadership might require the ability to think on your feet. Leaders who accept improvisation are convinced that it better positions them to expect the unexpected, profit from their mistakes, and respond to change.

Wrapping Up

Birth of The Cool - Miles Davis Leadership & Life Lessons - Final Thoughts
Being rebellious and black, a nonconformist, being cool and hip and angry and sophisticated and ultra clean, whatever else you want to call it — I was all those things and more. But I was playing the fuck out of my horn and had a great group, so I didn’t get recognition based only on a rebel image.Miles Davis

In our fast paced environment, leaders, like jazz musicians, need to interpret vague cues, face unstructured tasks, process incomplete knowledge and take action anyway. Musicians prepare themselves to be spontaneous. Leaders and executives must do the same.

Take risks. Experiment. Be comfortable making mistakes. Learn from your mistakes.

Of course, there are some areas where mistakes are intolerable. But, most of the time, allow exploration and experimentation. Follow sometimes and lead at others. Courage is the presence of fear and willingness to take action.

Yes, improvisation can be intimidating. Outcomes are unclear, and nobody wants to be embarrassed.

But when it comes to situations requiring improvisation, those are the crucible moments in our lives, the once that create our true identity. Say yes to the mess.

As a leader, your attitude comes through in everything you do and is magnetic.

Anyone can play. The note is only 20 percent. The attitude is 80 percent. Once your attitude changes — for good or bad — everyone in your orbit will alter their attitude around you and toward you. This will have a direct impact on your team mates and your organization.

Surround yourself with incredible talent, from any background. This is the key to creating something so much larger, greater, and more expansive than yourself.

In this dynamic age where uncertainty is a new norm, jazz leadership and its magic components encourage innovation, supported autonomy, shared leadership, improvisation, and clear communication. How can jazz leadership guide your organization into the next decade? Share your thoughts in the comments below!

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🌀 Birth of The Cool – Miles Davis Leadership & Life Lessons

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