Why Miles Davis Was The Ultimate Product Leader

Trevor McLeod
Mic Product Blog

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Nine Grammy Awards, spanning over three decades. More than 80 albums. Several standing out as transformational moments in the evolution of music. One in particular, Kind of Blue, widely considered to be among the greatest albums of all time and what became the highest selling Jazz record ever. Miles Davis is unquestionably a legend.

But Miles wasn’t just a musical genius, he was also the ultimate product manager. If you study his work, you’ll come to realize that he knew exactly what he was doing and his creative formula will change the way you think about leadership, teamwork, and yes — your product.

Isn’t Kind of Blue what every product manager wants? To change the world? Sell more than anyone else?

How can we recreate that level of success? Is there a process to something like that? Here’s what I’ve learned from Miles Davis so far.

Be a voracious student

Miles obviously made music, but he also obsessively studied music. These days, we don’t tend to dive deep into disciplines, electing rather to “skim the surface” and pick at various options. It’s nice at a dinner party to know a little about a lot — but Miles new a gargantuan amount about music.

He studied the history, theory, techniques, chords, notes, composers, and most importantly, styles. To be in the same arena as Miles, you have to be obsessed with your craft.

The first stage in this process is to take the time to study the problem you are trying to solve. Don’t act like you know anything. Assume you know nothing.

“It took me twenty years of study & practice to work up to what I wanted to play in this performance.” — Miles Davis

Go straight to the top

When Kind of Blue was recorded, people were looking for the “next Charlie Parker.” When Miles first came to New York as a 19-year-old kid, he played trumpet for — you guessed it — Charlie Parker. Miles knew exactly who the best was and he wasn’t too proud or distracted to waste his time elsewhere. Charlie was playing music that no one else was even thinking about at the time. So why would you train anywhere else?

The internet makes it too easy to source information. At this point, your challenge is to filter that information. The second step in this process is to 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.

“I can tell whether a person can play just by the way he stands.” — Miles Davis

Do whatever it takes to make sure people care

Great, so you have the knowledge and you’ve studied the best people in the world. You’ve earned the respect of your teammates — now what? This is when most people get lost and Miles is just getting started.

I’ve always wondered what the look on everyone’s face was like when they first showed up to record Kind of Blue. It would be like if Michael Jordan, Isiah Thomas, Kobe Bryant, Lebron James, and Steph Curry all showed up to lead the same team, not realizing the others had been invited. They’d all be looking around the room at each other like “wait, what is he doing here?”

If you gave a team like that the task of winning championships, without the right coach, how long do you think it would take before each of them left to start their own championship team? They’d all bash into each other. The only way to get a team like that playing together is if they all care about winning that championship together.

Miles assembled a group of people who were all at the top of their game. They were all-stars, who probably knew they were all-stars. So, how does he plan for this team to work together? Get them to play nice?

He must have had an amazing plan. He must have known beforehand what his team was going to build. Naw — all accounts describe the situation such that Miles gave them basically no requirements at all, just a few ideas he had and the confidence that he invited them for one reason — he believed they could help make great music.

John McLaughlin, who worked with Miles on In a Silent Way (among several other albums), described the process as Miles wanting his musicians to “start with more space.” He didn’t want them constrained in the beginning, focused on music. He wanted them free and focused on playing, solving, enjoying the challenge. He wanted the full potential of each of his all-stars to come to life. “He wanted to bring the unknown in us out”, as McLaughlin says. He got them to be their best.

There’s this unfortunate tendency within product teams to immediately put forth “what needs to happen” or “what the product should be”, instead of starting with more space — and focusing on the problem — and helping each person be their best. The third step in Miles’ process is to get out of the way. Not to box people in. Give them the challenge and let them enjoy the thrill of solving it. Do whatever it takes to make them care.

“he would get people to play and get music that would make them happy because he never wanted to impose his will, his musical will, on his musicians. I never ever seen that. He wanted them to be themselves.” — [McLaughlin on Miles’ process]

Experiment constantly, even if it costs all the money

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.”

Constantly experimenting is a nice thing to say you do, but is it really part of your culture? When is the last time your CEO said “I pay you to experiment at work.” Are you willing to spend your money breaking, changing, throwing things away?

But wait, you say — there’s such a thing as experimenting too much dude. Probably. But, a lot of people felt Miles did. And it’s not like he was a one-hit-wonder. He obviously knew something about perfecting products. Can you honestly say you’re breaking enough rules?

The fourth step in the process is to build a culture that loves to test and encourage your colleagues to think this way.

“Do not fear mistakes. There are none.” — Miles Davis

Simplify

Building any incredible product starts to get difficult once it’s time to finalize all of it’s incredible features. They just keep growing and revealing new and “better” and more shiny opportunities.

Miles 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.

As the leader, it’s easy to critique other people’s ideas. But who’s critiquing your ideas? It has to be something that’s done across the board, everything is put through the same filter and scrutiny. Is this feature something customers need? Or is it just something we want to build? Or worse of all, is it just something other people build?

It’s not only about the final product, it’s also about the resources you’re consuming to build it. Miles didn’t like unnecessary notes because it distracted him from playing the necessary notes. The last step to this process is simple. But it sure is hard.

“I always listen to what I can leave out.” — Miles Davis

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