What music taught me about teams

daniel debow
Helpful.com
Published in
7 min readAug 3, 2017

People endlessly compare business to sports or war. These analogies have never really resonated for me. I’m not much of an athlete. And thankfully, I’ve never been to war. Instead, I relate to music. And I think that the creation of music has some great lessons for teams in business.

I love improvisational forms of music, like jazz, in which artists create unique interpretations on the spot. Musicians can seemingly read each other’s minds as they adapt and synchronously respond to each other.

Through my experience as a co-owner and bassist at The Root Down Studio, I found out that these moments of flow — i.e. hyper-collaborative, zero-pressure, max-focus sessions — produce some of our best sounds. Obviously creativity has a part to play here. But creativity is a just part of the story. It’s also a symptom, not a cause.

So I reflected on why these sessions, and our musical space in general, are so effective. I had a hunch that there were lessons for entrepreneurs in there somewhere. Turns out there are five big ones.

1. Play with people who are better than you.

When you’re not a professional musician, playing with professionals is terrifying. They know you’re worse. You know it. It’s uncomfortable.

The right thing is to keep doing it until it doesn’t feel uncomfortable anymore.

I learned this: if you’re not showing your skills to the people to whom you aspire, you’re holding yourself back.

So, to skyrocket your business skills, you should “play” with two types of people:

1. Those who are more experienced than you in a general sense, like CEOs and successful entrepreneurs. Spend time with them. Watch them. Engage with them.

2. Individuals who are better at your particular skill, such as coding or public speaking.

For example, you can attend events and trade ideas with successful business owners. You can also find a mentor, collaborate with your higher-ups on a project, or take someone you admire out to lunch. If you choose to reach out to mentors, think of it like a rehearsal. Come with specific questions that will help you with an imminent decision, just like showcasing a particular piece of music or a particular skill. This is because you’ll get high-impact, relevant feedback.

Volunteer for projects and activities that are beyond your comfort zone. It’s the same principle: if you’re not pushing yourself into situations in which you feel deficit in your skills, you won’t get better.

2. Practice. Practice. Practice.

Your favourite musicians might sound effortless when they take the stage.

But their “effortless” playing is the result of years of practice.

Musicians have an expression called “shedding” — i.e. going alone “to the woodshed” to practice something until it’s perfect. They often play slowly at first and only pick up the tempo once they’ve improved. A musician can spend hours practicing the same scale, technique, or song.

Shedding is solitary. It’s sometimes painful or mentally exhausting. You keep on going over the same skill again and again until the skill becomes second nature. Even then, you’re not done. There has never been a musical legend who just stopped innovating. Keep going again and again.

By contrast, many business professionals think that school is the place for practice. Once they are in the real world, they just want to get stuff done. This is common, especially with people who want to be “a great speaker”. They don’t realize that the best speakers in business are people who have spent hours shedding. I don’t just get up on stage to speak. I practice, repeatedly. I video myself. I do the same talk over and over in a mirror. I write it down, then memorize. All of this — so that when I’m up on stage, it seems effortless. Just like a musician.

Shedding allows you to fail fast. When you shed, you can quickly identify mistakes and practice until you stop making them. As soon as you have the buds of a new skill, try it out at work (see point 1).

Take time after hours to shed. Take classes. Read. Listen to podcasts. Blog. Join a group like Toastmasters. Don’t think too hard — just choose one fast and start practicing ASAP.

3. Show your work before it’s perfect (because it’s never perfect).

Many professionals won’t share their early-stage work with their colleagues. For example, they may write three drafts of a blog post before they show it to their team. To many, this “feels” right because they avoid negative feedback.

But musicians know that the first take is never the final result. They suggest ideas, and the band works together to turn the raw parts into a deliverable, polished product. When jamming, a musician might throw out a musician phrase, or idea, to see how others react. That musical idea might inspire another artist to respond with something even better, or harmonious. This can’t happen if every player withholds their ideas until they’re fully thought through.

Musicians who admonish half-baked ideas and phrases don’t last long in the jams at the Root Down. Instead, we encourage musicians to feel safe enough to throw things out. At the same time, we don’t laud every new sound. The key is to listen for the good ideas and keep iterating on them until they take off (or, sometimes, peter out).

A rule of thumb here: if you feel uncomfortable showing your work, it’s the right time to show it.

4. Listen. Listen. Listen.

You know when a band is in the groove. All of its members are locked in — each instrument and voice comes together to create one arrangement. Musicians will often call this “playing in the pocket” — everyone is aligned. But how do bands create this feeling?

Broken down, the question is really how to get individuals to independently and volitionally contribute their sound while simultaneously leaving enough space for others to do the same. Team managers will recognize that I have just described working on a team.

So how does the drummer know when to start a solo? It’s simple.

Each band member listens to everyone else. A great musical drummer — one who listens — can hear subtle suggestions made by the singer and the guitarist. When she gets the right cues, she knows it’s time to begin her solo. If she zoned out and only listened to her own drums, she would overtake the band.

Listening is the secret skill of all musicians who play with others.

Listening is the secret skill of all great team players at work.

When I started as a musician, I only listened to my own guitar. This is human nature. I wanted to avoid making mistakes. Therefore I could only focus on myself. I just kept doing this. As I got better, I played louder. Eventually I drowned out the other players. This created a reinforcement loop: I listened to myself even more. This spiral results in a terrible musical experience.

Then a pro told me, “You need to stop listening to yourself when you play.”

His comment made me realize that I was selfish. I didn’t understand that it doesn’t matter how good or bad I am. What matters is how the group sounds as a whole.

It’s the same for teams. Instead of just optimizing yourself, optimize your entire team. Focus not only on your own work, but instead on how you can make the entire team perform better. Your team might not need all of your ideas, work, and efforts all over your collaboration. Sometimes, you might need to add just the slightest of support, help, ideas.

As Miles Davis said: “It’s not the notes you play, it’s the notes you don’t play.”

5. Drop your ego.

During my first years in music, I sucked.

But I was somehow lucky enough to play with great musicians. I didn’t understand why. I asked them, “Why do you play with me? I suck.”

They replied, “Because you have fun. And you have feel.”

Me — in the midst of vibing with the group

People who enjoy their craft raise the energy in the group. If newer musicians have passion, their band mates will adjust how they play to make the sound work. They know that it’s more important to play great music than to show off their technical skills. As John Coltrane said, “”All of the technique doesn’t matter… only if the feeling is right.”

Business is the same thing.

People who show off or don’t listen to others cause dissonance and lower their team’s morale. The most junior employee, or the newest team member must be allowed to express their “feel” for a project, to project their joy into the team. If only the “experts” contribute, the “feel” gets misaligned. Share your good vibes. Even more important: let others share theirs.

More Ideas?

If you’ve got some new sounds on this subject, I’d love to hear them. Comment below.

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P.S. Helpful is a new company I’m working on. Check it out here to learn more.

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daniel debow
Helpful.com

Dad of 4, CEO of Helpful.com, ex-Salesforce SVP, founding team at Rypple & Workbrain, angel investor, bass player, adjunct prof @UofTLaw and curious person.