The Art and Craft of Improvisation at Work

Photograph of Le pianiste américain de jazz McCoy Tyner en concert à Deauville (Normandie, France) en 1989.
Le pianiste américain de jazz McCoy Tyner en concert à Deauville (Normandie, France) en 1989.

About five minutes into John Coltrane’s famous recording of My Favorite Things, the pianist, McCoy Tyner, one of the greatest jazz pianists of all time, hits a wrong note. A “clam” as we used to call it at Berklee College of Music where I studied music in the late 1990s.

I’ve listened to this passage dozens of times and with each listening, I have more and more respect for what a master of improvisation Mr. Tyner was. He doesn’t lose a beat. He accepts the flub and dances around the melody two or three more times as if to say, “I know I did that. Let’s try it again. And here it is one more time for good measure.” It’s a dance that pulls your ear back out of the dissonance before moving on to the rest of the song.

I graduated college in 1997. I was a good musician, but not great. I was lucky though, the Internet was just starting to take off and I had enough background in technology that I got a job as a web developer a couple of years after graduating. People sometimes ask me if I ever still play. I don’t. I never found my voice playing music, but I did find my voice as a technologist. One of the things I did take with me from my experience as a musician was the art and craft of improvisation.

A few words about improvisation

Improvisation is not “flying by the seat of your pants” or “faking it until you make it.” And please don’t say “close enough for jazz.” Improvisation is knowing your craft so well that you can adapt your practice in real-time to unpredictable scenarios. Improvisation at work means going into an important meeting, a workshop, or a leadership presentation with one set of plays in mind and nimbly shifting to another when things aren’t going the way you expected. Best of all, being good at improvisation means bringing creative thinking and innovation to the table instead of falling back on additional process.

I lean into this skill a lot and I frequently advise my teammates to work on ways they can improve their own improvisational craft in safe, low-risk settings. Here are a few examples where it comes up a lot in day-to-day work:

Re-aligning stakeholders

A few years ago, a teammate and I were facilitating a design workshop for a healthcare client and their software vendor. We had run many of these workshops before. We were well prepared, and we assumed we had this one under control. About 30 minutes into the first session, however, we learned that our client and their software vendor were wildly out of alignment. There was a major disagreement about the primary problem we were solving in the workshop.

We were stuck. Without alignment, the workshop could not move forward. My teammate recalled an alignment exercise that worked well for them in the past and we modified our agenda so we could gain this important alignment before moving forward.

Adapting to unforeseen events

When the pandemic was full-on and everyone locked down, we could no longer do our workshops in person. We had to adapt quickly to keep things on track. At the time, we were primarily using virtual whiteboarding tools like Miro and Figjam for internal, low-stakes work. Being able to adapt our in-person workshops quickly and bring stakeholders into virtual whiteboard environments proved to be effective. Engagement definitely took a hit, but scheduling became a lot easier since people no longer had to travel to our office.

Rebuilding trust when things go wrong

Try as we may to always play our A game (or all the correct notes as in McCoy’s case), sometimes we’re playing B at best. Maybe you’re stretched too thin and juggling too many things. Maybe a change of strategy happened that you weren’t informed about beforehand.

When we do play the wrong note, or a bad game, being able to improvise won't get us out of being accountable for the way we performed, but it will help us to start rebuilding trust that we can refactor and get the job done right.

You’re innovating with a team

Saving the best for last… Being good at improvisation at work means creating opportunities to jam i.e., being innovative with your teammates. Having a shared vocabulary of your craft means being able to mix and match to build new combinations of how to do things, especially when working with ambiguity.

I had to get particularly creative in a workshop I was running shortly after the pandemic lockdown. I was working with a team to redesign data workflows and it meant treading on some sensitive and political areas of the business. Doing in-person icebreakers can help get folks into an empathetic mindset, but with everyone working remotely, how was I supposed to do this? I solved this by getting everyone to position their zoom window as close to the center of their screen as possible and look directly into their camera for a few minutes. It was the closest thing we had to real eye contact with our co-workers for months and it worked great to get us into an empathetic headspace.

Practicing Improvisation

Venn diagram illustrating how improvisation sits at the intersection of technique and creativity.
Improvisation sits at the intersection of technique and creativity

In addition to being great at your craft, improvisation at work takes confidence that you can bring your stakeholders along with the new, creative direction you’re taking. There’s no magic here, it just takes practice. For me, I isolate the practice in safe, low-stakes situations; cooking and testing things in my garden. For you, it could be one of these, or taking a dance or theater improv class. The key is breaking down the practice of improvisation into two parts:

  1. Your professional craft — technique
  2. Building confidence in adapting to unfamiliar situations — creativity

When cooking something new, I practice the recipe once or twice – technique. After that, I purposely put aside the recipe and adapt the dish to things that are either in season and/or on hand in my kitchen – creativity. It doesn’t always work out – I have a few jars of salsa in my pantry that are pretty bad – but my cooking gets better each time I try something new and I gain confidence in my ability as I work through my mistakes.

So, give it a try. Isolate times in your work where the stakes are low and you can practice and get honest feedback from a buddy. When you make inevitable mistakes, learn from them, and keep moving forward. Dance around it and your audience will love it!