Improvisational Leadership

10 March 2020

Improvisation gets a bum rap.

Many people equate “improvisation” with simply making things up on the spot without preparation. This, however, could not be further from reality. A lifetime of preparation goes into being able to successfully improvise, whether it be stand-up comedians, jazz musicians, or even leaders.

The true masters of improvisation are pulling from experience, intuition, and principles that they have internalized so well that it is second nature. Take jazz musicians, for example. They understand the difference between dissonance and harmony and the appropriate time and place for each. They understand the importance of being able to tell a musical story that others can follow, and they know how to bring others along for the ride. And they know how to read the room: not everything’s going to come out the way it sounded in their head, and they know when to change course or double-down.

Leading teams requires the same toolbox. Like jazz, the people we are leading can be messy, chaotic, and unpredictable — and much of the time, we’re expected to react in the moment to changing circumstances. We learn to expect and embrace conflict and collaboration, and recognize the importance of both. We learn the art and power of storytelling and how to lead through that narrative and influence others. We learn how to react when things don’t go according to plan.

There Is No Sheet Music, Only Chord Changes

Leaders face unique situations every single day.

Let’s say, for example, there are two people working together who are not, well, working together. There are differences in opinions, differences in philosophies, and differences in approach. It has gotten obstructive enough that the situation has escalated to a manager.

What is the manager to do? One completely acceptable approach would be to strive for immediate harmony, and mediate to get the team back onto a constructive path. Another reasonable approach may be to coach the individuals through the dissonance and conflict, delaying the inevitable resolve. There are benefits to both, and there may not be an obvious “right” solution. These types of in-the-moment decisions pull from the personal experiences and intuition the manager has. And regardless of the decision made, it could very well turn out not to work, and the manager has another decision to make: do they try again, or change their tactics? How about a third time?

While it’s impossible for a manager to foresee every possible situation they are likely to face, they will continually catalog and learn from the experiences they have. Some of these decisions will work, and some will fall flat. There will be decisions that evoke rational responses, and some will trigger unexpectedly emotional ones. Some tactics will drive the team to success, and some will end up as categorical failures. Regardless, these events and outcomes are all learning opportunities and will influence how someone will be able to improvise in future situations.

Yes, and…

A subtle nuance to the power of improvisation is the underlying intention to keep future options open. Just like any decisions we make, the outcome can either open up possibilities or back us into a corner. Just as a musician crafts a melodic phrase or an actor leverages “yes, and,” they are deliberately leaving the door open to be able to handle upcoming and unknown situations. For those just starting out on their journey, having so many possible outcomes can seem terrifying, and the instinctual response may be to play out every conceivable “if this, then that” scenario. For these leaders, they may only feel comfortable moving forward with a plan when they have 80% or 90% confidence that they will achieve their objective. Short of that, they may fall prey to “analysis paralysis” and/or shy away from risk.

"If you stumble, make it part of the dance."


However, with experience comes confidence and assurance; the culmination of past experience gives leaders the ability to confidently move down one path with the assurance that they will be able to handle any situation that arises. This is not to say that experienced leaders don’t consider the possible outcomes of their decisions. However, it does mean that more experienced leaders are comfortable with broader stroke future projections and are inherently accepting of more risk. These leaders may not need 80% or 90% confidence in the success of their plan; 30%-40% confidence in addition to their ability to improvise may be enough. Or, as they say: close enough for jazz.

Getting Better, Stronger, Faster

Mastering improvisation is a function of exposure and time. The more experiences we are able to have over years of practice, the more adept we will be at handling whatever future situations may hold. But as we can’t speed up time, there are a few things we can do to increase our exposure, and therefore accelerate growth.

The first strategy that leaders should employ is to build teams with diverse backgrounds and experiences, both professionally and personally. Life experiences, as well as career experiences, influence the way we solve problems. Leaders must hire people who have different experiences from the rest of the team, and from themselves. These outside perspectives will help the team identify blindspots in their approach and will open the doors to new problem-solving strategies in the future. This reduces risk, improves confidence, and increases resilience within the team.

A second key strategy is to hire for a growth mindset. The growth mindset is a fortuitous mix of attitude and inclination. These are the individuals who embrace challenges and the unknown with the knowledge that there are infinite opportunities for learning along the way. Find people who can give examples of, and are proud of, experiences where things didn’t go according to plan and can articulate how they adapted in-the-moment (and how they may have responded differently in hindsight). Individuals with this mindset have the advantage of a bias for action — an improvisational imperative — as growth only happens through doing. This leads into a third strategy.

Take more risks. With a team of diverse perspectives whose members are eager to learn and grow, it is critical for leaders to set the example for what it looks like to forge ahead, even when the path and the guarantee of success are unclear. This means embracing the philosophy of Disagree and Commit. This means maintaining open lines of communication within and beyond the team to respond quickly to changing circumstances. This means embracing failure and failing fast. And this means taking new information and responding with “Yes, and…

A Team Activity

There’s a lot in common between leadership and the improvisation that you find in music and comedy. Improvisers aren’t just “making it up.” They are crafting a story in real-time that represents everything they’ve learned over years of honing their skills. They are moving forward even though they don’t know what’s coming up next — but with the confidence that they will be able to handle it. But the most important thing to remember is that success in mastering improvisation, just like leadership, is much more than a solo activity.

“When I'm playing, I'm never through. It's unfinished. I like to find a place to leave for someone else to finish it. That's where the high comes in.”

Miles Davis

That quote sums up leadership better than I ever could myself. Miles, truly one of the best musicians to ever live, understood that the value of leadership comes from the group as a whole, not the most accomplished or most visible person. He understood that it’s up to the leader to lay the groundwork, to craft the narrative, to provide inspiration, and to create space for the magic to happen. It’s not about telling the team where they’re going to end up but rather give them a path to figure that out. Just like a musician leans on their ensemble or a comedian engages with their audience, someone’s ability to lead is only as strong as their ability to work collaboratively and respond in real-time.

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