Imagination is a Foundational Leadership Skill

I define leadership as the act of taking responsibility for something.

However, one crucial element that underpins effective leadership is frequently overlooked: imagination. From my experience, both personal and professional, I have learned that taking full responsibility for a project or goal requires the ability to vividly imagine its realization. This power of imagination is not just a lofty concept but a practical and essential skill for leaders.

To inspire a team to bring our vision to life, we must articulate it clearly and compellingly. This act of sharing our imagination is what we commonly refer to as having a vision. Whether you are a CEO, product manager, entrepreneur, artist, politician, or parent, the ability to communicate your vision is fundamental to effective leadership.

Imagination operates on three distinct levels when we take responsibility for a project. To illustrate, consider the creation of a running shoe. The first level involves envisioning the product itself. What does the shoe look like? How is it designed? What makes it unique and special? This product vision is the core of what we aim to create, whether it’s a shoe, a family, a city, or a store.

The second level of imagination is what I call the market or cultural vision. This involves envisioning the broader impact of our product or project on the world. For our running shoe, we must consider who will be using it. Are they solo runners or part of running clubs? How does running with our shoe change them as individuals? What new stories do they tell themselves because of their experiences? How do these runners interact with others differently? Envisioning this broader impact helps us understand how our efforts contribute to making the world a slightly better place.

The third level of imagination is the internal vision, which focuses on the process and team dynamics required to bring our vision to life. For the running shoe, this means imagining the manufacturing process: How will the shoe be made and designed? Who will be part of our team? What kind of culture will we cultivate within our team? What will our interactions look and feel like? If a documentary were made about our journey, what key moments and values would it highlight? This internal vision ensures that we have a clear roadmap for achieving our goals.

In essence, a leader is someone who takes end-to-end responsibility for a project or goal. To do this effectively, the ability to imagine and share what’s in our mind’s eye is essential. Without this, we risk merely replicating someone else’s vision instead of creating our own.

This brings us to two key “how” questions: How do we get better at imagining, and how do we assess imagination in others?

To improve our imagination, we need practice. However, imagination cannot be practiced in the abstract. We must engage in the act of creation—whether it’s building a custom shelf, writing a book, painting a picture, or organizing a street festival. The process of imagining often unfolds naturally as we commit to building something. We don’t set out with the intent to imagine; instead, we follow our instincts, commit to the project, and let the imagination flow.

Assessing imagination, particularly in an interview setting, is relatively straightforward. Ask candidates to share their dreams—whether for their current company, their family, or their community. Encourage them to elaborate with follow-up questions. If, within 5-10 minutes, you can vividly see what they envision and feel excited about it, they likely possess a refined ability to imagine and communicate their vision. Chief James Craig, who led the Detroit Police Department while I was there, emphasized this principle: “We have to talk about our dreams.” I wholeheartedly agree.

To ground this discussion, which may seem abstract, let’s envision a world where people are committed to making their corner of the world a bit better by bringing their dreams to life. Achieving this requires the ability to imagine and clearly communicate what’s in our mind’s eye. How do we cultivate this capability? By building things and talking about our dreams.

Mastering the Mind: How Artists and Athletes Think and Feel Simultaneously

Have you ever wondered what sets elite artists and athletes apart from the rest of us? I sure have.

Over the years, I’ve reflected on their mindsets, which, on the surface, appear quite different. (Check out this post on athletes and this one on artists).

But there’s at least one big thing that elite artists and athletes have in common: they can think and feel at the same time. Let’s take the example of a tennis player and a stage actor.

A tennis player has to think and make snap decisions with every stroke, fluidly, in real-time. When you’re playing tennis, you’re constantly thinking about your game plan, your opponent, the match's momentum, and your tactical strategy—and then putting it into action on every single point.

Additionally, a tennis player must manage their emotions because the sport is an emotional roller coaster. Clinging to bad shots or failing to ride the momentum can hinder their performance. To be a great tennis player, you have to be able to think and feel at the same time.

Consider a moment in a high-stakes tennis match. The player is down a set and facing a break point. The crowd holds its breath as the player takes a deep breath, silencing the noise in their mind. In that instant, they must trust their training and instincts, feeling the weight of the moment while calculating their next move.

A stage actor must also access their emotions. Characters become believable and storytelling compelling only when it comes from a genuine emotional place. As a stage actor, you have to delve deep into your inner world to tap the emotional reservoir necessary for an outstanding performance.

At the same time, a stage actor has to think deeply. The actor has to think about their lines and their cues, of course. But also, the stage actor has to think about their technique, body movements, intonation, and their interplay with all the other actors onstage - especially if something goes wrong and the ensemble has to start improvising. To be a great stage actor, you have to think and feel at the same time.

This skill of simultaneous thinking and feeling applies to many domains of our lives. As a parent, we have to think about our actions and principles while deeply empathizing with and listening to our children. At work, we have to think analytically about problems but feel and attune to human dynamics and emotions within our teams. This skill - which artists and athletes possess - is broadly applicable.

The trick lies in the “how.” How do we cultivate this dual skill of thinking and feeling simultaneously?

As I contemplate this, I think of two martial artists who spar inside our heads: “The Thinker” and “The Feeler.” The key, I believe, is letting these fighters go at it. Not in an antagonistic way, but in a symbiotic, we’re-on-the-same-team, iron-sharpens-iron kind of way when we do hard stuff.

In practice, this means two things. First, we have to do novel, challenging things. We need new, difficult stuff for The Thinker and The Feeler to work on. Maybe it’s a new project at work, or training for a race, or resolving to be a more patient parent.

Second, we have to ensure that The Thinker and The Feeler aren’t just going through the motions. We can’t let ourselves go on autopilot and do things the way we always do. The Thinker has to be trying new stuff to become a better thinker, and The Feeler has to be trying new stuff to be a better feeler. In any novel situation where we’re trying to “train,” we should periodically ask ourselves, "Am I on autopilot, just going through the motions? Should I be?"

If we aim for excellence in any field—be it artistry, athletics, parenting, or our vocation—we cannot afford to be pushovers. We need The Thinker and The Feeler in our minds to be strong, agile sparring partners, ready to tackle any challenge in real-time. By continuously training both, we forge a path to mastery.

We Are Everyday Artists: Seizing the Canvas of Daily Routine

What is an artist?

Three things define an artist: a point of view, refined craft, and canvas. This is my interpretation, and I'll elaborate shortly. Here’s a thread on ChatGPT for a summary of different schools of thought on what an artist is.

We can be artists in our day to day lives. Parenting can be artists’ work. Leadership can be artists’ work. Yes, artists create plays, music, paintings, and dance - but fine and performing artists are not the only artists there are.

We are all capable of being artists within our respective domains of focus. We should.

Artist = point of view + refined craft + canvas

Artists have a point of view. A point of view is a unique belief about the world and the fundamental truths about it. Put another way, an artist has something to say. A point of view is not necessarily something entertaining or popular, but I mean it as a deeper truth about life, the world, ideas, or existence itself.

A point of view might be and probably should be influenced by the work of others, but it’s not a point of view if it’s copied. To be art, the artist must internalize their point of view.

Artists have a refined craft. Artists must be able to bring their point of view to life and communicate it in a novel, interesting, and compelling way. Bringing their point of view to life in this way takes skills and practice. And it’s not just technical skills like a painters brush technique or a writer’s ability to develop characters, part of the skill of being an artist is the act of noticing previously unnoticed things, or, the ability to connect deeply with emotions, feelings, and abstract concepts.

A refined craft might be and probably should be influenced by the work of others and exceptional teachers, but it’s not a refined craft if it’s mere mimicry of someone else. A refined craft is something that the artist has mastery in.

Artists have a canvas. The point of view that an artist brings through their refined craft must be manifested somewhere. Painters literally use canvasses. For dramatic actors, their canvas is a stage performance. For muralists, their canvas is the walls of large buildings.

However, those mediums do not have to be the only canvas. For a corporate manager, their canvas might be a team meeting. For someone cooking a family dinner, their canvas might be the dinner table - both the food and the surrounding relationships. For a parent, their canvas might be their nightly bedtime routine. For someone just trying to be a good person, their canvas might be their bathroom mirror or journal, where they reflect on how their actions have impacted others.

And for what it’s worth, a canvas doesn’t have to be the center of a performative act. A canvas is merely the medium. Who sees the medium, and its level of public transparency, is an entirely different question.

Examples really bring what I mean to life. I’ve asked ChatGPT to apply the Artist = point of view + refined craft + canvas framework to a handful of people. This link will take you to an analysis of Frida Kahlo, Jay-Z, Steve Jobs, JK Rowling, Oprah Winfrey and others.

We need artists

What I find so compelling about artists is they move society and culture forward. In some ways, people who operate as artists are among the only people who can progress us forward. Why? First, artists operate in the realm of beliefs, which means they can change the deepest parts of people’s minds. Second, because artists bring a novel perspective to the table, they’re people who cut against the grain and challenge long-held norms, by definition. Artists make a difference by making things different..

This is exactly why I think we ought to operate as artists, especially in our daily lives as parents, colleagues, and community members. I believe things ought to be different and better. Kids, on average, deserve better parents. People working in teams, on average, deserve better colleagues and leaders. Communities, on average, deserve a better quality of life.

We are fortunate to be alive now, but there is room for improvement. Daily life for children, workers, and citizens ought to be much better because there is still so much unecessary drudgery and suffering.

Moreover, there is insufficient abundance for everyone to pursue a career as a fine artist or performing artist. Conventional art is invaluable, but not feasible for most to pursue professionally or as a hobby. For most of us, the only choice for us is to act as artists at home, work, or in our communities.

Again, I think examples bring it to life. Here are three personal examples that illustrate that we can think of ourselves not just as parents, leaders, or citizens, but as artists. (Note: my examples don’t imply that I’m actually good at any of these things. It’s an illustration of how one might think of these disciplines as art).

As an artist-parent…

I believe…that I am equal in worth to my children and my job is to love them and help them become good people that can take care of themselves and others. I’m merely a steward of this part of their life, and that doesn’t give me the right to be a tyrant.

Part of my craft is…to reflect questions back at them so they can think for themselves. So if they ask, “Should I ride my bike or scooter on our family walk?” I might reply, “What should you ride, buddy?”

My canvas…is every little moment and every conversation I have with my kids.

As an artist-leader at work…

I believe…our greatest contributions come collaboratively, when we act as peers and bring our unique talents together in the service of others.

Part of my craft is…creating moments where everyone on the team (including our customer) has time to speak and be heard - whether in groups or 1-1 behind the scenes..

My canvas is…team meetings, 1-1 meetings, and hallway conversations where I am in dialogue with colleagues or customers.

As an artist-citizen…

I believe…we will reach our ideal community when there is leadership present on every single block and community group.

Part of my craft is…find new people in the group and ask them to lead something, and commit to supporting them.

My canvas is…neighborhood association meetings, conversations while walking my dog, and the moments I’m just showing up.

We can be artists. Even if we can’t paint, even if we can’t dance, even if we can’t write poetry - we can be artists.

How we become everyday artists

The hard question is always “how”. How do I become an artist-parent or artist-leader? This is an important and valid question. Because these ideas of “point of view” and “craft” are so abstract and lofty.

What has made these concepts practical to attain is starting with my mindset. We can act as if our environment is a canvas.

So no, the team meeting at work isn’t just a meeting - it’s a canvas. And no, the car ride to school isn’t just 15 minutes with my sons to kindergarten or daycare drop off, it’s a canvas. These are not ordinary moments, I need to tell myself that I’m an artist and this is my canvas.

Because when I treat the world like a canvas, it goads me into considering what my point of view is. Because what’s the use of a canvas without a point of view? The existence of a canvas persuades me to form a point of view.

And when I think about my point of view, it nudges me to consider and hone my craft. Because what’s a point of view without the ability to bring it to life? Once I have a point of view, I naturally want to bring it to life.

Treating the world around me like a canvas is both under my control and the simple act which snowballs me into practicing as an artist in everyday life.

If you think being an everyday artist has merit, my advice would be to pursue it. Just start by taking something ordinary and make it a canvas. Because once we have a canvas and take our canvas seriously, an artist is simply what we become.

Photo by Anna Kolosyuk on Unsplash

Artists Must Wander

There are, roughly speaking, three types of bands. Any of the three is a legitimate way to make a living as a musician, but they’re different and require different skills and mindsets.

To be successful at any, we must choose and know what we’re signing up for. The biggest mistake we can make and the surest way to be average is to not choose.

The job of a tribute band is to be as close to the original as possible. At a tribute band’s show, the audience very explicitly doesn’t want anything new. The whole craft of being a tribute band is mimicking, with intense fidelity, what has come before. To be good at this, we have to listen, with unrelenting meticulousness, the artist we are paying tribute to. The key question for a tribute band is, “does it sound like the original?”

The job of a cover band is to play hit after hit, across artists and genres. Cover bands take the songs people like and play the hell out of ‘em. To do this requires great musicianship and an ability to find the balance between preserving the original and putting just enough of a twist on it to make it feel new and exciting. Cover bands have to be good at listening not to the original artists, but to the audience in front of them. Their key question for a cover band is, “does it sound like something the audience wants to hear?”

And then there are those bands who want to be artists. The job of this last group is to be new, to be original, and to bring a new point of view - catching lighting in a bottle, if you will. To be an artist, an original artist, is an entirely different proposition than being a tribute band or a cover band.

To be an original artists requires wandering around lost, often for significant periods of time. An original artist has to find the songs that only they can write and only they can sing. Original artists cannot listen, too much, to what’s come before them. Instead, an original artist needs to listen to their own voice and to the rhythms and melodies out in the world that nobody else is hearing yet. The key question for an original artist is, “What does my voice sound like?”

I think we underestimate, still, how much our culture indoctrinates us to avoid wandering. We have curriculum and an education system. We have college majors with specific requirements. We have board exams and certification tests. We have career plans and linear project plans. In the corporate world, we have competitive benchmarking and the application of “best practices.” We’re told, ‘Don’t recreate the wheel.”

All these things, in aggregate, seem to just scream sometimes, ‘Wandering is bad! Bad boys wander! Those who wander are lost!”

To be original artists, we have to unlearn this indoctrination and replace it with a new belief, “Not all those who wander are lost. On the contrary, if being an original artist is what we choose to be - wandering, to where it is quiet enough to hear our own voice for the first time, is the surest way forward.”

Photo Credit: Unsplash @yvettedewit