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.

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

Leadership as artistry

In a second, I’m going to suggest that leadership can be considered artistry. But first, what is an artist?

I’ve been thinking non-stop about this take from the comedian, writer, and producer Hasan Minhaj.

Here’s a clip (link to Instagram Reel) from his appearance on the Colin and Samir podcast (heads up: there’s some profane language in the clip). Here’s a key blurb:

It’s artistry vs. the algorithm…An artist is someone who has something in their head or their heart that they gotta SAY. And they want to get it out - that’s an artist. I have to get this out into the world. You’ve got a short film? Let’s show it in the park TONIGHT.

I love this framing: an artist has something to say. They have a point of view that they have to share out into the world.

And then there’s the algorithm. Serving the algorithm is not expressing a point of view, it’s putting something out based on whether other people will like it. Whether other people will click it. Whether other people will buy it. You’re not serving up a point of view, you’re serving up something that optimizes some variable.

Like Minaj says in the clip, I’m not trying to be disparaging about living by the algorithm or pejorative. Choosing artistry over the algorithm (or vice versa) isn’t necessarily better…but it is a choice.

Is leadership artistry? I know it can be, because I’ve seen leaders communicating a point of view through their leadership. I’ve seen leaders who have something in their heart that they’ve got to say. A recent example I’ve encountered is Alan Mullaly’s interview (he’s a former Boeing and Ford CEO) on The Knowledge Project podcast.

The entire interview is worth listening to, but I’d summarize Mullaly’s point of view on leadership with his phrase “love by design.” It’s clear that his whole worldview on leadership - from the language he uses, to his framework of key ideas, to the management operating system he uses to manage the process of leading a team - all come down to loving and serving others.

Mullaly has a point of view, that he needs to communicate. He’s an artist. His medium just happens to be leadership.

I’ve found that many successful leaders I’ve observed also express a unique, personal, cohesive point of view through their leadership.

Like a colleague of mine who’s one of the founders of Joybird furniture: his point of view, which I learned within an hour of meeting him, is to create growth - for people, for enterprises, and for customers.

Or there’s Reese Witherspoon, whose entrepreneurship founding Hello Sunshine centers around the importance of telling stories that celebrate women and puts them at the center of the story.

Or there’s former Joint Chiefs Chairman and Secretary of State Colin Powell whose point of view centers on solving problems and taking care of people. When I was an intern at the State Department, I heard personal tales from my colleagues about Secretary Powell embodying this through behaviors like eating in the canteen with everybody else or personally seeking out the families of personnel who died or were injured in action and finding ways to help them.

Of course, the alternative to leadership as artistry is leadership by algorithm.

We can do what makes the most money with the lowest risk. We can do what optimizes for a social metric. We can do what gets us promoted the fastest. We can copy the generic management system we learn in graduate school. Whatever variable we choose, there’s there’s a leadership algorithm to optimize for it.

Leadership by algorithm is a legitimate choice, and maybe even the right one for the circumstances. And just like on social media, playing to the algorithm works if you do it well enough.

But like Minhaj opined in the clip above - leadership by algorithm may work well, I just don’t want to live like that.

In my experience and study of organizations and leaders for the past 25 years, algorithmic leadership has consequences I’m not willing accept.

Just like social media, algorithmic leadership leads to “inflammatory content” like when ego-maniacal leaders develop cult followings with their extreme tactics.

Just like social media, algorithmic leadership leads to “content mediocrity” - like when the leadership quality of the entire cadre of listless middle-level managers in the world seems to mirror the endless supply of mediocre cat videos on the internet.

Leadership by algorithm can work, but it has consequences.

Behavior Is communication

The hard part, as is usually the case, is the “how.” How do we actually do this? How do we actually develop a point of view that we can express through how we lead?

Robyn, my wife, recently shared a concept she learned during her training to become a high school teacher: behavior is communication. In the education (or parenting) context, the lesson is simple: when kids are acting out, they’re actually trying to say something that they aren’t capable of expressing in words. Their behavior is communication.

If we want to think of our leadership as artistry, we can apply the same lesson. Our behaviors - when we’re trying to lead a team or make a positive contribution - say something. The beliefs we have in our hearts are represented in how we act. Our point of view is reflected in how we operate.

Just like artists can express a point of view with their scripts, paintings, or music - we can express a point of view with how we behave in the organizational world.

If we want to think of our leadership as artistry with a point of view, we first have to explore and try new things. We have to listen and observe. We have to hone the fundamentals of our craft - like communicating, being authentic, delegating, and more. And then, we have to reflect, and do deep introspection about what we’ve experienced and form a point of view.

That practice of introspection can take many forms, but I think this question is as good as any to start: when I try to behave in a context of leadership and organizations, what am I trying to say? What am I trying to communicate, from deep within my heart, through my behavior?

If we explore as artists do and introspect as artists do, we can practice leadership as artistry.

Photo Credit: Unsplash @timmossholder