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.

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