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.

From Standing Ovations to Silent Smiles: How My Daydreams Changed

What I visualize has changed over the years, and I can’t figure out why.

When I was younger, I always used to visualize myself being applauded.

In those days, I regularly imagined myself being sworn in as a U.S. Senator, or perhaps being elevated to CEO of a publicly traded company. Sometimes, I wouldn’t even just imagine myself giving a TED talk, I imagined myself watching a video of myself giving a TED talk.

This is objectively vain and narcissistic stuff. These delusions fueled my motivation and ambition. I craved moments of being “awesome” or being “ the guy” and that’s a large part of why I worked hard and tried to achieve success in my education and professional life.

Somewhere along the way that changed.

To be clear, I still have moments where I imagine myself winning something, succeeding, or receiving some sort of promotion. But it’s not only that anymore. Sometimes, now, I visualize others experiencing joy.

Sometimes, for example, I imagine Robyn and I being older and we’re making pizza and chocolate chip cookies with our giggling grandchildren. Or maybe we’re holding hands at church, seeing families of five hugging each other in the pew in front of us, and we feel remember our own joy because we see theirs.

Other times, I imagine our adult sons, joking and laughing with each other, while we’re all having a beer around a campfire. Sometimes, I imagine a time when the world is kinder and more verdant, and I am walking through the park, breathing clean air and passing by birthday parties with loads of youngsters singing and eating cake. They are all strangers and I don’t talk to them, I just notice their glee and I am smiling as I stroll past.

Sometimes, too, I imagine some of the former gang members I met at community meetings dropping their kids off at school or cooking a Friday night dinner, being attentive and loving fathers. Sometimes, I imagine some of the people who buy La-Z-Boy furniture just sitting, and catching their breath in moments of ease.

Again, I’m still self-centered, I’m just not solely that anymore. Now, I imagine others’ joyous moments sometimes too.

The problem is, I don’t know what caused this change to happen.

Was it gratitude journaling or prayer? Was it marriage and kids? Was it losing my father? Was it travel to places, like India, where I witnessed slums with unimaginable poverty? Was it just something that happened because I lived more life? What was it that caused my visualizations to change?

This post doesn’t have a solution, only a question for those of y’all who made it this far. Has this change in perspective happened to you? What do you think did it?

It’s something that I would love to understand enough to recreate on purpose. If I can pinpoint what sparked this shift in me, perhaps we all can learn to intentionally foster a more outwardly compassionate perspective.

Photo by Clay Banks on Unsplash

A practitioner’s take on goals and dreams

There is a time and a place for SMART goals.

Like when we want or have to achieve something that’s specific, measurable, attainable, relevant, and timely. (See what I did there?)

Put another way, sometimes we need to outline a goal like this: “I will publish my book in 2023, and have 1000 people download or purchase it within 6 months of publication.”

But there are times when SMART goals are precisely the wrong approach to take.

Sometimes we have to dream. And a good dream is probably the inverse of a SMART goal: A audacious, unorthodox, and slow to achieve.

Put another way, sometimes we need to put a dream out there, something like: “I dream about a day when America is a more trusting place, probably because our government is innovative and citizen centric, we have skilled leaders on every block, and our culture becomes one where everyone reflects on their own actions and is committed to developing their own character.”

Here’s what I’ve learned about both, as a real person, living a real life, trying to achieve goals and dreams for real:

First, dreams are a paradox. The most visionary dream feel too crazy to talk about - and so we often don’t talk about them. At the same time, the surest way to never achieve a dream is to keep it a secret. The only way our dreams become a reality is if we talk about them even when it feels awkward.

Second, it’s really important to know whether the situation at hand requires a goal or a dream. If the situation is well understood and we need to “get it done”…goals all day.

But if we’re trying to imagine a better future, and contemplate a new way of being, dreams are the only way.

Third, both goals and dreams are worthless if they are not specific. If the finish line is blurry, collective action grinds to a halt, especially when there’s no hierarchy to scare people into action.

Finally, and perhaps most importantly, both dreams and goals require an action which deviates from the status quo. That’s why we dream and set goals in the first place, we want something to be different.

A good question is: “Do my goals and dreams require me to act differently? If so, how? If not, how do I get better goals and dreams?”

That’s there’s the unlock.

Photo by Estee Janssens on Unsplash.