Imagination Isn't a Soft Skill. It's How Leaders Reconnect With Themselves.

When was the last time someone asked you what's most important to you?

Not your boss. Not the strategy doc. Not the performance review.

You.

I'm asking because I had a podcast conversation recently with executive coach Dawn Kasey Lovelace. We were talking about leadership and imagination — two words that don't usually land in the same sentence. But Dawn made a wonderful case for it:

Before leaders can create something new externally, they often have to reconnect with something internally.

Most leadership content skips that part.

Most leadership advice is about output

Take a look around you. Most of what passes for leadership content talks about execution.

How to give better feedback.

How to run a tighter meeting.

How to make faster decisions.

How to scale your communication.

All of it’s useful, and none of it’s wrong.

But Dawn was pointing at something underneath all of that — something that doesn't make it into most leadership playbooks.

If you're disconnected from yourself, you're going to lead from that disconnection. And no amount of optimization will fix it.

Imagination isn't what you think it is

When most people hear "imagination," they think of creatives: designers, writers, musicians. Then the next thought is brainstorming sessions and vision boards. Things that are nice to have but not central.

“Soft skills.” But Dawn took it in another direction.

She defined imagination as the movement from "what is" to "what could be." Not a creativity tool, but a way of being in our jobs and in the world.

"You have to imagine yourself outside the box before you can think outside it."

A lot of people are stuck inside their current self-concept, stuck inside who they were three jobs ago, and stuck inside who they were told to be.

And until they can imagine themselves differently, no plan is going to take them anywhere new.

What disconnection actually looks like

Here's what this shows up as in real life:

The director who can't take a vacation without checking Slack.

The VP who hasn't taken a full breath since 2019.

The senior leader who's started dreading the work they used to love and can't tell anyone, because the title still looks good on paper.

A lot of folks come into coaching looking for a tactical answer. A new resume. A LinkedIn refresh. A sharper pitch.

But underneath that, something else is usually going on. Fatigue. Disconnection. An identity that's been shaped entirely around being useful.

What they actually need isn't another system. It's enough quiet to remember who they are.

Stillness is where imagination becomes available

At one point in our conversation, Dawn asked me how I deal with writer's block. My answer was quick: I get away from my desk.

I go for a walk, or even a run. Maybe grab some coffee at the shop up the street. Anything to break the force. Because continuing to sit at that desk and stare at the screen pretty much never works.

And leadership can work the same way.

We've been sold the idea that the answer is always more: more effort, more hours, more optimization. More more more.

But some breakthroughs don't arrive through forcing them. They arrive when you stop trying to forcing.

Maybe it looks like taking a walk between meetings. Maybe it looks like closing the laptop at six instead of nine. Maybe it looks like a Saturday without an agenda.

Whatever it looks like for you, the principle remains the same: clarity needs space before it needs strategy.

The leader who can't imagine shrinks the room

Dawn said something else worth sitting with:

“Leaders who cannot imagine beyond their own worldview often shut down contribution without realizing it.”

Read that twice.

Because most of the time, this isn't intentional. The leader doesn't think they're shutting anyone down. They're just defaulting to what they already know. What they're already comfortable with. What worked last time

But the team feels it.

They feel whether their half-formed idea is going to be welcomed, or dismissed. Whether bringing something risky to the room will be rewarded, or punished. Whether you as a leader can hold uncertainty long enough for a real answer to emerge.

You can't bolt psychological safety onto a leader who can't imagine. It comes from the inside out.

But imagination without action becomes avoidance

Here’s the thing, though: I’ve seen this go the other way, too. Because imagination becomes its own trap if you don’t have it grounded.

Possibility can be a wonderful place, but you can’t stay there forever. At some point, the imagined future has to meet your feet on the ground.

The vision you hold for you and your team still calls for action. Stillness still has to lead somewhere. The key is learning how to move between the imagining and the doing.

Who do you say you are?

I want to leave you with this question — the one Dawn kept coming back to in our conversation, and the one I think most leadership advice never gets to:

“Who do you say you are?”

Not your title. Not your LinkedIn headline. Not the role you're currently performing.

You.

Because if you've tied your identity to your job, then any disruption — a layoff, a transition, a quiet voice telling you something needs to change —is going to feel like everything's collapsing.

But if your role is just one expression of a fuller self, then there's room. Room to imagine, to shift, to become something you haven't been yet.

So tell me:

Who do you say you are this week?

Hit REPLY. I read every response.

I’m Richard Taliaferro. I’m a certified career coach specializing in helping mid-stage professionals gain clarity on their career journey. I’ve written a guide on how to escape the work hamster wheel. Click here to download yours.