Navigating Ambiguity: Shaping What's Next

What if leaders navigated ambiguity as a creative process?

In my coaching work, I often invite leaders to look beyond traditional models and draw from other disciplines to navigate ambiguity. The creative process, particularly how an artist approaches a blank canvas, offers a meaningful lens. This article explores that process and how it applies to leadership in practice.

The Power of a Portrait

 I found myself thinking about leading through ambiguity while standing in front of a painting. It asked something of me: to stay with what wasn't immediately clear. 

That moment unfolded at the Museum of Modern Art, where I paused before a painting by Wilfredo Lam, whose work I had encountered before at the MALBA in Buenos Aires and the Hirshhorn Museum in Washington, D.C.

Wilfredo Lam was a Cuban artist whose work sits at the intersection of Afro-Cuban culture, modernism, and Surrealism, shaped by spiritual traditions that run through his work. He studied in Europe and worked alongside Picasso. His paintings pull you in while leaving space for continued discovery. Figures that are human and otherworldly at once. Images that hold your attention without fully revealing themselves.

Lam’s approach to his practice is firmly rooted in his identity, deliberately drawing together the complexities of his heritage, education, and experience into something unified. Rather than holding these influences apart, he integrates them into a cohesive body of work.

There’s a parallel here to leadership, particularly in how leaders draw from multiple perspectives and influences. Lam didn’t wait until his influences felt resolved before he painted. He worked from the tension itself. The question then becomes: how do you actively bring those perspectives together into something coherent?

The Creative Process

In conversations with fine artists I'm close to, I've come to appreciate this:

They don't begin with a fully formed picture.

It starts with a sense.
A partial idea of what might take shape.

And then they start.

With each brushstroke, something becomes clearer.
Not all at once.
But progressively.

A direction begins to emerge.

That's what it looks like as something comes into view.
Through this unfolding, different elements begin to come together.

What it Feels Like to Be in it

One of those conversations turned into something more.

An artist friend encouraged me to try it for myself. A small canvas. Nothing ambitious.

We had a full discussion on materials.

Acrylic? Watercolor? Oil? What kind of paint to use?
Canvas or poster board?

We talked through how colors blend. She even gave me a color wheel, and I was still a bit lost.

Overwhelmed. Unsure.  Well outside my comfort zone.

It’s awkward to be in that place of not knowing. No roadmap.

I admitted to her that my artistic range is mostly limited to stick figures, Snoopy, and the occasional snowman.
In a joking, yet truthful way.

Still, I gave it a try.

Music on. A few images for inspiration. No clear plan.

And something interesting happened.

I got into it.

Not because I knew what I was doing. But because I didn't.

I felt like a kid again. Crayons in hand, coloring outside the lines. All possibilities at my fingertips.

What surprised me was how much I was drawing on without realizing it. Music. Places. Feelings. It wasn’t empty improvisation. It came from somewhere.

From Waiting to Shaping

Artists don't wait for clarity before they begin.  They create, and momentum builds. 

Leaders often do the opposite. They wait for clarity before they act.

It is not about perfection or a fully formed strategy. It's the step that begins to shape what's next.

The answer isn’t simply outside of you.

It’s in how you take in what’s around you and bring it together with your experience, judgment, and what matters to you.

No one else brings the exact combination that you do. That distinct mix becomes your advantage, giving you a way to engage ambiguity and begin shaping what comes next.

What This Looks Like in Practice

There’s a creative capacity within each of us, a way of working that allows something to come into view even when

the path isn’t fully clear.

Here's what it looks like in practice:

🟩 Clarify what is known and what is still evolving.
🟩 Define your next move, not the full plan.
🟩 Create short feedback loops.
🟩 Experiment and learn as you go.



The ability to create and shape is not limited to master artists. You have access to it.

Talent matters, and so does the willingness to step into the unknown.

The question becomes:

What is your first brushstroke into ambiguity?