What if doubt isn't a weakness, but the birthplace of clarity?

What if strategy didn’t begin with the solution, but with the courage to say “I’m not sure yet”?

In business, and in life, there’s a strange pressure to always know.

Know where you’re going. Know what to do next. Know how to answer the question before it’s even asked.

But here’s something we’ve learned at Memorable: the best strategies don’t begin with certainty.

They begin with doubt.

The kind of doubt that doesn’t paralyze, but invites inquiry. The kind that whispers: something doesn’t feel right here, and instead of brushing it off, you lean in.

What’s the problem?

That’s the question that Richard Rumelt puts at the center of his book Good Strategy/Bad Strategy. He argues that bad strategy often starts with vague goals, generic mission statements, and feel-good mantras that don’t mean much. It skips the hard part. The part where you name the real issue.

Good strategy? It begins with a diagnosis.

Not a goal. Not a slogan.

A problem.

Because until you can articulate the problem clearly, any solution is just noise.

“Strategy is about overcoming obstacles. And the first step in overcoming obstacles is to understand them.” — Richard Rumelt

It sounds simple. But we’ve seen this play out in dozens of organizations: teams sprinting toward execution before pausing to really ask what they’re solving for. Innovation workshops that start with “Let’s brainstorm ideas!” without aligning on the tension they want to resolve. Leadership teams building roadmaps before understanding the terrain.

What doubt makes possible

Here’s the twist: doubt doesn’t slow creativity, it activates it.

When the brain recognizes a gap in knowledge, or a tension between what is and what could be, it lights up. Neuroscientific research shows that confronting a problem, especially one we don’t immediately know how to solve, stimulates regions of the brain associated with associative thinking, lateral connections, and creative insight.

In other words: doubt opens the door to new ideas. Certainty often closes it.

So what if we gave ourselves permission to begin projects, strategies, even entire business models with a question rather than an answer?

What if our meetings began with:

“What are we not seeing?”

“What’s the real friction underneath this?”

“What are we assuming that might not be true anymore?”

At Memorable, we treat doubt as a starting point

In our work with teams and leaders, we don't rush toward the "how."

We spend time with the "what" and the "why."

We surface tensions, explore contradictions, challenge assumptions.

We might begin a strategy session not by asking “What’s the plan?”—but by asking “What feels unclear?” Or even more provocatively: “Where are we pretending to be sure?”

And it’s in those moments, where someone says “I don’t know” out loud for the first time, that the real work begins.

That’s when you feel the shift in the room. The air gets lighter. People lean in.

Because when doubt is allowed, people get honest. And when people get honest, clarity follows.

Questions that move us forward

At Memorable we start every project with a Company Diagnosis. A session were we ask questions to understand the weaves of each company. What works, what does not work, what the client knows and what the client does not know. We’ve learned to trust a the method of questioning before designing or defining. The kind of questions that don’t ask for fast answers, but open space for reflection.

Intentional questions that aren’t theoretical. They’re real. And they’re hard to answer. But they’re the kind of questions that move teams from alignment theater to actual insight.

Doubt + dialogue = momentum

If you’re a leader, founder, or facilitator reading this: you don’t need to have all the answers.

(You probably shouldn’t.)

What you do need is the ability to hold space for better questions.

To model curiosity. To slow down before speeding up.

Because when doubt becomes part of the culture, something else emerges: trust.

And trust, more than any framework, is what fuels real strategic clarity.

Feel you need a Diagnosis Session?

You can book a Diagnosis Session for free on this link!