Episode Details

Reflections from host Sarah Olivieri ...

Imagination: The Missing Ingredient for Better Strategy

Have you ever experienced a strategic planning process where you get a room full of smart, committed people? They agree on the words. They nod at the plan. And then six months later, everyone is pulling in slightly different directions.

In my experience, this happens when the plan was created without real clarity and alignment around where exactly we are trying to go.

Clarity and alignment come from shared understanding. And shared understanding starts with how clearly people can picture what "done" looks like.

And in order to "see" what "done" looks like, we need … IMAGINATION!

I recently had a conversation about this with imagination expert and strategist Rebecca Sutherns.

Imagination skills are critical for great strategy planning and execution.

Are You Planning Backwards?

Most planning processes are built around looking in the rearview mirror.

We review last year's data.

We evaluate what worked.

We talk about what didn't.

None of that is wrong.

But it's incomplete.

Because strategy is not about explaining the past.

It's about building the future.

Rebecca said something that stuck with me:

"Our strategies ought to be forward-facing, not backward-facing."

That sounds obvious. But it's not how most organizations actually operate.

What happens instead is this:

We take what we've already done.

We make incremental adjustments.

We call it strategy.

That's not a strategy. That's iteration without intention.

And when you build a plan this way, you end up with a partially built system. It functions—but it doesn't move you meaningfully forward…

Because you haven't clearly imagined, as a collective, what the future looks like, tastes like, feels like.

Why Alignment Breaks Down

Even when teams do talk about the future, they often still don't align.

Because they're using the same words… but imagining different things.

Rebecca put it this way:

"If people are not watching the same movie in their heads, there's a good chance you're using the same language but moving in different directions."

I see this often. We assume other people are thinking what we are thinking when we talk to them, but actually getting them to think what we are thinking is a much harder feat.

When we talk, we usually communicate only a tiny fraction of what we intend to.

Ask a leadership team what success looks like, and you'll get five versions of the answer.

None of them are wrong.

But they're not the same.

And when that happens,

execution becomes messy.

What Actually Creates Alignment

If you only take one thing away, it's this:

Alignment is not about agreement. It's about shared imagination.

You need people to be able to picture the same outcome.

Not just intellectually—but concretely.

That means moving beyond vague language like:

• "Make a bigger impact"

• "Expand our reach"

• "Strengthen the organization"

Those sound good. But they don't mean anything operationally.

Instead, you need to ask:

• What do