Better Imagination = Better Strategy with Rebecca Sutherns [Episode 410]

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. 

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.

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.

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 does this actually look like? Draw it!

• What’s happening differently when we’ve succeeded?

• What would we see, hear, and feel if this worked?

This is where imagination becomes a leadership skill—not a nice-to-have.

Most nonprofit leaders struggle with this.

And it makes sense.

They’re operating at capacity.

They’re dealing with real constraints.

They’re trying to make payroll.

So when you ask them to imagine a bold future, you often get:

“I just want enough money to pay my staff.”

That’s not a lack of ambition.

It’s a reflection of the state of being under-resourced.

But constraints can actually enhance our ability to be creative.

Rebecca shared a simple but powerful idea:

Instead of removing constraints entirely, define them clearly.

For example:

“We have $50,000 and six months. Now what could we build?”

This changes the conversation.

It gives the brain edges to work within—without shutting down possibilities.

Imagination is not a personality trait.

It’s a muscle.

And like any muscle, it gets stronger with use.

One of the most useful insights Rebecca shared is that imagination is built from memory.

We don’t create from nothing.

We recombine what we’ve already seen, experienced, or learned.

That means the fastest way to improve your strategic thinking is not another framework.

It’s more inputs.

• Talk to people outside your sector

• Read widely

• Change your environment

• Expose yourself to different ways of thinking

This expands your “pantry” of ideas.

And the bigger the pantry, the better your ability to combine ingredients and imagine something new.

There’s one more piece here that I don’t want to skip.

Imagination changes how leaders show up.

Because when you can imagine better, you start asking better questions, and better questions lead to better answers.

Also, we can't be great at imagining if we don't get great at being curious.

When leaders come in with curiosity, people open up.

And when people open up, you get better thinking.

Better thinking leads to better decisions.

And better decisions lead to better results.