The Art of Strategic Uncertainty

The Journey

When I’m briefed about a strategy project, my client will often say they desire ‘clarity’, or ‘focus’, or ‘a roadmap’.

But here’s the thing. People don't want to be handed a finished plan like some corporate Christmas present. They want to be taken on a journey.

It’s like a Marvel movie you might watch with your kids. You don't just want to see the final battle, as exciting — and as predictable — as it is. You want the origin story, the character development, the "how did we get here?" Because without the journey, there's no buy-in.

I'm currently working with a 20,000-employee organisation where we're doing something radical. We’re formally "imagining" their future across 12 real-life business areas — from delivery models and digital platforms to employee engagement and translating research to real-world applications. But here's the twist: we're not doing this in some ivory tower boardroom.

We've gathered 100 senior leaders and said, "Help us imagine what's possible." Not "review our recommendations" or "provide feedback on our analysis." Actually imagine. Together.

What I've learned is that collective imagination requires two things: leadership brave enough to say "We don't have all the answers" and a structured invitation for people to contribute their wildest, most thoughtful ideas.

The magic happens when people realise they're not just implementing someone else's vision—they're co-creating it.

Question: When did your organisation last invite people to imagine together, rather than just execute someone else's imagination?

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Everyday magic

Grimes (yes, the musician) claims that the Third Law of Witchcraft states: "Any sufficiently advanced magic is indistinguishable from technology." She simply reversed sci-fi writer Arthur C. Clarke’s maxim, who lifted it from St. Augustine: "Miracles aren't contrary to nature, just contrary to what we know of nature."

Translation: invention is just everyday magic.

Think about it. Your smartphone would get a medieval peasant burned at the stake. Talking to invisible people? Summoning knowledge from thin air? Consulting AI oracles? Pure witchcraft.

So why do most organisations act like imagination is some rare, mystical gift instead of a learnable skill?

Consider these "impossible" business moves: Patagonia telling customers "Don't buy our stuff." Apple deleting the keyboard from handheld phones (because typing on glass makes total sense). Airbnb convincing people that sleeping in strangers' bedrooms beats hotels.

Each required leaders to still the voices in people’s heads that said "That's not how we do things" and imagine something different. Here's what I've learned from my clients: imagination isn't lightning striking — it's deliberately questioning every assumption about "how things work."

The best strategic breakthroughs I’ve seen happen when you stop asking "Is this possible?" and start asking "What if?"

Question: What "impossible" thing could your organisation start doing tomorrow if you stopped believing your own limitations?

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Frisson

Of course, asking 'What if?' means getting comfortable with something most businesses fear: uncertainty itself.

But think about what most people actually like — we like not knowing. When you’re listening to your music streaming service, often the joy is that delicious moment between songs, wondering what you'll discover next. Or at IKEA, where getting lost in their deliberately maze-like layout isn't a bug, it's a feature. The treasure hunt feeling keeps you discovering.

That feeling has a name: frisson. That pleasant agitation when you're on the edge of discovery.

Yet some organisations treat uncertainty like a disease to be cured immediately. I've watched leaders — especially those who suffer from a crippling condition called ‘premature understanding’ — rush to declare "the answer" before they've even understood the question properly.

My mentor Alan Weiss nailed it: "Find those who are seeking the truth. Run a mile from those who say they've found it."

The best strategic work I do happens with clients who can sit comfortably in not knowing. They ask better questions. They stay curious longer. They don't mistake early assumptions for final answers.

A CEO client opened a recent strategy workshop with these words: "Here's what we don't know yet..." Not "Here's what we know." That small shift changed everything: suddenly the room was full of explorers, not defenders. The air was charged with frisson, not frustration.

Question: What would happen if your organisation celebrated not knowing as much as it celebrated knowing?

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So there you have it: strategy is spell-casting. If this resonated (or even if you think I'm talking complete nonsense!), hit the heart below or drop me a line. I promise to respond with more questions than answers.

From tomorrow, I’m sailing the Ionian Sea for a few weeks, getting respite from Melbourne’s wind and cold. But I’ll be here with you in spirit — and you’ll get a 5MSM at the usual time next Friday.

Until then, keep wondering,

Andrew