Her CEO had been clear: slow down, take a breath, make sure we're stable before we go again. At the same time, her commercial director had asked her team for a 20% lift in results, with no additional budget.

She'd been carrying both instructions, trying to honour each one. It took a retreat, away from the office, and probing questions, for the tension to become clear. “I hadn’t put those two things together, it seems obvious now.” The conflict wasn't hers to solve. It was a decision that needed to be made.

And nothing in how the business ran would have surfaced it. The plan was set for the year. There was no fortnightly moment where those two instructions had to sit on the same table in front of the same people.

I've spent most of the last twenty years around product and tech teams, where agile became the default way to work with uncertainty.

We made delivery agile. Why is strategy still waterfall?

Agile stopped at the boardroom door

Think about what agile teams already believe. You can't predict what people will want, so you ship something small and learn. You plan, but you replan every couple of weeks. You treat the roadmap as a set of bets, and you expect some to lose.

No self-respecting product team would build for two years without talking to a customer. Yet plenty of leadership teams still write a strategy once a year, put it in a deck, and bring it out again at the next away day. In between there's no rhythm for testing it, no review of what's been learned, and no easy way to change course.

You get a strange picture: brilliant, adaptive teams, sprinting hard, in a direction nobody stress-tested.

Agile is a way of making decisions under uncertainty. So is strategy. They're the same problem at different altitudes. We just never took the method up the mountain.

Who we put in the room

Part of the answer is who ends up at the top table.

Simon Wardley describes three kinds of people an organisation needs. Pioneers explore the unknown and build the new thing. Settlers take the rough idea and make it real and repeatable. Town planners industrialise it and run it efficiently at scale. All three matter. The trouble is the order they arrive in.

Early on, pioneers run the show. As a business grows it rewards the people who make it predictable, and town planners rise. For roughly forty years management has prized operating excellence, so leadership teams fill up with excellent operators.

That isn't a criticism of operators — we need them badly. But Michael Porter drew the line years ago: operational effectiveness has a frontier your competitors can reach, while strategic positioning is much harder to copy. A top table built entirely from town planners is very good at running today's business, and often uneasy with the exploration that finds the next one.

Then we ask that table to set strategy in the most uncertain conditions any of us have known. People who are brilliant at reducing uncertainty, asked to decide inside it. No wonder the result looks like a plan.

Deciding too fast

When leaders are uncomfortable with uncertainty they rarely freeze. More often they do the opposite: grab the first credible option and move.

Paul Nutt spent years studying how organisations decide, and the Heath brothers popularised his work in Decisive. The finding, broadly, is that most decisions only ever weigh one real option — and the ones that weigh several tend to turn out better.

I see it most in boardrooms. A proposal lands. It's reasonable. Nobody wants to be the one slowing things down. So the first idea on the table becomes the plan, and the challenge that would have improved it never gets heard.

Deciding too slowly is a real risk. Deciding too fast is the one I see more often.

The better move is to hold the problem open a little longer. Generate a second and third option. Ask what you'd need to believe for each one to be right.

The leader I was coaching had the mirror image: two decisions issued, neither reconciled. Deciding too fast and not deciding at all are the same failure. Both happen when a board has no rhythm for holding a question open and coming back to it with evidence.

What an agile board would look like

Two thinkers help here.

Nassim Taleb argues we should stop trying to predict the future and build things that gain from surprise. His barbell keeps most of what you have safe while placing many small bets where one good outcome pays back many times over.

Rita McGrath argues that lasting competitive advantage is largely a myth now. Winning organisations build a stream of temporary advantages, riding each one while it lasts and starting the next before it fades. Her discovery-driven planning treats a plan as a set of assumptions to test, cheaply and early.

Put them together and you get something any product team would recognise: strategy as a portfolio of bets, reviewed on a rhythm, with the riskiest assumptions tested first. In practice, an agile board might:

• review strategy every quarter as a live set of bets, with the evidence in front of them
• fund a few small experiments alongside the big commitments
• ask for two or three genuine options before any major decision
• name the trade-offs out loud, including what it will stop doing
• make room for a pioneer's voice at the table, even when the business is mostly settlers and planners

None of that needs a new framework. It needs the board to hold its plan the way a good walker holds a map. You plot the route before you set off. Then, when you find a bog in the middle of the path, you go round it. Hold the map too tightly and it walks you straight in up to your knees.

Back to the leader who felt stuck

Once she saw that the two instructions couldn't both be true, she had something to take back to her leaders: a clear choice between stability and growth, with the cost of each. Trade-offs are the foundation of strategy.

A team that replans every fortnight would have caught that contradiction in weeks. It took a retreat and an outsider's questions to catch it at all.

That's the work. Better decisions, turned into action. Agile teams already know how to do it. The boardroom is the last place that hasn't caught up.

So here's the question to take into your next leadership meeting. If your delivery teams worked the way your board does, how long would it take you to notice?

A big number goes up on the wall. The resources to reach it go down. Everyone is expected to find the gap somewhere, usually through longer hours and quiet heroics. It might even work for a quarter. But the experiments stop, because nobody has time to try anything, and you buy this year's number with next year's future.

A target is a destination. Strategy is the route — and the route only exists once someone has done the hard thinking about what's possible, what has to change, and what you'll stop doing to make room. Without that, a goal is a wish. Put a few in a deck and you've got a hope list.

The tell is one question: what are we going to stop doing to get there? A clear answer, and you might have a strategy. A pause, and you've got a number plucked from the air.

A proposal lands. It's credible, it's been worked on, and nobody wants to be the one who slows things down. So the first reasonable option quietly becomes the plan. The challenge that would have sharpened it is never voiced; the second option that might have been better is never written.

Uncertainty makes this worse. When the future is unclear, grabbing the first credible answer feels like leadership. It relieves the discomfort. The leaders I rate do something harder: they keep the problem open a little longer, ask for a second and third option, and ask what they'd need to believe for each to be right.

Speed matters. But a fast decision on the wrong option just gets you lost more quickly.

Watch what happens as a business grows. The early years belong to the pioneers. Then the organisation starts rewarding predictability, and the people who deliver it rise. Over time the top table fills with brilliant operators — which is fine, right up until you ask that table to set direction in deep uncertainty. People whose gift is removing uncertainty, asked to decide inside it.

The fix isn't to replace your operators. It's to make sure the explorers still have a seat, and that someone asks them what they can see ahead. Who on your leadership team is looking furthest out — and how often do they get the last word?