Nearly every leader I talk to knows the old planning model doesn’t make sense anymore. Multi-month cycles. Layers upon layers of initiatives. Budgets that quietly replace strategy as the plan. By the time it’s all done, the competitive landscape has already shifted under their feet.
And yet, many companies still do it this way. They can feel the mismatch as they strive to move fast. They just don’t know what to do instead.
The old game was setting direction. Decide where to go. Communicate it. Cascade it down. It made sense when the future looked enough like the past that you could be certain of your choices.
But certainty is gone. In its place: disruption, surprise, and acceleration. Which means the work of leaders has shifted. The new game is adapting direction.
What needs to be new and different
If strategy execution today is about improv, then strategy setting is no longer about choreography. It requires a more flexible approach.
Here are four flaws of traditional strategy planning, and what leaders can do differently:
1. Stop pretending there’s only one future.
We know the future won’t unfold exactly as envisioned. Customer needs shift. Competitors surprise you. Economies wobble. So why do we plan for just one version of what’s next?
When one “winning” idea emerges too fast, it often gets momentum without being stress-tested. A better approach: evaluate multiple distinct directions at the same time.
One executive team we worked with had five competing visions for doubling the business in three years. Instead of forcing consensus, we worked with them to think through the core choices for each, including customer focus, product bets, and geographic expansion. Once leaders saw the real implications, they quickly ruled one option out. The eventual plan blended elements of the others, with contingencies built in. Thinking through alternatives gave them confidence and resilience when the inevitable twists came.
2. Make choices real before you announce them
Too many strategic plans race to the declaration moment at the Town Hall: here’s the big idea, now go execute. The problem? Leaders rarely know what they’ve actually signed up for, or what needs to change in how the work gets done. If you believe that strategy execution requires improv, then even in setting strategy you need to imagine what comes next and rehearse moves, implications, and ripple effects across future time horizons, albeit in a simpler but realistic form.
One client we worked with knew that acquisitions were essential to their growth. They had several targets in sight and negotiations underway, but no imminent deal. Instead of waiting, we ran the extended leadership team through a series of acquisition scenarios with different strategic intent that examined variables such as deal size, level of integration, and adjacency of the added business. As they worked through each scenario, they not only got a view into the nature of potential targets but also what changes they, as the leaders of the organization, needed to make now. They were choosing what kind of organization they would become. Based on what they were learning, they were able to make key decisions to position themselves for future success. They agreed on new hiring profiles, streamlined decision processes, leadership shifts, so they’d be ready when the right deal came. Strategy shifted from a conceptual statement to a real, lived preparation for a different future.
3. Work across time horizons.
People can change fast. Infrastructure and capital cannot. Budgets, board approvals, and physical assets move slowly. Leaders need to intentionally plan for what can change now, what will take time, and what’s locked in, while still identifying the opportunities at each stage.
Take a pharma company with a pipeline bursting with new drug development. If even half their drugs made it through approval, their manufacturing capacity would be insufficient. Together we built an adaptable manufacturing plan, anchored on essentials, with clear trigger points for future decisions. When 70% of the drugs cleared approval, they were ready. Without that horizon-based thinking, they would have been caught flat-footed.
4. Align at the right level of detail.
Here’s a trap: mistaking varied interpretation of the strategy for purposeful improvisation. They are not the same. Without clarity and alignment at the top, every leader fills in gaps differently. That isn’t agility, it’s chaos.
Leaders must turn the conceptual strategy into something tangible and real, in order to be able to align and lead the organization in the same direction. Strategic modeling allows leaders to test choices at the right level of fidelity, so they know what they’re actually agreeing to. Growing “a lot” versus growing 37% are not the same thing. The detail that is uncovered in the modeling exercises provides enough clarity to shape coherent execution, while still leaving room for adaptive moves over time.
From map to compass
Old strategy setting was about certainty. New strategy setting is about clarity of intent and readiness to adapt. It’s less a map and more of a compass.
If your strategy and planning process still looks like a marathon toward a finished plan, ask yourself: are you preparing for the world you wish you had, or the one you actually face?
The trick is helping leadership teams shift from setting direction to adapting direction—so strategy setting and execution can adapt. The future won’t wait for your plans.
