A few years back, I identified an interesting paradox when it came to planning and uncertainty. I had noticed among my clients—and in organisations more broadly—that times of high uncertainty often led people to lower their gaze. Instead of scanning for disruption and staying alert to changing conditions, leaders tended to think shorter-term, become more operational, and ultimately, more reactive.
The Paradox of Planning in Uncertainty states:
“In times of high uncertainty, the need for strategic planning (or more specifically, strategic thinking) goes up, yet our appetite for strategic thinking goes down.”
Or more directly: when we need leaders to do more strategic thinking, they tend to do less.
But why is this the case?
An(other) Ocean Analogy
In 2018, I sailed in the Darwin–Ambon Yacht Race. Unsurprisingly, the race runs from Darwin in northern Australia to Ambon in Indonesia—a distance of around 600 nautical miles. What was most memorable about this trip was the weather. As any sailor can attest, it’s rare to spend five days on the ocean and get consistently great conditions, but that’s exactly what we experienced.
The wind started as a light southerly leaving Darwin Harbour, but once we cleared the lee of the land,* it picked up. After rounding Bathurst Island, we pointed our yacht at Ambon, raised our two spinnakers, and didn’t take them down or deviate course until we reached the mouth of Ambon’s harbour.
*If the wind comes from across the land, it can create a wind shadow on the lee (non-wind) side. In the shadow, winds tend to be lighter and less consistent.
By and large, our five days to Ambon looked like this:
This was taken by a drone I launched from the yacht. The horizon is crystal clear, and I’ve circled the only other boat we could see—they were also in the race.
A leader’s ability to think strategically is the ability to see the big picture: to look to the horizon, pre-empt change, and prepare their people for it. Being strategic is easy when conditions are calm, but conversely, when conditions are calm, there isn’t a pressing need to think strategically. Just point your organisation toward your intended destination, organise and align your crew… and then head down to the galley for some G&Ts.
In Times of Stability, Strategic Thinking Can Feel Wasteful
In business school, you’re taught that good strategy often involves a combination of efficiency and specialisation: find the one thing your customer wants that you can do better than anyone else, then do it as cheaply and quickly as possible. This type of thinking is perfect when conditions are stable and predictable.
In fact, you could argue that in such conditions, spending too much time scanning the horizon, checking the radar, or reviewing the weather reports can feel wasteful. Honestly, if the crew has that much spare time, perhaps a round of redundancies should be on the cards (notwithstanding the impracticalities of off-boarding people in the middle of an ocean).
Somewhat ironically, doing big-picture thinking in this type of environment is super easy. The horizon is clear, gathering clouds are easy to spot, and change happens slowly. Even if we get things a little wrong, the outcome is unlikely to be catastrophic. It’s very easy to be strategic when you don’t need to be and there’s little at stake.
…But in Times of Uncertainty, Strategic Thinking Is Required
Why? Because in times of heightened uncertainty and volatility, conditions can change quickly, and plans become outdated fast. The ability to pre-empt and prepare becomes crucial, as does the capacity to remain flexible and continuously identify and assess new options.
Here’s a comparison shot from the 2004 Sydney–Hobart. The horizon is barely visible through the windscreen as waves break over the boat.
But the conditions that make strategic thinking critical are also the conditions that make it hard. The same uncertainty and volatility that destroy existing plans also make it harder to create new ones. And uncertainty has both physiological and psychological effects on us: we experience greater fatigue, higher anxiety, and a tendency to avoid ambiguity—even though avoidance doesn’t make the uncertainty go away.
This is why organisations may still go through three or four-year planning cycles, but the plans themselves become less strategic and more operational (regardless of what words appear in the document title). At a personal level, leaders micromanage more. As discussed in a previous post, if people feel overwhelmed or can’t make sense of what’s coming toward them, they seek control over whatever they can—focusing on the immediate and operational, rather than the long-term and strategic.
Meanwhile, some big waves are starting to build out the back.* Some are industry-specific, but common ones include the impact of uncertain weather events, cyber security risks, regulatory changes, geo-political instability, and everyone’s favourite: the unknown impacts of AI.
*In surfing terms, “out the back” refers to the area beyond the currently breaking waves—the place where you can spot new waves forming and where the really big waves tend to break.
Uncertainty Requires a Structural Response
So how do you overcome the physiological and psychological forces that push leaders toward short-term thinking? To be effective, the response can’t just be one of skill or will (though both are required); it must be structural.
Just like pre-race briefings, scheduled watches, crew changes, logging and plotting positions, and attending scheduled radio check-ins are all part of safe navigation in a yacht race, something similar is required in organisations.
What are the non-negotiable weekly, monthly, quarterly, and annual activities that provide cues for your leaders to look upward and outward? Which should be done individually, and which collectively?
Perhaps most importantly: how would you implement this? What are you willing to invest in time and resources to build and maintain organisational resilience, even when competing short-term pressures threaten to undermine long-term success*?
*I’ve previously been asked to justify the value of my work. I tend to answer: “What’s the value of one great opportunity seized, or one major issue avoided? Do you think we could achieve either by thinking a little more critically and carefully about the future together?” For most organisations, the value is many multiples more than anything I will ever be paid. And aiming for just one improvement is a remarkably low bar to clear.
Thinking Strategically Takes Time—But It Doesn’t Have to Be Hard
At the end of last year, I wrote another post challenging the assumption that big-picture thinking is inherently hard. The logic seems obvious: the bigger we think, the more information we encounter, the more uncertainties arise, and the more overwhelming it feels.
But this isn’t true—or at least, it doesn’t have to be.
Good strategic thinking begins by gaining clarity on what really matters, then focusing energy there. Maps are a great analogy. As the saying goes, the map is not the territory, which is exactly the point. Maps simplify the world—showing land heights, road networks, weather conditions, population densities, or voting patterns, for example. The benefit of the map is its simplicity at the exclusion of other information. Add too much, and the map becomes overwhelming—and ironically, less useful.
The same is true for strategic thinking. Large amounts of information must be excluded to focus on what genuinely matters. The first step in a strong strategic process is identifying those priorities.
Creating a map of the trends, risks, and opportunities your leadership team faces—and using it to determine what truly requires your time and attention—can be remarkably insightful. I recommend all leadership teams do this at the start of a new year to build shared understanding and align activity for the year ahead. As an annual ritual, it also forms part of a structured approach to encouraging strategic thinking across the leadership team.
Like sailing, conditions won’t always be calm. But with the right structures and habits in place, leaders can lift their gaze and be strategic when it matters most.
Simon
