by Robyn Bolton | Feb 2, 2026 | AI, Leadership, Strategic Foresight, Strategy
It was a race. And the whole world was watching.
In 1911, Captain Robert Scott set out to reach the South Pole. He’d been to Antarctica before and because of his past success, he had more funding, more expertise, and more experience. He had all the equipment needed.
Racing him to fame, fortune and glory was Norwegian Roald Amundsen. Originally heading to the North Pole, he turned around when he learned that Robert Peary had beaten him there. He had dogs and skis, equipment perfect for the Arctic but unproven in Antarctica.
Amundsen won the race, by over a month.
Scott and his crew died 11 miles from the South Pole.
When the Playbook Stops Working
Scott wasn’t guessing. He’d tested motor sledges in the Alps. He’d seen ponies work on a previous Antarctic expedition. He built a plan around the best available equipment and the general playbook that had served British expeditions for decades: horses and motors move heavy loads, so use horses and motors.
It just wasn’t right for Antarctica. The motors broke down in the cold. The ponies sank through the ice. The plan that looked solid on paper fell apart the moment it met the actual environment it had to operate in.
The same thing is happening today with AI.
For decades, when new technologies emerge, executives have followed a similarly familiar playbook: assess the opportunity, build a business case, plan the rollout, execute.
And for decades it worked. Cloud migrations and ERP implementations were architectural changes to known processes with predictable outcomes. As time went on, information grew more solid, timelines became better understood, and the playbook solidified.
AI is different. Executives are so focused on picking the right AI tools and building the right infrastructure that they aren’t thinking about what happens when they hit the ice. Even if the technology works as designed, you have no idea whether it will deliver the intended results or create a ripple of unintended consequences that paralyze your business and put egg on your face.
Diagnose Before You Prescribe
The circumstances of AI are different too, and that requires a new playbook. Make that playbooks. Picking the right playbook requires something my clients and I call Calibrated Decision Design.
We start by asking how long it will take to realize the ultimate goals of the investment. Do we need to break even this year, or is this a multi-year bet where results slowly roll in? Most teams have a sense of this, so it allows us to move quickly to the next, much harder question.
What do we know and what do we believe? This is where most teams and AI implementations fail. To seem confident and indispensable, people present hypotheses as if they are facts resulting in decisions based on a single data points or best guesses. The result is a confident decision destined to crumble.
Where you land on these two axes determines your playbook. Apply the wrong one and you’ll either waste money on over-analysis or burn through budget on premature action.
Pick from the Four Playbooks
Go NOW!: You have the facts and need results now. Stop deliberating. Execute.
Predictable Planning: You have confidence in the outcome, but the payoff takes patience. Build a flexible strategy and operational plan to stay responsive as things progress.
Discovery Planning: You need results fast, but you don’t have proof your plan will work. Run small, fast experiments before scaling anything.
Resilient Strategy: The time horizon is long and you’re short on facts. The worst thing you can do is go all in. Instead, envision multiple futures, identify early warning signs, find commonalities and prepare a strategy that can pivot.
Apply it
Which playbook are you using and which one is best for your circumstance?
by Robyn Bolton | Jul 16, 2025 | Leadership, Strategic Foresight
You’ve done everything to set Strategic Foresight efforts up for success. Executive authority? Check. Challenging inputs? Check. Process integration? Check. Now you just need to flip the switch and you’re off to the races.
Not so fast.
While the wrong set-up is guaranteed to cause failure, the right set-up doesn’t guarantee success. Research shows that strategic foresight initiatives with the right set-up fail because of “organizational pathologies” that sabotage even well-designed efforts.
If you aren’t leading the right people to do the right things in the right way, you’re not going to get the impact you need.
Here’s what to watch out for (and what to do when it happens).
Your Teams Misunderstand Foresight’s Purpose
People naturally assume that strategic foresight predicts the future. When it doesn’t, they abandon it faster than last year’s digital transformation initiative.
Shell learned this the hard way. In 1965, they built the Unified Planning Machinery, a computerized forecasting tool designed to predict cash flow based on trends. It was abandoned because executives feared “it would suppress discussion rather than encourage debate on differing perspectives.”
When they shifted from prediction to preparation, specifically to “modify the mental model of decision-makers faced with an uncertain future,” strategic foresight became an invaluable decision-making tool.
Help your team approach strategic foresight as preparation, not prediction, by measuring success by the improvement in discussion and decision-making, not scenario accuracy. When teams build mental flexibility rather than make predictions, wrong scenarios stop being failed scenarios.
People are Paralyzed by Fear of Being Wrong
Even when your teams understand foresight’s purpose, managers are often unwilling “to use foresight to plan beyond a few quarters, fearing that any decisions today could be wrong tomorrow.”
This is profoundly human. As Webb wrote, “When faced with uncertainty, we become inflexible. We revert to historical patterns, we stick to a predetermined plan, or we simply refuse to adopt a new mental model.” We nod along in scenario sessions, then make decisions exactly like we always have.
Shell’s scenario planning efforts succeeded because it made being wrong acceptable. Even though executives initially scoffed at the idea of oil prices quadrupling, they prepared for the scenario and took near-term “no regrets” decisions to restructure their portfolio.
To help people get past their fear, reward them for making foresight-informed decisions. For example, establish incentives and promotion criteria where exploring “wrong” scenarios leads to career advancement.
Your Culture Confuses Activity with Achievement
Between insight and action, the Tyranny of Now reigns. In even the most committed organizations, the very real and immediate needs of the business call us away from our planning efforts and consume our time and energy, meaning strategic foresight is embraced only when it doesn’t interfere with their “real” jobs.
Disney’s approach made strategic foresight a required element of people’s “real jobs” by integrating foresight activities and insights directly into performance management and strategic planning. When foresight teams identified that traditional media consumption was fracturing in 2012, Disney began preparing for that future by actively exploring and investing in new potential solutions.
Resist the Tyranny of Now’s pull by making strategic foresight activities just as tyrannical – require decisions based on foresight insights to occur in 90 days or less. These decisions should trigger resource allocation reviews, even if the resources are relatively small (e.g., one or a few people, tens or hundreds of thousands of dollars). If strategic foresight doesn’t force hard choices about investments and priorities, it’s activity without achievement.
How You Lead and What People Do Determine Strategic Foresight’s Success
Executive authority, challenging inputs, and process integration are necessary but not sufficient. Success requires conquering the deeper organizational and human behaviors that determine whether strategic foresight is a corporate ritual or a competitive advantage.
