How often have you found yourself saying, "I should have known"? That moment of realisation when hindsight reveals that the warning signs were there all along—you just didn't have the right tools or framework to recognise them, let alone act on them. This phrase, uttered in boardrooms, project meetings, and strategy sessions across the globe, represents one of the most costly failures in modern business: the inability to prepare for what seems obvious in retrospect.
The true cost of "I should have known" extends far beyond the immediate crisis. When organisations are caught off guard by events they could have anticipated, the price tag includes not just the direct financial impact, but also the erosion of stakeholder confidence, the loss of competitive advantage, and the demoralisation of teams who feel their concerns were ignored. Consider the company that watched a competitor launch a disruptive technology they'd seen coming for months, or the project manager who watched a critical deadline slip because of supply chain issues they'd discussed in passing but never properly planned for.
Reactive planning—the practice of responding to events after they occur rather than preparing for them in advance—creates a cycle of perpetual crisis management. Teams become so focused on putting out fires that they never have the bandwidth to prevent them. Budgets get consumed by emergency responses, leaving nothing for proactive measures. And perhaps most damaging of all, organisations develop a culture where planning for uncertainty is seen as pessimism rather than prudence.
Leaders often do see the warning signs. They notice market shifts, hear concerns from team members, read industry reports, and sense that something is changing. Yet despite this awareness, they find themselves paralysed. Why? Because traditional planning methods don't provide the tools to translate vague concerns into actionable strategies. When you can't quantify uncertainty or structure multiple possibilities, those warning signs remain abstract worries rather than concrete planning inputs.
Consider the executive who knew that regulatory changes were coming but couldn't get budget approval for contingency planning because they couldn't articulate what "might happen" in terms that finance teams could understand. Or the project manager who sensed that weather patterns might delay shipments but had no framework to create multiple plans for different scenarios. They saw the signs, but without the right tools, they couldn't act on them effectively.
This gap between awareness and action is where "I should have known" takes root. It's not that leaders are blind to potential problems—it's that they lack the structured approach to turn that awareness into preparation. The warning signs are visible, but they remain disconnected dots rather than a coherent picture of possible futures.
Beyond the immediate crises, reactive planning creates a deeper organisational problem: it trains teams to wait for problems rather than anticipate them. When planning processes only address the single, most likely future, teams become conditioned to ignore alternative possibilities. This creates blind spots that compound over time, making organisations increasingly vulnerable to disruption.
The financial impact is staggering. Research consistently shows that organisations that prepare for multiple scenarios recover faster from crises, maintain better stakeholder relationships, and preserve more value during turbulent times. Yet many businesses continue to invest heavily in single-outcome planning, betting everything on one version of the future and leaving themselves exposed when reality takes a different path.
Some organisations have found a way to break this cycle. They've developed approaches that allow them to prepare for multiple futures simultaneously, creating flexible strategies that work regardless of which scenario unfolds. These organisations don't try to predict the future—they prepare for several possible futures, ensuring they're ready whether the market shifts, regulations change, or unexpected disruptions occur.
What sets these organisations apart isn't superior forecasting ability or access to better information. Instead, they use structured frameworks that help them identify key uncertainties, map out different scenarios, and develop contingency plans for each. They've learned to think in terms of possibilities rather than probabilities, creating strategies that remain relevant across multiple outcomes.
These forward-thinking organisations have discovered that the key to avoiding "I should have known" moments isn't better prediction—it's better preparation. By acknowledging uncertainty and planning for it systematically, they transform vague concerns into concrete strategies. They create a culture where discussing multiple futures isn't seen as pessimism but as strategic thinking.
The good news is that this approach isn't reserved for large corporations with extensive planning departments. The principles can be applied by individuals, small teams, and organisations of any size. The challenge isn't the complexity of the method—it's having access to a framework that makes multi-scenario planning practical and actionable rather than overwhelming.
The organisations that avoid "I should have known" moments share a common characteristic: they've moved beyond single-outcome planning to embrace uncertainty as a planning input rather than a planning obstacle. They've found ways to structure their thinking about the future that allow them to prepare for multiple possibilities without getting lost in analysis paralysis.
"I should have known" represents a failure of preparation, not a failure of awareness. The warning signs are often visible, but without the right tools to structure thinking about multiple futures, leaders find themselves unable to translate concerns into action. The organisations that avoid this trap have learned to prepare for uncertainty systematically, creating flexible strategies that work across multiple scenarios.
The question isn't whether uncertainty exists—it's whether you have the framework to plan for it effectively. Those who do find themselves better prepared, more resilient, and less likely to utter those expensive words: "I should have known."
If you're ready to move beyond reactive planning and develop the skills to prepare for multiple futures, there are structured approaches that can help you transform uncertainty from a planning obstacle into a planning advantage.
Check out this course to help you prepare for multiple futures: The Future Matrix - Master the Art of Planning for Uncertain Futures