In Alice in Wonderland, the Cheshire Cat delivers one of the most quoted—and misunderstood—lessons in leadership:
“If you don’t know where you’re going, any road will get you there.”
It sounds whimsical. Harmless, even. But in business, this mindset is dangerous.
Modern leaders are navigating markets that shift overnight, technologies that disrupt entire industries in months, and workforces that expect meaning—not just marching orders. In this environment, many organizations cling harder to strategy documents, multi-year plans, and rigid frameworks, hoping structure will restore certainty.
Instead, those plans often become obsolete the moment reality intervenes.
The problem isn’t a lack of intelligence or effort. It’s that traditional strategy assumes a world that no longer exists.
Why Traditional Strategic Planning Breaks Down
Classic strategic planning was designed for relatively stable environments—where change was incremental, competitors were known, and forecasting was reliable. In that world, leaders could analyze, predict, and execute with confidence.
Today’s reality looks very different.
Volatility compresses decision timelines. Ambiguity clouds data. Complexity multiplies interdependencies. And uncertainty makes long-range prediction more guesswork than science. In these conditions, traditional strategy often fails for three reasons.
First, it over-indexes on prediction. Leaders are asked to forecast markets, customer behavior, and competitive moves years in advance—when even months can be uncertain.
Second, it rewards precision over adaptability. Plans become polished, detailed, and difficult to revise, creating friction when course correction is needed.
Third, it confuses certainty with clarity. Leaders mistake having a plan for having direction, even when that plan no longer reflects reality.
Like Alice asking the Cat which way she should go, many organizations seek the right path—when the more important question is whether they agree on the destination.
Strategy Without Certainty Is Still Strategy
Abandoning rigid plans does not mean abandoning strategy.
The most effective leaders today don’t operate without direction—they operate with a different kind of compass. Instead of relying on fixed roadmaps, they anchor themselves to three stabilizing forces:
- Vision – Where are we ultimately trying to go?
- Principles – How do we choose when trade-offs arise?
- Strategic intent – What are we prioritizing right now, given what we know?
This shift changes strategy from a static document into a living practice.
Vision provides orientation without over-specification. It defines the future state you’re moving toward without dictating every step required to get there. A strong vision is emotionally resonant and directional, not overly detailed.
Principles act as guardrails. When conditions change—and they will—principles help leaders decide what not to do as much as what to do. They shape behavior under pressure and prevent reactive decision-making.
Strategic intent focuses energy. It clarifies what matters most in the current chapter, allowing teams to align their efforts without waiting for perfect information.
Together, these elements allow leaders to move forward confidently—even when the path keeps shifting beneath their feet.
The Difference Between Rigid Plans and Adaptive Strategy
Rigid plans assume stability. Adaptive strategy assumes movement.
In a rigid model, deviation is treated as failure. In an adaptive model, adjustment is expected—and valued.
Adaptive strategy is not reactive chaos. It is disciplined flexibility. Leaders continuously scan the environment, test assumptions, and adjust course while staying anchored to their core direction.
This requires a different leadership posture. Instead of asking, “Are we following the plan?” adaptive leaders ask, “Is this decision aligned with who we are and where we’re going?”
Instead of locking teams into detailed execution paths, they empower teams to respond intelligently to new information.
This doesn’t reduce accountability—it reframes it. Accountability shifts from rigid adherence to plans toward thoughtful decision-making in context.
In Wonderland terms, the Cat doesn’t give Alice a map. He gives her awareness.
Strategic Thinking in the Fog
Leading strategically in uncertainty means learning to decide without full clarity. That can feel uncomfortable—especially for leaders trained to minimize risk and maximize certainty.
But waiting for perfect information is its own risk.
A useful way to navigate decision-making in foggy conditions is to return to a simple sequence of reflection:
- What direction are we aiming toward, even broadly?
- What values or principles must guide this choice?
- What is true right now—not hypothetically, not ideally?
- What is the cost of action versus inaction?
- Does this move keep us aligned with our intent?
These questions don’t eliminate uncertainty. They make it manageable.
Importantly, they also create shared language across leadership teams. When everyone understands how decisions are made, trust increases—even when outcomes are imperfect.
Giving Teams Direction Without Micromanaging
One of the most overlooked benefits of adaptive strategy is how it empowers teams.
When leaders obsess over controlling every step, they unintentionally signal distrust. Teams become dependent, cautious, and slow to respond to change.
But when leaders clearly articulate vision and principles, they create space for autonomy. Teams understand the destination and the boundaries—and are trusted to navigate the terrain.
This approach mirrors the Cheshire Cat’s wisdom. He doesn’t tell Alice where to go. He helps her realize that clarity of purpose matters more than the specific path.
Leaders can ask themselves:
- Have I clearly communicated what success looks like?
- Do my teams understand why this work matters?
- Have I defined principles strongly enough to support decentralized decisions?
When the answers are yes, teams move faster, adapt more effectively, and feel ownership over outcomes.
Strategy as a Living Conversation
Perhaps the most important shift in modern strategy is recognizing that it is not a one-time event. It is an ongoing dialogue.
Effective leaders revisit assumptions regularly. They invite dissent. They listen for weak signals at the edges of the organization. They treat strategy less like architecture and more like navigation.
This doesn’t mean constantly changing direction. It means staying awake.
In Wonderland, logic bends and rules shift—but Alice’s growing self-awareness allows her to stay grounded. In business, leaders who remain clear on who they are and what they stand for can navigate even the most nonsensical environments.
Finding Direction When the Path Disappears
The Cheshire Cat fades away, but his message lingers.
Direction doesn’t come from certainty. It comes from intention.
In chaotic environments, leaders who thrive are not those with the most detailed plans—but those with the clearest sense of purpose, the strongest principles, and the courage to adapt without drifting.
If you know where you’re going—and who you want to be along the way—you don’t need every answer upfront.
You just need the confidence to take the next step.
And in a world that looks increasingly like Wonderland, that may be the most strategic move of all.
References
- Bishop, Parker (2025). Wonderland Guide to Business Strategy: Navigating Change in a Nonsensical World. Tin Roof Publications.
- Mintzberg, H. (1994). The Rise and Fall of Strategic Planning. Free Press.
- Reeves, M., Levin, S., & Ueda, D. (2016). The Biology of Corporate Survival. Harvard Business Review.
- Snowden, D. J., & Boone, M. E. (2007). A Leader’s Framework for Decision Making. Harvard Business Review.
- McGrath, R. G. (2013). The End of Competitive Advantage. Harvard Business School Publishing.