If you’ve spent time in strategy post-mortems, or even in high-stakes “war” rooms, you’ve probably heard the same lines: “We had all the data, but no real insight.” “The logic felt right, but no one tested it.” “We assumed X would hold, and we never questioned it.”
Sound familiar? I hear versions of this often, from CEOs, executives, founders, and boards with access to talent, capital, and experience. These aren’t failures of intelligence or capability; they are failures of thinking under complexity.
After facilitating over 1,000 strategy workshops, reviewing more than 4,000 strategic initiatives, and sitting on boards across multiple industries, I’ve seen a consistent pattern: the most talented teams fail not from lack of effort, but from gaps in reasoning.
A Necessary Caution on Executive Confidence
No CEO or C-suite, no matter how capable, gets it right all the time. Under complexity, consistent correctness is mathematically impossible. What matters is not brilliance, but whether the organization’s thinking system can surface and correct error early.
This is why worldview matters. A small flaw in a logic chain, one untested assumption or an elegant but incomplete narrative, can compound over time and become destructive long after the executive who made it is gone. Strategies may look sound, balance sheets may even improve, yet unintended consequences often emerge later when conditions change and incentives shift.
Boards and teams must also be wary of being impressed by articulate leaders and compelling presentations. Persuasion is not proof. Fluency is not rigor. Short-term performance can mask long-term fragility if the underlying reasoning was never examined. This is where disciplined, integrated thinking becomes essential, not to replace judgment, but to protect organizations from inevitable human error under uncertainty.
The Cost of the “Type 1” Strategic Error
Across thousands of business reviews, one pattern became painfully clear: most failures we call “bad strategy” are not execution failures. They are Type 1 errors, the act of doing the wrong thing very efficiently. In statistics, a Type 1 error is a “false positive”; in strategy, it is a “false conviction.”
These errors generally fall into one of four categories:
- The problem is misframed – Solving the urgent, not the strategic.
- Insights are shallow – Obvious observations that cannot guide unique choices.
- Logic is not defensible – Gaps or hidden leaps in the “if-then” chain.
- Assumptions are invisible – The strategy is fragile because its foundation is unexamined.
By the time budgets are spent and timelines met, the failure has already happened, quietly, before anyone could intervene.
Introducing PILA: Problem, Insight, Logic, Assumptions
PILA is a reasoning stack, a disciplined way to examine whether a strategy deserves belief before it earns investment and support.
- Problem: Agree on the real problem before exploring solutions.
- Insight: Generate leverageable understanding that forces trade-offs.
- Logic: Connect choices and outcomes explicitly.
- Assumptions: Make critical bets visible and testable.
Let me be clear: nothing in PILA is individually revolutionary. The power is in the integration and sequence. A strong insight cannot rescue a misframed problem. Elegant logic cannot fix false assumptions. Confidence cannot replace rigor. Each element is necessary, but none are sufficient alone.
When Is Each Element “Enough”?
To ensure rigor, we must define the “Pass” criteria for each layer of the stack:
- Insight: Deep enough if it changes a choice or trade-off you would not otherwise make. Shallow insights, like “customers want low prices,” don’t count.
- Logic: Defensible if it is stepwise, falsifiable, and survives skeptical review. Persuasive logic sounds good; defensible logic can be tested and challenged.
- Assumptions: Keep the critical 1–3 explicit and ranked by impact. More than five untested assumptions? The strategy is a gamble, not a plan.
PILA as a Fiduciary Shield
PILA provides what many organizations skip: a pre-commitment checkpoint. In a professionalized corporate environment, this isn’t about micromanagement; it is about governance excellence.
For the Board of Directors: It is a fiduciary shield. It moves the Board away from passive oversight of “results” to active validation of “thinking.” By using PILA, directors can identify the “weakest link” in a proposal before capital is deployed. This provides a neutral, professional vocabulary to ask, “What is the critical assumption that makes this entire proposal work?” It protects the collective responsibility of the board without undermining management’s vision.
For Startups: It is a burn-rate guardrail. Startups often fail because they solve problems that don’t exist. PILA forces founders to identify the “leap of faith” assumptions that can be de-risked with small experiments rather than massive overhead.
For Function Leaders: It is a silo-breaker. Marketing might find the Insight, while Finance validates the Logic. It ensures that every department is working off the same “reasoning stack” rather than fragmented goals.
Navigating Organizational Pressures
High-stakes strategy rarely fails solely from reasoning gaps. Authority, fear, groupthink, and incentives all influence outcomes. PILA works because it provides a structured lens to bypass these pressures:
- Authority & Politics: Leaders can dominate decisions, but explicit reasoning makes challenges safer and more objective.
- Groupthink: Structured discussion around the stack encourages dissent by focusing on the mechanics of the plan, not the personality of the planner.
- Environmental Complexity: PILA makes assumptions explicit, allowing for rapid scenario testing when markets shift.
Operationalizing PILA
For managers and leaders, the goal isn’t more meetings, it’s better thinking. They can:
- Run pre-mortems: Ask “why will this fail?” using the PILA stack before committing.
- Use independent review: Use PILA to give contrarian perspectives a way to validate logic.
- Score your strategy: Track problem clarity, insight leverage, and logic defensibility.
Why PILA Is Attack-Proof
Critics may call PILA “common sense.” That is exactly the point: PILA is not a magic bullet; it’s a guardrail for reasoning. Its power lies in integration and discipline, not novelty. It forces leaders to surface hidden bets and align teams before major commitments.
In short, PILA strengthens thinking where confidence, authority, and momentum often lead teams astray. It enables strategy to survive scrutiny, uncertainty, and high stakes, without claiming to control the uncontrollable.
Bottom line
Strategy fails not because leaders lack intelligence or vision. It fails because reasoning, assumptions, and insights often don’t integrate under uncertainty and organizational pressures. PILA fixes the cognitive layer, empowers teams, and provides the structure to surface critical questions early.
When Problem, Insight, Logic, and Assumptions work together, strategy becomes more than a plan on paper, it becomes a defensible, adaptable, and focused approach to winning. Discipline in thinking matters more than confidence alone. PILA is the framework to make that discipline actionable.
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Josiah Go is a business thought leader, speaker, mentor, entrepreneur, blogger, columnist, and independent director. He is a record-breaking, bestselling author of 20 books on marketing and entrepreneurship.
Interested in having your team learn about PILA? Register Here: https://bit.ly/BDA2026.
