In hindsight, most strategic failures look obvious. From the outside, they appear naïve, rushed, or poorly thought through. But from the inside, at the moment they were made, they usually felt reasonable.
That is what makes them difficult to spot in real time.
In my experience, the most costly mistakes in business rarely arrive as bold gambles or reckless moves. They come disguised as sensible decisions, supported by data, framed by logic, and reinforced by internal agreement. The plan looks coherent. The numbers line up. Nothing immediately triggers an alarm.
And yet, something is often missing.
Right before certain decisions — scaling the organization, making a senior hire, raising capital, acquiring another company, or committing to a major strategic shift — the quality of conversation inside a team tends to change. Questions soften. Assumptions become implicit rather than examined. Doubts are acknowledged, but rarely pursued.
Speed starts to feel like progress.
What’s notable is that these moments are rarely driven by a lack of information. More often, the opposite is true. There is an abundance of data, projections, benchmarks, and narratives. The challenge is no longer gathering information, but distinguishing what actually matters from what merely looks convincing.
Teams begin to confuse internal alignment with external truth. Agreement inside the room becomes a proxy for validity in the market. The logic holds, but only within the boundaries of assumptions that remain unchallenged.
By the time reality intervenes, the decision has usually hardened into commitments — headcount, burn rate, contracts, expectations. At that point, revisiting the original logic feels like retreat or failure, rather than judgment. Execution is expected to compensate for what was never fully tested.
It rarely does.
What makes these situations particularly dangerous is how unremarkable they feel while unfolding. There is no visible crisis. No urgency. Just a steady sequence of reasonable steps taken without enough friction, without an external perspective, and without someone whose role is not to agree, but to slow the decision down long enough to see what is actually happening.
Only later, when consequences accumulate, does the gap become visible — the gap between how a decision felt when it was made and how it looks once its outcomes are irreversible.
That gap is where most strategic risk lives.
And it is also where many organizations underestimate how fragile even the most reasonable logic can be when it has not been meaningfully challenged.