We treat contingency planning like an admission of doubt. Real conviction, we tell ourselves, means committing fully to the one plan.
Then deadline day arrives, the plan collapses in the final hour, and we discover what that conviction was hiding: a refusal to prepare for anything but success.
Transfer deadline day in sport is theater precisely because it strips away the polish. Deals that look certain at nine in the evening are dead by midnight. A number moves. A medical raises a flag. A player changes his mind. None of this is rare. It’s the norm, dressed up as the exception.
We build organizations the same way we build transfer strategies, around the ideal outcome, not the range of outcomes. We chase the one candidate, the one client, the one deal, and we call the chasing “focus.”
But focus without a fallback is fragility with better branding.
The clubs that manage deadline day well aren’t the ones with the deepest pockets. They’re the ones who assumed early that plan A might not survive contact with reality, and built plan B before they needed it. When the deal falls through, they make a second call instead of an excuse.
We rarely ask, in the boardroom or the transfer room, what happens if the sure thing isn’t sure. Silence is usually the answer, and silence is expensive.
The organizations built to last aren’t the ones that never lose the deal. They’re the ones that never let one deal own their future.
