The library
Search by the shape of the decision
Every case carries the same twelve field groups, so a procurement decision in logistics and a pricing decision in payments can be compared on the constraint they share rather than the industry they sit in.
We killed a feature after six months of build. The reasoning held; the timing did not.
Adoption sat at 4% of target after two quarters. Four options on the table, three rejected. The decision to discontinue was defensible on the evidence available — the error was waiting two months longer than the criteria required.
One senior engineer or two juniors on the same budget
A Series B team with one open requisition and a delivery commitment eight months out. The decision turned on who would do the mentoring, and that question had no good answer.
We took a down round instead of an acquisition offer. Eighteen months later the company closed.
An offer on the table at roughly half the last valuation, against a bridge at a 60% markdown. The reasoning was documented at the time. It did not survive contact with the following year.
Renewing a fleet contract three months early to lock a price
Fuel and lease rates were moving in opposite directions. Renewing early cost a negotiating position and bought eighteen months of certainty. The spreadsheet said yes; the counterparty relationship said be careful.
Cutting 12% of staff nine months before the runway required it
The model said we could wait two more quarters. We cut early anyway, on the argument that a smaller cut now beat a larger one later. That argument is harder to defend than it sounded in the room.
We ended the contract with the client that was 41% of our revenue
No board, no runway, no second opinion. The decision took eight months to execute and the replacement revenue arrived four months later than the plan assumed.
Rewriting the billing system instead of patching it for another year
The estimate was five months. It took nine. Whether that counts as a failure depends entirely on what the patching path would have cost, and that number is unknowable.
A 40% price rise with no grandfathering for existing customers
Grandfathering was the obvious kindness and the obvious mistake. We chose against it, lost more customers than the model predicted, and would make the same call.
Moving the warehouse night shift to four ten-hour days
Proposed by the shift supervisors, resisted by scheduling, and measured for six months before a permanent decision. The pilot design mattered more than the change itself.