Before You Say Go: Seven Questions That Expose a Project's Fatal Flaws
Photo: executives in strategy meeting reviewing project plans with sticky notes on whiteboard, via img.freepik.com
There is a well-documented quirk of human psychology that plagues every planning process: once a group has drafted a plan, the room tilts toward optimism. Gary Klein, the psychologist who popularized the pre-mortem, described the phenomenon neatly — imagine it is twelve months from now and the project has failed catastrophically. Now explain why. That single reframing gives dissenters permission to speak and forces hidden assumptions into the open.
At Mr. Lee Projects, we have watched enough initiatives stumble to know that the failure was usually visible at the start — to anyone willing to look. The seven questions below are our adaptation of the pre-mortem discipline. Run them before your next greenlight. A no to any of them is not necessarily a veto, but it is a flag that deserves a conversation, not a shrug.
1. Can every stakeholder state the project's definition of success in one sentence?
Scenario: A mid-sized manufacturer launches a warehouse automation initiative. Operations says success means fewer picking errors. Finance says it means lower labor cost. The CEO said it means a showcase for the investor roadshow. Six months in, the vendor builds to the wrong target. If the answers diverge, the project does not have a goal — it has three, and only one of them will be met.
2. Who owns the project full-time, and do they have the authority to match the responsibility?
Scenario: A regional healthcare provider assigns its director of IT to lead an EHR migration — while she still runs her entire department. Accountability without authority produces escalation paralysis. If the answer to this question is a person with a title but no decision rights, the project will stall exactly when speed matters most.
3. What is the single assumption that, if wrong, kills the project?
Scenario: A retailer assumes its legacy inventory system can export clean data to a new platform. Nobody validates this until month three. Naming the load-bearing assumption — and testing it early — is the cheapest insurance available in project management.
4. What would make our best people quietly conclude this project is doomed?
Scenario: The team knows the timeline was dictated by a press release date, not by the work. Nobody says it aloud, but the strongest performers quietly begin disengaging. Attrition of belief precedes attrition of talent. Ask what the unsaid thing is, and then say it out loud in the room.
5. If this slips by six months, what breaks?
Scenario: A software launch tied to a regulatory deadline has no slack. A product launch tied to a trade show has none either. Knowing the hard dependencies in advance lets you build buffers where they matter — or renegotiate the constraint before it becomes a crisis.
6. Who has veto power, and have they actually agreed?
Scenario: Legal, compliance, or procurement was cc'd on the plan but never formally signed off. Their objection arrives at the worst possible moment. Silence is not approval. Get the explicit yes — or surface the explicit no — before resources are committed.
7. What did the last three similar projects get wrong, and what have we changed?
Scenario: An organization has launched three process-improvement initiatives in five years. All three faded after kickoff. If nothing structural has changed, the fourth will follow the pattern. History is the most honest consultant in the building.
A Repeatable Discipline
None of these questions requires a consultant, a framework license, or a two-day offsite. They require an hour, a whiteboard, and the willingness to hear uncomfortable answers while the project is still cheap to fix. That is the entire promise of the pre-mortem: it converts hindsight into foresight, one greenlight at a time.
