Most project plans are quietly optimistic. They map out milestones, assign owners, set deadlines, and completely ignore the voice in the back of your head whispering “but what if this all goes sideways?”
That’s the gap this prompt fills. The author, u/Glass-War-2768, shared a sharp one-liner in r/PromptEngineering that turns your AI into a brutally honest critic before you’ve spent a single dollar on execution.
The Prompt (copy this exactly)
“Here is my project plan. Imagine it is 6 months from now and the project has failed. List the 3 most likely reasons why it failed and how to prevent them today.”
That’s it. Paste your plan after this instruction and let the AI do the uncomfortable thinking you’ve been avoiding.
Why it works
This technique borrows directly from a well-established decision-making method called a pre-mortem, a concept popularized by psychologist Gary Klein. Instead of asking “will this succeed?”, you assume failure and work backwards. It’s cognitively very different, and that difference matters.
Here’s what makes each piece of this prompt pull its weight:
- “Imagine it is 6 months from now”: temporal anchoring. It forces the AI (and you) out of present-tense optimism and into a concrete hypothetical future.
- “The project has failed”: assumption of failure. This unlocks critical reasoning the AI might otherwise suppress when trying to be “helpful.”
- “3 most likely reasons”: a hard constraint that prevents vague, exhaustive risk lists. You get the top threats, not a 40-point spreadsheet.
- “How to prevent them today”: action orientation. The output isn’t doom; it’s a to-do list.
The community pushback from u/VorionLightbringer, who points to risk matrices, is fair. But a formal risk matrix takes hours to build and requires a team. This prompt takes 30 seconds and works solo. They’re complementary, not competing.
Use Cases
- Freelancers scoping a new client project and worried about scope creep
- Startup founders stress-testing a product launch timeline
- Team leads pressure-checking a quarterly roadmap before presenting to leadership
- Solopreneurs launching a course, cohort, or service and second-guessing the plan
Two variations worth trying
Variation 1: Stakeholder lens
“Here is my project plan. Imagine it is 6 months from now and a key stakeholder has pulled their support. What did they see coming that we missed, and what should we change now?”
This shifts the frame from internal execution failure to external relationship failure, often the real killer on complex projects.
Variation 2: Scale the timeline
Swap “6 months” for whatever matches your project’s horizon. A 2-week sprint? Use “3 weeks from now.” A 2-year product build? Try “18 months from now.” The temporal anchor should feel slightly beyond completion, not so far it’s abstract.
Prompt of the Day
“Here is my project plan. Imagine it is 6 months from now and the project has failed. List the 3 most likely reasons why it failed and how to prevent them today.”
Head over to the original r/PromptEngineering thread to see the full discussion, including the debate about whether this replaces or just shortcuts traditional risk management. Both sides make points worth reading.
Frequently Asked Questions
Q: Isn’t this just a risk matrix in disguise?
Not quite. A risk matrix maps known risks systematically (likelihood vs. impact). This prompt flips the script: instead of listing what could go wrong, you imagine the project already failed and work backward. Same goal, different mental model — the pre-mortem forces you to think like a critic rather than an optimist, which often surfaces blind spots traditional risk matrices miss.
Q: How do I actually identify which 3 reasons are “most likely”?
Involve your team (not just leadership). Run the pre-mortem in a meeting: have everyone imagine failure, then vote on the reasons that resonate most. You’re looking for consensus on what keeps the team up at night, not a mathematical probability calculation. Common themes usually surface quickly.
Q: What about transparency and data — how does that fit in?
Great catch. The pre-mortem works best when your team has visibility into what’s actually happening (status, blockers, risks). Without transparent communication and reliable data, you’re guessing at failure modes. Before running this prompt, make sure stakeholders are sharing real information, not just rosy updates. That’s your foundation.
Q: Can this replace my existing risk management process?
Use it as a complement, not a replacement. The pre-mortem is fast and team-friendly — good for catching blindspots early. Formal risk matrices are better for large, regulated projects that need audit trails. Many teams do both: run the prompt in week one, then build a risk matrix from the results.
The ‘Anticipatory Reasoning’ Prompt for project managers.
by u/Glass-War-2768 in PromptEngineering