Activity · Pre-Mortem · Copilot Tool
It is 12 months from now. The initiative stalled. What happened?
This is a pre-mortem. We are not predicting failure — we are using the assumption of failure to surface the risks we are not seeing clearly enough right now.
What This Tool Does
A pre-mortem is one of the most powerful planning tools available — and one of the least used. Instead of asking "what could go wrong?", it asks you to assume the initiative has already failed and work backwards to explain why. This reframe bypasses optimism bias and surfaces the risks that are hardest to name when you are inside the work. Use this prompt on any initiative, project, or change programme you are currently leading or contributing to. Paste it into Copilot. Replace the placeholders with your specific context. The output will surface the failure modes that are easiest to miss when momentum is high.
How to Use This Prompt
Replace every [BRACKETED PLACEHOLDER] with your specific initiative context before pasting into Copilot. The more specific you are, the more useful the output. Vague inputs produce generic risks — the ones you already know about. Specific inputs produce the uncomfortable ones.
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What the Prompt Will Surface
Eight Dimensions of Initiative Failure
The prompt is structured to push Copilot across eight distinct failure dimensions. These are the areas where initiatives and change programmes most commonly stall, underdeliver, or quietly die — and where the warning signs are most often visible in hindsight but invisible in the planning phase.
Dimension 1
Stakeholder Alignment
The sponsors who lost interest, the stakeholders who were never truly on board, and the competing priorities that quietly displaced this one.
Dimension 2
Operational Readiness
The processes, systems, and capabilities that weren't ready when the initiative needed them — and the assumptions we made about how quickly things could change.
Dimension 3
Resourcing & Capacity
The people, time, and budget that were committed on paper but absorbed elsewhere — and the workload that was underestimated at the start.
Dimension 4
Change Resistance
The teams or individuals who adapted slowly, the cultural patterns that reasserted themselves, and the informal systems that outlasted the formal ones.
Dimension 5
Technology & Integration
The systems that didn't connect, the data that wasn't available, and the technical dependencies that created delays we didn't fully anticipate.
Dimension 6
External Environment
The market shifts, regulatory changes, or external pressures that changed the context in which the initiative was operating — and that we didn't build enough flexibility to absorb.
Dimension 7
Governance & Escalation
The decisions that were delayed, the concerns that weren't raised in time, and the review points that passed without the honest conversations they required.
Dimension 8
Communication & Narrative
The story that didn't land, the teams that didn't understand why this mattered, and the momentum that was lost when communication became inconsistent or stopped.
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The Initiative Pre-Mortem Prompt
Copy · Paste Into Copilot · Replace Placeholders
Paste this prompt into Microsoft Copilot. Replace every bracketed section with your specific initiative context. The more detail you provide about the initiative, the stakeholders, and the key assumptions you are currently making, the more targeted and useful the output will be.
Why this framing works: Asking "what could go wrong?" activates defensive optimism — we generate risks we feel comfortable naming. Assuming failure has already happened activates a different cognitive mode. We stop protecting the plan and start explaining the wreckage. This is where the real risks live.
You are helping me conduct a pre-mortem on an initiative I am currently leading or contributing to. A pre-mortem works like this: instead of asking what might go wrong, we assume the initiative has already failed — it is now 12 months from now, and the initiative has stalled, underdelivered, or been quietly abandoned. Our task is to work backwards and construct the most plausible, specific explanation for what happened. This is not a pessimism exercise. It is a rigorous planning tool. The goal is to surface the risks that are hardest to name when momentum is high and commitment is strong. HERE IS THE INITIATIVE I AM WORKING ON: Initiative name: [Name of the initiative or project] What we are trying to achieve: [Describe the core objective in 2–3 sentences. What does success look like? What problem are we solving?] Current stage: [Where are we right now? Planning, early implementation, mid-delivery, approaching launch?] Key stakeholders: [Who are the main sponsors, decision-makers, and affected teams? Who needs to change their behaviour for this to work?] Key assumptions we are making: [What are we assuming about resources, timelines, stakeholder support, technology readiness, or team capacity that we have not fully tested?] The biggest pressure on this initiative right now: [What is the main constraint, tension, or risk that is already visible?] YOUR TASK: It is now 12 months from today. The initiative has failed to deliver what we intended. It may have stalled, been deprioritised, produced the wrong outcomes, or quietly lost momentum. Please construct the most plausible, specific failure narrative. Work through each of the following eight dimensions. For each one, describe the specific way this initiative could have failed — not generic risks, but the failure modes that are most likely given the context I have described above. DIMENSION 1 — STAKEHOLDER ALIGNMENT Which stakeholders lost interest, withdrew support, or were never truly committed? What competing priority displaced this one? Who should have been more involved earlier? DIMENSION 2 — OPERATIONAL READINESS What processes, systems, or capabilities were not ready when the initiative needed them? What did we assume would be in place that wasn't? Where did the gap between plan and reality show up first? DIMENSION 3 — RESOURCING AND CAPACITY Where did the resource commitment break down? Whose time was absorbed elsewhere? What was underestimated at the start — workload, complexity, or the number of people genuinely needed? DIMENSION 4 — CHANGE RESISTANCE Which teams or individuals adapted more slowly than expected? What cultural patterns reasserted themselves? What informal systems or habits outlasted the formal change effort? DIMENSION 5 — TECHNOLOGY AND INTEGRATION What technical dependencies created delays? Which systems didn't connect as planned? What data wasn't available when it was needed, and what did that cost us? DIMENSION 6 — EXTERNAL ENVIRONMENT What changed in the external context — market conditions, regulatory requirements, organisational priorities — that we didn't build enough flexibility to absorb? DIMENSION 7 — GOVERNANCE AND ESCALATION Which decisions were delayed too long? What concerns were visible but not raised in time? Which review points passed without the honest conversations they required? DIMENSION 8 — COMMUNICATION AND NARRATIVE Where did the story break down? Which teams didn't understand why this mattered? When did communication become inconsistent, infrequent, or stop altogether? SYNTHESIS: After working through all eight dimensions, identify: 1. The single most likely root cause of failure — the one thing that, if it had been addressed earlier, would have changed the outcome most significantly. 2. The two or three early warning signs that would have been visible within the first 90 days if we had been looking for them. 3. One structural change to the current plan that would most reduce the risk of this failure narrative becoming real.
5 Follow-Up Prompts — Go Deeper
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"Now focus only on the people dimension. Which specific individuals or teams are most likely to be the source of friction — not because of bad intent, but because of competing priorities, unclear roles, or insufficient involvement in the design of this initiative?"
2
"Construct a partial failure scenario: the initiative delivered something, but not what mattered most. What did we ship that looked like success but wasn't? What did we optimise for that turned out to be the wrong thing?"
3
"Give me three falsifiable hypotheses — specific, testable predictions about this initiative that I could check within the next 30 days to know whether we are on track or already heading toward the failure narrative you described."
4
"Now run the pre-mortem from the perspective of the teams who will be most affected by this initiative. What would they say went wrong? What did they see coming that leadership didn't? What did they need that they didn't get?"
5
"Based on the failure narrative, what is the one conversation that the initiative lead most needs to have in the next two weeks — and with whom? What is the honest thing that needs to be said that is currently not being said?"
"The pre-mortem is not a pessimism exercise. It is the most rigorous thing a leader can do before committing to a plan — because it is the only tool that forces you to see the failure that is already baked in."
This tool is designed for individual reflection and team conversation. Use it before you finalise a plan, before a major milestone review, or whenever momentum is high and honest challenge feels harder to find.