The Regret Pre-Mortem

Run Your Pre-Mortem

How It Works – Step by Step

1. Enter Your Decision: Describe the big strategic move, pivot, or investment you’re considering.
2. Time-Travel Simulation: The AI projects you 12 months forward — where the decision failed.
3. Write the Post-Mortem: The tool prompts you to articulate how and why it failed.
4. Analyse the Insights: Review failure modes, missed signals, and underestimated stakeholders.
5. Refine the Decision: Adjust your plan, validate assumptions, or avoid the trap entirely.

Understanding Your Results

Your AI-generated Post-Mortem Report includes:

• Actual Failure Mode: The true reason behind the collapse, not the surface-level excuse.
• Second-Order Effects: Ripple consequences, such as morale loss or market erosion.
• Ignored Signals: Red flags you dismissed during planning.
• Underestimated Stakeholders: Groups affected more than anticipated.
• Misguided Optimisation: What you focused on that didn’t matter.
• Alternative Actions: What you could’ve done differently.

How to Use Your Analysis

• Before Major Strategic Shifts: Run a pre-mortem to expose untested assumptions.
• During planning phases, use the results to stress-test risk appetite and market readiness.
• For Team Alignment: Share outcomes to surface differing views early and address them effectively.
• When Seeking Investor Buy-In: Present both best- and worst-case models to build credibility.
• After Execution: Re-run the pre-mortem quarterly to track actual outcomes against expected ones.

When to Use This App?

• Before product pivots, fundraising rounds, or mergers.
• Before launching new business units or pricing strategies.
• When scaling to unfamiliar markets or industries.
• During leadership off-sites for structured reflection.
• As part of your quarterly decision review cadence

Decision Reflection Benchmarks 2025

Use these benchmarks to evaluate how your decision-making risk compares to industry averages.

Note: These benchmarks highlight how ambition often blinds strategy. Use them to recalibrate optimism with operational reality.

Example Output

Decision: “Pivot our B2C SaaS product to target enterprise customers.”

Failure Mode:
A mismatch between product-market fit, organisational DNA, and sales motion. We forced a lightweight consumer product into a complex enterprise world, resulting in poor adoption and wasted resources.

Second-Order Effects:
Neglected B2C customers churned, top talent left, morale plummeted, and the company ultimately lost both markets.

Underestimated Stakeholders:
Ignored existing loyal customers and internal product experts; overestimated the ease of convincing enterprise committees.

Ignored Signals:
Dismissed team warnings, long enterprise sales cycles, and lack of inbound interest were clear signs that the pivot was premature.

Misguided Optimisation:
Chased prestige metrics like high ARR and “enterprise credibility” instead of deepening product value for paying customers.

Growth Tips & Strategic Impact

• Make Failure Your Teacher: Every imagined failure is a saved resource in real life.
• Rehearse Regret to Build Clarity: Leaders who visualise failure make better long-term decisions.
• Turn Emotion into Insight: Writing the post-mortem forces objective analysis of ego-driven calls.
• Integrate with Other Tools: Use alongside the Opposite-Day Audit to explore both regret and inversion perspectives.
• Build a Decision Archive: Keep pre-mortems as part of your strategic documentation to measure and improve decision quality over time.

Strategic Impact:
Leaders who use the Regret Pre-Mortem avoid catastrophic pivots, strengthen validation loops, and build emotionally intelligent decision-making cultures.Consequence Chain reduce strategic blind spots, shorten feedback loops, and make more resilient long-term decisions.