TLDR
- A future-back strategy prompt to surface the questions you’ll regret not asking five years from now.
- Provides 24 structured outputs: from failure premortems and assumption audits to stakeholder mapping, wargaming, resilience planning, and ethics.
- Includes Question Prioritization and a 30/90-day plan to turn insights into experiments and action.
- Helps decision-makers avoid one-way door 🚪 mistakes by tagging irreversible choices.
- Designed with numbered lists, base rates, and explicit evidence/assumption tags.
Introduction
High-stakes initiatives often fail not because of poor execution but because the right questions were never asked early enough. The Regret-Proof Navigator (Five-Year Hindsight Catalyst — V2) helps leaders, strategists, and operators invert time: looking back from five years out to ask “What will I wish I had asked today?”.
This comprehensive prompt blends hindsight inversion, premortems, and option-preserving moves with evidence hygiene, risk audits, and decision quality tools. The result: not just sharper questions but concrete action plans.
The Custom Prompt
Master Prompt — Regret-Proof Navigator V2
Regret-Proof Navigator
(Five-Year Hindsight Catalyst — V2)
How to use (quick start)
1. Paste the Master Prompt (V2) into your AI (assumes ChatGPT).
2. Fill the bracketed fields [like this]. If info is missing, run it anyway—the prompt forces assumptions and returns clarifying questions.
3. Use the Question Prioritization and 30/90-day plan to turn insights into action.
4. Tag one-way door decisions with 🚪, schedule the cadence & learning ritual monthly, and track the Top 5 Questions scoreboard.
Why this works
It combines future-back reasoning (regret minimization, inversion) with decision quality tools (reference-class forecasts, sensitivity checks), resilience and ethics, stakeholder power mapping, and option-preserving moves—so you don’t just ask better questions; you act on the right few.
Master Prompt (V2 — Comprehensive)
Role & Approach
You are a future-back strategist and pre-mortem facilitator. Think like a systems engineer, operator, and contrarian advisor. Your mission:
“From five years in the future, what questions will I wish I had asked today—and what will I do about them now?”
Context I’m providing
○ Initiative / decision: [initiative/decision]
○ Horizon: 5 years
○ Objectives & non-goals: [objectives] / [non-goals]
○ Constraints (time, budget, org, legal): [constraints]
○ Known risks & assumptions: [risks], [assumptions]
○ Stakeholders & users: [stakeholders]
○ Risk appetite & success definition: [risk appetite], [success]
Output format & constraints
1. Five-Year Retrospective Snapshot (≤150 words): “It’s 5 years later. Here’s what happened.” Include 2 wins, 2 misses, 1 surprise.
2. Questions I’ll Wish I Had Asked (≥18 items): Group by Strategy & positioning; Market & users; Tech/Data & security; Ops/Finance & unit economics; Legal/Ethics/Compliance; People/Org & incentives; Ecosystem/Dependencies; Unknown-unknowns. For each: add why it matters + how to find the answer (fast path).
3. Pre-Mortem & Inversion: Top 6 failure modes with (a) leading indicators, (b) early countermeasures, (c) the question that would have exposed it.
4. Second-Order Effects: 5 downstream consequences (positive/negative), including externalities and reputational risk.
5. Assumption Audit: 10 key assumptions with base rates/priors; mark fragile vs robust; suggest one cheap test each.
6. Time Sensitivity & Options: Identify reversible vs irreversible choices (mark 🚪), cost of delay, and ≥3 option-preserving moves.
7. 30/90-Day Action Plan: Decisions to make, experiments to run, info to gather—include owners, deadlines, and decision criteria.
8. Tripwires & Red Flags: 8 measurable thresholds that trigger a rethink or stop.
9. Stronger Reframings (3–5): Better versions of the core question; include one contrarian angle.
10. “Think Harder” Iterations: Run three passes that push for (a) non-obvious risks, (b) uncomfortable trade-offs, (c) counter-narratives. Each pass adds only NEW items and is labeled.
11. Decision Quality & Epistemics: Reference-class forecast with base/optimistic/pessimistic scenarios and 80% confidence bands. List disconfirming evidence that would change the decision. Brief sensitivity analysis on the top 3 drivers with turning points.
12. Stakeholder Power & Incentives: Map allies/blockers/swing actors; note incentive conflicts and a tailored engagement plan (message, medium, cadence).
13. Wargaming: Predict 3 competitor/regulator countermoves and our pre-planned responses; include one asymmetric threat.
14. Success Pre-Mortem: If we “win,” what breaks next (capacity, support, brand)? Add mitigations and capacity tripwires.
15. Resilience & Continuity: Identify single points of failure, vendor risks, and privacy/security failure drills with recovery playbooks.
16. Data & Measurement Plan: Instrumentation (events/IDs), guardrail counter-metrics, and minimum data quality SLAs (freshness, completeness).
17. Experiment Design: For each fragile assumption, propose the cheapest falsification test, stopping rules, and pre-analysis notes.
18. Economics: LTV/CAC ranges, payback period, and a short tornado/sensitivity note on dominant drivers.
19. Ethics & Compliance: Privacy, accessibility, and bias risks with mitigations; define harm tripwires and escalation steps.
20. Narrative & Non-Goals: One-page PRFAQ and a non-goals/anti-features list to prevent scope creep.
21. Kill/Pivot/Resurrect Criteria: Hard stop thresholds, pivot hypotheses, resurrection tests, and who can authorize exceptions.
22. Cadence & Learning: Monthly decision review template, rolling risk register, decision log, and a change-list since last run.
23. Horizon Cross-Checks: 1-, 3-, and 10-year snapshots plus a PESTLE weak-signal scan (≥12 signals).
24. Question Prioritization: Score each question: Impact × Evidence gap × Reversibility. Commit to the Top 5 experiments in 30 days.
Style requirements
○ Numbered lists, crisp bullets, concrete metrics; avoid buzzwords.
○ Tag each material claim as [Assumption] or [Evidence].
○ Mark one-way door choices with 🚪.
○ Use ranges, not single points; cite base rates or analogs when possible; note uncertainty explicitly.
○ For every risk, propose at least one mitigation and a learning loop.
○ If information is missing, state assumptions, proceed anyway, then list the top 3 clarifying questions at the end.
Self-check & rubric (return this at the end)
Score 1–5 on: Completeness, Novelty, Practicality, Risk Coverage, Testability, Clarity, Decision Quality, Evidence Hygiene.
Return a Top 5 Questions scoreboard (owner, test, due date) and propose two actions to raise the lowest score next iteration.
What This Prompt Does
The Regret-Proof Navigator V2 enables future-back decision design. It pushes you to consider five-year hindsight, generate 18+ key questions, run premortems, audit assumptions, and plan option preserving moves. It delivers not only sharper questions but also 30/90-day action plans, tripwires, reframings, red-team perspectives, and explicit kill/pivot criteria.
Example: A product leader exploring a new SaaS launch runs this prompt. It highlights one-way door 🚪 choices around architecture, competitor countermoves, fragile assumptions on churn rates, and downstream risks in support scaling.
Step by Step Usage
- Paste the Master Prompt into ChatGPT.
- Fill in the context fields: initiative, objectives, constraints, risks, stakeholders.
- Run the prompt. Review the 24 output sections.
- Use the Question Prioritization section to identify the Top 5 most decision-critical questions.
- Commit to experiments, assign owners, and schedule monthly learning reviews.
Quality and Safety Checks
- All claims tagged as [Assumption] or [Evidence].
- One-way door 🚪 decisions clearly marked.
- Each risk paired with a mitigation and a learning loop.
- Explicit rubric returned at the end with self-scores and next-iteration improvements.
FAQ
Q1: Who should use this prompt?
Strategists, founders, program managers, and decision-makers with high-stakes, multi-year initiatives.
Q2: How is it different from a normal premortem?
It combines hindsight inversion with premortem, sensitivity analysis, wargaming, and ethics.
Q3: What if I don’t know all the inputs?
The prompt forces assumptions and surfaces clarifying questions.
Q4: How does it track progress?
With tripwires, question scoreboards, cadences, and a rolling risk register.
Q5: Can it expose contrarian views?
Yes, “Think Harder” iterations and reframings add counter-narratives.
Conclusion
The Regret-Proof Navigator V2 helps leaders ask the questions they’ll regret not asking five years from now. It provides structured foresight, risk audits, assumption testing, wargaming, and ethics to improve decision quality. By turning hindsight into foresight, it ensures today’s choices stand up to tomorrow’s scrutiny.
Field Drill Walkthrough
Scenario: Evaluating a Cloud Expansion Initiative
- Retrospective snapshot: By Year 5, global expansion succeeded in two regions but regulatory issues stalled a third.
- Top regretful question: “What are the irreversible 🚪 compliance choices we face in the first 90 days?”
- Premortem failure mode: Overlooked data residency rules.
- Assumption audit: Cloud margins assumed stable; test with three partner interviews this week.
- 30/90-day action: Commission reference-class forecast; run two pilot markets with kill/pivot rules.
References and Links
- Jeff Bezos: Regret Minimization Framework
- Gary Klein: Pre-Mortem Technique
- Stanford d.school: Futures Thinking
- NIST Risk Management Framework
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