🧭 Decision-Making Prompts Pack — 30 Prompts From Daily Choices to Life Decisions

Decision Type Diagnosis

High-stakes + partially-reversible + affects multiple stakeholders + 10-day timeline = proper deliberation warranted. Don't satisfice; don't rush.

Reversibility is key: fully reversible → be fast. Fully irreversible → maximum caution. Partially reversible (your case) → significant analysis + willingness to delay 24-48h even past original timeline if needed.

Prompts I'm Selecting

Prompt 1: The Pre-Mortem (Klein)

Imagine it's 18 months from now and the new-job decision went spectacularly wrong. Write specifically what happened:

• What specifically made the new job bad?
• What did you discover about the company / role / people that wasn't visible in interview?
• What did you miss that was obvious in hindsight?
• What happened to your wife's career / kids' schools that made it worse?
• What's your honest reconstruction of WHY you took it despite signals you now see?

Then: write a parallel pre-mortem for staying going wrong:

• 18 months from now, still at current company, decision went wrong — what happened?
• Stagnated? Missed growth? Company changed? Competitor won market?
• What did staying cost that wasn't obvious?

Compare both failure scenarios. Which failure is MORE survivable + learnable from?

Prompt 2: Regret Minimization (Bezos)

Project to age 80. Look back at this decision from there.

• Which option will I regret less?
• Is there a version where I try the new job AND preserve optionality (e.g., 1-year evaluation explicitly, with ability to return)?
• What version of 'taking chances' will I be proud of at 80?
• What version of 'preserving stability' will I be proud of at 80?

The regret-at-80 perspective sidesteps loss-aversion bias (Kahneman: we overweight losses 2.25× vs. gains of same size, making status-quo feel safer than it is).

Pre-Mortem Specific

For 18-month-failure of taking new job, most likely specific scenarios:

1. Role was misrepresented. 'More responsibility' meant 'you manage a team that's exhausted + about to quit.' Or 'new initiative' that gets cancelled 6 months in.

2. Cultural mismatch. Established processes at current company; competitor has chaotic culture that your style doesn't fit.

3. Family friction. Wife's career took hit from relocation. Kids struggled. Marriage strained. You resent the job for it.

4. Manager/team dynamics. New boss is micromanager; team resents outside hire.

5. Company financial trouble. Layoffs 12 months in. Not just you — structural.

For 18-month-failure of staying:

1. Company reorg. Your 'trusted + established' position is eliminated in restructuring.

2. Skill stagnation. You realize after 18 months you were ready for more 18 months ago + compensation gap widened significantly.

3. Missed opportunity. Competitor company grew dramatically + your network-path is now through old colleagues who took similar offers.

4. Inner resentment. You blame self / spouse / circumstance for not taking it.

Neither failure is clearly worse. Both are survivable. That's the key signal: this isn't a life-or-death decision; it's a direction decision with recoverable failures.

The Full 30-Prompt Library (Copy Ready)

CATEGORY 1: Cognitive Bias Audit (Kahneman-informed)

1.1 The Confirmation Bias Check — list evidence for AND against your lean. Are you weighing them fairly?

1.2 The Anchoring Audit — is the first number / first option you heard unduly influencing you?

1.3 The Sunk Cost Check — how much of this decision is about past investment vs. future value?

1.4 The Availability Heuristic Check — are recent / vivid examples distorting your probability estimate?

1.5 The Loss Aversion Awareness — are you weighing losses 2× gains? Is that fair for this decision?

CATEGORY 2: Pre-Mortem (Klein)

2.1 The 18-Month Failure Scenario — imagine it went wrong; reconstruct.

2.2 The 'What Would Make This a Disaster' Audit — specific disaster scenarios.

2.3 The Hindsight Bias Inversion — imagine you chose the OTHER option + it failed. What would you say?

2.4 The Red Team Exercise — argue the opposite of your lean as strongly as possible.

2.5 The Worst-Case + Coping — worst case happens. Can you survive / rebuild?

CATEGORY 3: WRAP Framework (Heath)

3.1 Widen Options — 'whether X' is too narrow. What 3rd, 4th option exists?

3.2 Reality-Test Assumptions — get data. Talk to people who've made similar decision. Tiny experiment.

3.3 Attain Distance — advice you'd give a friend in this situation. Future self in 10 years.

3.4 Prepare to Be Wrong — how will you know if you made the wrong choice? Pre-committed re-evaluation trigger.

3.5 The 10-10-10 Rule (Heath) — how will you feel in 10 min / 10 months / 10 years?

CATEGORY 4: Regret Minimization (Bezos)

4.1 The Age-80 Perspective — which option will I regret less at 80?

4.2 The Status-Quo Bias Check — are you preferring current because it's known, not because it's better?

4.3 The Missed-Opportunity Audit — specific missed opportunities from status-quo preference.

4.4 The Values Alignment — which option better fits your actual values (not performed values)?

4.5 The 'Decisions vs. Outcomes' Distinction — good process + bad outcome still good decision. Separate.

CATEGORY 5: Small Daily Decisions

5.1 The Decision Fatigue Audit — what's eating your decision-making capacity daily?

5.2 The Satisficing Protocol — when 'good enough' beats 'best.' Criteria for which.

5.3 The Default-Setting Design — eliminate daily decisions via defaults.

5.4 The Batched Decisions Approach — decide weekly, execute daily.

5.5 The Decision-Energy Protection — save decision-making for high-stakes; auto-pilot low-stakes.

CATEGORY 6: Reversible vs. Irreversible

6.1 The Door Classification — 1-way (irreversible) vs. 2-way (reversible). Bezos framework.

6.2 The Minimum Viable Commitment — how to test decision with smallest commitment first.

6.3 The Exit Strategy Pre-Design — for irreversibles, what's the exit if it goes wrong?

6.4 The Timeline Check — am I treating reversible as irreversible (over-cautious)?

6.5 The Optionality Preservation — how to decide AND preserve future flexibility.

Timeline Recommendation

10 days is tight for this magnitude but workable:

• Day 1-3: Pre-mortem both scenarios. Cognitive bias audit. Widen options (is there negotiation with current OR with new?).
• Day 4-5: External reality-testing. Talk to 2-3 people you trust outside immediate circle. Especially people who've taken similar offers.
• Day 6-7: Spouse deep conversation. Her career + life impact isn't secondary. Pre-mortem from family perspective.
• Day 8: Sleep on it. No decision-making. Let it settle.
• Day 9: Write out final decision + reasoning. Read aloud. Does it sound right?
• Day 10: Communicate decision.

If by Day 9 you're still genuinely torn: ask new company for 3-5 additional days. Most reasonable employers grant this for senior hires; the ask itself signals thoughtfulness, not weakness.

Watch-Outs

Likely biases in play:

• Loss aversion: staying may feel 'safer' than it actually is
• Status quo bias: current company is knowable; new is uncertain
• Sunk cost: 5 years invested at current — shouldn't drive future
• Availability bias: recent positive moments at current company may outweigh systematic concerns
• Anchoring: 30% raise is anchoring positive. What if raise was 10%? Would you still take it?
• Family-pressure bias: wife may advocate either direction based on HER needs without full decision-context