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Moderator Discussion Guide
Scenario Planning
This assessment asks participants to imagine different futures—both challenges and opportunities—and think through how they'd respond. Scenario planning isn't about predicting the future; it's about building mental and practical readiness for uncertainty. It reveals where someone is vulnerable, where they might be overconfident, and where they have real optionality.
PROMPT 1
If the market dropped 40% next month, what would you do in the first 48 hours?
This tests financial resilience and decision-making under stress. Listen for panic versus preparedness. Some people will say "I don't know," which is honest and important. Others will have a plan. Ask: "Have you thought about this before?" and "What would trigger you to sell or hold?" This reveals whether they have a philosophy for market volatility or whether they'd react emotionally. Follow up with: "How is your portfolio actually positioned for this scenario?" Many people are exposed in ways they don't realize.
PROMPT 2
What personal scenario — health crisis, divorce, family emergency — would most destabilize your current life?
This surfaces real vulnerabilities. Everyone has them; the question is whether they've thought about it. Once they name it, ask: "How would your life actually change if that happened?" and "Are there things you're doing now that depend on that situation staying stable?" Sometimes the answer reveals that a key relationship, career, or health assumption is more fragile than they realized. That awareness matters. Then ask: "What could you put in place to reduce that vulnerability?" Not to prevent it, but to mitigate it.
PROMPT 3
What's the best-case scenario for the next five years, and are you positioned for it?
This is an optimistic question about preparedness. What does success look like? Maybe it's a business opportunity, a major life transition, a health transformation, or a major project completion. Once they describe the best-case scenario, ask: "What would need to be true for that to happen?" and "Are you actually building toward that?" Often people have a vision but haven't made deliberate choices to move toward it. Help them see the gap between their best case and their current trajectory.
PROMPT 4
How would a sudden windfall change your plans — and would that be a good thing?
This reveals whether someone has clear priorities or whether they'd be reactive. If a windfall would radically change their plans, ask: "Why wait for a windfall to make those changes? What's stopping you now?" Sometimes it's financial (they need more money); sometimes it's permission or clarity. If they say a windfall wouldn't change much, ask: "Does that mean you're already positioned exactly where you want to be, or that you don't know what you'd do with more resources?" That distinction matters.
PROMPT 5
What scenario have you never planned for that you probably should?
This is an open-ended gap-finding question. Often people realize they've been thinking narrowly—they've planned for one kind of disruption but missed others. Maybe they've planned for market downturns but not for a disability. Maybe they've planned for business success but not for business failure. Once they name it, ask: "What would it take to plan for that?" Sometimes it's just thinking about it; sometimes it's concrete action. Help them move from "I should think about that" to "Here's what I'm going to do."
Tips for the Moderator
- Scenario planning can feel heavy or anxiety-inducing. Frame it as prudent, not paranoid. Smart people think through possibilities.
- Many people avoid thinking about bad scenarios because they're uncomfortable. Validate that discomfort, but help them see that thinking through scenarios reduces anxiety long-term, not increases it.
- Watch for people who've catastrophized in one area (over-prepared for one scenario) but are blind to others. Help them see the pattern.
- Some people are naturally imaginative about scenarios; others aren't. For the latter, help them concretize: "If your income disappeared, what would happen to your mortgage payment?" specificity helps.
- Scenario planning can surface real gaps (no emergency fund, no insurance, no will, no business succession plan). Don't try to fix these in the conversation; just help them see the gaps and point them toward who can help.
- End by asking: "Which of these scenarios feels most urgent to think through?" and "What's one step you could take toward planning for it?" Make it actionable.