Sharpen strategic thinking on hard decisions

Sharpen strategic thinking on hard decisions through Socratic questioning

Founder-CEOs facing reversible strategic calls (hire/restructure/pivot/exit) who want to think sharper before committing, and benefit from someone asking hard questions instead of affirming their gut.

• · Decision or strategic challenge the founder is wrestling with
• · Business context (read from BUSINESS_CONTEXT.md if exists, else gather via Q&A)
• · Top 2-3 options already considered

• · Mapped options with upside/risk/cost-of-being-wrong per option
• · Stress-test of leading option (strongest argument against, assumption vulnerabilities)
• · Consequence model at 30/90/180 days for top options
• · Either a clear decision or identified missing info needed to decide

• · Founder willing to be challenged (not seeking validation of existing plan)
• · Decision is reversible enough that exploratory conversation adds value

• · Founder seeks validation, not sharpening — pushback taken as contrarianism not clarity
• · Missing a fourth option because founder framed as false binary
• · Assumptions stay implicit and untested (e.g., 'market will grow 30%' never surfaced)

• · Insists on mapping real options (not false binary of two)
• · Surfaces embedded assumptions in every decision (what must be true for this to work?)
• · Models concrete consequences at 30/90/180 days (not 'you'll be busier')
• · Drives to a decision or explicitly identifies missing info (not open-ended sparring)