The Family Office Sherpa The Power Of Saying "I Don't Understand" To The Finance Industry
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Feb 2, 2026 A practical take on using the phrase "I don't understand" to demand clarity in financial conversations. Short scenarios show how questioning momentum can reveal weak explanations and misaligned incentives. Tips cover committee dynamics, due diligence, onboarding advisors, and retesting inherited portfolios. The focus is on forcing accountability and clearer decision processes.
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Insist On Plain Explanations
- Ask directly what you're investing in and insist on clear explanations rather than accepting jargon.
- Demand clarity so managers explain the product plainly and show they truly understand it.
Clarity Signals Mastery
- Simple explanations are evidence of mastery and build understanding rather than shutting down questions.
- Good managers welcome questions and use them to educate rather than becoming defensive.
Treat It As Your Money
- Remember it is your money and you are entitled to understand how risk is managed and what failure looks like.
- Ask specific scenario questions about cycles, liquidity, and counterparty risk to reveal manager thinking.