Big Fat Questions

Big Fat Questions:

Why advisors ask personal questions — and how to make the conversation more comfortable.

In this episode of The Financial Prosperity Podcast, Ellen Bessner and guest Brendan Monahan explore a common challenge in financial planning: the discomfort investors feel when advisors ask personal questions about income, savings, debt, and goals. These details are essential for building a financial plan for the future, yet many adults hesitate to share them.

Ellen introduces her “Big Fat Questions” — open-ended, human-first questions that help financial advisors understand clients as whole people, improving money management conversations and strengthening advisor–client communication. Brendan shares why this approach builds trust, reduces anxiety, and leads to better outcomes for investors seeking long-term financial prosperity.

Key topics:

• Why investors avoid sharing personal financial information
• Why advisors legally and practically need these details
• How assumptions lead to poor financial outcomes
• How “Big Fat Questions” help close the communication gap
• How advisors can earn the right to ask sensitive questions
• How clear communication supports better financial planning and wealth-building

Order Ellen’s Books: 
Advisor at Risk: A Roadmap to Protecting Your Business 

Communication Risk: How to Bridge the Client-Advisor Gap to Protect and Grow Your Business 

Contact us: [e-mail] | www.babinbessnerspry.com  

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