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Ellen Bessner's Financial Prosperity Podcast episodes
- 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: [email protected] | www.babinbessnerspry.com
Follow us: @TheFinancialProsperityPodcast
Subscribe to our Financial Services & Securities blog
31 min
About Ellen Bessner's Financial Prosperity Podcast
From the publisher's feed
The Financial Prosperity Podcast identifies, analyzes, and solves the most common gaps between investors and financial service providers so that you can build long-term financial prosperity, strengthen your financial literacy, and make informed decisions about your money management and future financial planning. Because investors and financial service providers—whether online platforms, individual financial advisors, financial planners, or Portfolio Managers—sit on the same side of the table, the success of one depends on the success of the other.
Each episode uncovers a real-world disconnect between investors (around their savings, investing decisions, financial goals, and confidence in sharing information) and financial service providers (their ability to communicate clearly in person, online, or by email by asking the right questions and using the right language and tone). We explain the gap, why these gaps exist, and offer practical, actionable steps to close them—whether you're trying to understand how to choose a financial advisor, evaluate advice, improve communication, or start building long-term wealth.
Hosted by lawyer, author, and industry expert Ellen Bessner, the Financial Prosperity Podcast breaks down financial conversations and services in a way that's human, honest, and easy to apply. Listeners gain clarity and confidence on essential topics such as retirement planning, wealth-building strategies, finding the right advisor, and making informed decisions that lead to real, lasting financial prosperity.
Ellen Bessner is a leading Canadian lawyer, author, and expert in financial services practices. With decades of experience advising and defending wealth firms and financial advisors, she brings a clear, practical lens to how investors and financial service providers can better understand and bridge communication gaps. Her focus: helping people make confident, well-informed decisions about their money so they can truly achieve financial prosperity.