Picking the wrong wealth manager at a critical financial moment can cost a family millions. Michael Gold, who founded Gold Family Wealth in Westport, Connecticut, has spent more than 25 years helping families avoid exactly that outcome by teaching them how to evaluate advisors before committing.
His core insight is counterintuitive: the most useful information comes not from what advisors say about themselves, but from what they ask about you.
The Questions Advisors Should Be Asking
Gold argues that a high-quality advisor will prioritize discovery above everything else. Before a recommendation is made, the advisor should have a thorough understanding of the client’s business, family structure, net worth, risk management approach, and long-term personal goals. An advisor who skips this phase and moves quickly to product recommendations is showing you something important about their process.
He uses a surgical analogy he knows personally. After three spine surgeries over multiple years, Michael Gold Westport observed that his neurosurgeon ran exhaustive tests before recommending any treatment path. “They did a suite of tests, MRIs, CAT scans, x-rays, and all that. And then they laid out all the options, from conservative to aggressive.” An advisor who does not operate with comparable discipline should prompt serious questions.
In his Westport practice, Gold asks clients and prospects about everything: “their business, their family, what’s going on on their net worth statement, their risk management, their kids, all the things.” Only then does the advisory work actually begin.
Why Transparency About Tradeoffs Matters
A second warning sign is an advisor who presents a perfect picture with no tradeoffs. Gold’s firm explains priorities and alternatives clearly. “We can lay out the things that need to be solved in priority order and say, look, this is most pressing and this is least pressing. These are the two or three ways to do them. None of them are perfect, so there are pros and cons.”
Families who hear only enthusiasm and certainty from a prospective advisor should push harder. Michael Gold of Westport holds a CFP, a Certified Exit Planning Advisor designation, and an MBA from NYU Stern. His 2025 Forbes Best-in-State recognition was built on a process that values clarity and honesty over polish. Read this article for more information.
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