Most families treat the wealth manager interview as an audition a chance to hear what the advisor knows and how well they present. Michael Gold, the Westport, Connecticut-based founder of Gold Family Wealth, suggests flipping that frame. The real information, he argues, comes from watching how the advisor runs the process.
Do they arrive with a presentation, or with questions? Do they explain options with their tradeoffs clearly stated, or steer toward a favored product? Do they ask about the client’s business, family dynamics, estate structure, and risk exposures before recommending anything? The answers to those behavioral questions reveal more about an advisor’s actual orientation than any pitch ever could.
Selectivity Is Growing
This scrutiny matters more than ever. Ultra-high-net-worth families are asking more pointed questions: Who coordinates all the specialists? Who has managed this level of complexity before? Who stays engaged through transitions not just the ones that are pleasant? Gold describes an industry being reshaped by increased selectivity among families who have learned, often through hard experience, what poor advisory coordination costs.
The numbers behind that lesson are significant. An estimated $10 to $14 trillion in wealth tied to privately held businesses is expected to move through transitions over the next decade. Mistakes made during those critical moments from tax missteps to structural errors can permanently diminish what families pass on to the next generation.
Michael Gold Westport offers a counterweight to that risk through a practice built on coordinated, comprehensive financial planning. He holds an MBA in Quantitative Finance and Leadership from NYU’s Stern School of Business and maintains both a Certified Financial Planner designation and a Certified Exit Planning Advisor credential. In 2025, Forbes named him a Best-in-State Wealth Advisor.
Gold’s framework for advisor evaluation is simple: watch what they do, not just what they say. “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.” That kind of transparency, he argues, is the most reliable signal that an advisor is working in your interest. Refer to this article to learn more.
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