Trust is the single factor investors say matters most when picking a financial advisor, yet few people know how to measure it beyond a firm handshake and a tidy office. Michael Gold, founder and CEO of Westport-based Gold Family Wealth, says the clearest signal comes from watching how an advisor behaves before any recommendation is made.

He built his firm around what Gold calls a diagnosis-first approach, developed over more than 25 years working with business owners and multigenerational families. He describes the industry’s common failure bluntly: too many advisors treat their job as making clients feel reassured about a headline from cable news, rather than building a plan tied to what that family actually needs.

What to Watch For

According to Gold, the most telling moment in choosing an advisor happens early, before any portfolio talk begins. Does the advisor ask detailed questions about a family’s business, net worth, and the people who depend on that wealth? Or do they jump straight to products and performance numbers?

Ultra-high-net-worth families, Michael Gold Westport notes, are asking sharper questions than they used to. They want to know who takes responsibility for coordinating every specialist involved, who has handled comparable complexity before, and who will remain engaged once circumstances change. Gold sees this scrutiny as a sign that families are getting smarter about how they select advisors.

Beyond the Numbers

Gold holds an MBA in Quantitative Finance and Leadership from NYU’s Stern School of Business, along with Certified Financial Planner and Certified Exit Planning Advisor credentials. He was named a Forbes Best-in-State Wealth Advisor in 2025. Even so, he cautions families against choosing an advisor based on titles or a strong track record alone.

Michael Gold points out that this scrutiny extends well past the first meeting. Families should expect the same curiosity from an advisor a year in as they experienced on day one, he says, since circumstances change and plans need to keep pace with them.

The real test, Gold argues, is whether an advisor can coordinate legal, tax, and investment specialists into one coherent plan rather than leaving a family to stitch the pieces together themselves. For families weighing a Westport advisor against competitors elsewhere, that coordination ability may matter more than any single credential. Refer to this article for additional information.

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