Three Questions to Ask a Financial Advisor to Tell If You Can Trust Their Advice

(Most advisors claim expertise. These three questions reveal whether it’s real.)

“Trustworthy advice comes from specialists with training—not generalists with confidence.” - Paul Powell

These questions are taken directly from Financial Self-Defense: 27 Questions Every Investor Must Ask Before Hiring a Financial Advisor — the same framework I used for years evaluating advisors inside institutions, long before I ever shared them publicly.

In this industry, almost every advisor says the same thing:

“We do comprehensive planning.”

It sounds well-rounded, but inside the business “comprehensive” often means something very different:

“I’m a generalist.”

Generalists are excellent at conversation but thin on depth. They rarely go deep enough into any area to build true expertise. And when your financial future depends on precision — retirement income, tax timing, business exits, stock compensation — depth matters more than friendliness.

These three questions, taken from the Specialty section of Financial Self-Defense, reveal instantly whether an advisor’s advice is trustworthy.

1. “What area of financial planning or investing do you specialize in?”

A trustworthy advisor has a specialty.
A generalist has a brochure.

Most advisors try to signal versatility: “We work with everyone.” It sounds good; it’s meant to. But real expertise is narrow. Specialists earn it through repetition, pattern recognition, and years of solving the same problems for the same kind of client.

A strong advisor should be able to describe their specialty clearly — retirees, business owners, corporate executives with stock comp, physicians with complex income structures, etc. They should talk about the problems they handle repeatedly and the decisions they’re trained to make.

A weak advisor will resort to vague language: “I help people at all stages of life,” or “My specialty is relationships.”

If you would choose a specialist for your health, legal issues, or business — why settle for a generalist when your financial security is on the line?

2. “What designations or advanced training do you have in that specialty?”

Anyone can claim to be a specialist.
Credentials prove it.

Designations are not a trophy wall — they’re evidence. They require difficult exams, continuing education, ethical oversight, and a demonstrated understanding of complex planning or investment issues.

CFP®, CFA®, CPWA®, CLU®, ChFC®, CPA/PFS — these are real indicators of expertise, not marketing tools.

A trustworthy advisor can clearly explain why they pursued their designation, how it applies to your situation, and what decisions it prepares them to make. Someone without training will work hard to make credentials sound unimportant — because they don’t have them.

Institutions never rely on untrained advisors.
Neither should you.

3. “How does your specialty fit my specific situation?”

This question moves everything from theory to reality.

Most advisors will tell you they can help. Very few can explain precisely why they are the right fit for you.

A strong advisor connects your lived situation — your business, your retirement timeline, your assets, your benefits, your goals — to their area of specialization. They explain the problems they’ve solved repeatedly for people like you and the mistakes they help clients avoid.

A weak advisor will simply say, “We work with a lot of people in similar situations,” which usually means they haven’t thought about it deeply at all.

When advice fits your situation cleanly and logically, trust increases.
When it’s generic, trust should decrease.

Why These Three Questions Reveal Trustworthiness

These three questions do not measure whether you like the advisor. They measure whether the advisor has:

• depth instead of generalist breadth

• training instead of jargon

• a clear, logical fit instead of a sales script

They reveal more about an advisor’s trustworthiness in five minutes than an entire year’s worth of friendly conversations.

That’s why they form the core of the Financial Self-Defense Specialty section: because trust must be built on competence, not charisma.

Trust is earned through structure.
And structure begins with the right questions.

Bottom Line

You don’t need to understand the markets to determine whether an advisor is trustworthy.
You simply need questions that force clarity.

If you want the complete framework — all 27 institutional-grade questions covering experience, investment process, fees, incentives, and accountability — download the Financial Self-Defense Checklist.

Your financial life deserves a specialist, not a generalist.
And these three questions reveal which one you’re dealing with.