Three Questions That Reveal a Financial Advisor’s Real Experience

(Because in a sales-driven industry, sounding experienced is easy. Being experienced is not.)

“A polished conversation can hide inexperience. The right questions reveal everything.” - Paul Powell

Most financial advisors look experienced.

They dress like professionals. They speak confidently about “the markets” and “long-term strategy.” They know how to drop terms like diversification, risk management, and asset allocation in ways that feel reassuring.

Inside the industry, people know better.

A polished surface doesn’t tell you whether an advisor has actually guided real clients through real decisions. It says only that they’ve learned how to present well in a business that rewards presentation.

If you want to know whether an advisor is truly experienced—or simply sounds that way—you don’t need a finance degree. You need a few precise questions that cut past the story and into the record.

Here are three of them.

1. “How long have you been directly responsible for advising clients, not just working in the industry?”

Most investors ask some version of, “How long have you been doing this?” It sounds like the right question. It isn’t.

In financial services, “doing this” can mean almost anything: processing paperwork, answering service calls, sitting in a training program, wholesaling products to other advisors, or working in a bank branch where the real decisions are made somewhere else.

None of that is the same as being the person across the table who gives the advice, signs their name to the recommendations, and lives with the outcome.

That’s why the wording matters: How long have you been directly responsible for advising clients, not just working in the industry?

Many advisors enter the field mid-career. They may say they’ve “been in financial services for 20 years,” and that might be technically true. But those 20 years may include insurance sales, branch administration, mortgage work, or any number of related but very different roles. Their time actually advising individuals—choosing allocations, setting strategy, managing risk, adjusting plans—might be only a small slice of that.

You’re trying to uncover how long they’ve had real accountability, not just proximity.

The way they answer tells you almost as much as the number itself. A seasoned advisor will answer plainly: “I’ve been in the industry 18 years and directly advising clients for 14 of those.” Someone less secure in their record is more likely to blur the lines between “industry experience” and “advisory experience,” because it sounds better when the two are blended together.

Markets test advisors. Downturns test them even more. You want someone who isn’t just around money, but has actually been through difficult environments with clients whose lives were affected by every decision.

2. “What are your current assets under management?”

This question makes many investors uncomfortable, in part because it feels like asking someone their income. In reality, it’s far closer to asking for a résumé than a bank balance.

Assets under management—often shortened to AUM—is simply the total value of investments an advisor manages for clients. It doesn’t tell you everything, but it tells you something important: whether other people over time have trusted this person with meaningful responsibility.

An advisor with substantial assets has usually had to build systems, withstand scrutiny, and retain clients through both good years and bad. They’ve seen more scenarios, more emotions, more difficult decisions. Their process has been tested by more than theory.

On the other hand, an advisor who speaks fluently about markets but has very little in actual client assets may be long on language and short on lived experience.

The industry makes this tricky because jargon is easy to learn. Advisors can sound sophisticated very quickly. It doesn’t take long to memorize phrases like “sequence of returns risk,” “downside volatility,” or “Monte Carlo analysis.” It does, however, take time to understand those concepts deeply enough to design portfolios around them with real consequences if they’re wrong.

That’s the difference AUM helps illuminate. It isn’t a quality score in itself—plenty of smaller advisors are excellent—but it is a reality check. If someone has been “helping clients” for 15 years and is still managing a very small amount of money, that doesn’t automatically disqualify them. It does invite further questions about why their practice hasn’t grown.

Again, you’re not looking for a perfect number. You’re looking for coherence between the story you’re hearing and the footprint they’ve actually built.

3. “Have you ever received a formal client complaint or regulatory action?”

This is the question almost no one asks and almost every institutional decision-maker insists on.

Advisors operate in a regulated environment. When things go wrong—suitability issues, miscommunication, aggressive sales tactics, improper documentation—clients sometimes file complaints. In more serious cases, regulators get involved.

Most advisors have clean records. Some don’t. The point of the question isn’t to catch anyone in a “gotcha” moment. It’s to see how they handle accountability.

A direct, professional answer might sound like this: “No, I’ve never had a complaint,” or, “Yes, I had one early in my career. Here’s what happened, here’s how it was resolved, and here’s what we changed as a result.”

What you’re listening for is not perfection, but maturity. Responsible people can explain a difficult situation without becoming defensive or evasive.

If you see visible discomfort, a long, tangled explanation that never quite lands, or an attempt to change the subject, pay attention. The content of the record matters, but so does the advisor’s comfort with being examined. You are, after all, deciding whether to let them examine your entire financial life.

In institutional settings, no one skips this step. Neither should you.

The problem with “general experience”

Even when an advisor passes all three questions—reasonable tenure, meaningful assets, no troubling record—another issue still remains: the difference between generalists and specialists.

The financial industry rewards broad claims. “We handle all your needs” sounds appealing. It suggests simplicity and convenience. The reality can be less reassuring.

Generalists tend to know a little about a lot. They talk comfortably about investments, insurance, retirement planning, college savings, long-term care, business transitions, tax strategies, and estate issues. For basic conversations, that can be useful. For real decisions with six and seven figures at stake, it can be dangerous.

The phrase that often fits is: a mile wide and an inch deep.

Institutions don’t hire generalists to manage serious money. They hire specialists with focused experience in the area that matters: fixed income, large-cap equity, alternatives, liability-driven investing, and so on. The expectation is that when complexity appears, the specialist has seen it before.

As an individual investor, you should think similarly.

If you’re a business owner, you want someone who understands liquidity events, exit planning, and tax-efficient cash flow. If you’re five years from retirement, you want someone whose daily work revolves around income planning, Social Security timing, and risk management in the distribution phase. If you’re a corporate executive, you want someone fluent in equity comp, deferred comp, and concentrated stock risk.

Experience only matters if it’s relevant. General experience fills a brochure. Specialized experience protects your future.

What these questions really do

These three questions are not trick questions. They’re structural ones.

They help you distinguish between:

Someone who has been around finance versus someone who has been accountable for advice.
Someone who can speak the language versus someone who has managed real assets.
Someone whose record matches their story versus someone whose story is doing most of the work.

You don’t have to challenge or confront. You just have to ask, then stay quiet long enough to hear the full answer.

Strong advisors are not threatened by questions like these. They expect informed clients. They welcome due diligence because it gives them an opportunity to show the depth behind the presentation.

Weak advisors, or those whose experience is thinner than it appears, are much more likely to be rattled.

You don’t need to be an expert

Investors often assume they’re at a disadvantage because they don’t “speak the language.” In practice, the opposite is often true: the right plain-language questions are more powerful than any technical debate.

You don’t need to understand portfolio theory. You don’t need to forecast markets. You don’t need to inspect every fund.

You need to know who you’re dealing with.

These three questions will tell you more about an advisor’s real experience than an hour of polished conversation ever will.

If you want to go further, the Financial Self-Defense Checklist lays out 27 due-diligence questions that expand beyond experience into incentives, process, and accountability—the same kind of framework institutional clients use to evaluate advisors before hiring them.

You don’t have to become an industry insider.
You just have to stop relying on the surface and start asking the questions that reveal what’s underneath.