Most advisor-shopping conversations are too polite. The prospect is nervous, the advisor is selling, and the questions that would actually reveal whether this is the right relationship never get asked. Here are ten direct ones — and what an honest answer sounds like.

1. Are you a fiduciary at all times?

A good answer is a plain yes, ideally followed by “and I’ll put that in writing.” Anything equivocal (“well, it depends on which hat I’m wearing”) means they operate under dual registration and are a fiduciary only sometimes. That’s the opposite of reassuring — it means specific recommendations may come from the non-fiduciary side.

See Fiduciary vs. Suitability for why the distinction matters.

2. How do you make money?

You’re listening for three things: (a) advisory fees paid by clients, (b) commissions on products sold, (c) any third-party compensation (referral fees, revenue-sharing, insurance trails). Ideally only (a). The Form ADV Part 2A, Item 5 spells this out — ask for it.

3. What is my all-in cost in dollars and percent?

Not just the advisory fee. The sum of the advisory fee, underlying fund expense ratios, platform fees, and any commissions — expressed as both a percentage and an annual dollar figure at your portfolio size. See How Advisor Fees Actually Work for the framework.

A good advisor will do this math with you. An uncomfortable one will give you an advisory fee and move on.

4. Who holds my money?

The answer should name a large independent custodian — Charles Schwab, Fidelity, Pershing. If the answer is “we hold it here” or names the advisor’s own firm, that’s a meaningful concern. Custody and advice separate for a reason.

5. Can I see your Form ADV?

Every RIA files one. The firm-level Brochure (Part 2A) covers fees and conflicts; the Brochure Supplement (Part 2B) covers the specific individual advising you. Any advisor should be able to produce both on request or point you to adviserinfo.sec.gov.

6. What’s your investment philosophy?

You’re not looking for a specific answer — you’re looking for a coherent answer. “We use whatever our firm recommends” is not coherent. “We build diversified, low-cost portfolios using evidence-based research, tilted toward X for these reasons” is. Ask them to show you an actual sample portfolio for a client like you.

7. Who will I actually work with?

Some firms sell with senior advisors and deliver with junior staff. That can be fine — but you should know. Ask: when I call with a question, who picks up? When there’s a plan review, who leads it?

8. How often do we meet, and what’s covered?

Good answers are specific: quarterly check-ins, annual comprehensive review, ad-hoc for life events. Bad answers are “whenever you need us” (which in practice often means “rarely”).

9. What does the onboarding process look like?

Document requests, risk questionnaire, plan draft, account opening, transfers, initial rebalance. How long does it take? What’s expected from you vs. from them? An advisor who can’t walk through a clear onboarding sequence probably hasn’t onboarded many clients.

10. Why should I not hire you?

This is the question that sorts. An honest advisor has a clear answer: we don’t do X, we’re not the right fit for Y, our minimums are Z, our style doesn’t suit someone who wants A. An advisor who says “we’re a fit for everyone” hasn’t thought carefully about their practice — or is selling.

What to do with the answers

Ask the same ten questions of two or three advisors. The patterns emerge quickly. The right advisor isn’t the one with the slickest pitch — it’s the one whose answers are specific, written, and internally consistent.

If you want to run these by us, we’d be glad to talk — no pressure. Contact us.