Debt Free Dr
Debt Free Dr
To help other dentists obtain financial independence within 5-7 years by investing in passive real estate investments.
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What to Ask a Financial Advisor Before Hiring

What to Ask a Financial Advisor Before Hiring

9/23/2026 7:03:00 AM   |   Comments: 0   |   Views: 81
If you’re wondering what to ask a financial advisor, start with three key questions:

  • Are you a fiduciary 100% of the time?

  • How exactly do you get paid?

  • What will I pay in total each year?

Those answers tell you whose best interest the advisor is really working for, and everything else builds from there.

In this article, I’ll walk you through the 15 questions I’d ask any potential advisor, grouped by conflicts of interest, fees, strategy, services, and the working relationship. I’ve also included two that most people never think to ask, like whether the advisor can help you build income outside the stock market.

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What I’ve Learned From Sitting Across the Table From Advisors

To be honest with you, I don’t use a financial advisor today. Right out of residency in 2005, a deal to join a group practice fell through, and I learned pretty quickly that nobody was going to care about my money more than me, so I took it upon myself to learn.

That said, I’ve used advisors in the past when I had specific questions about estate planning and taxes.

The bigger lesson came when I sprained my wrist on a ski trip around age 40. I’d already paid off $300K in student loans following Dave Ramsey, but I realized my income lived entirely in my hands, and the traditional advice I’d followed never talked about building income that didn’t depend on me treating patients.

What Are the Most Important Questions to Ask a Financial Advisor?

The most important questions to ask a financial advisor cover conflicts of interest, fees, investment strategy, and the working relationship. Get clear answers on those, and you’ll know whether you’re looking at a good fit or a sales pitch.

Here’s a quick cheat sheet you can bring to your initial meeting (or pull up on your phone in the parking lot).
#Question to AskWhat You’re Listening For
1Are you a fiduciary 100% of the time?A clear yes, in writing
2Are you a registered investment adviser, a broker, or both?Which standard applies to each service
3Can I see your Form ADV and your record?A clean BrokerCheck or IAPD history
4How do you get paid?Fee only, flat fee, or full disclosure
5What will I pay in total each year?One dollar figure, including fund expenses
6Do you earn anything from the products you recommend?No commissions, or complete transparency
7What’s your investment philosophy?A simple, repeatable process
8How will you build a plan around my specific situation?Questions about you before products
9What do you do when the market drops?A plan, not promises
10What services are included in your fee?A written list
11Do you work with practice owners, CPAs, and attorneys?Real experience with business owners
12How often will we meet, and who will I work with?A named person and a set schedule
13Can you give me references from clients like me?Longtime clients in your career stage
14Can you help me invest outside the stock market?Openness, even if it’s not their specialty
15How do I replace my monthly expenses with passive income?A real answer, not a blank stare
Now let’s walk through each one.

What Should You Ask About Fiduciary Duty and Conflicts of Interest?

Ask whether the advisor is legally required to act in your best interest at all times, and how they’re registered. These questions come first because they tell you whether the advice is built around your financial goals or around their paycheck.

1. Are You a Fiduciary 100% of the Time?

A fiduciary has a legal duty to put your interests ahead of their own. Some financial professionals only act as fiduciaries part of the time, such as when they’re giving advice but not when they’re selling insurance products or other financial products.

I want you to think about it like taking your car to a mechanic who earns a bonus on every part he replaces. He might be a great mechanic, but you’d still want to know about that bonus before you say yes to new brakes.
What a Good Answer Sounds Like
You want to hear a clear “yes, all the time, and I’ll put it in writing.” Answers like “I follow the fiduciary standard when I give advice” or “I follow a suitability standard” mean they may wear more than one hat, and that’s worth a follow up question.

2. Are You a Registered Investment Adviser, a Broker, or Both?

In the United States, a registered investment adviser (RIA) owes you a fiduciary duty, while a registered broker dealer follows the SEC’s Regulation Best Interest when making a recommendation. They sound alike, but they aren’t the same standard.

Some advisors are registered as both, so ask which hat they’re wearing for each service. It’s a simple question, and a good advisor won’t mind answering it.

3. Can I See Your Form ADV and Your Record?

Every registered investment adviser files a Form ADV with the Securities and Exchange Commission or their state, and Part 2 spells out fees, services, and conflicts of interest in plain English. You can check any advisor’s background and disciplinary history for free on FINRA’s BrokerCheck or the SEC’s Investment Adviser Public Disclosure site.

If they say they’re a CFP, you can verify that with the Certified Financial Planner Board of Standards at cfp.net. It takes about five minutes, and I’d do it before the first meeting, not after.

What Should You Ask About Fees Before Hiring an Advisor?

Ask how the advisor gets paid and what your total cost will be each year, including the fees you’ll never see on a bill. Fee structure is where most conflicts of interest hide, and small percentages turn into big dollars over a career.

4. How Do You Get Paid?

There are three basic fee structures. Commission based advisors are paid when you buy a product, fee based advisors collect fees plus some commissions, and fee only advisors are paid directly by you and nobody else.
Fee StructureHow They’re PaidConflict of Interest RiskFollow Up Question
Commission basedCommissions on products you buyHighestWhich products pay you, and how much?
Fee basedAdvisory fees plus some commissionsMediumWhich services earn you commissions?
Fee only (percentage)A percentage of assets under managementLowerWhat’s my total cost in dollars?
Fee only (flat or hourly)A set fee or an hourly rateLowestWhat’s included, and what costs extra?
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A flat fee or hourly advisor can make a lot of sense if you just need a plan or a second opinion, not ongoing portfolio management. That’s closer to how I’ve used advisors myself, for specific questions rather than a lifetime arrangement.

5. What Will I Pay in Total Each Year?

Ask for one number, in dollars, that includes the advisory fee plus the expense ratios on the mutual funds or other investment products they’d use. A lot of people only hear the advisory fee and never add up the rest.
The Kitchen Table Math
Let’s say you’ve got a $1 million portfolio and the advisor charges 1% of assets under management. That’s $10,000 a year, and it comes out whether the market’s up or down, before you count any fund expenses.

Now I want you to think about what happens as your portfolio grows. At $2 million, that same 1% is $20,000 a year, so it’s a bit like a subscription that raises its price every time you get a raise.

6. Do You Earn Anything From the Products You Recommend?

This question brings out commissions and third party payments that don’t always come up in the first conversation. It matters most with insurance products, annuities, and proprietary funds.

Whole life insurance is the one I’d watch closely. I only use term life insurance myself (I mention it in my list of tax deductions for doctors), and if an advisor pushes whole life hard in the first meeting, I’d want to know exactly how they’re paid on it.

What Should You Ask About Their Investment Strategy?

Ask how they build a portfolio, how they match it to your risk tolerance and long term goals, and what they do when markets fall. You’re looking for a clear, repeatable process, not a pitch built on past performance.

7. What’s Your Investment Philosophy?

Some advisors try to beat the market with active management, and others use low cost funds that track it. Ask how they set your asset allocation, how often they rebalance, and how they handle taxes on capital gains.

There isn’t one right answer here, but there should be a clear one. If they can’t explain their investment strategy in a couple of minutes, that tells you something.

8. How Will You Build a Plan Around My Specific Situation?

A good advisor asks about you before talking about products, including your income, your net worth, your family members, your practice, and when you’d like work to become optional. If your plan looks exactly like everybody else’s, it probably is.

Doctors and dentists have a unique financial situation (big student loans, a late start, high taxes, and sometimes a practice to run). Ask what type of clients they usually work with and how many look like you.

9. What Do You Do When the Market Drops?

Ask what they did for clients during the last big downturn and how they’ll keep you steady when your account is down 25%. Market volatility is when a good advisor earns their fee, because keeping you from panic selling can matter more than any fund they pick.

Also listen for how much they lean on past performance. Past performance is no guarantee of future results, and any advisor who promises returns (or brushes off the possible loss of principal) is telling you something about how they operate.

What Services Should a Financial Advisor Provide Beyond Investments?

Beyond managing your investment portfolio, a good advisor should help with retirement planning, taxes, insurance, and estate planning. Ask exactly which of those advisory services are included in the fee and which cost extra.

10. What Services Are Included in Your Fee?

Here’s what full financial planning services usually cover:

  • Retirement planning, including when you can afford to cut back

  • Tax planning, like Roth conversions and capital gains strategy

  • Insurance review for disability, life, and liability coverage

  • Estate planning coordination

  • Education planning for your kids

Get that list in writing. A holistic approach sounds great in a brochure, but you want to know what you’re actually paying for.

11. Do You Work With Practice Owners, and Will You Coordinate With My CPA and Attorney?

Small business owners need help with retirement plans for staff, entity structure, and eventually an exit plan. Ask whether they’ve done this before and whether they’ll work alongside your CPA on tax advice and your attorney on legal advice.

Most advisors can’t give legal advice, and many aren’t CPAs, so the best ones know where their lane ends. I trust a professional a lot more when they tell me what they don’t do.

What Should You Ask About the Working Relationship?

Ask how often you’ll meet, who you’ll actually work with, and whether clients like you will vouch for them. Even a brilliant advisor isn’t much help if you never hear from them.

12. How Often Will We Meet, and Who Will I Actually Work With?

Some advisors meet quarterly, and others meet once a year with calls in between. Ask whether you’ll keep working with the person across the table or get handed off to a junior team member after you sign, and how quickly they return calls and emails.

Their service model should fit your life. If you’re with patients all day, you need someone who respects that and reaches out when there’s a real reason to.

13. Can You Give Me References From Clients Like Me?

Ask for two or three clients at a similar career stage, ideally ones who’ve been with the advisor for years. Ask them what the advisor does well, where they fall short, and whether they’d recommend them to a colleague.

If an advisor hesitates, or only offers prospective clients who signed up last month, that’s worth noting.

If you want to learn how to build income outside the stock market before you ever sit down with an advisor, join the Passive Investors Circle. It’s free, and it’s where I share what I’m learning about passive income.

Don’t Miss Any Updates. Each week I’ll send you advice on how to reach financial independence with passive income from real estate.

Sign up for my newsletter

What Questions Do Most People Forget to Ask a Financial Advisor?

Most people never ask whether an advisor can help them build income outside the stock market, or how to replace their monthly expenses with passive income. Those two questions are where the traditional plan (max the 401(k), fund the 529, and retire at 65) tends to leave a gap.

14. Can You Help Me Invest Outside the Stock Market?

Ask how they feel about real estate and other alternatives, like investing passively in real estate syndications. Many advisors are paid a percentage of the assets they manage, so money that goes into a private deal leaves their books, and that’s not a knock on them, it’s just how the model is built.

I invest as a passive investor in syndications, and I also own mobile home parks with my business partner, so I’ve seen this from both sides of the table. An advisor who’s open to the conversation (even if it’s not their specialty) is a lot more useful than one who waves it off, and if you’re not sure you qualify for these deals yet, start with how to become an accredited investor.

15. How Do I Replace My Monthly Expenses With Passive Income?

This is the question I wish somebody had asked on my behalf early in my career. Most financial plans focus on a big number at 65, but what gives you options sooner is income producing assets that cover your monthly expenses.

I call that target your Freedom Number, which is simply your monthly expenses times 1.1, and it’s part of my 7 WOW Steps. Ask your advisor how their plan gets you there, and if they’ve never thought about it that way, you’ll learn a lot from the answer (I cover seven ways to get started in my guide to passive income for doctors).

What Red Flags Should You Watch For in the First Meeting?

Walk away if you hear a vague answer on fiduciary duty or feel pressure to sign that day. Here are the other red flags I’d watch for:

  • Promised returns or “you can’t lose” language

  • A plan that’s all stocks and whole life, with no questions about your goals

  • Reluctance to put fees in writing

  • A focus on high net worth individuals when you’re just getting started

It’s the same rule I use with any investment. When someone works harder to make you feel good than to show you the math, it’s time to go.

The Bottom Line

Knowing what to ask a financial advisor comes down to making sure the person across the table is working for you. Start with fiduciary duty and fees, then dig into strategy, services, and how they’ll take care of you over time.

The right financial advisor will welcome these questions and answer them in writing. If they get defensive, you’ve already learned what you need to know to make an informed decision.

And remember, even the best advisor won’t care about your money more than you do. The more you learn on your own, the better your questions get, and the better your financial future looks.

If you want to keep learning how to build income that doesn’t depend on your hands, join the Passive Investors Circle. It’s free, and it’s where I share what’s working for me (and what hasn’t).

This article is for educational purposes only and is not financial, tax, or legal advice. I’m a periodontist, not a financial advisor. Always consult your own financial advisor or CPA before making any investment decisions.Join the Passive Investors Circle
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Category: Financial Planning and Investments
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