10 Questions to Ask Before Hiring a Financial Advisor

A few years ago, I sat down with a couple in their late 70s who had been working with the same financial advisor for almost 20 years.

I asked them to walk me through their accounts. What came out was this: twelve different fixed annuities. Six for the husband, six for the wife. Rates between 2.5% and 4%. Every time one annuity finished its term, the advisor rolled them into a new one, collected a new commission, and started the cycle over. It had been disguised as a tax-saving estate plan. In reality, it was product sales. The advisor had made a lot of money. The clients had been locked up in low-yielding, high-cost products for two decades.

I almost lost my mind.

Here is the hard truth about hiring a financial advisor: most people have no way to tell whether the person sitting across from them is a true fiduciary planner, a salesperson in a fiduciary costume, or somewhere in between. Every advisor is going to say they act in your best interest. Every advisor is going to talk about planning. The difference is in the answers to the specific questions you ask.

When I meet clients who have been with a big-bank advisor for 5, 10, or 20 years, the most common thing I see is that they have zero idea what actually goes into the tax planning for the different stages of their life. Not pre-retirement. Not the year of retirement. Definitely not post-retirement. They can't tell me the order in which they should be pulling from their accounts. They don't know how Social Security should integrate with their pre-tax and post-tax distributions. Their "plan" is a pie chart. That is not planning.

So here are the 10 questions I would bring to any first meeting with an advisor. Whether you end up working with us or someone else, these are the answers you need before you write anyone a check.

1. Are you a fiduciary 100% of the time, in writing?

The word "fiduciary" gets thrown around a lot. What you actually want to know is whether the person sitting across from you is legally obligated to put your interests first at all times, or only some of the time.

Broker-dealers and dually-registered advisors can switch hats mid-meeting. A true RIA is a fiduciary 100% of the time, on every account, in writing.

The question to ask: "What are the different options and plans that you normally work with, and are there products incorporated into those plans? Can you show me every single product you, your firm, or your broker-dealer have access to?"

That one question flushes out whether you're sitting across from a planner or a salesperson. If the answer is a long list of insurance products, annuities, and proprietary funds, you have your answer.

2. How do you get paid, and by whom?

There are three ways advisors make money: commissions, fees, or a blend. If your advisor can't explain their compensation in one sentence, that's the answer.

At Baskets Capital, our fees are fully transparent and include both comprehensive financial planning and investment management, with no product commissions, no surrender charges, and no hidden layers. Our maximum fee is 1.5% on the first $500K of assets under management, and 1% on everything above $500K per household.

No commissions. No kickbacks. No product push. One fee, one firm, one team doing the work.

3. What credentials do you actually hold?

CFP, CFA, CPA, and ChFC all mean something. "Financial advisor," "wealth manager," and "retirement specialist" often mean whatever a firm lets someone put on a business card.

I hold a Series 7 and a Series 66. Ask any advisor you meet with to tell you exactly which licenses and designations they hold, and then look up what those actually require. Some take years of coursework and continuing education. Others take a weekend.

4. Can I see your Form ADV Part 2A?

Every registered investment advisor files a Form ADV with the SEC or their state regulator. It lays out their fees, services, conflicts of interest, and disciplinary history. If an advisor hesitates to share it, that's your answer.

You can also pull any advisor's ADV yourself at adviserinfo.sec.gov. It takes 60 seconds.

When you read it, start with the disciplinary disclosures section. If your potential advisor has been in disputes with former clients, arbitration, or regulatory actions, that is a serious red flag and you need to understand exactly what happened before you go any further.

5. Who is your custodian?

Your advisor should not be holding your money. A third-party custodian holds the assets. The advisor manages them. That separation is one of the most important protections you have as a client.

At Baskets Capital, we use Schwab and have access to other custodians as well. We don't push any specific custodian. Instead, we talk with each client about their situation and what fits best. What matters is that your money is held at a reputable, independent third-party institution, not at the advisor's firm.

6. Who actually works on my portfolio?

At a big firm, the person selling you is often not the person managing your money. You meet with a senior name. Your account gets handed to a junior associate or kicked to a model run by someone in another state who has never heard of you.

At Baskets Capital, we are the investment team for every single client. We do not outsource portfolio management to third-party managers or off-the-shelf models. We trust our own research and expertise, and we put in the hours to choose specific positions and stocks based on each client's custom portfolio and goals.

We love doing this work. We are not the kind of firm that puts every client into the same five mutual funds with high expense ratios because we don't understand how the markets actually work. We understand how markets work, how they move, and how to build portfolios that reflect that understanding.

7. How often will we meet, and what will we actually cover?

Vague answers like "as needed" or "quarterly-ish" are a red flag.

Our standard is a minimum of four meetings per year, but the cadence is fully up to the client. Some clients want to talk every few weeks during a specific life event, like an inheritance, a business sale, or a large liquidity event. Other clients are busy and prefer once a year. Both are fine. What matters is that the option is yours, and that when you want to talk, we pick up.

8. What's your investment philosophy in one paragraph?

If an advisor can't explain their investment approach in plain English in under 60 seconds, they either don't have one or they don't want you to know what it is.

Baskets Capital's investment philosophy is a completely custom and catered strategy for every client. We have clients in their 70s with the same aggressive risk tolerance as clients in their 30s. Just because someone is a certain age doesn't mean they get pushed into a certain bucket. Our philosophy is to find out exactly where a client wants to be invested, and then do real research into the specific stocks and companies that match those goals.

If you want an income and dividend strategy, we can build that. If you want an aggressive growth strategy focused on high-quality companies, we can build that. If you want something in between, we can build that too. What we will not do is give you an off-the-shelf portfolio and call it custom.

9. How do you handle taxes, estate planning, and insurance?

Investment management is table stakes. The real value of a good advisor is coordinated planning across taxes, estate, insurance, and cash flow. Ask how they work with your CPA and attorney. Ask them to describe the types of situations they have handled before.

We have worked with clients through complex events, including business sales in the eight-figure range. When you sell a business for $12M, the tax bill is not a small decision. Can you stretch earning years? Can you structure the sale to change the character of the income? Can you coordinate the sale proceeds with a trust, a DAF, or an installment structure so the after-tax outcome is dramatically different? That is the kind of coordinated work that separates real planning from product sales.

We coordinate with third-party estate attorneys, either ones we work with regularly or the ones our clients already have relationships with. The point is the integration. Your tax return, your estate plan, your insurance, and your investment portfolio should all tell the same story.

10. Who do you work best with, and who do you not?

This is the question almost nobody asks, and it tells you everything.

A good advisor has a clear picture of who they work best with and who they don't. If they tell you "we work with anybody," run. If they give you a real answer, you've found someone with a philosophy.

Here is my honest answer. We work best with business owners and families navigating a complex tax picture. If you are approaching a liquidity event, an inheritance, a business sale, or a major transition into or through retirement, and you want an advisor who will coordinate the tax, estate, and investment sides of that picture, we are very good at that work.

If you are looking for someone to help you build a monthly budget, talk through spending habits, or get organized at the starter-saver stage, we are probably not the best fit. There are excellent advisors who specialize in that, and I'm happy to point you to them.

The meta-question behind all 10

If I could give you one piece of advice when you're evaluating advisors, it's this.

Ask the person across from you whether they can deliver a fully custom, comprehensive financial plan that accounts for your tax planning, estate planning, retirement planning, and every other specific goal in your life, while at the same time giving you their own internal investment management. Not a plan built by one person and then handed off to off-the-shelf funds with high expense ratios. A real, integrated portfolio built on the thousands of hours of research their team does internally, dedicated to the specific stocks and positions that fit your plan.

In my opinion, everyone should pick an advisor who does both. The planners who don't manage money tend to leave your portfolio in a mess. The investment managers who don't plan tend to miss the tax and estate pieces that actually drive long-term outcomes. You want one team doing both, and you want them coordinated.

Ask the 10 questions above. If the answers feel honest, specific, and human, you've probably found someone worth working with.

(As always, these are my thoughts and observations. This is definitely not financial advice. Do your own research!)