Before You Hire (or Keep) a Financial Advisor, Ask These Questions

If you’ve been following along, you know this already.

I had a bad experience with a financial advisor early in my career. During a strong bull market, he lost me thousands of dollars, made it extremely difficult to release my money from his firm, and tried to sell me a Variable Universal Life (VUL) insurance policy that would have paid him significant fees and simply did not make sense for my situation at the time.

That experience changed how I think about financial advice, not because all advisors are bad, but because misaligned incentives and lack of transparency are very real.

Since then, I’ve met countless women who are working with a financial advisor by default, often a family advisor, without ever really choosing that person.

Many of those women have been sold products they don’t fully understand. They feel behind, confused, or disengaged from their finances, even though they’re earning well and doing many things right.

Most women I speak to don’t need a financial advisor, yet.

If I had to put a number on it, I’d say you start to seriously consider a traditional financial advisor when you’re north of $2 million in investable assets. Even then, some people still manage perfectly well on their own.

Most women in my network simply aren’t there yet.

That doesn’t mean hiring an advisor is wrong. It means it should be a deliberate choice, not a default one.

If you are choosing to work with a financial advisor (or already are), the questions below will help you determine whether you’re actually getting good service or simply outsourcing your confidence.

First: Are You Interviewing a New Advisor or Evaluating Your Current One?

Some of these questions are best asked before hiring a financial advisor.

Others are just as important if you’re already working with one and want to pressure-test the relationship.

If asking these questions feels uncomfortable, that’s information in itself.

General Fit & Philosophy

How are you compensated?

Are you fee-only, commission-based, or a mix? You should clearly understand how your advisor is paid and where conflicts of interest may exist.

Are you a fiduciary at all times?

The answer must be "always".

Do you have experience working with professional women or clients with similar goals?

Ask for specific examples of success working with women that sound like you - same industry, similar goals, similar amount of assets.

Investments

This is where many women disengage and where advisors can quietly take over without explaining much.

How do you decide what I should invest in?

What inputs matter? What doesn’t matter?

What’s your approach to risk, and how do you assess mine?

Risk tolerance should evolve as your life and goals evolve.

Will you help me choose what I’m investing in, or will you manage it entirely?

There’s no right or wrong answer, but you should be clear on what you want.

How do you monitor and adjust my portfolio over time?

They should articulate what needs to happen for them to buy or sell investments for you. Their answer should include some examples around both market conditions, and life events.

How will you help me decide WHEN and HOW MUCH to invest?

If this can’t be explained simply, that’s a problem. They should articulate whether they would advise around dollar-cost averaging (ie, taking a certain amount from each paycheck), or lump sum at various times.

Goals & Planning

Investments are just tools. The plan is the critical point.

How will you help me prioritize short-term and long-term goals?

Buying a home, building flexibility, retiring early, etc - these trade-offs matter.

Can you help me model different timelines for financial independence?

They should be able to show you how your investments can track to your financial independence goals, especially if you are looking to expedite that before traditional retirement age.

How do you factor in kids, career breaks, or geographic moves?

If the plan assumes a straight-line career, it’s not realistic for many women.

Accounts & Taxes

Good advice isn’t just about returns. It’s about what you keep.

Should I be contributing to a traditional or Roth IRA/401(k)? Why?

You deserve a clear explanation on which is best for you, based on your income and tax bracket.

How do you consider tax efficiency in your recommendations?

Asset location, timing, and withdrawal strategy all matter.

How will you coordinate with my CPA?

These professionals should work together. If they brush off the need to coordinate with your CPA - that's a huge red flag.

Ongoing Support

How often will we meet or check in?

And what level of support exists between meetings?

What happens if I want to pause or stop working together?

You should know this before you need to. If they become defensive or snarky in response to this question, that's also a huge red flag.

Can I reach out with questions, or only during scheduled meetings?

Get them to commit to a specific response time for your questions.

Education & Transparency

This is my personal line in the sand.

How will I know if I’m on track?

What metrics actually matter? What will they show you in terms of your progress? What are we tracking against?

What tools or dashboards are available to track my progress?

If it's hard to log into, or in a format you can't understand, you'll lose visibility - which is CRITICAL when someone else is managing your money.

Should I Hire a Financial Advisor? A Simple Decision Framework

Before you interview advisors or keep the one you have, ask yourself these five questions and answer honestly.

1. Do I understand where my money is today?

You don’t need to be an expert, but you should be able to name your accounts, roughly how much is in them, and what they’re invested in.

If you can’t, that’s a organization gap, and not necessarily something an advisor will help.

2. Am I accumulating or optimizing?

Most women in their 20s-40s are still in the accumulation phase. Full-service advisors tend to add the most value in the optimization phase.

3. Are my finances truly complex, or just intimidating?

Complex usually means multiple income streams, business ownership, significant taxable investments, or advanced tax strategy needs. Intimidation can be solved with education.

4. Do I want to stay involved or fully delegate?

Neither is wrong, but clarity matters. If you want to stay informed, you need an advisor who is a teacher.

5. What am I really paying for?

If you can’t clearly articulate the value you’re receiving and why it’s worth the cost, it’s time to reassess.

Bottom line:

You don’t hire a financial advisor because you “should.”

You hire one because the value clearly outweighs the cost.

One Final Thought

Hiring a financial advisor should feel like partnering with someone who helps you build wealth smarter and faster than you could alone.

If you're working with an advisor and feel in the dark about your money, that’s not a sophistication gap, it’s a service gap - and you deserve better.

And if you’re not ready for an advisor yet, that doesn’t mean you’re behind. It often means you’re early, capable, and better served by building confidence and clarity first.

That’s exactly the stage most women I work with are in. Her Wealth Collective is designed for women who want to learn how to invest, understand their options, and stay actively involved in their money without handing everything off to an advisor. If that sounds like you, you can learn more and join us here.