Polite Women Finish Last: Tough Questions I Wish I’d Asked My Financial Advisor Sooner

Balancing risk, trust, and long-term goals can feel like walking a wire. Here’s how to stop being polite and start getting answers that protect your financial future.

I’ve pissed off my financial advisor. Badly enough that he’s thought of “firing” me.

Why?

Because I failed to ask the right questions when we first started working together—the kind you should be asking, too. We never laid out clear mutual expectations, and over time, communication slipped. Misunderstandings grew. Kinda like a lot of marriages.

After years invested in the relationship, are we now headed for a financial divorce?

Splitting us up now would be a mistake on his part. According to McKinsey, women in the U.S. controlled more than $18 trillion in 2023, projected to be $34 trillion by 2030. That’s more than a third of retail financial assets. Our financial power is only increasing.

That’s why, after years of making women feel unseen, major brokerages are now scrambling to cater to us. Better late than never. They’ll chase money wherever it is, of course, and they’re starting to pay special attention to our age group: Women over 50 are the fastest-growing segment of women’s wealth holders, and they’re more willing than younger women to pay for personalized investment advice.

How We Got Here

My own relationship with my advisor started off great a few years back, when my husband and I were referred to an advisory team. They typically worked with high-net-worth families. Our assets were on the low end of their client spectrum, so we felt lucky to be taken on. We clicked well with the lead advisor and were fine letting him handle most of the investment decisions. Problem was, we didn’t know what we didn’t know, so we failed to cover some very important topics.

During COVID, we halted in-person meetings (understandable), but we haven’t seen our advisor face-to-face since—and our financial plan became seriously outdated. I kept asking for more … more planning, certainly, and ways to invest in different sectors that I thought had potential. But nothing seemed to change. Whether it was true or not, I felt like the advisor had more important things to do than deal with me.

And despite having an MBA, I found it hard to understand how our investments were performing. I had to request a special report to see the full picture—it wasn’t something I could access on my own. Once I received that report, I still couldn’t tell how much we were paying in fees. WTF? Am I being an idiot, or is it just too opaque?

It’s You, but It’s Also Me

To be completely fair, I haven’t been an easy client of late. I asked my advisor to raise cash (by selling stock) to provide me with more security, but then I turned around only months later and invested that cash in something speculative. I had my reasons, of course. But he made it clear he wasn’t happy with my risky move while he was trying to protect my assets.

I get that. I do. But it’s my money, and I’ll do as I please with it, thank you very much.

I made things worse, though. When an investment I had wanted to make—but didn’t, based on his advice—reached a new high, I expressed mild frustration in an email. Nothing at all dramatic, I promise. Little did I know that our email exchanges are scanned for regulatory violations. My message was flagged as a “complaint”—which instantly puts an advisor under the compliance microscope. In other words, I unintentionally got the guy in real trouble. I felt guilty … and embarrassed … and angry … and defensive, all at once. How was I to know someone (or some bot!) was reading our email?

The Breaking Point?

So, he’s frustrated and annoyed. And I’m feeling neglected and about ready to bolt. Where does that leave us?

For now, we’re in limbo, but we’ve scheduled several meetings to hash things out. As a journalist, asking tough questions isn’t difficult for me. But for many women—especially those who are divorced, caregiving, widowed, or managing money on their own for the first time—it’s much harder. Finance is still a bro club: 85 percent of financial advisors are men, and too many still intimidate us or bury us in jargon. (This handy financial terms dictionary can help.)

Older women, especially those who came of age before the Equal Credit Opportunity Act (ECOA) of 1974, may have to fight long-standing habits in order to take control of their own finances.

A little wiser now, I’ll clarify expectations in these meetings—for both of us—by asking the questions I didn’t know to ask when we first met. Questions that can’t easily be answered with “Of course we do that” or “That depends.”

Who’s Really Managing My Money?

Most advisors sound great on paper—until you realize you don’t know who’s actually making the decisions, how often they’ll talk to you, or what they do behind the scenes.

These questions help pull back the curtain.

1. Does your fiduciary role apply to all parts of our relationship, or only for certain types of accounts? (Fiduciary: legally required to act in your best interest—not theirs or their firm’s.)
2. What credentials do you hold? (For example, CFP, CRPC, or ChFC. This list from FINRA explains these terms and more.)
3. How many clients do you personally handle? How often will we meet? Might I get passed off to someone else?
4. How would you approach building or adjusting a portfolio for someone new to managing money?
5. Do you handle the financial planning, portfolio construction, and execution yourself? If not, who does?

What Am I Paying for—Exactly?

Between fees, fund charges, and vague promises about tax strategy, it’s easy to feel like you’re overpaying—or getting duped.

6. Can you walk me through what fees I’d be paying—both for your services and for the funds you recommend—and where I’d see those on a statement? What might I expect as a total “all-in” fee each year?
7. How exactly are taxes in my portfolio managed—through asset location, withdrawal strategy, or tax-loss harvesting? Can you give an example of what you’ve done for other clients? Who reviews these decisions, and how often?
8. What other professionals (tax experts, estate attorneys, etc.) are on staff? Is any of their advice included in the fees?

Do You Really Understand Women’s Needs?

Women have different life transitions, risks, and family roles. These questions reveal whether an advisor has deep experience with the issues you might face.

9. Can you provide examples of how you helped women go through major life changes like divorce, caregiving, widowhood, or long-term care needs?
10. What did you do to help women prepare who were about to receive—or leave—a significant inheritance?

Keeping Options Open

Of course, I didn’t stop at just writing a list. Before the meetings with my advisor (and in case things go south), I researched discount brokerages, where fees are more transparent (and likely lower). I also interviewed an advisor who has advanced certifications and works in a nearby office every day, where I can easily meet with him. He was clearly enthusiastic about educating his clients. That resonated strongly with me.

Still, it wouldn’t be easy to leave my current advisor. Despite the recent sturm und drang, we’ve built a strong bond over the years. He’s a genuinely good guy, and after a frank and honest conversation in our first meeting, I have faith that he’s working to do what’s best for me and my money. If we can lay all the issues on the table and agree on what our professional relationship should look like, I might put this volatile chapter in the rearview and move forward. Finance is complicated, and I’m not about to jump ship unless I’m sure it’s the right move.

But it’s not just about me. Despite the rush to accommodate women’s financial needs, too many women still walk into meetings only to be talked over, brushed off, or treated like someone else is calling the shots. That’s not just outdated; it’s bad business.

So don’t let that happen to you. After you meet with a financial advisor, ask yourself:

Did you feel understood and respected?

Do you trust them with your financial future?

Do they communicate in a way that feels easy for you?

If you can’t answer a resounding “yes” to all, just move on to the next advisor. Because the truth is, they’re lucky to have us—not the other way around.

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