Top Financial Questions Clients Ask, According to Advisors

Money shapes nearly every part of life, yet it often leaves people with more questions than answers. As you work with an advisor, it’s normal to have questions about your financial well-being or progress. These can lead to meaningful discussions and enable a professional to better assist you in a more personalized way.

In this article, we’ll discuss several important questions clients often ask their advisors early in the relationship or along the way. This includes real-world insights from experienced financial professionals on how they approach these conversations and work with clients for optimal outcomes.

1. Will My Money Last Through Retirement?

The thought of retiring and giving up a steady paycheck is intimidating. Before or after you retire, it’s common to doubt whether you’ve saved enough to live comfortably for the rest of your life. Many people find themselves asking their advisor: “Will my money last?”

Thomas J. Brock, CFA, CPA, an expert contributor at Annuity.org, notes that this question is one that “arises early in most client relationships,” but is “a paramount concern for anyone embarking on their retirement planning journey.”

To help clients answer it, Brock walks through a structured process that emphasizes “transparency, open communication, and education.” His approach includes:

• Building a realistic retirement budget that reflects current expenses and desired lifestyle.
• Identifying reliable income sources such as Social Security, pension payments, or required minimum distributions (RMDs).
• Listing supplemental income streams, including Roth withdrawals or taxable asset liquidations.
• Optimizing the investment portfolio to ensure asset allocation aligns with income needs and risk tolerance.
• Running scenario analyses to test how savings perform under different market conditions, inflation rates, and spending patterns.
• Implementing a withdrawal strategy that balances tax efficiency with portfolio sustainability.

Brock’s method provides clients with a foundation for understanding their current financial situation and how long their savings might last under various scenarios. And, importantly, it helps them feel more confident in their retirement plan.

2. Am I Doing This Right?

No matter your stage in life, it’s easy to wonder if you’re making the right financial decisions. You might be doing all the right things, like saving or investing, but it can be hard to know. Simply asking an advisor if you’re on the right track is both valid and important.

Michelle Taylor, a financial advisor at GFG Solutions and founder of the Women and Wealth Initiative, says this is the question she hears most often. “It’s the quiet anxiety behind nearly every money conversation,” she says. “My response is always: ‘Let’s make sure your money is working for the life you actually want, not the life you think you should have.’ Once clients understand their cash flow and priorities, they stop second-guessing themselves and start feeling in control.”

When you work with a financial advisor, it’s as much about empowering yourself as it is about the dollars and cents. Taylor highlights that, with a “clear plan,” working with a professional “gives you the power and puts you in the driver’s seat.” She adds that a “good financial advisor doesn’t take control of your money; they give you the tools and confidence to take control yourself.”

3. Should I Be Saving or Investing More?

Even if you’re managing your money responsibly, it’s common to wonder if you should be saving or investing even more. Part of the challenge is that your progress, especially at first, is incremental and can take months or years to realize.

According to Taylor, this question often stems from fear of loss. “What they’re really asking is whether they’re safe to focus on growth that comes with risk,” she explains. Relating it to her practice in helping women with their finances, she says, “So many women have been conditioned to save diligently but invest cautiously. I help them shift from fear of loss to confidence in growth, showing how consistent, intentional investing builds quiet wealth over time.”

Taylor adds that many clients hesitate to start investing altogether because they believe they need a large sum of money before taking the first step. She recalls helping one client who overcame that mindset by automating small contributions. “She started automating small monthly contributions and as a result, she built a six-figure portfolio within five years. That changed everything: progress over perfection.”

No matter how much you’re investing, making any progress can help you reach your goal. Just as Taylor illustrates above with her experiences, a financial advisor should serve as a resource to motivate you and offer perspective so you can keep building.

4. Is My Money Safe?

As you invest, however, it’s natural to worry or stress about losing money. Even if you’re in it for the long haul, market downturns can shake your confidence and stir panic. This fear causes many clients to ask their advisor: “Is my money safe?”

Brock explains that this question is crucial because it tends to reveal a client’s most notable fear regarding money: “Hands down, this is the question that reveals the typical client’s biggest financial worry. It is an especially pronounced concern during volatile periods, such as the one experienced during the onset of the COVID-19 pandemic.”

To address those fears, Brock offers perspective. “I remind clients about the strategic nature of their asset allocation,” he explains. “I highlight the value of the liquidity provided by his or her cash reserve, and I stress the resilient nature and additional liquidity provided by any allocation to high-quality, fixed income investments.”

With that in mind, Brock notes that his “goal” revolves around helping clients “understand they have the capacity to ride out near-term market declines and to avoid knee-jerk liquidations that could have a debilitating effect on long-term financial health.”

Finances can become very emotional, especially when significant risk is involved. Working with a professional brings you someone to keep you grounded and aware of your strategy, even if times get tough.

Bottom Line

From the examples above, the common denominator is fear or anxiety about one’s finances or their progress toward a goal. Money can stir emotions, especially when there’s uncertainty. This can lead you to question yourself and your strategy.

A financial advisor can be an invaluable resource to keep you on track and allay your fears when necessary. They often accomplish this in an objective way, by “providing facts over feelings,” says Alajahwon Ridgeway, EA, MBA, CPWA^®, CDFA^®, owner of A.B. Ridgeway Wealth Management. Offering objective information, he explains, empowers clients to see what’s really happening with their money and make informed decisions.

Asking questions about your fears or anxieties can help you confront them directly. Whether you’re just starting to work with a professional or have been a client for years, open conversations can reveal new opportunities and remind you why trusting the process matters.