The Critical Questions Every Retiree Must Ask Their Financial Advisor in 2025

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As we settle into the new year, many adults are making a resolution to finally get serious about their retirement planning. Whether you’re seeking professional guidance for the first time or looking for a second opinion after years with your current advisor, knowing the right questions to ask can make all the difference in your financial future.

We meet with prospective clients every day who feel something is missing from their current financial strategy. They have that gut feeling that they should be getting more value, more attention, or more comprehensive planning. If that sounds familiar, you’re not alone—and more importantly, there are specific questions you can ask to determine if you’re truly getting the guidance you deserve.

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Beyond the Surface: What Really Matters in Your First Meeting

Most people assume the first conversation with a financial advisor should focus on technical details like fees and investment philosophy. However, we’ve learned that these technical questions, while important, often miss the mark entirely. As we tell our clients, if we’re discussing receipts and portfolio specifics in the first 15 minutes, we’ve already failed at leading the conversation well.

The most valuable questions you can ask are actually personal ones. You should be asking personal questions to see if these are the kind of people you want to engage with for the next 15 to 30 years. After all, we meet with our clients every single quarter for check-ins. If you don’t genuinely like your advisor, those meetings will be uncomfortable for everyone involved.

Think about it this way—would you want to run into your advisor at a restaurant and hide your face? We want our clients to feel comfortable approaching us anywhere, whether it’s at a local restaurant or a community event, because we live, work, and play in the same community.

The Question We Wish More People Would Ask

There’s one particular question that we wish prospective clients asked more often. It demonstrates deeper understanding and opens up meaningful conversations about what really matters for your financial future:

“How can I assess how things are going with my investments and retirement planning?”

This question reveals whether you’re thinking beyond the basic “did my account balance go up or down?” Most people assess their financial progress solely based on the number at the bottom of their statement, or perhaps compare it to the S&P 500 or their neighbor’s portfolio. However, this approach misses the bigger picture entirely.

What we really want to know is: How is your portfolio getting better over time at producing the income you’ll need during your potentially 40-year retirement? Are you accomplishing this without taking unnecessary risks or exposing yourself to taxes you don’t need to pay?

We’ve seen countless examples of people coming into our office saying, “I’m killing it! Look at my statement—I’m up 30% this year!” Then we dive into the details and discover that 20% of that “growth” actually came from their own contributions. They weren’t really up 30% at all.

The Interest Rate Risk Question That Creates Awkward Silences

Here’s a question that will likely create some uncomfortable moments with many advisors, but it’s critically important given today’s economic environment:

“What are you doing to protect me from interest rate risk?”

We have a feeling this question is going to get awkward for a lot of people. Why? Because most advisors aren’t doing much to protect against interest rate risk, especially if your “safe money” position consists entirely of bonds.

If you’re in or approaching retirement, you absolutely should have a safe money position—a portion of your portfolio in less risky investments. To not have one is frankly irresponsible. However, if that safe money position is completely tied up in bonds, your advisor isn’t protecting you from interest rate risk at all.

Consider this sobering reality: One of the biggest bond funds in the world lost over 15% of its value in 2022. If your advisor’s solution for safety is bonds, and you’re paying the same management fee for those “safe” investments as you are for your growth investments, where exactly is the value?

The Fee Structure Question That Reveals Everything

This leads us to another revealing question:

“Am I paying you a lower fee for managing my less risky investments?”

The answer, unfortunately, is almost always no. Think about this logically: On one hand, you have investments shooting for 14% returns where active management might justify higher fees. On the other hand, you have conservative investments targeting 4% returns. Why would you pay the same management fee for both?

This is often why people come to our office feeling generally upset. They have that gut feeling that something isn’t right, that they’re not getting full value for what they’re paying.

The Hidden Danger of Stock Overlap

Here’s one more critical question that often reveals shocking information:

“How much overlap do I have in my different stock holdings?”

During our portfolio analysis sessions, we consistently find that people have far more exposure to individual stocks than they ever imagined. We regularly see situations where 45% of someone’s portfolio is concentrated in just eight stocks: NVIDIA, Apple, Microsoft, Google, Meta, Amazon, Broadcom, and Eli Lilly.

When we share this information, jaws drop. People say, “That can’t be true! My advisor has me in several different mutual funds.” Here’s what they don’t realize: All those mutual fund managers are competing against each other, and they’re not coordinating their stock picks. If you own a dozen mutual funds, you likely own NVIDIA, Apple, and Microsoft a dozen times over.

Why People Seek Second Opinions

The biggest reason people come to us for a second opinion is that they know something is missing. They might like their current advisor and feel they do a good job, but there’s a nagging feeling that they should be getting more value or more comprehensive service.

Often, they find themselves always being the one to initiate contact, always having to drive the conversation, always needing to come up with the right questions at the right time. That’s not how it should work—your advisor should be proactively coming to you with questions, opportunities, and strategies.

Additionally, as you get closer to retirement, you become more sensitive to topics you’ve never had to consider before, like taxes in retirement. Many of our clients in their late 50s and early 60s have never thought about how taxes will impact their retirement income, despite having decades of investing experience.

Moving Forward with Confidence

The questions we’ve shared aren’t meant to create confrontation with your current advisor—they’re meant to ensure you’re getting the comprehensive, proactive guidance you deserve as you approach or navigate retirement. If your advisor can’t provide clear, confident answers to these questions, it might be time to explore other options.

Remember, you shouldn’t have to be an expert in financial planning to get good financial planning. That’s exactly why professional advisors exist in the first place.

Take the Next Step Toward Financial Confidence

If these questions have sparked concerns about your current financial strategy, we invite you to experience our complimentary 3 Meeting Retirement Planning Process. During this comprehensive review, we’ll analyze your current situation, identify opportunities, and provide you with a clear roadmap for your financial future—regardless of whether you ultimately choose to work with us.

For those who want to start with a brief conversation to see if we might be the right fit, we encourage you to book a “Can We Help” call. This no-pressure discussion allows you to share your situation and learn about our approach without any commitment.

Book a ‘Can We Help’ Call

You can also visit our website at www.vincentplanning.com or call us directly at 770-485-1876 to schedule your consultation.

For personalized financial guidance, reach out to Vincent Financial Group today to schedule a consultation.

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