7 Questions to Ask When Choosing a Fiduciary Financial Advisor in The Villages

Nov 3, 2026

Smiling retired couple reviewing their financial plan together on a laptop at the kitchen table

Choosing a financial advisor is a personal decision, especially as you approach or enter retirement.

Maybe you’ve managed your investments yourself for years and are considering professional guidance for the first time. Or perhaps you’ve worked with an advisor for decades, but you’re beginning to wonder whether that relationship still meets your needs.

Whatever brings you to the search, there are several factors worth considering beyond investment performance and professional credentials.

Understanding how an advisor works, the services they provide, and whether their approach aligns with your expectations may help you make a more informed decision.

If you’re searching for a fiduciary financial advisor in The Villages, here are seven questions to consider.

1. Are You a Fiduciary?

You’ve probably heard the word fiduciary, but what does it actually mean?

Investment advisers are subject to fiduciary obligations when providing investment advisory services to their clients. These obligations generally include duties of care and loyalty, including acting in the client’s best interest within the scope of the advisory relationship.

When meeting with a prospective advisor, consider asking how their fiduciary responsibilities apply to the specific services they provide.

You may also want to understand whether the professional serves in different capacities depending on the services or products involved.

Understanding these distinctions can be a helpful part of evaluating an advisory relationship.

2. What Experience and Credentials Do You Have?

Financial professionals may have different educational backgrounds, professional designations, and areas of experience.

One credential you may encounter is the CERTIFIED FINANCIAL PLANNER® certification.

CFP® professionals must satisfy CFP Board’s requirements involving education, examination, experience, and ethics. Under CFP Board’s standards, CFP® professionals have a fiduciary duty when providing financial advice to clients.

Credentials alone don’t determine whether someone is the right advisor for you, but understanding what they represent may be a helpful starting point.

You might also ask about the advisor’s experience working with individuals and couples approaching or already enjoying retirement.

3. Will You Help Us Look Beyond Our Investments?

Investments are an important part of financial planning, but they may not be the only consideration during retirement.

Depending on your circumstances, you may have questions about retirement income, Social Security, required minimum distributions, Roth conversions, Medicare-related costs, or planning for a surviving spouse.

Ask a prospective advisor which areas they address and how their planning process works.

You may also want to understand whether, and under what circumstances, they coordinate with other professionals, such as your CPA or estate planning attorney.

The goal is to better understand what services are included in the relationship and whether they align with your planning needs.

4. How Often Will We Communicate?

Communication preferences can vary considerably from person to person.

Some people are comfortable with periodic reviews and occasional phone calls. Others prefer more frequent conversations or the opportunity to meet in person.

Neither preference is necessarily right or wrong.

Before establishing a relationship, consider asking:

  • How are review meetings typically scheduled?
  • Who should I contact when I have a question?
  • Will I work directly with you or with other members of your team?
  • What types of changes might prompt a conversation?
  • Are in-person meetings available?

For some people, particularly those who have recently retired or relocated, having a financial advisor nearby may be an important consideration.

What matters is understanding the communication practices of a prospective advisor and considering whether they fit your expectations.

5. How Are You Compensated?

Understanding how a financial advisor is compensated is an important part of evaluating a potential relationship.

Financial professionals may use different compensation arrangements, including asset-based fees, hourly fees, flat planning fees, commissions, or combinations of these methods, depending on their services and business model.

Consider asking what fees you would pay, what services those fees include, and whether there are additional investment or account-related expenses.

You may also want to ask about potential conflicts of interest and how those conflicts are addressed.

Reviewing an investment adviser’s Form ADV and other applicable disclosures may provide additional information about compensation, services, and potential conflicts.

6. Will Both Spouses Be Part of the Conversation?

For married couples, financial decisions often affect both partners, even when one spouse has traditionally handled most of the finances.

Retirement may provide an opportunity for both spouses to become more familiar with their accounts, income sources, financial priorities, and important planning considerations.

When interviewing an advisor, consider asking how they involve both spouses in the planning process.

It’s also worth considering whether both of you feel comfortable asking questions and participating in conversations.

We believe financial planning is most meaningful when it reflects the individuals and families involved.

7. What Happens During Our First Meeting?

Meeting with a financial advisor for the first time doesn’t necessarily need to begin with complicated financial statements or investment recommendations.

An introductory conversation may provide an opportunity to discuss your goals, concerns, current financial situation, and what you’re hoping to find in an advisory relationship.

It’s also an opportunity for you to ask questions.

You may want to learn how the advisor approaches planning, what working together might look like, and whether their services align with your needs.

An initial meeting may help both parties explore whether there could be a good fit.

Financial Planning Is Personal. So Is the Relationship.

At the office of Kelley C. Pyles, CFP®, we believe getting to know our clients is an important part of the financial planning process.

Kelley works with individuals and couples in The Villages and surrounding Central Florida communities, with a focus on retirement planning, investment management, and the financial decisions that often accompany this stage of life.

Some people come to us after managing their own investments for many years. Others have worked with financial advisors before and are interested in exploring a different relationship.

Whatever your experience, we believe it’s important to begin by listening, understanding your goals, and discussing what you’re looking for.

If you’re searching for a fiduciary financial advisor in The Villages, we welcome the opportunity to meet you, answer your questions, and explore whether our approach may be a good fit.

Contact the office of Kelley C. Pyles, CFP®, to schedule an introductory conversation.

Visit Either of Our Offices in The Villages

Prefer to call? (352) 766-1100


This article is provided for general educational purposes and is not intended as individualized investment, tax, or legal advice. Financial planning considerations vary based on individual circumstances. Investors should review an investment adviser’s Form ADV and other applicable disclosures when evaluating an advisory relationship.

Kelley C. Pyles, with Royal Fund Management is an Investment Adviser Representative of and investment services offered through Royal Fund Management, LLC, Royal Fund is registered with the U.S. Securities and Exchange Commission (SEC) and only transacts business in the U.S. in states where it is properly notice filed or is excluded or exempted from registration requirements. 401(k) Maneuver is another business name for Royal Fund Management, LLC. Registration as an investment advisor does not constitute an endorsement of the firm by the SEC or any other securities regulator and does not mean the advisor has attained a particular level of skill or ability. Insurance product guarantees are subject to the claims-paying ability of the issuing company. The adviser is paid commissions on the sale of insurance products only. Royal Fund Management and Kelley C. Pyles are not engaged in the practice of law or accounting and any advice provided should not be construed as legal or accounting advice. The information discussed and presented herein is intended to serve as a basis for further discussion with your financial, legal, tax and/or accounting advisors. It is not a substitute for competent advice from these advisors.