Your Financial Advisor Review: 9 Questions to Know If It’s Still the Right Fit

If you’ve been working with a financial advisor in Maryland—or more specifically here in Bel Air—for a while, it’s natural to pause and ask: Is this still the right fit? Life changes, financial goals shift, and expectations evolve. Whether you're planning for retirement or managing more complex needs, your financial plan should be growing with you.

Signs You May Have Outgrown Your Financial Advisor

Your needs today might not be the same as when you first hired your advisor, and that’s okay. The key is knowing when it’s time to reassess.

Here are a few signs that clients often notice when they begin to question the fit:

  • Lack of communication. You shouldn’t have to chase your advisor down - there should be pre-planned communication touchpoints.

  • One-size-fits-all advice. Your plan should be tailored to you, not templated.

  • More product talk than planning. If conversations are focused on sales, not strategy, take pause.

  • No collaboration with your other professionals. Your advisor should be willing to coordinate with your CPA, estate attorney, and others when needed.

You’ve started wondering if this is “as good as it gets.” That feeling may be a sign it’s time to explore other options.

9 Questions to Ask When Reassessing or Switching Financial Advisors

Already working with an advisor but starting to wonder if they’re still the right fit? These questions can help you evaluate the relationship more clearly.

1. How has my plan responded to any life changes?

Have you experienced a job transition, marriage, new child, or other major milestone since your plan was created? Has your advisor asked you about any of these life changes? When appropriate, your advisor should help ensure your plan reflects your current circumstances, always with care and intention.

2. Am I on track to meet my long-term goals?

Markets will move. But your advisor should be able to help you understand how your strategy supports your goals, whether that’s retiring comfortably, supporting your family, or giving back.

3. Is my risk level still appropriate?

Your risk tolerance may not change overnight, but risk capacity often does. As life circumstances evolve with new responsibilities and less time to recover from downturns, your portfolio should reflect the level of risk you’re truly able to take on.

4. What investment approach is being used and how is success measured?

You don’t need to know every market detail, but you should understand the general strategy and how your progress is being tracked.

5. Have there been any tax law or estate planning changes that I should be aware of?

Even small legal or policy shifts can have ripple effects. A proactive advisor will keep you informed and help you adapt when needed.

6. How and how often will we communicate?

Every client is different. Some want quarterly updates, others prefer annual reviews. A strong advisor will help you set communication expectations up front so you’re not left guessing (or stressing) in moments of uncertainty.

7. Has my advisor clearly explained how they’re compensated?

Financial advisors may be paid in a variety of different ways. What matters most is that your advisor has been transparent about how they’re compensated and that you feel confident their guidance is aligned with your best interest.

8. Does my advisor have the right training to guide me through this next phase?

Credentials like CFP®, ChFEBC℠, and others can give added confidence, especially when your financial life becomes more complex. Designations also signal a commitment to ongoing learning and ethical standards.

9. Does my financial plan reflect my personal values?

Financial planning should support the life you want to live. Whether that includes legacy planning, charitable giving, or helping loved ones, your plan should be aligned with your priorities.

Get a Second Opinion 

You don’t have to settle for “fine.”

If your current advisor isn’t giving you the support, strategy, or clarity you need, getting a second opinion is a smart next step. Whether you’re preparing for retirement, navigating a life transition, or simply wondering if your advisor is still right for you, our team is here to help.


The Kelly Group is a fiduciary financial planning firm based in Bel Air, Maryland and serving clients throughout Harford County, and the surrounding counties, including Cecil, Baltimore, and beyond. If you’re ready for a more collaborative relationship, one that puts your goals first, we’d love to start a conversation.

The Kelly Group is a trade name of Kelly Financial Group, LLC, a registered investment adviser with the Securities and Exchange Commission (“SEC”). Registration with the SEC does not imply any level of skill or training. For more information about our services, please see our Brochure and Relationship Summary, available on the SEC’s website atwww.adviserinfo.sec.gov, and on The Kelly Group’s website at www.kellyria.com

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