The 4 Questions a Financial Advisor Will Ask You—And Why They Matter

Jun 20

The first time you meet with a financial advisor at The Kelly Group, we don’t start with numbers—we start with what matters most to you.

For over 25 years, we’ve helped neighbors, friends, and families in Bel Air and Harford County navigate life’s biggest decisions by building relationships grounded in trust, clarity, and long-term support. As fiduciaries, we’re legally and wholeheartedly committed to putting your best interests first, always.

New to working with a financial advisor? Here are four questions we often ask when we start working with a new client. Each one helps us get to know you, so we can build a plan that fits your life and legacy.

What are your long-term financial goals?

Everyone’s long-term financial goals are different. For some, maybe it’s retiring early. For others, it’s being able to help your grandkids with college, travel freely, or giving back to the community. That’s why this is often our first question. We want to know what matters to you—not just in dollars and investments, but in life.

Our financial planners and advisors take a holistic approach to retirement and long-term financial planning, working with each client to tailor their plan to their individual needs, goals, and overall financial situation.

When do you want to retire–and what is your ideal retirement lifestyle?

Retirement is one of the most common goals that our clients and prospects bring to the table—but how you get there, and what it looks like once you do, is different for everyone.

That’s why we don’t just ask when you want to retire, we ask how you want to live in retirement. Are you hoping to travel more? Spend time with grandchildren? Purchase a vacation home, or stay where you are? The personal goals shape your plan just as much as the numbers do.

Our approach takes many factors into account, such as:

How far you are from retirement and what kind of preparation you might need.
The lifestyle you envision and how your savings and income align with it.
Your comfort with market risk as you shift from building wealth to drawing from it.

We don’t believe in one-size-fits-all solutions. Instead, we create a personalized roadmap that grows with you—adjusting over time as life and markets change.

What has been your investment management approach?

One of the most important parts of building your financial plan is understanding how you feel about risk. Not everyone reacts to market changes the same way—and that’s okay. Some people can ride out the ups and downs without worrying, while others feel anxious when things get uncertain.

We guide clients through a clear, long-term investment process rooted in discipline, diversification, and behavior coaching. We take the time to understand your personal risk tolerance and use it to build a plan that aligns with both your goals and peace of mind.

That way, when the market gets noisy or nerves creep in, you always have something steady to lean on. With our guidance, your plan acts as a reminder to stay focused on the big picture, not the day-to-day swings.

Our team of financial advisors are here to simplify the complex and give you confidence in the plan we build together.

Do you have any upcoming life or career milestones that could affect your financial plan?

People often think of financial planning as just retirement or investing, but the truth is: a great advisor helps you navigate so much more. Life rarely follows a straight line, and your financial plan should be flexible enough to move with it.

That’s why we take the time early on to understand what changes might be on the horizon. Whether it’s a new milestone or difficult transition, we help you prepare thoughtfully and clearly.

Some common situations we help clients plan for include:

Navigating a career change or early retirement
Caring for aging parents
Selling or transitioning ownership of a family business
Understanding federal benefits and retirement options when making a career pivot
Estate and legacy planning or helping support a family office

We’ve walked alongside families in Bel Air, MD for decades, and we’re here to help you plan with confidence—not just for today, but for the next generation and beyond.

Work with our Team of Financial Advisors in Bel Air, MD

If you’re thinking about working with a financial advisor for the first time, we know it can feel like a big step. That’s why we start by listening—to your goals, your concerns, and the future you want to build.

At The Kelly Group, we’re proud to be a trusted financial planning and wealth management firm in Bel Air MD, serving families across generations with clarity, care, and a steady hand. Whether you’re planning for retirement, navigating life changes, or simply want to feel more confident in your financial path, we’re here to help.

The Kelly Group is the trade name of Kelly Financial Group, LLC, a registered investment adviser with the Securities and Exchange Commission (“SEC”). Registration of an investment adviser 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 at www.adviserinfo.sec.gov and The Kelly Group’s website at www.kellyria.com.

Michele Wolbert