Discovery Questions for Financial Advisors: What to Ask Prospective Clients

Knowing a client’s goals, concerns, and preferences is the foundation of a strong relationship. Discovery questions allow financial advisors to understand what really matters to each person they work with. The results are more personal and long-lasting when the focus shifts from presenting a plan to having a conversation. Asking thoughtful questions and truly listening to answers helps shape strategies that reflect needs, not assumptions.

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What Are Your Top Three Financial Goals?

This question opens the door to what truly matters to your client. Some people want to retire early. Others might want to purchase a home, save for college, or pay off debt. Everyone has different priorities, and asking them to name their top three keeps the conversation focused and transparent. 

When someone says, “I want to travel in retirement,” or “I’d like to get rid of my student loans,” you now have something specific to work with. You can start creating timelines, estimating costs, and looking at the tools or habits that will help them meet those goals.

These answers give you and your client a good starting point for every other part of the plan.

What Keeps You Up at Night Financially?

This question cuts to the heart of your client’s worries. Some may feel uneasy about market fluctuations or be stressed about credit card debt, rising expenses, or not having enough saved. These concerns get in the way of progress, especially if they’re left unspoken.

Asking directly shows that you’re paying attention to what’s on their mind, not just to numbers. Once you know what’s causing stress, you can offer ideas to reduce it. That may mean building a better budget, reviewing investments, or considering insurance coverage. 

What Does Your Ideal Retirement Look Like?

Retirement means something different to everyone. Some people want to travel the world, while others want to stay close to home, spend time with family, or enjoy a slower pace of life. This question shifts the focus from a dollar amount to a lifestyle.

Once your client shares what they want their retirement to look like, you can figure out what it might cost. From there, you can discuss income sources like social security, saving goals, and steps to stay on track.

Who Depends On You Financially?

This question brings important responsibilities into the picture. Does your client have a spouse, children, or aging parents? Knowing who relies on your client helps you understand their day-to-day and long-term needs. 

These relationships influence decisions regarding insurance, savings, and estate planning. Caring for both children and parents can strain a person's budget and future plans.

You’ll need to factor those people into the bigger plan and help your client protect the people they care about.

What Are Your Biggest Financial Concerns Right Now?

Urgent needs must be brought to the surface. Maybe your client is worried about job security, rising costs, or not having enough saved. Whatever it is, these concerns are often top of mind, and they deserve attention early in the planning process.

Understanding what feels most pressing allows you to focus your first steps where they matter most. That may mean adjusting spending, looking at income options, or setting up an emergency fund. 

Have You Worked with a Financial Advisor Before?

This is a helpful question to understand your client’s past experiences. Some might have worked with an advisor they didn’t hear from enough. Others may have tried to manage everything on their own. Some might not know what to expect at all.

By asking, you learn what they liked or didn’t like, and how you can better support them going forward. If they had a bad experience, you can explain how your approach is different. If they’re new to this, you can walk them through what working together will be like.

How Do You Define Financial Success?

Everyone views success differently. For one person, it may mean retiring early. For another, it could be feeling secure, living debt-free, or leaving something behind for their family. 

Asking this question helps you learn what matters most to your client. It also gives you a clear direction for your planning. Instead of aiming for a general goal, you’re working toward something personal and meaningful.  Knowing how your client defines success, you can create a plan that fits them best.

See our guide to the average and median net worth by age.

What Are Your Expectations From a Financial Advisor?

This is the time to set the tone for your collaboration. Some clients want regular updates, while others prefer to check in only when something changes. Some value detailed reports, while others want quick, easy-to-follow summaries. 

Asking early is always the best strategy. You better understand how involved they want to be and how they like to communicate. 

Once you know what they’re looking for, you can explain how you work and where you can adjust to meet those needs. It’s an easy way to ensure you’re on the same page from the beginning.

What’s Your Risk Tolerance When It Comes to Investing?

Some clients are comfortable taking big swings, others like to play it safe, and many aren’t quite sure. This question helps you understand their comfort level and how they handle market ups and downs. 

Their answer will guide how you build their portfolio. If they’re cautious, you may lean toward more stable investments. If they’re open to taking risks, you can talk about options with higher potential returns.

You can also use simple questions to help them think it through. The goal is to match the plan to their personality, not force them into something they’re unsure about. 

Do You Anticipate Any Major Life Changes in the Next Few Years?

Life can change quickly, and big changes often impact income, spending, and goals. This question helps you plan ahead. Maybe your client is thinking about changing jobs, getting married, or growing their family. Knowing what’s on the horizon lets you build flexibility into the plan. You can talk through different scenarios and be ready if plans change. 

What Types of Investments Have You Used in the Past?

Your client’s experience level is an important element. Some may be familiar with stocks or mutual funds, while others might have tried alternative investments like real estate, or never invested at all.

Understanding what they’ve done before allows you to meet them where they are. If they’re uncomfortable with certain investments, that’s a good starting point. If they’re new to all of it, take more time to explain things transparently.

You want to know how to guide the conversation rather than test their knowledge.

What Does Your Current Insurance Coverage Look Like?

Insurance plays a big role in protecting your client’s finances, but it’s usually something people don’t think much about. This question helps you find out what coverage they already have, such as life, health, or disability, and what may be missing.

Some clients rely on what’s offered through work. Others may not be sure what they have, and that’s okay.

Once you know the basics, you can discuss whether a deeper review makes sense or if it might be helpful to bring in a specialist to review things.

Do You Have A Will, Trust, or Estate Plan?

It's important to discuss whether your client has a will, trust, or estate plan, even if it’s not easy. Having the necessary legal documents helps your client protect their family and wishes regarding money, property, or future care. 

Many clients may say they haven’t gotten around to it or are unsure if what they have is current. That’s a good place to start.

You don’t need to handle estate planning yourself, but you can suggest working with an attorney or reviewing what they have. It’s one of those things that doesn’t seem urgent until it suddenly is.

Are There Any Charitable Causes or Legacy Goals You Care About?

You’ll also want to uncover values that might not come up in other parts of the conversation. Some clients want to give to nonprofits, support a scholarship fund, or leave something meaningful behind for their family.

When you know what matters most to them, you can bring in ideas like donor-advised funds or gifting strategies. Your goal is to align their financial plan with what they care about.

Who Else Do You Work With Professionally (CPA, Attorney, Etc.)?

Financial planning often involves more than one expert, and you want to know if your client already has a team or if they may need one.

Some might have a CPA (Certified Public Accountant) they trust, but no legal support. Others may want introductions. When you know who’s involved, you can better coordinate efforts and avoid overlap

If they’re missing someone, you can offer referrals or help fill the gaps. Working together with other professionals makes things easier for your client.

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What Concerns Do You Have About Taxes and Tax Planning?

Taxes can be confusing, and many clients feel like they’re missing something or paying more than they should. This question gives them space to share what’s been frustrating or unclear.

Some might ask about how tax brackets work, while others may worry about a big tax bill or wonder if there’s a better way to manage income and deductions.

You don’t have to get into every detail, but you can offer general guidance and suggest bringing in a CPA if needed. It’s a good way to spot opportunities and help your client feel more informed.

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