What Your Financial Advisor Should Be Asking You: Key Questions to Listen For

When you’re choosing a financial advisor, there’s no shortage of advice about the questions you should ask—about their compensation model, their investment philosophy, and what differentiates them from their competition.

Those are important questions. We’ve even written about many of them ourselves. But there’s another side of the conversation that’s worth considering: What questions is your advisor asking you?

The answers typically reveal whether their advice is reactive or truly proactive:

• Are they primarily interested in your investment portfolio, or are they trying to understand your entire financial life?
• Are they focused on what your accounts look like today, or are they asking what could change five or ten years from now?
• Do they ask about your goals and concerns or move too quickly into recommendations?

Here’s what to listen for in each phase of your advisory relationship.

During the Interview: “What Matters to You?”

Your first conversation with a prospective advisor shouldn’t feel like a sales pitch followed by a discussion of investment returns. Instead, it should start with questions like:

• What matters most to you?
• What are your goals?
• What does financial success look like for you?

You may be trying to retire early or help your children with college. Perhaps your spouse hasn't been involved in the financial aspects of your life, and you want to set them up for success in the event of your passing.

Or like many of our clients, you may have reached a level of financial complexity that leads you to wonder if you’re making smart decisions or missing something important.

Beyond your goals, your advisor should be asking where they can provide some clarity in your plan:

Where do you feel like you’re missing opportunities or not making the most of your financial situation?

That question can help identify opportunities that may not be immediately apparent when the conversation is focused solely on existing challenges. Those opportunities could involve advanced tax planning, estate planning, charitable giving, equity compensation, or the timing of a major financial decision.

How do you approach investing?

A fiduciary advisor should also seek to understand your unique circumstances and preferences before recommending an investment strategy.

That means going beyond a standard risk tolerance questionnaire to explore your investing philosophy, your comfort with market volatility, and the beliefs and experiences that influence your financial decisions.

• Are you comfortable with a long-term, diversified strategy that accepts market volatility, or do you find yourself tempted to make changes when markets fall?

• Are you hoping to outperform the market, or are you more interested in participating in market growth while keeping things simple and disciplined?

What to listen for: Your advisor should spend more time understanding your goals, concerns, and priorities than discussing specific recommendations.

During Onboarding: “What Are We Missing?”

Once you’ve decided to work together, the questions should become much more detailed. The more your advisor understands your financial picture, the better equipped they are to see how each piece of your financial life affects the next.

Because your financial plan doesn’t exist in isolation. Your estate documents affect how your assets transfer. Your tax return can reveal planning opportunities. An attorney or CPA may be helping you make decisions that have significant financial implications. Your investment strategy needs to account for all of these pieces.

When those pieces are coordinated, your advisor can help identify planning decisions that might otherwise be missed if each area were handled separately.

They should also ask what you expect from the relationship. One of the most overlooked questions in an advisory relationship is deceptively simple:

What are your goals and expectations for working together?

Maybe you want someone to take the day-to-day investment decisions off your plate or develop a proactive tax strategy. Or you may be looking for someone to simply serve as a sounding board for major financial decisions and hold you accountable to a long-term plan.

The best advisor-client relationships aren’t one-size-fits-all. It’s a good sign when an advisor asks what you want the relationship to accomplish and revisit those expectations as your circumstances evolve.

They should also ask about the things that make your financial life personal.

What causes are important to you?

For some people, charitable giving is a major part of their financial plan. For others, supporting family members, leaving a legacy, or giving back to their community may be important priorities. Those priorities can influence a variety of planning decisions.

The questions an advisor asks during onboarding should ultimately help answer one larger question:

What does your entire financial picture look like, and how do all the pieces fit together?

What to listen for: Advisors should be working to understand how taxes, investments, estate planning, and other decisions fit together.

During Review Meetings: “What’s Changed?”

One of the most important questions your advisor can ask is also one of the simplest: What’s changed?

A financial plan isn’t something you build once and put in a drawer. It should evolve as your life evolves. That’s why review meetings shouldn’t simply be a report card on your investment portfolio. A proactive review meeting should help you connect what changed, what’s ahead, and what decisions may need to be made before they become urgent.

There’s another question that can be just as important but doesn’t always show up in a traditional financial review:

How do you feel about your financial plan right now?

You can have a mathematically sound investment portfolio and still feel uneasy about it. You can have a well-funded retirement plan and still worry that you’re not saving enough. You can understand intellectually that market volatility is normal and still feel tempted to sell when markets fall.

A good advisor helps clients navigate those emotions and build confidence in their financial plan.

What to listen for: Review meetings should include more than portfolio performance. Your advisor should be asking about changes in your life, priorities, concerns, and financial goals so the plan can adapt as circumstances evolve.

Looking Ahead: “What’s Next?”

A strong review meeting should absolutely look in the rearview at what has happened, but a good advisor is forward-looking.

What major decisions or changes are on the horizon?

You may be considering a home purchase, expecting a career change, preparing for a liquidity event, receiving an inheritance, or approaching a significant equity vesting date. Or maybe you’re approaching retirement and have new questions about income, taxes, and flexibility.

The earlier your advisor knows about an upcoming decision, the more opportunities there may be to plan for it.

That’s especially true when taxes are involved.

Questions About Tax Planning

Rather than waiting until tax season to look backward at what happened, these questions can help reveal opportunities to make decisions before the end of the year:

• What is your income likely to look like this year?
• What might it look like over the next several years?
• Are there changes coming that could affect your tax situation?

A five-year view can be particularly valuable because not every planning opportunity is about minimizing taxes this year. Sometimes the better strategy is about managing your tax picture across multiple years.

What to listen for: Tax planning conversations should focus on future decisions, not just past tax returns. Your advisor should be asking questions that help identify planning opportunities before important deadlines pass.

The Bigger Question: Is Your Advisor Listening?

Ultimately, you don’t need your advisor to ask every question on some rigid checklist. The bigger question is whether their questions demonstrate genuine curiosity about you and whether those questions lead to better advice.

Whether you're working with a CFP® (certified financial planner) or another fiduciary advisor, the focus should be on understanding your goals, concerns, values, investments, taxes, estate plan, family, professional relationships, and the decisions you’re likely to face in the future.

And just as importantly, they should keep asking questions because your financial life isn’t static. The priorities that mattered when you first became a client may look different today, and new opportunities and challenges will emerge over time.

So, the next time you sit down with your financial advisor, pay attention to the conversation.

• Are they asking about what’s changed and what’s coming next?

• What are you worried or excited about?

• What do you want your money to accomplish?

Or are you leaving with only a performance report and little clarity about what comes next? That difference may provide insight into whether your advisor's approach extends beyond investment management into a more comprehensive wealth management and financial planning relationship.

If your financial conversations rarely move beyond portfolio performance, it may be time to ask whether your advisor is seeing the full picture. At Plancorp, we believe thoughtful questions support more informed financial decisions, and more informed financial decisions help align your wealth with your goals, values, and the life you want to live.