5 Questions Every Advisor Should Ask

Matthew Jarvis, CFP®, answers five essential questions every advisor should ask to transform meetings from mundane to meaningful, uncovering clients’ true priorities and aspirations.

5 min read

Imagine walking into a client meeting armed with charts, graphs, and enough financial jargon to make anyone’s head spin. You’re ready to dazzle them with your expertise, but as you dive into the numbers, you notice something—they’ve zoned out. Why? Because you’ve missed the most important piece of the puzzle: who they are beyond their balance sheet.

Most advisors think they’re mind readers, assuming they know exactly what clients want without even asking. Spoiler alert: you don’t. But don’t worry, there’s a simple fix—asking the right questions. And no, I’m not talking about the bland, “How’s the weather?” type of questions. I’m talking about the ones that dig deep, the ones that get your clients talking about what really matters to them. You know, the stuff that turns a meeting from a snooze-fest into a genuine conversation.

So today, we’re going to break down five questions that will have your clients opening up like they’re chatting with an old friend. Not only will you uncover their dreams, fears, and everything in between, but you’ll also position yourself as the advisor who actually gets them. And trust me, that’s where the magic happens.

1. What is New and Exciting in Your Life?

This isn’t just your typical “how’s it going?” question. It’s an invitation for your client to share the good stuff—the things that light them up and make them tick. By asking what’s new and exciting, you’re giving them the chance to talk about the milestones, big plans, or even the small wins that matter most to them.

Why does this matter? Because these seemingly casual conversations can reveal crucial details that can shape their financial plan. Maybe their daughter just got engaged, and they’re thinking about a destination wedding. Or perhaps they’re eyeing a new vacation home. Whatever it is, this question helps you get to the heart of their current priorities.

But here’s the trick: ask the question and then zip it. Seriously. Lean back, give them space, and let them fill the silence. Your job is to listen, not just for the sake of listening but to catch those golden nuggets of information that will help you craft a financial strategy that’s as unique as they are.

And if they respond with, “Nothing much, same old, same old,” don’t be discouraged. Sometimes, it just takes a little warm-up before they start sharing the good stuff. So, stay patient and curious—you never know what might come up when you least expect it.

2. What Are Your Biggest Concerns Right Now?

Let’s cut to the chase—every client has worries, and they’re not always about market volatility or interest rates. This question goes beyond the surface to uncover what’s really keeping them up at night. Maybe it’s the fear of outliving their savings, or perhaps it’s the nagging anxiety about their kid’s college tuition. Whatever it is, getting them to voice these concerns is like shining a flashlight into the dark corners of their mind.

Now, here’s where most advisors fumble—they either gloss over these concerns or try to fix them immediately. But you’re smarter than that. You know that your role isn’t just to solve problems but to be a sounding board. So when they lay their worries on the table, resist the urge to jump in with solutions right away. Instead, acknowledge their concerns and show empathy. A simple “I hear you, let’s talk through this” can go a long way.

By taking the time to understand what truly worries your clients, you’re not just addressing their immediate fears—you’re building trust. And trust is the secret sauce to any successful client-advisor relationship. Plus, it gives you the opportunity to tailor your advice to tackle their concerns head-on rather than just offering generic solutions.

So, next time you’re in a meeting, don’t be afraid to ask this question. It’s the gateway to deeper conversations and, ultimately, to a financial plan that feels personal and reassuring to your clients.

3. What Does Financial Independence Mean to You?

Financial independence—it’s the Holy Grail of financial planning, but here’s the catch: it means something different to everyone. Some clients might dream of early retirement and endless travel, while others just want the peace of mind that comes from knowing they’ll never have to worry about money again. Asking this question lets you peek into their vision of financial freedom and, more importantly, how they define success.

Don’t assume you know the answer. You might be surprised. For some, financial independence isn’t about luxury or leisure; it’s about having the freedom to spend more time with family, volunteer, or pursue a passion project. For others, it’s about securing a legacy for their children or giving back to the community.

The beauty of this question is that it takes the conversation away from numbers and portfolios and places it firmly in the realm of values and priorities. It’s a reminder that financial planning isn’t just about amassing wealth; it’s about aligning money with life goals.

So, once your client starts sharing their vision, dig deeper. Ask follow-up questions like, “What does a typical day look like for you when you’re financially independent?” or “What’s the first thing you’d do if money were no object?” These responses will give you the insights you need to create a plan that’s not just about achieving financial benchmarks but about crafting a life they’ve always dreamed of.

Remember, you’re not just helping them reach a number on a spreadsheet—you’re helping them live their ideal life. And understanding their version of financial independence is the key to making that happen.

4. How Do You See Your Lifestyle Changing in the Next 5-10 Years?

This question is a bit like peering into a crystal ball, but instead of trying to predict the future, you’re inviting your client to imagine it. What changes do they see on the horizon? Are they planning to downsize their home, start a business, or maybe finally take that year-long sabbatical they’ve been dreaming about? This question helps you anticipate their needs and adapt their financial plan accordingly.

Life doesn’t stay static, and neither should a financial plan. By asking about their future lifestyle, you’re not just playing it safe—you’re being proactive. Maybe they’re considering moving to a different state to be closer to family or are thinking about transitioning to part-time work as they edge toward retirement. Understanding these potential changes allows you to adjust their investment strategies, cash flow planning, and even tax strategies ahead of time.

But don’t just stop at the broad strokes. Encourage them to think about the smaller, day-to-day changes as well. Are they planning to travel more frequently? Take up a new hobby that might come with a price tag? These details, while seemingly minor, can have a significant impact on their financial situation.

And here’s the kicker: by helping them plan for these changes, you’re not just managing their money—you’re managing their expectations. You’re positioning yourself as the advisor who thinks ahead, who sees the whole picture, and who’s ready to make their evolving lifestyle as seamless as possible. This isn’t just about meeting their current needs; it’s about anticipating their future ones and ensuring they’re prepared for whatever comes next.

5. What Legacy Do You Want to Leave Behind?

Now, we’re getting into the heart of the matter—the legacy question. This isn’t just about estate planning or making sure their assets are divvied up neatly. It’s about understanding what impact they want to have on the world and how they want to be remembered. Whether it’s leaving a financial cushion for their kids, contributing to a cause they’re passionate about, or ensuring their business lives on, this question taps into their core values and long-term goals.

Here’s the thing: legacy isn’t just about money. It’s about the stories, values, and lessons they want to pass down. Some clients might envision setting up a scholarship fund, while others might want to ensure their grandchildren have a solid financial foundation. Then there are those who see their legacy in non-monetary terms—mentoring the next generation or leaving a positive mark on their community.

By asking this question, you’re opening the door to some deeply personal reflections. And it’s your job to listen—not just to their words, but to the emotions and motivations behind them. This understanding allows you to guide them in structuring their estate, philanthropy, or business succession in a way that aligns with their vision.

But don’t forget the practical side. This is also the moment to discuss the nitty-gritty details: wills, trusts, charitable giving strategies, and the like. Your role is to ensure that their legacy is not just an idea but a well-thought-out plan that can be executed seamlessly.

So, when you ask this question, be prepared to have a conversation that might go beyond the usual scope of financial planning. It’s about helping your clients see the bigger picture and ensuring that their legacy is something they can be proud of. In doing so, you’ll solidify your role as not just their financial advisor but as someone who truly understands what matters most to them.

These five questions aren’t just conversation starters—they’re game changers. By asking what’s new and exciting, uncovering their biggest concerns, exploring their vision of financial independence, anticipating lifestyle changes, and understanding their legacy, you’re not just scratching the surface—you’re digging deep into what makes your clients tick.

This approach transforms client meetings from transactional check-ins to meaningful conversations that build trust and rapport. And trust me, when your clients feel understood on this level, they’re not just clients anymore—they’re partners in a shared journey.

So, next time you sit down with a client, put away the spreadsheets for a moment and start with these questions. You’ll not only gain invaluable insights, but you’ll also set the stage for a relationship that goes beyond numbers—a relationship built on understanding, trust, and shared goals. And that, my friend, is where the real value of financial advising lies.

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