6 Discovery Meeting Questions To Find Clients’ (Real) “Why” And Set Goals That (Actually) Resonate

Two Common Pitfalls In Early Planning Conversations

It's easy to assume that when a client engages with a financial planner, they already know what they want. They have goals, right? Retirement at 65. Paying off debt. Saving for college. The usual things people are supposed to want. And in an initial planning conversation, that's often exactly what they say.

But as many advisors know, financial goal-setting with new clients isn't always that straightforward. Especially when they're encouraged early on to list multiple goals and structure them using the "SMART" framework – goals that are Specific, Measurable, Achievable, Relevant, and Time bound.

These SMART early goals, as it turns out, often fail to connect with what motivates people to change – which is probably why advisors often see clients struggle to implement or stay the course.

SMART goals make perfect sense for execution. They break down big ideas into manageable, trackable steps. But that structure isn't built for inspiration. It's built for productivity. And that's a key distinction – because many financial goals, especially in the early stages of planning, don't naturally inspire change. They're often 'meh' to begin with, and making them SMART doesn't necessarily make them meaningful.

There are two common issues that can make early goal-setting conversations feel stuck. First, clients often can't articulate meaningful long-term goals beyond the immediate problem that brought them in. Second, even when they do surface other goals, they may struggle to follow through – particularly if those goals don't inspire them.

To be clear, SMART goals aren't the problem on their own – they can be incredibly helpful. The real issue is when and how they're introduced in the planning process.

And that's the key issue: When goals are set too early – and without a guiding vision – they aren't deeply motivating, so they rarely lead to meaningful change.

Imagine a new client who signs up and walks into the office. They're clearly stressed about their money, worried about retirement, and they've reached a point of frustration that they're ready to meet with an advisor for help. The advisor is warm, kind, and positive. They listen, ask thoughtful questions, and ask gentle follow-up questions like, "Retirement is a wonderful goal – tell me, what do you envision doing in retirement?" and "Describe what a typical day, week, month, and year look like when you think about retirement." So far, so good.

Then comes the pivotal question: "What else? Share with me another financial goal."

But in this moment, the client – probably feeling a bit overwhelmed and emotionally raw from the conversation – may find it difficult to answer. They've just shared the thing that brought them in and the source of their stress. Pushing further and looking for more goals too soon can be overwhelming, uninspiring, and demotivating. And if the conversation shifts into building a larger financial vision or turning early thoughts into a stack of SMART goals, the entire process can start to feel like a burden.

Instead of feeling inspired, the client walks away with a financial to-do list they weren't expecting – and are certainly not ready to follow through on.

When financial goals are introduced too early – especially in a generic, productivity-focused format – they rarely inspire the emotional investment that promotes lasting change. And the more goals an advisor tries to elicit in that first meeting, the more likely they are to create overwhelm rather than clarity.

The Risk Of Rushing Into Goals

The research behind goal-setting comes primarily from the field of organizational psychology. In the 1990s, Edwin Locke and Gary Latham studied how structured goals influenced employee performance. They found that workers with clear, challenging objectives performed better than those without them.

That's great – for managing productivity in the workplace.

But clients don't experience their financial lives the way an employee experiences their job. Financial goals are different. They require more than just clarity and structure; they require personal motivation, emotional resonance, and a sense of meaning. A clear goal alone won't lead to change if the client doesn't feel connected to it.

Consider the following examples:

• A retirement savings goal won't resonate if the client hasn't yet imagined what retirement will look like.
• A debt payoff plan feels restrictive instead of empowering if it's framed around sacrifice.
• A budgeting strategy lacks energy if it's just a spreadsheet exercise, not a path toward a meaningful outcome.

This disconnect is why advisors frequently hear comments like:

• "I know I should save more, but I just don't feel like it's urgent."
• "I set a financial goal, but I don't feel any closer to it than I did before."
• "I forget the goals we talked about in our first meeting."

It's not that clients lack goals. It's that those early goals – aside from the one that initially brought them in – don't feel meaningful. Turning them into a long list of SMART goals just creates more work. Instead of gaining clarity, clients often walk away with what feels like financial busywork. Which is why the timing of goal-setting – and the mindset clients are in when those goals are introduced – matters just as much as the structure of the goals themselves.

Why Clients Struggle To Follow Through — Even With SMART Goals

Think about the common goals clients tend to share early in the planning process:

• Save more for retirement.
• Pay off debt.
• Invest more consistently.

Technically, these are all 'good' financial goals. But there's something missing from each of them: They don't stir excitement. And when financial goals that just sound like obligations are unlikely to spark meaningful action. When stacked together, they can actually make people feel worse. A client who was already stressed about retirement now has a whole financial to-do list they didn't even see coming – they don't have a stronger sense of purpose, and they certainly don't feel any better.

This is especially problematic when financial planning conversations jump straight into lots of goal-setting before a client has a chance to process what they really want – beyond that initial pain or stress that brought them in. The dominant emotion in an initial meeting isn't necessarily hope – it's more often fear, stress, frustration, or confusion. Clients are anxious about running out of money, weighed down by debt, or unsure where to begin.

As I often say, most future financial planning clients don't wake up on a Tuesday and say, "Yes! It's financial planning day! I can't wait to call a total stranger and talk about money".

They don't engage because they're excited about financial planning. They engage because something is wrong – and they want help fixing it. So when asked what their goals are, they name the source of that stress: "I need to save more", or "I need to pay this off faster."

And that's the pain point that prompts them to pick up the phone.

But when someone is in an emotionally painful state, it's hard for them to think beyond the immediate stressor. Even if an advisor encourages them to think bigger or share additional goals, those broader aspirations tend to get pushed aside. The client can't think creatively about a broader financial vision. They are focused on the pain. They might say they want to fund college for their kids or update their estate plan, but those goals don't feel immediate or real. Instead, they just become more things to worry about. And too much stress and worry aren't good for motivation. When those early goals are quickly formalized into a SMART format – Specific, Measurable, Achievable, Relevant, and Time bound – the structure alone can't generate the emotional connection needed to motivate action.

Why It's Better To Wait Before Building The Vision

Clients need to be in the right emotional and cognitive space for goal-setting to be effective. Introducing multiple SMART goals before that happens can make change harder, not easier. Here's why:

1. Rigid planning can kill excitement. Asking clients to commit to structured goals too soon can feel premature, especially if they haven't fully processed what they want. That pressure can lead to avoidance rather than engagement.
2. People are motivated more by meaning than by metrics. A goal like "Save $10,000 this year" is less compelling than "Retire early and spend more time with family." Numbers matter, but meaning moves people forward and drives follow-through.
3. Stress narrows focus. When clients are in problem-solving mode, their cognitive bandwidth is limited. They tend to focus on short-term fixes and struggle to think creatively and dream big.

This is why the best time to introduce new goals – beyond the one that brought the client in – is rarely in the first meeting. A more effective approach is to revisit goal-setting later, once the initial stress has subsided and the client has had time to process their concerns.

This might mean:

• Using the first meeting to focus solely on the client's immediate stressor – helping them feel safe and heard – and avoid getting into anything else.
• Introducing vision-based questions in a second or third monitoring meeting, once there's more breathing room to think bigger.
• Collaboratively shaping new goals from that vision – goals that feel relevant, inspired, and actionable.

Clients generally aren't 'bad' at goal-setting because they lack discipline – they struggle because financial goals are different. These goals are personal, emotional, and can easily become overwhelming – especially when they're introduced too early or in a rigid format.

The traditional approach – starting with a long list of structured, measurable goals – misses some important psychological considerations. Before asking clients to identify multiple goals, it can be helpful to consider:

• Is the client in a mindset where they can think beyond their immediate stressor?
• Are the goals they're naming meaningful, or is the client just listing what they think they're supposed to say?

If a client is still operating from a place of fear, stress, or confusion, they're unlikely to connect with a big-picture vision. The conversation may feel hollow or even frustrating. What they often need first is relief, clarity, and a sense of control. Only then can the vision truly start to take shape.

When early goal-setting doesn't seem to land, it's often because clients haven't yet had a chance to feel relief or imagine something beyond their stress. Instead of pushing for full clarity right away, here are a few ways to meet clients where they are – and help them get where they want to go:

• Instead of jumping straight to SMART goals, try vision-building first – but only around the immediate goal that brought them in. Then, turn that vision into actionable steps.

• Instead of asking a client to define a list of additional financial goals or a broad vision in the first meeting, try waiting until a monitoring meeting or two later, once the initial fear has subsided and the client has more emotional space and trust in the process.

Ultimately, clients don't follow through on financial goals just because they're told to. They follow through because they want to – because the plan speaks to something that matters to them.

And the best way for advisors to help them get there isn't to start with all the goals, but with the right goal at the right time – whatever it was that excited them enough to call the advisor (their immediate pain).

The Role Of A Later Big Vision In Lasting Behavior Change

Dr. Richard Boyatzis, a professor of Organizational Behavior at Case Western Reserve University, has spent decades studying how people make real, sustainable life changes. His research led to the development of Intentional Change Theory (ICT), which suggests that change doesn't start with identifying gaps or setting logical goals. It starts with positive emotional energy – in financial planning terms, a clear and inspiring vision of the financial future.

The key idea: People don't change because they're told what they should do. They change when they see a future they want to step into.

ICT research shows that:

• People are more motivated by possibility than by problem-solving.
• When change begins with restriction or rules, people are more likely to resist.
• Emotional connection to the future increases the likelihood of taking action.

This is where traditional financial planning can run into trouble.

A client who walks into an advisor's office for the first time is rarely ready for big-picture visioning. They're usually in problem-solving mode – seeking relief, clarity, or reassurance. If an advisor jumps too quickly into a future-focused conversation, it can feel irrelevant or even frustrating to the client.

Think outside of planning for a moment. Imagine going to the doctor because of terrible headaches, only to hear the doctor say, "No problem. What other health concerns do you want to work on?" While those broader concerns might matter – and be connected, just like multiple goals in a holistic financial plan – the patient's immediate priority is simply to stop the headache.

When the headache is gone, then the patient may be more able to think – emotionally and mentally – about other changes they want to make for long-term health.

Financial planning is the same. The initial vision is often small: Fix the thing that brought the client in and provide some relief, hope, or clarity. And then, with that weight lifted, the next vision meeting can happen from a fresh, more open place.

A "Big Beautiful Why" Activates Different Brain Systems Than Logical Goal-Setting

Many advisors have probably seen this principle in action: Clients nod along with a financial plan but never act on it – not because they disagree, but because the plan doesn't spark motivation. That's because different brain systems are responsible for different types of thinking:

• Visioning taps into the Default Mode Network (DMN) – the part of the brain linked to creativity, imagination, and long-term thinking.
• Logical goal-setting activates the Task-Positive Network (TPN) – responsible for focus, problem-solving, and execution.

Both networks are important. But starting with logic alone (TPN) can make planning feel like a list of obligations rather than an exciting opportunity.

The most effective advisors help clients dream first, then plan. And this brain-based insight shows up in real-world financial planning, too.

When visioning conversations happen too soon, clients tend to forget earlier conversations about their values, money beliefs, and financial history – not because they're unimportant, but because they don't yet feel emotionally relevant.

Research supports this idea. In a KSU/Allianz study/Money Quotient study:

• Financial planners reported covering key context:

• • 68% reported covering cultural values;
  • 73% covered personality traits;
  • 80% covered money attitudes; and
  • 67% covered family values.
• But clients recalled less:
  • Only 41% recalled cultural values;
  • 38% personality traits;
  • 53% money attitudes; and
  • 53% family values.

The researchers were surprised by the disconnect – and many advisors may recognize this in their own client relationships. While there's no definitive answer, one possibility is that when clients are still in stress or problem-solving mode, vision-based conversations don't resonate. The information doesn't yet feel relevant, so it gets mentally pushed aside.

This isn't just an issue of whether to ask big-picture questions and introduce vision. It's a question of when. Because if vision-building conversations happen too early, there's a good chance the client won't even remember it later.

A Second Vision-Building Conversation May See Stronger Client Commitment

The first time that clients talk about their financial future, their answers are often vague, generic, or stress-driven:

• "I want to retire comfortably."
• "I just want to feel secure."
• "I want to be in a good place financially."

That's not because clients lack vision – It's because they don't yet know what's possible.

This is why monitoring meetings are often a better place for deeper vision-building. By then, the immediate stressor has subsided, the client has had more mental space to think clearly about the future, and trust with the advisor has grown.

When clients are asked about their ideal financial future in a second or third meeting, three things tend to happen:

1. Clients take more ownership of their vision. If they weren't emotionally invested the first time, they may have offered surface-level answers just to move the conversation along. Later, they're more likely to actually reflect.
2. The conversation feels more relevant. At this stage, clients begin to see financial planning as a process – not a quick one-time fix. That sets the stage for engaging in more meaningful vision-based discussions.
3. Clients commit to action more naturally. When they build their own vision, they're more likely to follow through. They've also experienced how the advisor relationship works and how financial planning can support their goals.

Vision isn't about asking the perfect question. It's about asking the right question at the right time – when the client is truly ready to engage.

That's why it often works better to hold off on asking about a client's ideal future in the first meeting and instead, revisit those vision-building conversations during a later (second or third) monitoring meeting – once immediate concerns have been addressed and a stronger foundation of trust is in place.

Likewise, money attitudes, values, and financial history may be better explored after the client has had time to settle into the relationship. When introduced too early, these topics can feel abstract and irrelevant. But brought at the right moment, they resonate more deeply – and often stick.

Clients don't need to be convinced to care about financial planning. They just need the space and timing to connect with it in a meaningful way.

Six Questions To Help Clients Create A Compelling Vision Before Setting Their Next Round Of Goals

Once clients are ready to think beyond their immediate financial stressors, advisors have an opportunity to guide them toward a vision that truly resonates. But asking the right questions is just as important as when they're asked. A well-timed, thoughtfully framed question can help clients connect emotionally to their future, rather than simply listing financial goals out of obligation.

Here are six questions designed to help clients explore their "Big Beautiful Why" and build a vision that fuels lasting change.

Question 1. What Would Your Ideal Life Look Like If Money Were No Object?

Most financial planning conversations start with constraints – budget limitations, investment returns, and market uncertainty. But vision-building isn't about solving problems. It's about imagining possibilities.

This question gives clients permission to step beyond those restrictions and dream freely. By shifting from "Can I afford it?" to "What do I actually want?", clients begin to uncover their true priorities, values, and aspirations – the foundation of a financial plan they'll actually want to follow.

• Some clients may describe a life full of travel, generosity, or creative pursuits.
• Others may realize they value security and stability over major lifestyle changes.
• Some may struggle to answer – which is useful, too. It means they've never had space to think this way before.

Why it works: Clients often default to practical, responsible goals. But goals without emotional weight don't inspire action. This question connects financial planning to something meaningful. (Variations like the miracle question – defined next – as well as the magic wand question and George Kinder's "dream of freedom" question also serve as powerful vision starters.)

Question 2. If You Wake Up Tomorrow And All Your Financial Worries Were Gone, What Would Change?

This is another version of the miracle question, a tool often used in coaching and therapy to help people envision life without their current stressors. Instead of asking clients what they should be doing, it invites them to think about what they want – without the weight of financial stress shaping their answer.

• If a client suddenly felt zero anxiety about money, what's the first thing they would do differently?
• Would they change careers? Spend more time with family? Travel more? Start a business?
• What would their daily life feel like if money were no longer a source of worry?

Why it works: Many financial goals come from a place of fear – I need to save more so I don't run out of money. But lasting change is easier when it's driven by excitement, not avoidance. This question helps clients focus on what they're moving toward, not just what they're moving away from.

Question 3. What's One Thing You Want To Experience In Life That You Haven't Yet?

Some clients struggle with long-term vision because it feels too abstract. But asking about a single experience grounds the conversation in something tangible.

• Maybe they want to take a year off to travel.
• Maybe they want to see their kids graduate from college debt-free.
• Maybe they want to launch a nonprofit, write a book, or spend more time in nature.

Why it works: Big-picture thinking can feel overwhelming. Focusing on one meaningful experience makes the future more real – and helps clients connect their financial decisions to something that excites them.

Question 4. Imagine Your Future Self Is Looking Back – What Financial Decisions Do They Thank You For?

It's easy for clients to get caught up in the present – the daily spending decisions, the short-term worries, the financial to-do list. This question shifts their perspective, helping them zoom out and think long-term.

• What financial habits would their future self be grateful for?
• What investments in relationships, career, or well-being would make them proud?
• What decisions would bring them peace, security, or excitement later on?

Why it works: People often know what they should do, but this framing helps deepen their emotional connection to their future self, making it easier to act today.

Question 5. What Legacy Or Impact Do You Want To Leave Behind?

Financial planning usually focuses on the individual – their retirement, their lifestyle, their needs. But this question shifts the focus to something bigger.

• What do they want their money to accomplish beyond their own life?
• How do they want to support their family, community, or causes they care about?
• What kind of financial example do they want to set for future generations?

Why it works: When clients connect money to meaning, they become more invested in financial planning as a tool for something beyond just wealth accumulation. This often sparks more purpose-driven financial decisions – whether that means philanthropy, family support, or aligning their spending with their values.

Question 6. What's One Change You Could Make Today That Moves You Toward That Vision?

After all the big-picture thinking, clients need a way to translate their vision into action – without feeling overwhelmed. This final question helps them identify a single, manageable step they can take now.

• If their vision is travel, maybe it's starting a dedicated savings account.
• If their vision is financial security, maybe it's finally setting up that estate plan.
• If their vision is more free time, maybe it's reevaluating their work-life balance.

Why it works: Change feels more doable when it begins with a small, meaningful step. This question keeps momentum going while avoiding the paralysis that can be created by making too many changes at once.

Bringing Vision Into The Room: Three Tips To Make The Second Meeting Sing

Once clients have had time to settle into the planning process, the second (or third) monitoring meeting becomes fertile ground for visioning. But even with the right timing and the right questions, the meeting itself still needs intentional structure. Here are a few ways to create the space for vision-building to unfold naturally and meaningfully.

Tip #1. Send an agenda in advance and explain why this conversation matters.

Giving clients a heads-up does more than just prepare them logistically. It primes them to reflect emotionally, and it signals that the conversation ahead is different from their typical review. Consider the following sample message:

Dear Carol Client,

You've made some huge strides over this past year – [insert personalized win]. I'd like to take some time in our next meeting to reflect on where you are and revisit financial goals.

Below are a few questions I'll be asking. I invite you to reflect on them in advance:

1. If you woke up tomorrow and all your financial worries were gone, what would change?
2. What's one thing you want to experience in life that you haven't yet?
3. What's one change you could make today that moves you toward that vision?

These questions offer a different lens – one of optimism and opportunity. Feel free to email me your thoughts before the meeting. I look forward to this conversation.

Cheers,

Penny Planner

This kind of pre-meeting message shifts the tone from 'goal-setting' to something more spacious, collaborative, and personally meaningful.

Tip #2. Consider building the meeting around a Statement of Financial Purpose.

One of the most powerful tools for this kind of meeting is Carl Richard's concept of the Statement of Financial Purpose. It's simple, elegant, and helps capture what really matters most to their client – in their own words.

This moment – when stress has eased and vision is starting to form – is the perfect time to introduce it.

Advisors Jeremy Walter and Andy Baxley have written about how to design a meeting around the Statement of Financial Purpose, and their work serves as a great resource. Feel free to borrow the questions they suggest, or mix them with those offered earlier in this article to create a custom flow.

Tip #3. Leave space for follow-up questions and shared reflection.

A big part of the financial planning experience is the act of discussing and brainstorming with the advisor. These conversations aren't about having all the right answers – they're about dreaming out loud, together.

Advisors can allow themselves to stay present in the moment. Ask follow-up questions. Reflect things back. Be curious.

The best planning conversations aren't transactional — they're co-created. And often, it's not the first thing a client says that holds the real insight. It's what comes after they've had space to think and feel their way into it.

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The best financial plans don't just help clients save more, spend wisely, or retire on time. They help clients feel excited about their future. But excitement and motivation are as much art as they are science. Advisors often get more done, more easily – and clients are more likely to remember and act – when conversations are well-timed and focus on possibility before locking into specific goals.

Vision-building matters. But only when clients are ready for it. They happen later – often in a second or third meeting – after the initial stress has been addressed, there's a bit more breathing room, and some trust has been built. That's when clients are more open to thinking about long-term visioning and what they actually want. And when that shift happens, the right questions can help clients move from vague, uninspired goals to something deeper and more personal – a financial future that truly resonates.

Ultimately, the key point is that when clients can see what's possible, and they feel connected to that vision, follow-through comes more naturally. And when advisors make space for those conversations – at just the right time – that's when planning really starts to feel meaningful!