“The art and science of asking questions is the source of all knowledge.”

Thomas Berger

*Click here to listen to the podcast version of this article or to check out other episodes on how to use behavior, psychology, and communication principles to master the human side of money.

We’ve all heard about the importance of first impressions. And this principle applies directly to the world of financial advice and planning.

There is no meeting, no conversation, no step of the process that influences both your client’s success and your own success more than a first meeting. (Or the first meeting after you’ve already qualified the person as a good fit for your practice. Some call it a “Discovery” meeting.)

The prospective client comes into that meeting and their brain is searching for the answers to these two questions:

  1. Do I like and trust this person?
  2. Can they give me the peace of mind I need to solve my financial problems?

The advisor comes into that meeting with a focus on two things:

  1. Establish likability and trust
  2. Uncover the information necessary to solve their problems and give them peace of mind

Flawlessly execute on both and you’ll convert the prospect into a lifelong client. Narrowly miss on one of the two, and you’ll jeopardize both your client’s and your own chance for success.

Asking Great Questions Is A Superpower

Fortunately, there’s one skill, or one path, that acts as a superpower for building trust and uncovering valuable information. Unfortunately, it’s counterintuitive and unnatural for most people.

Asking great questions.

Researchers have found that the most common complaints people mention after having a conversation, such as an interview or a first date, is “I wish he/she had asked more questions” or “I can’t believe he/she didn’t ask me any questions.”

A list of the reasons why we struggle to ask great questions and default to talking would certainly include: a desire to impress the person, assume we already know the answers, lack of curiosity, fear of being seen as rude or incompetent, etc.

All valid and all things we’ve experienced whether ourselves or in conversation with someone else.

But, the most likely culprit isn’t found on that list. It’s two-fold. One, we simply don’t understand how powerful question-asking can be. And, two, we don’t think it’s a skill that can be honed (or, if you do, you don’t know how to hone it).

People want to be asked great questions. They want to talk about themselves. Brain studies have shown that talking about yourself lights up the same area of the brain as eating chocolate and sexual activity.

To test just how effective questions can be, another group of researchers scrutinized thousands of conversations between people just getting to know each other. They had one group of people focus on asking questions (at least 9 in 15 minutes) and asked another to avoid asking questions (no more than 4 in 15 minutes). Not surprisingly, the researchers found that the group focused on asking questions were better liked and learned more about their partner’s interests.

In other words, asking questions does two things: establishes likability and trust while yielding valuable information. The foundation of a successful first meeting.

Questions are surprisingly powerful because they send a signal to the other person that it’s about them. Not you.

A great question can have far greater impact on your client’s lives than any investment ever could.

A great question will change the growth trajectory of your business in a way that a networking event could only dream of.

What follows is a guide for advisors on honing your question-asking abilities in a first meeting so that you can enhance client outcomes and forever change the trajectory of your business.

We’ll start with a couple principles of great question-asking and then include a menu of questions to choose from.

Principles for Asking Great Questions

Before we get to the actual questions you can start incorporating, let’s first address the key principles to making sure those questions are as effective as possible:

A Great Question Minus Listening Is Not A Great Question

These three form a cycle with one feeding into the next. But remove one element and the whole thing breaks down.

The Order And Structure Create Conversation Flow

Start with less sensitive questions and escalate slowly. A famous study of individuals on a blind date showed that those told to work through a progressive set of questions liked each other more. Always start with a question that allows the person to talk comfortably while focusing on positive feelings.

For example, on the podcast, my first question is always to have the guest tell us about their journey that brought them to where they are today. It’s a story they know, so it’s easy to answer and it elicits positive emotions.

Don’t Stress Over “Closed-Ended” Questions

There’s no doubt that open-ended questions yield more information. But closed-ended questions have a place, too. And, as long as you use the following list to come up with questions you know you’re going to ask, you’ll have plenty of open-ended questions and don’t need to sit in a meeting wondering “How do I not ask a closed-ended question here?”

The Most Powerful Question Of All Is A Follow-Up Question

Follow-up question are exactly like they sound. It’s a question seeking more information or clarity on what the person has revealed.

They are powerful because it signals to the other person that you are listening, that you care, and that you want to know more. Follow-up questions are especially effective as a guide to getting the person to improve their clarity and become more vivid on what they want to accomplish.

Two of the most powerful ways to start follow-up questions are: “I’m curious to hear more about…” and “It sounds like….” If you don’t believe me, try them with your significant other or someone close to you first and you’ll be amazed by what happens!

“Pre-Framing” The Question To Add Context

Anytime you feel hesitancy or concern around how your question will be received, “pre-frame” your question by establishing context and explaining why you’re asking.

For example, let’s say you want to ask your prospective clients “What’s important about money to you?” But, you’re worried that they’re going to be thinking, “What does that have to do with my old 401(k)??”

Try pre-framing the question this way:

“Mr. and Mrs. Corley, we believe that  money is simply a tool to fund the life that you want to live. So, in order to help us align your money with what’s most important to you, we want to make sure we spend some time talking about what’s most important in your lives…”

Explain WHY you’re asking the question paves the way to a better response

HOW You Ask Questions Is More Important Than WHAT You Ask

Think about the last time you were walking on a sidewalk passing a complete stranger on the other side who happened to flash a quick smile and wave.

If you’re like most people, before you even had time to think about it, you flashed a quick smile and a small wave back their direction.

Logically, it makes no sense that you would be waiving at a complete stranger.

But at a subconscious level, when you receive a friendly smile and wave, you almost can’t help but to reciprocate.

It turns out that our brains don’t just process words. They process feelings and intentions.

In other words, people don’t just hear WHAT you ask. They process HOW you’re asking it.

Your general demeanor and delivery will directly impact the quality of responses you get regardless of the question itself. That’s why the best questions are the ones fueled by curiosity.

Clients and prospects can process if you’re genuinely curious and eager to hear what they have to say based on how you ask the question.

Also, when asking questions, the most powerful tool is your voice. The FBI has figured out that the tone of your voice has the ability to reach into the brain and flip an emotional switch.

If you’re naturally curious, it naturally arises in your voice. But, the way the FBI teaches agents to use their voice is to use a “Positive/Playful” voice. It turns out when someone is in a positive frame of mind, it leads to better thinking and better collaboration.

The hallmarks of a great first meeting with a prospective client.

principles of asking great questions

The Best Questions for a First Meeting

This list is a combination of research, listening and reading the anatomy of a great question and a compiling of responses from advisors around the world on LinkedIn and Twitter when asked the question: “What is your favorite or best question to ask in a first meeting?”

It’s meant to be a list of questions that you can choose from. A menu, if you will. Some will resonate with you and others won’t. Focus on finding the ones you think will enhance your focus of building trust/credibility while uncovering the information you need to solve the client’s problems.

After reviewing hundreds of questions, a consistent theme emerged. The questions we ask in a first meeting can be categorized as seeking to do one of four things:

  1. Diagnosing Today’s Money Problems
  2. Clarifying vision, purpose, and values
  3. Understanding Money History
  4. Set Clear Expectations (a key component to any healthy relationship!)

Diagnosing Today’s Problems

  • What brings you in today? What’s on your mind?
  • What was the catalyst that led you to reach out and ask for help?
  • If you could wave a magic wand and change one thing about your financial life (or life in general) at this point, what would it be?
  • What is one thing that if we could help you solve would make everything we do together worth it?
  • When you are sitting around the kitchen table talking about money, what are you talking about?
  • On a scale of 1 to 10, how happy are you with your finances? Is there anything you’d like to improve?

Clarifying Vision, Purpose, and Values

  • Why is money important to you? (If you ask this question, it’s crucial that you use follow-up questions to get past the surface level responses you’re bound to receive.)
  • Let’s say you wake up tomorrow morning and have $10 million in your bank account. What do you do with it? How do you feel? (“Invest it all” is not an acceptable answer.)
  • If you found out today that you just received $20 million but only have 10 years to live, what does the next 10 years of your life look like? What would you do and what would you stop doing?
  • Imagine you are financially secure with enough money to take care of your needs both now and in the future. How would you live your life? What would you do? Would you change anything? (Kinder Question #1)
  • You’ve just visited the doctor who has delivered the news that you only have 5-10 years left to live. The good news is you’ll never be sick. What will you do with your remaining 5-10 years? What will you change and how will you do it? (Kinder Question #2)
  • This time your doctor shocks you with the news that you only have one day left to live. Notice the feelings that arise when you hear that news. What dreams will be unfulfilled? What do you wish you would have finished or done? (Kinder Question #3)
  • What is your desired future state?
  • Let’s say it’s five years from now. April 27th, 20__, and you haven’t accomplished (insert goal/vision here). What would you say are the one or two things that prevented you from getting there?
  • What do you love spending money on? What’s the best money you’ve spent in the last 6 months?
  • What is your “generosity philosophy?”

*If you like the Kinder questions, here’s a link to the episode where we talk about them in depth.

Understanding Money History

  • What’s a money decision you’ve made in the last 30 days where you experienced a lot of emotion, positive or negative? Could have been excitement, fear, joy, relief, etc.
  • Can you give me an idea of your financial life up to this point?
  • Beginning in childhood, what have been the financial events that have most shaped your life?
  • When you think about difficult financial times in the past, how well do you think you’ve bounced back financially and/or emotionally?
  • What is your first memory of money?
  • What was money like in your family growing up?
  • How would you describe your relationship with money and how does it make you feel?
  • What was your best experience with money? Have you had any bad experiences?

*Here are three podcast episodes where we spend some time talking about the importance of money history:

Setting Clear Expectations

  • What’s most important to you in a relationship with a financial advisor?
  • Have you worked with a financial advisor or planner in the past? What was that experience like? What did you like and what do you wish he or she would have done better?
  • What role do you want me to play in your lives?
  • How often do you want to hear from us? How often do you want to get together?

The “Staple” Question

The “staple” question is the one that should be asked at the beginning of every single meeting you ever have with a client.

There are a number of ways to ask it, but the core of the question is this:

“What’s on your mind?”

Other variations include:

  • What brings you in today?
  • What would you like to focus on today?
  • What would be the best use of our time together?
  • What led you to decide to invest your time and energy to be here today?
  • What’s the one thing you want to make sure we focus on today?

Placing this question at the forefront of your meeting does two things:

  1. Immediately signals to the client/prospect that it’s about them
  2. Allows them to release what’s on their mind to be more present

However, you have to be careful for one major mistake many advisors make. Never start the question with “Anything.”

For example, never say: “Is there anything on your mind?”

Our brains crave control, and thus, are wired to answer no any chance we get.

By using “What” instead of “Anything” it encourages an actual response instead of an easy “No.”

The Best Money Conversation

The ultimate first meeting consists of creating an unparalleled level of trust and peace of mind for the client while extracting all the valuable information you need to map their money to meaning.

The research shows that asking great questions is a superpower for doing just that.

Before your next meeting, review the principles for asking great questions. Then, pick one or two from each section that you like the best.

The prospective client will leave the meeting thinking, “That’s the best conversation I’ve ever had around money.”


Whenever you’re ready, there are 3 ways I can help you master the human side of advice:

  1. HSOA Masterclass: An 8-week group program on building trust & connection, aligning money and life, and delivering frictionless advice.
  2. The Ultimate Discovery Meeting: A proven framework to seamlessly convert prospects into life-long clients in one meeting.
  3. HSOA Community (COMING SOON!): An online space to meet, collaborate, discuss, brainstorm, learn and grow with other advisors passionate about the human side of advice

If you’re interested, let me know here.