Deeper Conversations From the Get-Go: How This Advisor Gets to Know Potential Clients Right Away

Jul 22, 2021 / By Sam Rodriguez, CFP®
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What’s Working Now: By asking more personal questions within the first half-hour of a potential-client meeting, this advisor gains a deeper understanding of people right away—and wins their business through his unexpected and genuine interest in them.

In this edition of What’s Working Now, an AdvisorRADIO feature in which Horsesmouth members tell us about recent success they have had running and growing their businesses, we hear from advisor Sam Rodriguez, who asks deep questions to really get to know clients—and allow them to realize they need his help.

Quick Overview

Guest: Sam Rodriguez
Allen, Texas

Years in business: 17

Firm: Foundation Wealth Partners

What’s working now: Asking challenging questions to understand clients’ deepest values—and letting them realize he knows them and can help them.

Everyone has a goal

When people come into our office, we already know that they have some sort of goal. Whether that goal be retirement, figuring out social security, etc. I think people expect that we’re already going to tell them that we can help them reach retirement.

But what I try really hard to do is spend a lot of time understanding how they think and feel about money. This helps me understand any motivating factors that are behind why they’re trying to achieve the goals they have in mind. I have found that the real problem we’re trying to solve is: how can we satisfy that emotional drive that made them want to create the goals they have—what experiences and feelings have driven our clients to those goals.

When we discuss these things with our clients, I mention how I have seen research recently that showed upward of 70% of the public, especially those that have investible assets, their main goal in retirement is to be financially secure and that is the context around which our conversation should happen.

Security tends to be a big factor, but what security means is different for everyone. Typically, I will ask a really vague question to start “Tell me what’s most important about your money to you right now.”

I get answers often of people saying something along the lines of “Well, I want to make sure I’m on track for retirement.” But sometimes, I’ll get a surprising answer that’ll be forthright right away.

Setting the stage for deeper conversations

I start the meeting by thanking them for coming in. I usually follow up with asking them how the drive was, if they found the place easily and if they’re from the area. This helps me get through the first letter of the acronym, H.O.M.E. (see the next section). Then, they will usually tell me if they grew up in the area, if they went to school in the area, or if they’re from somewhere else and where they met.

Then, I’ll just give a quick rundown of what we’re going to do. I’ll start by letting them know I’m going to ask some questions about what’s important to them about money, how they think and feel about it, and ultimately what the reasons were for coming in.

Then I’ll tell them a little bit about myself and more about our firm. After that, we’ll walk through the firm’s process of how we help our clients and talk about how that process may relate to what it is that they’re trying to achieve and our main goal throughout the first meeting is to figure out if I can help them and how I can best help them if I can.


I use the acronym H.O.M.E.:

H: Where you’re from

O: Occupation

M: Married/family?

E: Education

These things help ensure you and your client have something to talk about.

Additionally, in there it gives me some context of what their experiences have been, which helps me ask better questions when I am asking them about their money. A lot of times what you find out is, there’s some experience that maybe they didn’t personally have but they saw someone else go through. Either something that they’re trying to avoid or something that they aspire to, someone that they saw do something very well. You’re trying to find out what that is so you can get to the point where you really understand what security means to them.

Security means something different to each person

For some people security is not having anybody to answer to and the ability to do whatever they want with their days. Others have specific things like wanting to make sure they have enough money to travel and see their grandkids. You have to dive deep into what exactly security means to that person in front of you.

Something that I’ve seen from research is that there’s this notion of people wanting to feel “safe” and “secure;” the idea of being smart and responsible with their money. But the other key emotion is to continue to be optimistic about what the future holds for them.

They’re well-heeled enough to be sitting down with an advisor, and are able to be optimistic about the future, while also being proud about the things that they’ve achieved. It’s almost like they’ve made it to the big leagues. Now it’s time to figure out how to bring them to be their best self. As advisors, we need to not be intimidated by the fact that they’ll probably be OK without us.

It’s also OK to reassure them and let them know that they’ve done a good job up to this point, so that way you can give them advice on how to enhance their situation. When they are coming in, they already know that they’ve saved a good amount of money, so they’re looking for tips on how to do better. By complimenting them on what they’ve done so far, that allows you more acceptance when talking about areas of improvement.

Couples: getting them both to talk

Most of the time we don’t ask people deep questions. We don’t ask why hobbies are important or how they’re really feeling about something difficult. But what is really surprising is that typically couples or spouses don’t necessarily ask each other these questions, either.

Maybe they’ve talked about retirement, but many have never asked each other why they want to retire or what’s important to them for retirement. Usually, they’ve asked each other about what they want to do when they retire and leave it at that. Typically, one of the spouses almost completely checks out—they say something along the lines of, “You know, this is really their realm. I just sort of let them make the decisions. So now, as advisor, you should find out why that is and why the other has checked out.

A lot of times through these conversations with clients, they’re discovering things about each other that they necessarily didn’t know before. They’re maybe finding out that they don’t have the same views on things or you’re finding out that they already know they don’t have the same views and this is actually a point of contention in their relationship.

In a conversation like this, you’re playing with a little bit of fire.

This conversation happens within the first 30 minutes of our first meeting with a new client/prospect. I have found that getting into serious conversations rather quickly works extremely well, especially if you have someone who’s been shopping around a little bit. Because they definitely haven’t had this conversation with anybody else.

I always feel like people leave a meeting with me feeling very much like I understand what’s important to them before I even give them solutions. The way our first meeting works is that I help them figure out what’s important to them and then I explain the process I follow that solves their problems. Jumping in and finding the root to the problem or getting to know them on a deeper level is what’s important.

My experiences

I started my career about 17 years ago with American Express Financial Advisors before they broke off and became Ameriprise. How the job works is that you were basically in a classroom for half of your day practicing things and once you reached a certain production level you didn’t have to go to the classes anymore. I spent a lot of time in class because I started off so slow, so I got a lot of practice in.

They were teaching us this skillset of trying to understand what was driving the client, and then once I started actually seeing clients, it was just repetition. I always feel like I don’t have a lot to talk about so I’m going to try to get you to talk as much as possible. So, I just started asking a lot of questions and realizing that people actually have a strong emotional drive on these things. The first time it worked, it was sort of like a light-bulb moment. It was a really powerful meeting.

Not only does the client feel like I’m going to help them, but I feel fantastic about what I’m going to be able to do for this client. Knowing that you can help them scratch that emotional itch that’s been keeping them awake at night, that feels fantastic.

When you go to the doctor, you hope they ask you questions so that way they can get to what the issue is. The same goes for financial advisors; we need to be OK and confident enough to ask some really, really tough questions. I do find those questions are things like asking them what’s important about their money to them in that moment; this is a great opener. I follow that by asking them why and if they can tell me more about that particular thing. I have found that if they’re not giving me anything, asking something along the lines of if they’ve seen any examples of what they’re describing and to tell me their experience with those and if they’ve seen them in the past.

I don’t want my first questions to be extremely stressful personal questions, so I want them to relax and then I’ve asked a series of questions and now they’re used to just giving me answers. So, all of those first ones are very easy and then when we get into these others, it’s no big deal, because they have been answering questions for the past 10 minutes not realizing it.

More on working with couples

You’ve to be very, very conscious when you ask your questions with couples because you’re going to have one that is doing 90% of the talking. So when they stop talking, you just turn and then direct specific questions to the other one.

You do have to make sure that when you ask these questions and the dominating partner is answering, to consistently turn to the other and ask them if they feel the same way and what their feelings are on the topic you’re discussing. You have to keep pulling them into the conversation and you’ll find out, they have a lot more to say than anybody thought they did. They just have always deferred to the other, because the other is so dominating when it comes to finance.

I will often ask if money is a point of contention with them. The reason I ask that is because people have different attitudes, feelings, and thoughts about money. And what we have to realize is people have had experiences that have shaped those thoughts and those feelings. Something to remember is that the couple that’s in front of you, they haven’t been a couple their whole lives. They’ve only been together from a certain point in time, so before that they’ve had different life experiences that have shaped their thoughts about money and their goals in different ways, and so you want to find out, not only what’s driving the sort of dominating partner, but what are the emotional drivers for the other?

And so it could be as simple as always wanting to save. They’re always worried about the future, so they save, save, save while the other is trying to counterbalance that and keeps trying to spend. This is pretty common.

One of the great things that we do as advisors is we help them solve that problem. As an advisor, if I can show you exactly what you need to be putting away every month or every year for retirement and how that money needs to be saved so that you know what’s left over so that you can go out and live life for today and not feel guilty when you’re spending that money to help alleviate some of the stresses when couples deal with finances. That alone can be a marriage-saver for a lot of clients.


Budgeting is super important, but the way I approach it is a bit different based on experience, but it’s something that the firm as a whole is still working on.

Clients often don’t want to think about or look at their budget because it makes them feel bad. Especially when you have people who make a really good income that don’t even think about where they spend their money. Now you’re going to ask them to sit down and figure it out. So I don’t ask that anymore.

When in a meeting, I look at the money that comes in versus the amount of money that you save because that’s going to tell us what you actually are spending and then we can work on what you have to pay on a monthly basis. We first look at your basic expenses like their mortgage, electricity bill, and once we have the basics, we will know what their discretionary expenses are without knowing what you’re actually spending those things on.

When it comes to budgeting, the most important thing for clients to know is what it’s going to take for them to hit their goals. If they’re saving the amount that they need to hit their goals and they’re paying their bills every month, I don’t care what the extra money goes to as long as they’re not accumulating debt, and I let them know that from the start. Doing this helps avoid them feeling like they have to sit down and do a bunch of homework because they really don’t want to feel bad about how they spend their money.

Retirement goals for clients

I will often ask about their retirement goals when they talk about retirement. I can get a little annoying for them, because people will say, “Oh I’m going to do whatever I want.”

“Oh, OK. Well, what is that?”

“I’m going to golf all day.”

“OK. What are you going to do after that?”

“Well, whatever I want.”

“Well, what does that mean? You wake up. What are you doing? Are you going to watch all the game shows all day and then your shows at night and go to bed? Let’s really talk about how you’re going to be fulfilled.”

Those questions can be very difficult because people realize that they really have only scratched the surface of what’s important to them in retirement. Even if they say they want to travel, it’s not like they’re going to be traveling 365 days a year.

So you have to ask them, “What are you going to be doing when you’re not doing those things that you are looking forward to?” Because we all hear the same things. “I’m going to go visit my grandkids from time to time. I’m going to travel.” Recently, I have been getting a lot of people saying that they’re going to get an RV and see all the National Parks.

Loss of purpose and the challenge of fullfillment in retirement

The research I’ve been referring to introduces this concept as sort of describing what financial security means to them and the researchers teased out the phrase, “living the full life,” or, “a full life in retirement.” Then that’s a phrase that can mean a variety of things to people, but it seems like there is an expectation that there’ll be more than just golf, or more than just travel.

But I think people are very much rooted in their existing day-to-day life and if they stop working that’s a big chunk of time that, times seven, or five days a week that they didn’t have in the past. And it’s not like you can play golf 40 hours a week. You’ll wear yourself out, your back will be ruined. But not only that, if you’ve spent the last 30 or 40 years working, especially if you’ve been at one company for a long time, that’s also where your social circle likely is and now you’re going to be disconnected from that. So there can be this period sort of a depression.

When people go into retirement and they finally take that trip or do whatever it is for the first time, they come back and nobody is asking their opinion on things anymore. No one’s looking to them for answers, no one’s inviting them to things anymore and there’s this lack of fulfillment.

One problem that I see, is if there was only one working spouse, the spouse that’s been taking care of everything at home, the new spouse, or not the new spouse, but the spouse suddenly entering into the situation messes up their routine that they have and problems can actually start happening then because now they’re spending more time together than they ever have in the past.

The one that’s been working can get annoying because they’re searching for all that fulfillment that they received from work now from their partner and their partner is not used to them even being there. And so you do have to ask “What’s going to fulfill you? What’s going to make you feel like you have some purpose? What are you really going to do that makes you feel like you have some meaning behind your day?”

Retirement planning is more than financial

So this gets to this whole question of retirement life planning where it’s not income planning. We are looking at how to convert their assets into some sort of income plan where money will be there every month and all the other goals are achieved, but it’s the non-financial piece that I find particularly interesting. This is because I hear often of people not taking the time to think or have a vision for their own retirement, yet it’s something that advisors really aren’t necessarily suited to do other than encourage people to maybe think about it more.

The percentage of people that have no idea what they want their retirement to look like beyond financial security is very, very high and the number of advisors that are actually talking to people about these things is very, very low.

If you talk to these people and to your prospective clients about these things, I can almost guarantee you that whoever else they are talking to is not talking about these things and the thing also to realize is when you do talk about these things and you frame it in a way where you say, “I’m going to talk with you about some of the dangers I see when my clients enter into retirement.”

We’ve already tried to tell them, “Hey, we can help you.” As an advisor, you’re trying to display your expertise in income planning, in retirement planning, in investment planning. And you’re hoping the person believes you, and that’s what they want to know. They want to know that you have experience with someone that is experiencing the same thing that they’re going through at that moment in time.

Financial plans must fit the client’s values

You have to let people know, there is the dollars and cents behind making this work. But then the other piece is really having a good understanding of how you think and feel about money and what’s important to you about the way that this money works for you during this period of time along with what you are going to find fulfilling and satisfying in your life, and the reason that understanding their thoughts and feelings around money is not just buying an annuity and going forward like that.

There are so many tools that we as advisors can use, and I do tell clients this. I’ll say, “There’s so many tools that we can use to get you there, but what I promise you is whatever I recommend is not only going to be something that solves your problem but it’s going to be built based on the information that you have given me about what’s important to you during that period of time.”

So if someone says freedom—an annuity is probably not going to be the option for them. So, I will tell clients that, that what’s important to me is to understand how they think and feel about it so that way I find the way to get there. And then that actually was a hard lesson learned because I would design, early in my career, what I thought were these fantastic financial plans and no one was moving forward.

I wasn’t getting a lot of buy-in. I was showing them, “Here’s how fantastic this is going to work,” but I wasn’t connecting that emotional piece to it yet and understanding whether or not that solved the feeling that they were trying to achieve.

Talking about fulfillment and security

Beyond that it’s really just getting to know the person in front of you and it’s important to tell the clients that you want to understand not only how they think and feel but how to make sure they are financially successful in their retirement and are being fulfilled. Because if they’re not truly fulfilled, why would they retire? Asking them that is ok because it’s important.

And that’s OK to ask too. You can ask, “Tell me why you’re retiring.” You can even ask, “Do you not like your job?” Right? And they’ll start really thinking about, “No, I just want do these other things,” or, “No, I really don’t like it,” or, “No…”

Home in on what makes clients happy and why

Ultimately, what you should always be working towards is your client’s happiness and what clients need to understand is what makes them happy, or what alleviates the stressors in their lives so that way they can find happiness.

Honestly, we don’t think about that very often. We don’t think about what we really want. Before retirement, we all have different responsibilities. Well, when you finally hit retirement, a lot of those responsibilities are gone. So, we’ve got to think about what you’re going to do and what’s going to make you happy. What are you going to find fulfillment in? What’s going to give you the higher purpose?

You always have to ask yourself “Why.” Like, “Oh, I want this car.” Well, why do you want it? And maybe it’s this car that your client and their dad always talked about and dreamt of and sitting in it every day makes him think of his dad. Then yes, I get it. But if he goes, “Well, I don’t know. I just think it’s cool.” OK, well how long are you going to think that’s cool?

Or the beach house, I know that’s a thing for our family—as our kids are getting older, we would like to have a reason to bribe them to come see us with grandkids. And we want them to have those memories.

Some of the greatest things I hear are when clients tell me a personable story like them growing up and spending time with their grandparents, with everyone in the family together. I then remind them that finding that happiness is important. I often remind them that money can’t buy you happiness, but it can buy you the things that do make you happy. But I think what financial freedom or money buys you is options, and it buys you the ability to feel free to find what makes you happy.

When you’re struggling on a day-to-day basis and you’re barely making it, you don’t have a lot of options. And so it’s very hard to find the things that fulfill you and can make you happy because you’re just thinking about, “How are we going to get through the end of the month?”

Be different

When meeting with a client or a prospect, I can tell that they have not talked with other advisors about the things I bring up. You can tell when a client, or prospective client has been talking to other advisors because they have all their financial statements ready. And they want to get right to it and they want to know what your pitch is.

They say, “OK, I’m trying to retire by this time. What do you think I should do?” And you kind of have to take a step back and then reframe what the meeting is going to be about and what you’re going to do and they’re always a little taken aback and you’ll hear a lot like, “No one’s talked to me about these things.”

And every once in a while one will say, “well, I have a couple of other guys that I’m going to talk to,” which is fine because I’m sure they’re not going to have the same experience. But I have a lot of times where they have their stack of information, and even before I’ve talked about the process, it happens. When I’ve just repeated back to them everything that they’ve told me about what’s important to them, what there experiences are and how they feel about things—and then I ask, “Do you feel like I have a pretty good understanding of where you’re coming from and what you’re trying to achieve financially?” They’ll say, “Yeah,” and then that stack slides across and they say, “What do we have to do to get started?” So that makes me feel really, really confident in these conversations.

In their mind they’ve already decided, “I want to work with these guys.” And so this was actually an issue for us for a couple of years where we knew these people wanted to work with us, they’ve said yes, but then once we started going through the process, especially at the homework piece, things would begin to slow down, moving money over sometimes would slow down. So while they are still thinking about this and while this is still important to them, we want them to go ahead and take some sort of action. Even if that’s just signing an agreement that says, “We’re going to work together,” there’s something that makes them feel like, “OK, I’ve taken a step and so the process has started.”

So, we really try to make someone feel like they are now a client, right? Whether it’s just opening an account before we really know what exactly they’re going to do. We just know, “Hey, we’re going to help you. Let’s go ahead and make sure the account is open by the time you come into the next meeting we’ll talk about some of the options.” Right? But we really try hard for them to become a client in that first meeting.

Objections are OK

If someone is going to object to the kind of process we use, you will know right away. It’s not really an objection as much as it may be someone who is just looking for someone to manage their money.

So you have to decide what kind of advisor you are at that point in time because it’s hard to pass up additional income. But if you’re having to work with that person in a different way than you are everybody else, it’s going to take away from being able to help everybody else in the way that they deserve to be helped.

There’s not really any objections after you’ve gone through the process. Like I’ve said, if there’s an objection, it’s right up front and it’s somebody just saying, “I’m not into that. Just tell me what you can do with my money.”

Engage with more emotion

Don’t be afraid of emotion. I understand it can feel precarious, it can feel scary, it can feel like you’re stepping into some shark-infested waters. You’re not going to be good at it at first and you shouldn’t stop just because the first few times are not successful. It takes a lot of practice.

I’m 17 years into the business and I still have something written on my desk, where the clients can’t see: “Shut up and listen!” Because it’s important that the client is the one telling you what’s important to them. Know that after you get really good at it and you feel like you know what you’re doing, there’s really only about four or five different types of emotional drivers out there and you’re going to know within the first few minutes what is driving the person in front of you. But you can’t tell them until they tell you.

You have to let them come to the realization that, “Oh, this is what’s driving me,” And maybe that’s the reason this works so well is that what you want them to realize in this meeting is that they need your help instead of you trying to convince them that they need your help. Even though you know what you can do just keep asking questions until they realize, “Oh, I do need help. I do need this guy’s help.” Right?

That’s very difficult to do because as soon as you see a problem you can solve you want to jump on it and show value, but you really have to hold back and let the client discover it for themselves.

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