What Happens When Financial Planning Starts With Better Questions?

In many financial planning conversations, the loudest voices tend to shape the outcome.

Yet some of the most important perspectives in the room often go unheard.

What happens when we start asking better questions and make space for every voice to be part of the conversation?

On this episode of Get Ready Before Life Happens, I spoke with Colleen Bowler, entrepreneur, speaker, and creator of The Passport Package, about the human side of financial planning. 

We explore why listening is one of the most powerful tools advisors and families have, how planning conversations can bring out quieter voices, and why meaningful financial decisions begin with understanding what truly matters to the people involved.

🔹 Financial planning works best when advisors listen before offering solutions.
🔹 Asking thoughtful questions helps uncover what truly matters to clients.
🔹 Important perspectives can be missed when quieter voices are not invited into the conversation.
🔹 More than 70% of widows change advisors after losing a spouse when they feel unheard.

🔹 Engaging the next generation helps families prepare for transitions, many next-generation heirs move on when there’s no relationship.
🔹 Retirement planning becomes more meaningful when people move toward something purposeful.

💭Tony’s Take; Financial readiness begins with understanding people. When advisors and families create space for every voice and ask better questions about what truly matters, planning becomes more than numbers. It becomes a conversation about the life people want to build.

Connect with Colleen Bowler, CFP:

• Website: https://thepassportpackage.com
• LinkedIn: https://www.linkedin.com/in/colleen-bowler-cfp®-09576796/

Books:

• Generous Kids (Amazon: https://amzn.to/49zoitC)

Bio: 

Colleen Bowler, CFP® is an entrepreneur, speaker, and coach who transformed personal hardship — losing her father at 16, later navigating divorce as a single mom with a sick child — into a 25+ year financial planning career that took her from earning $14,000 her first year to building Strategic Wealth Partners into a top 1% Texas firm, managing half a billion in AUM. After successfully selling her practice, she co-founded C&J Innovations, LLC, where she created The Passport Package™ (patent-pending) — a proven framework that helps financial advisors grow revenue, referrals, and retention by embracing the human side of every financial decision, creating what she calls a "waterfall of impact" that lasts for generations.

☕ Support the Get Ready Movement.

If these conversations help you think differently about money or prepare for life’s what-ifs, your support helps expand financial readiness education and keep this work accessible.

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Transcript

SPEAKER_01 0:04

Get ready before life happens. The podcast helping you navigate life's what is.

SPEAKER_00 0:16

The future of financial planning is about asking better questions rather than having all the answers. Welcome to Get Ready Before Life Happens. I'm joined today by Colleen Bowler. Colleen, welcome to the podcast.

SPEAKER_02 0:31

Thanks, Tony. Thanks for having me.

SPEAKER_00 0:33

Yeah, I'm excited for this conversation. You're doing some really cool things. So to start off, tell us a little bit about yourself. What is your origin story and how did it lead you to creating the passport package?

SPEAKER_02 0:46

Oh, goodness, that's a long story that I'll that I'll try to make quick. Origin story in the sense of my upbringing, which habits are such a big thing in changing, which you were we were talking about change makers earlier. I grew up in this big family, six kids. My mom had this abundance mindset. It was one that there was always another person at the table. Someone is always invited. But I didn't actually realize that we were poor until my dad died when I was 16. And we had $187 in the bank. So that meant no college funds, no plan actually. And the impact on families when there is absolutely no planning is pretty huge. And um we got to live through that. And luckily, my mother also taught us and father um grit and perseverance and determination. And um, she started her own company because she needed to be flexible in all these things. Uh, my mom became an entrepreneur after being a nurse. So um we learned to just make it happen. And so that happened to me too when I was in the middle of a divorce. I had was in the middle of changing jobs and found out the job that I thought I had wasn't there. And so I'm in the middle of a divorce. I've got a sick three-year-old, no income, um, given all the debt because I was the one who did have a job. Um, I didn't create the debt, but I was given it. Um and somebody said, Hey, Colleen, you're good at math. Why don't you do this thing called financial planning? And I did. Um, I made $14,000 the first year. And then through grit and perseverance and determination and a lot of support, I um I when I sold my firm in 2020, I was in the top 1%, 7 plus figures, um, a fabulous firm. And um I wanted to give back. I wanted to help others learn easier or, you know, simpler than what I did, because it was a lot of school of hard knocks, as you can imagine, Tony, um, in the beginning of my career. And also, you know, there's only 15% women when I started in the industry. Now there's only like 17%. We haven't done very well on that thing. We need to be a change maker in that part. Um, but I really didn't have any guides or training on the human side. There was a whole lot on the financial side. There's a lot of instruments that you could use, but how could I make asking questions about someone else's future, which is what I learned really, when we can weave that together with their finances, then we have a sticky relationship and we can also help them, right? So that's how the passport package started. Somebody, um, Jeannie Hurlbert, PhD, much smarter than me, knew how to create assessments. I knew how the questions and um advisors now are using them, financial advisors with quick five-minute assessments with prospects or in with clients in their annual reviews. How's that for us?

SPEAKER_00 4:50

That that that is great. And you know, I appreciate you sharing the journey, is you know, I call it the origin story because I think that so many people, you know, when you ask them their bio and you go through the bio, it's not very interesting. But when you hear somebody's story, is it shows that you can, you know, change your circumstances, as you said, through grit and uh perseverance and that it is possible. And I think the story, especially as you point out, is I think for women to succeed in financial services can be extremely difficult. There's so many things. I mean, for people who watch and listen to the podcast, they've heard me have a lot of guests on who've discussed that. Um so I think that's such an important conversation. And and the thing that I'm hearing about women entering financial services is that a lot of them are going into financial coaching and financial therapy rather than financial planning. And so I think that's where some of the growth is. Um and I've had on a lot of financial planners who have become financial planners. They're they're CFPs, but they're coaching. So I I don't know if you've run into uh CFPs who've made that transition.

SPEAKER_02 6:10

They've made that transition. And I do believe they make that transition because they're doing it so much. If any financial advisor doesn't believe they're also not a therapist, a coach, a cheerleader, uh, they've missed the whole mark of what a really good financial advisor brings to the conversation. The financial side, especially with all of AI and the ease of doing investment allocation or figuring out what life insurance policy is really the best for this person, et cetera, that's become so much easier. So the advisor can actually spend more time on the human side, which is really, once again, that's what makes the relationship sticky. Um, that's what makes it that you really bring a lot of value to that relationship.

SPEAKER_00 7:12

And I think that's so important because you know, with the H AI, this is something that you know we've talked about a lot is like, okay, which advisors are going to succeed? You know, Microsoft did a study that financial advising is an industry that is going to have a huge amount of attrition uh due to AI. And I think it's because, as you point out, the financial planners who are the ones who are you know heavily focused on building portfolios and all those things, you know, AI can do the majority of that work now, now not always very well, and it's prone to hallucinations. However, it's getting there and it will be there very quickly. So, you know, as you point out, I'm a huge believer that the human side. I did want to touch on one thing because I do remember that powdered milk, and there is nothing yuckier than that powdered milk.

SPEAKER_02 8:08

It's disgusting, especially if it's not made the night before. And we had we rotated jobs, and it was always somebody's job to make it the night before, and it was four gallons of powdered skim milk. Oh man, if they didn't make it that night before the next day, it was disgusting to have to bring it.

SPEAKER_00 8:26

Yeah, so for anybody out there listening and you've had powdered milk, you know what we're talking about. So, but fortunately, I don't even know if they still make it.

SPEAKER_01 8:37

Um I saw it on a shelf. I saw it on a shelf. Yeah, I had I had nightmares, but when I walked by.

SPEAKER_00 8:46

So anyway, so we yeah, I I did take a detour there. Is you know so thanks everybody for bearing with us. Um, so you know, one of the things that you talked about is asking questions. And for me, after all this time, I believe the core thing that we can do to help people with their money is to empower them to be able to ask questions. Is in your mind, why is asking questions so powerful? Because it sounds like it's very central to your work as well.

SPEAKER_02 9:20

Yeah, it is very central to the assessments that um our clients, advisors, financial advisors give their prospects and clients. Because I think the further and further along you go in your career, the more and more you know, and the more and more you think you know what Tony should be doing in his life. Well, you see this list of stuff, but until you ask questions, you really don't know. And so our assessments cover eight mindsets about where they are now and where they want to be in the future. And I'll give one example. One advisor who was using our assessments with a high net worth client thought for sure they would be very focused on philanthropy. And when they looked at the assessments, it's a one to 12, you know, they were like a six on purpose. They really, that wasn't where they were at, right? It is where the advisor thought they were at, but it's not where they were at. What is more important to them was longevity, like what happens if something happens to me? And he was thinking, why would they be concerned about that? They know they have so much money, but he didn't ask the question. And having the assessment ask the question in the privacy of their own home that allowed them to. So whether you use the assessments or it's just asking the questions, it is about the client's future and where they want to go, um, not about where you think they should go. Like, what is it that is most important to them? This is also Tony White. I don't think AI, in the sense of a good advisor, the human side. Um, we call we say, keep it simple, keep it human. Um, you know, I have a blended family. I went through a divorce. I met my current husband when my son was in college. So I was a single mom the whole time I built my business. Um, his first wife had passed away. He's got three kids. We were just on the phone last week with our financial advisor, because even though I am one, having someone ask us the questions makes all the difference. It's that partnership of someone that can see outside of the little box that is our life or the big box that is our life. They can see around the corner. They've had experience with other people in your situation. So by asking the questions, they get such richness in how they really can support you.

SPEAKER_00 12:20

Yeah, that's it. That resonates so much. I was just taking a couple notes, is you know, we tend to forget that it really is about where the client wants to go, not where you think they want to go. And that's a trap that's so easy to fall into because you know, we get excited about planning technique. And you know, I know early on you even get excited about certain products, and you know, and you sort of start to think, you know, like, you know, if you have a hammer, every problem is a nail. And you know, and you tend to it it's an easy trap to fall into as an advisor, is to start thinking about what you think the client should do rather than thinking about where the client wants to go. And as you point out, the only way to know is to ask some questions and you know, and really to dig deep. Um, so you know, before we move on, is um do you want to share about what the passport package is since we're talking about it?

SPEAKER_02 13:20

Oh, sure. Thank you, Tony. It is um a two simple assessments, one for ages 45 and under who are accumulating, and one for 46 and above who are in that walkaway. I no one that I ever worked with wanted to retire, unless it is retire from what you don't love to do, right? You want to go to something, right? You want to walk away towards something. And maybe it is walk away to only certain parts of what you're doing right now. Maybe it is walk away to a volunteer position, maybe it is walk away to working with grandkids, whatever that walk away is. So there's two assessments, and each one covers eight mindsets, eight core mindsets. Where are you now on a scale of one to 12? And where do you want to be in your future on a scale of one to 12? And you can see with each one of those mindsets, if somebody rates themselves uh eight right now in one of the mindsets and they want to be a 12, and another one they're an eight, but they want to be an eight, you know where they really want to be is with the 12. And that's where the conversation needs to start with where they want to go in their future. Um, same thing with um with annual reviews. It's funny, Tony. I just finished my 30 hours of CFP CE, and um you're supposed to, as a CFP, do both quantitative and qualitative um review every year, minimum every year. And we all know the return on investment, we all have all the financial things, but where do they where do we show them the progress or backsliding of where they are on the human side, on that personal side? This is a way that they can do it. They take these assessments every year, quick five minutes in their own home. They get to sit with it and breathe with it. Uh during one of the one of the mindsets is wellness. During COVID, weight gain was 29 pounds on average, right? Wellness numbers came down. Imagine that, right? Um, one of the, and maybe for your change maker listeners, one of the biggest aha moments for me as a female, longevity mindset is about who's gonna take care of us if something happens to us. And interesting because the women tend to be the ones taking care of the older generation and the younger generation. That number, they are much, you know, they want to know what's gonna happen to them. Men aren't as concerned about it. So, as an advisor, that's something for me to know, right? That's something that's important in that conversation if that's where they are. So just questions, all questions.

SPEAKER_00 16:38

Yeah, well, I think that's really interesting, is you know, as you talk about longevity and the differences between men and women, it is there are differences. Um, you know, I mean, we can't stereotype and say every woman is thinking about this or every man, but but overall we do see some trends is um recently I completed the Impact Philanthropic Advisor, and that was a huge part of the curriculum was about how women think differently about philanthropy and how the philanthropic advisory community needs to shift to understand that. And it was interesting, is because out of my cohort, I was the only male. Um that's it's something about who's interested.

SPEAKER_02 17:25

Yeah. You know, the other thing, um, you know, I sold my firm in 2020, but I was in practice for I don't know, 28 years. In every couple that we work with, there's always a quieter voice in the conversation. There always is. One is always leading the conversation. And how do we um bring that quieter voice out? And the assessments is one way because each partner answers the assessment themselves, and then the advisor can go through it with them. I think that's really important for all of us, whether we use the assessments or not, to ask questions. I used to say, you know, okay, Tony, you're the one who always answers first. You be quiet. I'm going to ask the question, right? I would just make it a game to ask the question to the quieter voice first. Because the other one I was gonna hear from, right? We just right now, I think the average is 70%, somewhere around there, of widows leave their current advisor. I just want to take a deep breath on that one. My best friend just lost her husband a couple years ago, four different advisors. All four of them have been fired because no one had listened to her, they had always listened to him, right? And why does somebody want to stay? But it is the it is such a painful time, and you know, I lived it with my mother, we had no assets, so that wasn't an issue, but it's such a painful time. None of those decisions should be having to make be made right away, right? And that a widow doesn't feel in partnership, and then the other number is 84% of the next gen is leaving the current advisor. So, how are those questions in the conversation with the parent not including the next generation? So we've got a lot of work as an industry in those big numbers.

SPEAKER_00 20:00

Yeah, and I've heard even bigger numbers um on the percentage of widows. So I guess probably depends on the study. And I and that's not really important. So it's sad.

SPEAKER_02 20:10

No, but it's sad, isn't it? Yeah.

SPEAKER_00 20:13

It it is, and um it says a lot about listening to both partners. And I think that's something, as you point out, it's easy to listen and have a conversation with a person who is louder. You know, it's a squeaky wheel, you know, they're they're talking, and as an advisor, you're working for both partners, hopefully. And so, you know, listening to both partners is very important.

SPEAKER_02 20:44

Um I I think Tony, if I could say one thing. When you talk about your audience of change makers and financial fluency, um that's one thing that everybody could pay attention to, no matter what they're doing in their life, right? Listening to the voices in the conversation and making sure whatever conversation they're in, the quieter voices get listened to.

SPEAKER_00 21:16

Yeah.

SPEAKER_02 21:17

And making sure there's a there's a path, whether it is everybody asks a question around the table, or you know, you ask the quieter voice first. I mean, it is we all know, we all know that it happens. It's what can we do to break that habit? It's just a habit. That's all it is. We just need to break it.

SPEAKER_00 21:41

Definitely, definitely. And you know, and as you point out, I think the other part that's even you know, something else that advisors really need to pay attention to as well is that next generation and not engaging the next generation. For me, that always really that that. Puzzled me as much as not talking to both partners. Um, I I I'm in the San Francisco Bay Area, so I worked with a lot of same-sex partners. So that's why I keep saying partners.

SPEAKER_02 22:11

Yes, yes, absolutely.

SPEAKER_00 22:14

So, and that same holds true. Um, because as you said, it's that's listening to both voices, because no matter, you know, what relationship there is always that more engaged, louder voice. Um, so you know, do you have any oh sorry?

SPEAKER_02 22:32

I'm sorry, Tony. It doesn't change. And yes, same sex, you know, um heterosexual, two sisters in a room, four brothers in a room. There's always, right? So it it is paying attention in those group conversations. Absolutely.

SPEAKER_00 22:54

I I love that. Pay attention in group conversations because it can be hard. And it, you know, it's a muscle that you have to build where you're consciously engaging everybody in the conversation. And uh, you know, that is a leadership skill as well, is making sure that you're a leader, and even in your own firm, is to listen to all your employees because I've had on so many female financial planners who've left their financial planning firm to found their own. And almost always their financial planning firms are all women are pretty close to all women. And so, you know, that is a trend also that I've seen.

SPEAKER_02 23:42

Yeah, it it is. Um, and there's always people on your team. I've had big team, there's always people on your team that are quieter than others or don't think their opinion, they haven't been here long enough, which is actually a good reason to listen to them because they'll hear, see things that we wouldn't necessarily see. They're very, very important. Um, yeah.

SPEAKER_00 24:05

So yeah, so that's that's really important. So, you know, um, do you have any tips to engage um the quieter voice in the room? Um, what tips do you give people to to actually start doing that?

SPEAKER_02 24:20

As I said, the question, it's always in questions. And it is a asking the quieter voice first and you know, making a joke saying, okay, you're the one who's always talking. Just um I tend to make a joke however you do that. In a team, it's the same question going around the room to everyone, right? And if someone on your team is not, I mean, some people don't like to talk in public. So it is sometimes with our teams ahead of a meeting, we do it, you know, every quarter, every year. We do it with our team now. What worked last month? Well, this is something we learned from strategic coach. Uh, what worked last month, what didn't work last month, what do we need to put in place for next month for the team and for you individually? So that is a way that everybody can do it ahead of time because some people, you know, Tony, you're really good thinking on your feet, right? But there are some people that need time to digest the question and put things in order, right? So paying attention to their style as well. For the next gen um of clients, I think getting them in the room as soon as possible with the parents, most of our clients did not want to tell their adult kids the exact amount of money that they had. But going through the conversation about what will happen at somebody's passing, what how the things are in place, what we know about, what questions they have. Um, what is it about your own planning that you really like? What are do you have questions on your own planning? And sometimes those are okay to be in front of the parents, and sometimes they want those questions in a different meeting, which is great. That's when you know um that you've got them as a client because they want to have a meeting with you separate than their parents. And it is, we always had younger advisors with that next gen because, you know, I'm in the grandparent phase. I'm talking about grandkids, and the next gen is talking about new babies. And having a young advisor that is also talking about new babies or is also talking about new things with work or something like that is really helpful.

SPEAKER_00 27:08

Yeah, I think that's a great point is you know that the advisor should sort of not necessarily match up, but that there is something to be said. People like working with people who are somewhat like themselves, and you know, being in a different phase of life is something that's a little bit different. However, the main thing you say that I think is a super important message is it's all about communication, yeah. Is getting them in a room, having a conversation. And yeah, you don't need to have the parents talk about the exact numbers. That's not the important part of the conversation. You know, knowing that an account exists, perhaps at a certain institution is important, or understanding why the parents have made certain decisions, that's the important fact, not the details. The account balances don't matter.

SPEAKER_02 28:02

Um Yeah, and it's details. You as the advisor can help take a lot of the pressure off of the family in knowing who's going to be the executor, who would be this, who would be this, where are the passwords? Those things that are um critical at a time when someone, you know, is in the hospital or is not able to do it, who has power of attorney, who has power of health care. Those things, you know, no matter what age, are really, really important to have. And no matter what the structure is in the family.

SPEAKER_00 28:39

Yeah, that that is so important, is to know the roles. So, Colleen, to wrap up, I have what's called the get ready hot take trio. These are three quick questions that I ask all of my guests. Okay. The first one is what's one money myth you're trying to break?

SPEAKER_02 28:56

A money myth now. I have enough. Um, I have this thing in the back of my head. That's a really great thought. Um that we have enough, which we do. Um, and there's always room to to make such a difference with money. I I think we have I from my background, I think I have some some money things about that. That's really interesting. Yeah, that it's great, that more is fine. More is great.

SPEAKER_00 29:34

Yeah. I and I want to go back to, you know, the the topic of enough is I think that's something that we overlook is, you know, you know, we're constantly saying, okay, accumulate, accumulate, accumulate, save, save, save, save. But, you know, sometimes there's just enough. And, you know, the client can switch over to their walkaway, you know, phase of life because they have enough, and that's different uh for everyone. And as you also said about making a difference with your money, is you can have an impact with your money, both with your values and what you support. And so I think that's such great advice is to think about the difference you can make with your money. And Mackenzie uh Scott, Jeff Base's former wife, is the perfect example, is she's giving away just an incredible amount of money, but having just such a huge positive impact on so many organizations. Um that you know, it's incredible.

SPEAKER_02 30:41

And a lot of it had to do with people who gave to her at a time when she didn't have anything. Right? So, yeah, it is what a role model.

SPEAKER_00 30:57

She is. I mean, she's a role model for impact giving. Um, so Colleen, let's get out the time machine for a minute. If you could go back in time, knowing what you know now about money, what advice would you give your younger self?

SPEAKER_02 31:14

Um that money is a habit. Money is a habit. I've worked with um a couple lottery winners and stepped left from a couple lottery winners. And what I learned then was if you have the habit of spending more than you make, it doesn't matter how much of a lottery you win, like 60 million dollars, it's still gone. If you have a habit of saving, you'll have it. You'll have that money, right? It doesn't matter how much it is. So I would tell myself that money is a habit.

SPEAKER_00 31:53

I I love that. And, you know, I've had um guests who, you know, work with professional athletes, and they've said the same thing, you know, the professional athletes make an incredible amount of money, but they they spend an incredible amount of money. And, you know, it's and I've heard about, you know, I mean, we've heard about the lottery winners who go broke. Um, and you think, well, how could that possibly happen? You know, and I think you know, you explain it very well. So the final question is what is your number one tip to change the way we think about money?

SPEAKER_02 32:33

I would go back to habit. Um, it's an Aristotelian quote. People are probably tired of hearing me say this, but it is we are what we repeatedly do. Excellence then is not an act, but a habit. And that we use money, that it's a habit, that it's not about us being good or bad. It's just a habit. And we can change those habits. We can become more conscious of money, we can become more conscious of the spirituality of money, we can become more conscious of all those things that money can do. Um and it it is, it's a habit.

SPEAKER_00 33:15

I love that. That's such great advice. So, Colleen, where can people learn more about you and the passport package?

SPEAKER_02 33:22

Yeah, you they can go to thepassportpackage.com. We'd love to talk to you. Um, and also I am on LinkedIn under Colleen Bowler and CNJ Innovations has a LinkedIn page as well. And we have a website, like I said, thepassportpackage.com. You could take it for yourself. Um, there's some great action items on there to do.

SPEAKER_00 33:47

Yeah, I took it and it was very insightful. So um I appreciate the resource. And for everybody watching and listening, if you do have access to the show notes, you can go to the show notes and you'll find links to the passport package, uh, CNJ Innovations, as well as Colleen's LinkedIn profile. Um, so Colleen, thanks for joining us on Get Ready Before Life Happens.

SPEAKER_02 34:08

Oh, Tony, I really, really appreciate it. And to all those change makers out there um that are listening to this, that are fans of Tony, thank you for listening and so appreciate all the amazing work that you are doing and being. Thank you.

SPEAKER_00 34:28

I really appreciate it. And I appreciate all the work that you're doing as well. So um that's fantastic. And thank you, everyone, as always, for tuning in to this episode of Get Ready Before Life Happens. If you learned something today to change the way you think about money, please be sure to subscribe and to share with a friend. You can also go to my website at tony steward.com to join the get ready movement and receive my newsletter and access to free resources. Because when life happens, the way you think about money matters, we're gonna be able to do this.