Hiring & Talent

How Women Can Break into Financial Services Careers and Why They Should with Stephanie McCullough

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We talked with Stephanie about:

  • The power of a human-first approach and how she creates a safe space for clients
  • Tips for finding the right fit financial advisor to meet your specific needs
  • How she provides support and education to help make financial planning less intimidating 

About Stephanie McCullough:

Stephanie McCullough is a veteran financial advisor with 27 years of experience. Inspired by her father, a long-time financial advisor, she transitioned into the financial sector at age 30. Recognizing the value of his work, she decided to join his business. A pivotal moment in 1998, when she met a coach at a chamber of commerce event, significantly shaped her professional journey. Stephanie founded Sofia Financial in 2011 to focus on empowering women to confidently take control of their financial futures. She creates a safe space for open and vulnerable discussions about financial matters.


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Full Audio Transcript:


Lauren (00:05):

Stephanie, welcome. Glad to have you here today.


Stephanie (00:07):

Thanks, Lauren. I'm excited for the conversation. 


Lauren (00:10):

Yes, I'm excited to hear your story and how you have landed in the financial services world as an advisor, a firm owner. You are a podcast host as well. So many things, and I'm also excited to really pull back your story with the bend of how that can help others who are interested in landing in financial services and the plethora of things folks could get involved with. So I'm going to hand it over to you, if you don't mind just sharing a little bit about your background and journey and how you got to where you are today.


Stephanie (00:43):

Sure. So I'm a 27-year financial advisor. I was a career changer, so you can start doing the math, right? I was 30 years old when I changed careers and I really didn't know what I wanted to do. I had grown up with a father who was a financial advisor, and I literally did not want to do what he did. Then I got into the real world. I'm like, oh, I kind of see how this could be beneficial to people. Maybe I can pitch to him that I could work with him. And of course, he was like, one of my kids is into the business; you had me at hello. I didn't really need to make my whole big pitch but it wasn't all sunshine and roses from there.


Lauren (01:21):

Okay, so tell me more. I think it's fascinating that your father was an advisor, so you grew up in this world and you saw what the lifestyle was like and just that day to day, okay, so how did that all go? So you gave the pitch, it was like, yes, please, and then where did it go from there?


Stephanie (01:39):

Right. Then I started in and I had to get all my licenses and everything, and there was one role model. I mean, there were some other advisors in the firm but really it was kind of silos and everyone had their own thing. So my father was my role model, and he has an MBA from a fancy school, and I do not, and he's a natural born salesperson and I am not. I was like, oh, shoot, I can't do this work. I'm not like him. Now I'm in this life sentence called family business. What the heck am I going to do? How am I going to make this work?


Lauren (02:11):

We actually just did a recent interview too, where we talked about bringing folks in on the family business side and the complexity of that. So what did that feel like? I mean, how did you navigate those waters, right? Because there's this internal pressure, external pressure, and then this optics to manage that is a little different than just joining a company as an employer.


Stephanie (02:33):

Totally. The optics were really big to me. He had long-term employees. I worked for a couple months after I graduated from college, so eight or more years before, and some of the employees are still there, so I want them to think well of me, and I really made it a practice to ask lots of questions, try to learn as much as possible. I had nothing to bring. I had no knowledge or anything but my father had a partner at the time and his son had joined and he'd come from an MBA background, and he worked at a big company, and so he had suggestions right away, and I saw how that was received versus the more curious part. So it was kind of a blessing and a curse. The good thing was I wasn't getting fired because I was the boss's daughter. Yes, that's a privilege. And it was tricky also but my father had a lot of corporate clients. He did a lot of retirement plans and non-qualified types of benefit plans, so I didn't have to be in a sales role right away. Thank goodness I could be support for the plans, do the enrollment meetings, do one-on-one meetings with participants, where thank goodness I didn't have to sell anything because I was terrified of selling.


Lauren (03:48):

Yeah, I feel like it's funny because in this space you think you get into the numbers side of it, which there's a component of that, but the more and more I talk with advisors, there's so much more, there's a psychology side. You're working with people on really personal deep issues. There's a sales side as you alluded to too. It's such a people business. So how did you create that environment for you that felt safe to be able to lean in to kind of find your way despite all these other pieces going on?


Stephanie (04:16):

Yeah, early on I met someone, so this was 1998, I met someone at a chamber of commerce event who called himself a coach. I'm like, coach, what do you mean? You coach volleyball? I don't understand. And then he said, just do a free session with me and you'll get it. And by the end of the 20 minutes I was weeping. I'm like, I need to work with you. Help me, help me. Because I felt so stuck and I didn't know how to do it my way, and I didn't know how to get out. So that was really helpful. I worked with him for a couple of years just kind of thinking through all the parameters of it while at the same time still doing the work. And it really was a gift to be able to have so many one-on-one conversations. We did the retirement plan at a hospital, and I would sit outside the cafeteria and talk with anybody who walked by or I would have one-on-one meetings with everyone from the CEO to the people who cleaned the rooms. And I felt confident in that type of environment because I understood the retirement plan and they understood their life. So I felt like I could help in that way. So it was kind of learning by doing. And if I messed up one meeting, I wasn't going to lose the whole client. There were like 3,000 employees. So it was a low stakes way for me to learn, which was really helpful.


Lauren (05:32):

So sort of getting that outside counsel to be able to have that, I don't know, it's easy to be very in the woods kind of thing, to have that bird's eye.


Stephanie (05:41):

And I had no direct colleagues. Everyone else was either an employee or an advisor who's been doing it for 40 years.


Lauren (05:49):

There's too much of a gap. I know. I like that. That's an observation, right? Because sometimes when you come into your particular role, if you don't have someone who's sort of adjacent just a little bit, a few steps ahead of you, it's hard to be able to relate. Yeah, I did that. Just come on, get it kind of thing. And that upkeep. So we always sometimes also talk about it's changing but there's still a lot of men who are in this world. I know you have a focus on specifically working with women, just sort of non-judgmental approach as well. How did you get to that just over your career and what did you observe to be able to anchor in on that focus?


Stephanie (06:35):

Yeah, that experience with the hospital really was instructive because back then below the C-suite and the doctors, you had majority women. You had maybe a couple women up in the executive ranks and women doctors but not as much as it is today. But everyone else — the nurses, the technicians, the people working in the cafeteria — it was mostly women. So I had so many conversations with women who had let some man in their life handle the big financial decisions, like the long-term stuff, the investments, they probably pay the bills, but anything bigger or future oriented a lot of them delegated and it didn't always turn out well, whether it's the husband who left for the younger girlfriend or a brother-in-law who picked the investments that were right for him but not right for the woman. It just didn't always go well. And then I heard lots of sad stories about people being poorly treated by our industry, sadly, whether they were sold a high commission annuity and then the guy never answered the phone again, just too much of that. And then the head-in-the-sand approach. I always remember meeting with this one housekeeper who was 62 years old. She had worked at the hospital for nearly 30 years and never signed up for the 403(b) because it scared her. She was terrified to come meet with me.


Lauren (07:56):

It was the educational component.


Stephanie (07:58):

It was like, I don't understand what this means and how I sign up. So she came in, we walked through the forms, I helped her figure out the decisions, and at the end she gave me the biggest hug. She's like, I was so scared to come see you today. And I thought, oh my goodness. That gave me a lot of confidence. I don't understand everything and I can't answer every question under the sun but I can help women like her get on the right track. That was a catalytic moment for me.


Lauren (08:28):

Are there things you do that you feel like are unique in the way you propose questions, the way you help to educate this group target you work with? I mean, because being able to sit down and to be able to say, here it is, here's my story. That takes a certain skill set and a nuance to be able to pull that out in a way that feels like honest truth, to really pull it out, and then that's going to impact the quality of work you do. So if you can't pull it out, you're not going to get to the right end result. And then that's going to have an impact. So how do you help to nurture and pull that out so it does feel non-judgmental, and so folks do feel comfortable having these conversations with you, or are there certain things you're even doing to educate yourself so you know how to pitch those right questions?


Stephanie (09:18):

Well, I think you said unique at the beginning, and I don't think I'm unique. All the financial planners I hang out with have a similar approach, and I have found those people over the years who really have that kind of human-first approach and the life planning. I took some George Kinder training. I was like, ooh, this is cool. That all helped me. But I think it's creating a safe space to talk about things. And I say right upfront to someone who comes in — they don't come in off the street anymore but they google me and set up a free chat. I'm like, we're going to have to talk about all the things, because money is a means to an end. It's connected to all the most delicate parts of your life, your feelings of security, your relationships, your career, all these things.

It's going to be emotional. I just try to lay that out there right upfront. And I tell them in the first couple of meetings we're not going to talk about numbers at all. I'm going to ask questions, and the reason we do it is because the money should be in service of everything. I want to get at what's important to you, what your priorities are, what your values are, what you worry about, who your people are. So we're going to talk about it all. So I don't hide it and sneak it upon them. It's just on my website. I think it's very clear this is the approach we're going to take, and people self-select then if they're willing to have those conversations; it's a very vulnerable conversation. They have to get financially naked and talk about all the stuff. So I don't even know if I've had that many people who weren't into it. It's just if they're there . . .


Lauren (10:58):

They're ready to talk.


Stephanie (10:59):

I think. So I have had people who've tried to refer people like, oh, my cousin totally needs to talk to you. She'll come when she's ready. You can't force it.


Lauren (11:09):

Yeah, there's a firm we've worked with and they have a centerpiece in their office. It's this coffee table. It's a really ornate coffee table, and they've got chairs around it, and it's very purposely set up that way because it's more of a conversation table; it's circular with people all around it. It's not this sort of big thick table between you and the advisor, what have you, to just be able to just have these honest conversations and then you can go to the conference table and go through all the numbers or what have you. So I like that there's a warm trust-building component.


Stephanie (11:43):

I used to imagine having a series of offices around the country in houses. So do you want to have this meeting on the front porch or do you want to walk around? But then of course, everything went remote, online. A lot of my clients are all over the country so I don't need a space.


Lauren (12:00):

That's right. And sometimes it's just about having those conversations wherever you are, which is also a benefit to that as well. Okay. So you shed a little bit of light on what that day-to-day is, how you built up your career. Could you share a little bit more about someone who, I don't know, maybe they're thinking about getting into this space, they're thinking about getting into the advisor community. Maybe it's not even being an advisor, it might be on an ops team or in a different capacity. Where do you even start and what kind of things were you looking for to help just learn along the way and get that fit?


Stephanie (12:37):

Yeah, I think it's so interesting because when I first came in, I saw the one model being my dad, and I thought every advisor was like him. And every advisory firm was like that. And I've spoken to women who've come into different structures of doing this work, and maybe it's felt like a good fit or maybe it hasn't. And they've been like, oh, this doesn't feel right. I guess the industry is not for me. Goodbye. And I'm like, we still want you. We still need you. Right? So that's one. I think one thing I would say is there's lots of ways people do this work, even advisors in the same company, in the same overall structure might have very different approaches. So talk to as many people as you possibly can and kind of suss out like, oh, does this feel right to me? Does this feel kind of icky? Because we all know in every industry there are those who maybe do things more the way you would like and those who don't. And they might be sitting in offices right next to each other.

And I think with anything, right, I advise my clients this. Step zero is to get clear on what's most important to you, what you want, what you are hoping to get out of this. Why would you like to work in this industry? Is it because you think you make a lot of money? Okay, that's one route. Or is it because you’re fascinated by investing? Okay, that's interesting. Or do you really like the people conversations? There's lots of different ways. I love it because there's always something new to learn, and I love talking to people and hearing their stories. That's fascinating to me. But I think we have this reputation problem that it's all about numbers and spreadsheets and math and investments, and that's not it. Like you said, it's a very human conversation, a very human business.


Lauren (14:29):

We had a dinner with a young woman, I don't know, maybe two years in her career or something like that, as entertaining, shifting offices, and we were, my husband and I were giving the advice of just, why don't you just reach out to cold out to people and just say, I'm new in this space and I'd just love to learn from you that maybe your best place is to work at a company or you did this. Do you mind just giving me 30 minutes of your time to just share a little bit more? It's that giving back component and paying it forward to be able to help others. I've often spoken to undergrad classes and you see eyes light up when even questions like, okay, what do you need to put on your resume and this and that? And I'm like, sometimes it's just about putting your neck out there. There's that piece of it too but just asking questions as you're alluding to as well.

Stephanie (15:20):

Do you mind? Totally.


Lauren (15:22):

Yeah. There's so many industry groups too. Where would you recommend people start to even be able to learn a little bit more online resources or maybe conferences or things? Maybe people are already in their career and they're in their seat but where do they help to continue to learn and be able to build these relationships with others?


Stephanie (15:39):

Yeah, I mean, one resource I think is really fabulous, and it can be for people new in the industry or people who've been doing it a long time, is the externship that Hannah Moore and her company does, Amplified Planning. It used to be associated with FPA, and now I think it's just Amplified Planning and doing it. It's a low ticket, pretty intensive, really window inside to what the work is actually like. And they have advisors in different capacities speaking, and you learn different softwares. I think it's kind of a low stakes way to try it out, to be able to sit in the seat or simulate sitting in the seat of an advisor, of a financial planner, and see what that's like.

At the same time, that's not the only way to do it. So that's one interesting way. It goes over the summer. I think it's starting up soon this year for 2024. And then there's groups. There's all kinds of groups. There's the Financial Planning Association. I belong to a group called the AGC — Advisor Growth Community. We've done a mentorship program with students at Michigan State in the financial planning program. I think if you have one or two conversations and it doesn't feel right, don't give up. And I remember when I was doing informational interviewing back in school, always ask the person you're talking to, who else could I speak with? Who else do you think would be a good idea for me to have a chat with? And then your tree kind of builds from there.


Lauren (17:08):

Yes, there's so many conferences. Kitces has got a bazillion conference list directory.


Stephanie (17:14):

And a lot of them have free tickets for students if you're in that phase.


Lauren (17:21):

NAPFA, of course, is a great resource. Any other thoughts for folks who might be kind of going through an interview process? They always say they're just not interviewing you but you're interviewing them — things you think folks should look for to be able to feel out if it's the right fit or not.


Stephanie (17:49):

If you can ask, what does an average day look like? What are the responsibilities of this task? Who will I be interacting with on a regular basis and what's the path from here? Is there a career path? In a lot of the smaller firms that might be difficult for them to lay out for you but it's still a good question to ask. You can say something like, I value continuing to learn and develop. What opportunities might there be a couple years down the road? What can this grow into?


Lauren (18:20):

Yes, yes. So true. I know for folks, we're at a place where we're going to or we've offered them the position too. We've often offered, do you want to talk with someone else on the team just to feel what it's like? So if you're in a place where I feel like you've got multiple offers, you're trying to figure out what's the right energy, because when you commit to something, you're committing. Just like when you work with an advisor, most advisors, especially in the fee-only space, I mean, they're working with folks for a long time, so it's a long-term relationship, just like a career. You're working with them for a while, so it’s important to be able to figure that out. I think so.


Stephanie (18:57):

Right. How big is the team? I mean, my father used to say, we're a small group, everyone does a little bit of everything. Or in a bigger firm, you might be really in a small slice of the business, which could be fine but maybe even will I have an opportunity to see other parts of how this whole business works? And to me, I don't want to put judgment on it but a certain type of boss will be like, yeah, you're interested. I want you to see the whole thing and really have an understanding of this career because they want you to stick around. They're investing in you.


Lauren (19:34):

Yep, absolutely. Well, I also just really appreciate, just to sort of take a step back, I know we've been talking about getting into your career in this industry but you called out that part of your growth story was like you invested in yourself, you got to a coach early on, and then now where you are today you're paying it forward. And then to be able to continue; I'm sure that theme continues. How do you continuously invest in yourself? As I tell my team, we're always learning. I'm like, I'm learning. I don't have it perfect. I'm not over here on some pedestal. I'm like, I totally am learning all the time. We're learning together. So I really appreciate you're like, I'm also constantly learning and being able to share some of those lessons learned along the way.


Stephanie (20:20):

Yeah, I mean, I think that's exciting. And also at the beginning it gave me fear like, oh, shoot, I don't know enough yet. I can't go advise a client. I don't know all the answers. And I remember the day I was talking to a surgeon at this same hospital, and I was so terrified he was going to ask me a question I didn't know the answer to, and he asked me a question and I asked him a clarifying question back, and it turns out what he really wanted to know wasn't the initial question that I was like, I don't think I know the exact tax treatment of this exact thing.

I said, oh, that's interesting; why do you ask? It was something totally different. I was like, oh, even with my knowledge, which I feel like isn't big enough, it's still more than this surgeon knows. I can be helpful to this person.


Lauren (21:09):

And be able to help kind of guide them down that path. Sometimes I feel like folks, they'll say things but it's about the listening and the being able to, as you said before, kind of guide people down that right path because of experience.


Stephanie (21:23):

Yeah, totally. And I don't know, my approach is always like, I'm not telling the clients what they have to do. We're collaboratively coming up with a plan together.


Lauren (21:32):

Absolutely.


Stephanie (21:33):

They know their life and what they're trying to accomplish, and I know the language of the financial world and the different tools and the different tradeoffs and pitfalls, and together we come up with the action plan, so I don't have to know all things.


Lauren (21:44):

Yep. Well, Stephanie, thank you so much for sharing about your background and your journey to get to where you are today but also some tips and tricks for folks thinking about potentially getting into this industry, maybe even thinking about making a shift and where to start or what have you. Any other final thoughts you think would be helpful to share?


Stephanie (22:04):

Oh, I would just say I've talked to women before and I tell them what I do and they're like, I can't do what you do. I'm bad at math. I was like, I got calculators, I got computers. The math is not the thing. It's really diving in and asking questions and then just shutting up and listening. Money is so fraught, right? It's a neutral thing in principle but it's not neutral. We have so much baggage attached to it. So many stories we picked up from our childhood, so many kinds of valuations the world puts on it that it really makes decisions challenging for people. And if they don't have someone to talk to to help them figure it out, they can just cycle around in their own heads. So it really is a lot of that, right? Walking with someone, like you were saying, as opposed to directing them. And that's so fulfilling when you can see someone take steps forward when they’d been frozen before. It's really a very rewarding career.


Lauren (23:03):

I love that. Thank you for sharing too. And also for folks who are listening, takebackretirement.com is where your podcast is at. So to get more in-depth tips and tricks, I'm sure a little bit more technical or maybe a little bit more different topics or what have you is a great place to start to hear more. So thank you again for joining us today.


Stephanie (23:23):

Absolutely. Happy to.

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