Sheryl Hickerson on ‘Sistering,’ Females and Finance, and Money Dates

Journal of Financial Planning: April 2021

WHO: Sheryl Hickerson

WHAT: CEO of Females and Finance

WHAT'S ON HER MIND: “There’s a lot of focus today on the profound diversity needs out there, and yet we’re asking these same professionals who are already taxed out to be the voice of the change.”


What are some of the challenges that women in this profession face and how can they address them?

I’m going to answer it from two places. First, our Black and brown professionals are already taxed. There’s a lot of focus today on the profound diversity needs out there, and yet we’re asking these same professionals who are already taxed out to be the voice of the change. It’s double taxing them. It’s not right. 

Many times, organizations realize, ‘We have this diversity problem. So and so, you’re a person of color, you should be the voice of our company on this topic.’ I’m speaking to professionals who come to me and confide, ‘I’m exhausted of this, Sheryl.’

The other part of the issue is we have our non-people-of-color professionals—however they identify—who are trying to navigate how to best support everyone.

I think that’s an interesting problem because we’re telling everybody they should be building better, more diverse practices, yet we’re not providing education around how to do that.

An example: we’re asking white professionals to go into an underrepresented community and they’re not even certain if they’re supposed to say Black or African-American, so they’re going to do nothing because they don’t want to make a mistake.

We need to be providing more soft skill resources to all professionals. I think we need a lot more emotional quotient training to understand when and where to pull on or to give space to our professionals. There’s just an awful lot being asked of some [and] not enough being asked of others, and we need to find harmony.

As a community, financial services has never really had difficult discussions around the issues. In fact, at Females and Finance, we brought a racial equality specialist into the group after the George Floyd murder. Zaneilia Harris, CFP®, connected us with this amazing expert on this topic and we had a two-hour Saturday deep dive into how we could support each other through this. The women in our community were shocked that we were providing a resource like that and said, ‘We want more.’

And so we continue to provide more. We had a high-functioning anxiety webinar for our members. This webinar was with a business therapist and a mindset coach who came in to work with our members. A lot of women are operating with high-functioning anxiety—especially right now with homeschooling and families and running businesses—so we’re trying to meet their needs.

We need more of those kinds of resources. That’s where sponsorship really helps bring in and support women.


In a recent interview, you talked about how female planners can pick up on non-verbal communication and read into what’s really going on with clients. How do all planners sharpen that skill?

Women—and I realize I’m overgeneralizing here—do a good job of hearing the personal currency conversation much more than just looking at the numbers.

An example of personal currency is when we started off talking, I shared with you [that] one of my deepest loves in my life are my nine grandkids. I love being a grandmother. I will make the time; I will show up. Anybody who knows me knows that’s a really important part of who I am. Women hear those things differently.

Men have told me, ‘I hired a woman in my office because I don’t hear those things so well.’

This is where I think men and women are better together. I think we can really help those who don’t have the gift of sixth sense—hearing those little subtleties—when we partner with somebody who has more emotional depth and can connect to it. It’s just going to help improve your bottom line all around.

And vice versa—as somebody who hears the little things, I love when big-idea people come in and help frame some of it, too. We work together well that way. I think having more conversations and more dialogue around this would be really smart.


Tell us why you established Females and Finance.

I have been a professional speaker on social and digital marketing for many years. I was showing up at a lot of events—about 25 to 40 a year. In 2017, I spoke at an event in San Antonio, Texas, and as I stood up on stage, looking out at 300 cheeks in the seats, I remember not seeing a single person of color—but there were four women.

As I was standing up there, I realized I kept waiting for someone to ripple the pond of change and I decided I needed to be the rippler.

I left that conference and I spent most of 2017 interviewing hundreds of women in a variety of subject matter expertise roles within financial services to ask them how they got here, [and about] their training and advancement desires because I was intimately concerned with our retention and attrition rate.

I’d heard [author] Glennon Doyle, who’s Abby Wambach’s wife, speak and she had said the idea of taking architecture—whether it’s people or organizations—that are unstable and bolstering it, is called ‘sistering.’ I wanted to create a community where we sistered professionals who are most at risk. Who is most at risk? Anyone outside of what financial services has historically been built on—which is white, middle-aged or older-age professional males. For example, if you have a Black female who speaks a second language or who is gay, the further they are from that [traditional image of financial services], and the less sistering is going on. And that’s what Females and Finance is doing—drawing the circle around them and bolstering up the community.


How has the Females and Finance community grown?

When I first started, I don’t know why but I had a goal of 200 women. It was just this made-up number, and at day eight, I had 200 women that I had reached out to and said, ‘Would you like to do this? Join me.’

I was so pleased with the response, but I was also a little bit shocked. When you look at the numbers, month after month, our average growth ranges from 76 to 123 [new members] per month. I do vet every woman who comes into our community … because for change in our profession to happen, we need those who want to dynamically make financial services different. And I have that. As proud as I am of the numbers, the engagement tells the bigger story.


What are your future goals for Females and Finance?

When I first started the group, I had no idea where we were going. I just knew I got tired of being served what has always been given and I wanted to create something fresh. I went to the women and asked them, ‘What would you like? What would be different?’

I want to continue to keep our networking part free. I don’t know of very many places where you can go and get quality networking today that you’re not paying a premium cost. In an environment in financial services, we’re paying for so many things, between fees and offices—everything has something tied to it. I was very concerned about keeping networking free, so we can keep everybody engaged.

The first two years I paid for this 100 percent out of pocket. I took no sponsorship dollars and that was on purpose. I was offered it and I declined because I really wanted this to be completely grassroots growth and activism going forward.

Now, where we are, I can go back to organizations and very clearly articulate, ‘This is what the women—and the men, because we do have men on our platform as well—want.’

One example of how the community works: if members have a question about software or financial technology, they come into our ecosystem and ask the question, and then the women crowdsource that information based on their own experience with that particular software or situation.

I had one woman who reached out to me and said, ‘What I love about this organization is I can ask a question, and I can go get coffee or drive to the office and I can come back an hour later and 17 women gave me the answers I needed, and then some. I can’t get that if I were to drop a ticket and wait for a support person to give me the answer.’ This is much more holistic help.

As far as our long-term goals, I’m really excited to see the women grow their individual education and business practices and be able to foster better relationships that cross-pollinate. What I mean by that is when COVID-19 happened, our insurance and investment people were great resources, but it was our bankers who were stellar. Our bankers totally rocked it. They were like, ‘Here’s how you get PPP money. Here’s how you file a forbearance on a home without wrecking someone’s credit. Here’s how you restructure debt so that people don’t go under.’ The bankers really shined, and it helped our insurance and investment professionals be able to be better stewards of finances and act as better fiduciaries.


Talk to our readers about ‘money dates’ and how clients can use them.

At the Hickerson house, Fridays are our movie night, but on Sunday afternoons, we have our money dates.

My husband, Darrell, is also a financial service professional. We were both divorced around the same time, so we both experienced financial frustration in our previous relationships. And I’ll never forget when I was dating Darrell, he would go into his office and sit down, and he had his own little date with himself to do his finances. I was like, ‘I do that, too!’

When we got married, we dedicated anywhere from one to three hours—usually on the weekend—where we sit down and we talk about our money. Is this the best place for our money? How are our investments looking? Where is our debt-to-income ratio? We really look at it all. Bank account balances. Our loans. Is it time to do refinances?

We already had one money date this week and we’re having another one on Sunday because we want to put a deck on the house. Decks apparently range [in price] from $9,500 to $42,000—who knew? So we’re trying to sit down and figure out: are we going to stay in this house long enough to get the return?

Money dates are so important because we’re on the same page. We don’t fight about who spent money on this and who spent money on that.

Adam Grant’s book, Give or Take, says there are three types of people in the world: givers, takers, and scorekeepers. A large percentage of our working population is scorekeeping. That usually comes in the sound of, ‘You spent that, so I’m going to spend this. You got lunch last week, so I’ll get it next week.’ We like to keep score because there’s a balance sheet to it—we’re trying to keep the balance.

Money dates are so critical to get rid of the scorekeeping. If you can get the scorekeeping down and decide you’re on the same page, you go forward. The best part? We have very few disagreements about money.


Is there anything you want to add that we didn’t ask?

One of the things I hope for people is [that] we can all just influence one person in financial services to stay in financial services, or to bring one person in and give them a platform. For example, give a college student, or a veteran coming in as a career changer, a community they can be welcomed into, so they’re not left alone.

I really think we could all make financial services so much better, bigger, broader, and really get into the communities where there isn’t enough representation today. But it’s going to take a commitment for all of us to do that one right thing. Sometimes, that’s a little bit more difficult, but I sure try every day