Leadership, Delegation, & Time: Preparing Your Financial Advisory Business for the Next Gen with Daralee Barbera

Introducing Daralee Barbera, a trailblazing leader in financial services, who’s on a mission to elevate the profession through collaboration, personal development, and inclusion. 🌟 Recorded live at the NAIFA e3 conference, Daralee Barbera and host Amber Stitt dive into practical leadership strategies, building community, and the power of letting go to grow.

In this episode, you’ll get her take on succession planning, executive coaching, time management, task delegation, and why the “3 C’s” (Community, Connectivity, Communication) are game changers for your business and relationships. Whether you’re new to the industry, or a seasoned advisor, these insights will inspire you to take action and create a lasting impact—for your clients, your team, and future generations.

Let’s talk leadership, legacy, and designing a business where everyone truly belongs and thrives. 💪

📽️ To watch this podcast:  https://youtu.be/Q0kG46aMAyM

🔗 To connect with Daralee Barbera:

📲 Website #1: https://divprocoach.com

📲 Website #2: https://www.daraleebarbera.com

📲 LinkedIn: https://www.linkedin.com/in/daraleebarbera

#financialservices #naifae3 #taskdelegation #successionplanning #diversityandinclusion #womeninfinance #pathwayswithamberstitt #amberstitt #daraleebarbera #diversifiedprofessionalcoaching #divprocoach

📻 Thank you for tuning in to Pathways!

🔗 Connect with Amber on Social Media:

• AMBER’S INSTAGRAM
• AMBER’S LINKEDIN
• AMBER’S FACEBOOK

📲 Be sure to visit Amber's website:

www.AmberStitt.com

🎬 And remember, let's take action today!!!

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Transcript

Daralee Barbera [00:00:00]:
This is what helps us just be better. And I think that everyone I know who's in this profession, they just want to be the best that they can be. Because really, if you think about it, it's such a responsible field and profession to be in, because so many people are counting on us and counting on everyone to just be the best version that they can be because they're relying on their financial professional for things that are not only important in their life at that moment, but it becomes multi-generational. And if you're a business owner, so many families are counting on you. And so to get it right is like that positive domino effect that just goes around the world.

Amber Stitt [00:00:41]:
Hello and welcome to Pathways e3, a special edition of Pathways with Amber stitt. The Pathways e3 podcasts were recorded with special guests who were attending and collaborating at the NAIFA e3 conference in Newport Beach, California in September 2025. Let's join the conversation. We are live at e3 with one of

Amber Stitt [00:01:02]:
my friends, Daralee, and I'm so excited to have you with us today during conference.

Daralee Barbera [00:01:07]:
And I'm so glad that you invited me to come visit for a little bit.

Amber Stitt [00:01:10]:
We get to spend time here and also on a panel. So I'm so fortunate because we don't get to see each other really at all. But we are intertwined in different ways, so I'm glad we could spend some time. You are a prominent figure in our industry. I can't even name the accolades and different things that you have done. We will surely support you in the description box in our post production. So I want to jump into the goods of why we're here and the mission behind e3 and NAIFA. So coming into this week, we've talked through email and we were just kind of getting ready for the week.

Amber Stitt [00:01:44]:
But what's really been on your heart, like energizing you? What's been on your mind? Why are you excited to be here?

Daralee Barbera [00:01:49]:
Well, besides that this is a fabulous location from the moment that you pull up and just the energy is wonderful and it reminds us why we need to get out the door and go to conferences. It just helps it, and especially e3 Collaborate. The agenda is so full. I was just looking at the marquee outside and taking a picture of both sides of it because I don't know that I've seen so many sessions in such a short period of time.

Amber Stitt [00:02:16]:
There are so many. I'm like, I can't go to this. I'm meeting some amazing people and getting private time. But I'm like, I'm missing some of it because it's so good.

Daralee Barbera [00:02:23]:
Exactly, and this is what helps us just be better. And I think that everyone I know who's in this profession, they just want to be the best that they can be. Because really, if you think about it, it's such a responsible field and profession to be in, because so many people are counting on us and counting on everyone to just be the best version that they can be, because they're relying on their financial professional for things that are not only important in their life at that moment, but it becomes multi-generational. And if you're a business owner, so many families are counting on you. And so to get it right is like that positive domino effect that just goes around the world.

Daralee Barbera [00:03:07]:
But if we just don't get something right, it can just go wrong in so many ways.

Amber Stitt [00:03:12]:
So, in education, but then also meeting other thought leaders, learning from each other.

Daralee Barbera [00:03:16]:
Absolutely. And so far, because this is just our first day here, the presentations from the main platform have been very personal and about personal development. And you'd think it was about some basics, but people were taking pictures of the screen. Like basics about setting goals, figuring out that if one of your team members can do that task, instead of you, let them do it. So that then that frees you up to do the things that only you can do, which I can't count the number of times that I've talked about that because it's so important that the leadership role that everyone here has.

Daralee Barbera [00:03:57]:
It all varies. The important thing is that we still got the same stakeholders who are counting on us, the stakeholders from being the clients to the teams, to certainly our family, and then also to this profession and the organization to just get the jobs done that we need to get done so that we can just be the best that we can possibly be.

Amber Stitt [00:04:17]:
So you're seeing people snap in the photos, in the audience. So it's like, when we come out of this and we need to implement. And I talked with Jason about that, too. It's like the 4th "e" could be "execution". So if we're talking to maybe 2 people here, maybe the NAIFA member, maybe it's somebody new coming in, or not everybody's members that are coming to some of these events, but it's what can we do to execute? And you're talking about leadership, I'm guessing, because I don't have the same experiences, but you're talking about delegation and paying attention to being okay with letting something go to the right place. So I'm assuming there's a little bit of executive coaching that comes into play to make sure that you're allowing that to happen, because there's a control feeling there. But if your client needs the best of all, everyone needs to be in the right role. And I think that's part of the work that you've been doing is making sure people are looking at that, maybe for themselves or their team.

Daralee Barbera [00:05:08]:
Yes. And I do have a little bit of a saying that, "If you're going to grow, you got to let go." And that is often what I find that leaders are probably most challenged with.

Amber Stitt [00:05:18]:
I've been there.

Daralee Barbera [00:05:19]:
Yeah. Because you know how well you do it. But indeed, we really have a responsibility to help other people build those skills because that will make them better. And then indeed, that will make the whole organization better. And then if you just kind of what I encourage people to do as leaders, do the math. If you can free up only 20 minutes a day, what if it's 30 minutes a day of allowing someone else to do that task instead of you? You end up adding weeks and weeks into your 12 month year.

Amber Stitt [00:05:52]:
Yep.

Daralee Barbera [00:05:53]:
So, you know, I have one coaching client and his task is before we meet next week that he's going to tell me what thing is he letting go of. I said, "Good, because I want to be your wife's favorite person."

Amber Stitt [00:06:04]:
Okay.

Daralee Barbera [00:06:05]:
And so we agreed it's going to be like 30 minutes and that's going to get him close to a month.

Amber Stitt [00:06:09]:
Well, okay. I was thinking more business, but if you get in a good habit of that, there is some things you can bring home to your personal relationships, too. To your families.

Daralee Barbera [00:06:18]:
This is a leader who, he couldn't even tell me when he went on a vacation last.

Amber Stitt [00:06:22]:
It's not the first time I've heard that in these episodes.

Daralee Barbera [00:06:24]:
And in fact, a very successful individual with a big team. I actually met him because I conducted a mastermind session and we ended up having him be our person that we masterminded because he has a time allocation challenge, which was fascinating.

Amber Stitt [00:06:39]:
He let you do it, so he's letting go. This is first steps. He's actually saying, "Yes, we're doing this." Good for him. But can you repeat that?

Daralee Barbera [00:06:47]:
Yeah, he said, "I just can't manage my time."

Amber Stitt [00:06:49]:
And you said, "No, that's wrong."

Daralee Barbera [00:06:51]:
Well, yeah, let's get started on how do we manage time, right?

Amber Stitt [00:06:56]:
He's like, "You got a team. We can do this."

Daralee Barbera [00:06:59]:
But in the Mastermind session, not to digress, but there were about 12 people. It was at a conference, about 12 people in the Mastermind session. So then the rest of the group, they asked him questions about what is he doing now? And so he got so much out of it. And then we've continued to coach, but now I'm going for being his wife's favorite person.

Amber Stitt [00:07:18]:
And I'm sure everyone's loving that kind of open dialogue and then you can have some grace with yourself, too, and have a laugh.

Daralee Barbera [00:07:24]:
Yes, but everyone learns from that Mastermind environment. But it's kind of a great example because this was a very seasoned leader and that's the top of mind, most urgent thing that he wants to address.

Amber Stitt [00:07:37]:
Oh, good.

Daralee Barbera [00:07:38]:
I know.

Amber Stitt [00:07:39]:
Do you always see that in your coaching?

Daralee Barbera [00:07:41]:
I say there's always surprises. Yes, because upon meeting him, that's not what I would have guessed.

Amber Stitt [00:07:47]:
Interesting. So this is a successful tenured person. What are you seeing people doing to help? Maybe I don't want to go succession plan, but like creating more talent on their team. Is there any advice for the listener? They could be new in the business, or maybe they need to hire, or delegate, or maybe it's a tenured person, one of our colleagues even. What would you recommend for them to kind of pull in new talent? Male, female, that could help evolve and iterate.

Daralee Barbera [00:08:11]:
Well, a couple things. When we think about succession planning, what I see are advisors who have teams, leaders saying, "Oh, we'll just do it later. Now's not a good time." But I always like to say, the sooner you start thinking about your succession plan, like it's never too soon, because what will happen, you'll put better systems in place, you'll get better people in place. And what happens to your current market value of your business as your valuation...it's going to go up. Sooner than later. That's a good thing. And it just gets more efficient.

Amber Stitt [00:08:44]:
Well, and I wasn't even thinking about talking about this because I'm in kind of the middle. Like I was saying to someone earlier, I'm closer to 50 than 40. But you could always start thinking about your succession, or what you'd want in 10 years. But a lot of my friends are considering the retirement, or I can see they're going to do it, but then here they are still hanging on. And it's interesting, digitizing, websites. There's things that are not monetary, that X-factor your company. And so the sooner you can start allowing the team to kind of build that out. That's kind of where I was going.

Amber Stitt [00:09:13]:
I'm kind of worried for a lot of people that are like, "I'll get to that later. I don't want to learn that new tech." It's not really about tech anymore. It's about everything needs to be systematized, your worth more.

Daralee Barbera [00:09:21]:
Well, and there is so much to your point, so much readiness that has to go into effect, from the personal readiness, to the team readiness, to the business readiness. And it all matters. Nothing happens quickly, nothing happens overnight.

Amber Stitt [00:09:35]:
Everybody on the team's ready for it. So you might have to put in some other people that could help, or get people on board and find out maybe who's really interested about the legacy of the company, too.

Daralee Barbera [00:09:44]:
Yeah, it's just a good process all the way around because it really gives the business as a team a chance to reflect on why are they there, about their true vision, their true mission, what do they really need to do to get to where they need to go? And so then that gives you...kind of back to your question, in thinking about who do you add to the team and why? And that makes me think about, especially for financial planning, any part of what we do, it is about creating community for our clients. Clients want to belong to your community. That's why they chose you as their advisor. And so to get to that place, the best thing we can do is really whether we can assess it on our own, or we bring in coaches, or we have a personal board of directors, or have your friends come in. Does your practice reflect the community you serve?

Amber Stitt [00:10:39]:
Interesting.

Daralee Barbera [00:10:39]:
And then let's do everything we can do to make sure that happens. And it's not just the walking in the door. If you have a physical location, which even more so, I just saw a great study that was done, and out of 600,000 client conversations or something, 41% of the meetings happened in the office. I just saw that a couple days ago and I went, "Oh, that's interesting." And then like 30% were virtual, and then the rest were random places. So the majority were in the office. So that means that our physical location is really important. And I like to say it's not from when the client walks in the door, or the recruit walks in the door, or the advisor walks in the door.

Daralee Barbera [00:11:20]:
It's from the moment they drive up, park their car. That whole kinesthetic experience, it matters so much because you want everyone that you want to be serving your community. To walk in that door and feel like they belong, that they're part of that community and they want to be part of it.

Amber Stitt [00:11:41]:
Thank you for joining us on this episode of Pathways. Please consider giving us a "Like" and subscribing to the channel. Your support goes a long way towards helping us bring you more compelling content. Remember, let's take action together! Now let's jump back into the conversation.

Daralee Barbera [00:11:59]:
And so that kind of brings us to...I mean, we're both with WIFS, and there's so much important work to be done there. And I did write a book several years ago called "Women Matter: The Why and How of Gender Diversity in Financial Services". It's so surprising to me and disappointing that our representation of women in the profession has not increased. And I think one of the things we can do about that...

Amber Stitt [00:12:23]:
I mean the stat hasn't moved at all. I don't really think in the last...maybe its been 4 or 5 years now and I've heard a lot of things when I first jumped in. Not WIFS specifically, but I'm just saying. You mentioned a statistic earlier today about women. Can you bring that up again? Because I think if I'm picturing this aesthetic, this experience, which we've kind of gone automated in life, like the Walmart, the Amazon, but I think some of this "mom and pop" feel is coming back a little. I know that kind of sounds strange, but I think people are craving that, like you said, that more in-person, tangible experiences. So I'd really like to see what your philosophy is on the females that are managing the money. How do we help them and have them approach us to get help?

Daralee Barbera [00:13:07]:
Well, and if we just look at the...I think the statistics we were talking about is that really the majority of financial decisions are made by women. And we can look at that all different ways, but that's really what the research shows, and it has been that way for quite a while. So that the majority of financial decisions are actually being made by women. And the majority of wealth, if it's not now, it will be controlled by women. If you're looking at the strength of your practice, wouldn't you want to be sure that your practice caters to women? That when they walk in your front door, or they look at your website...

Daralee Barbera [00:13:42]:
And it's not just...Well, certainly gender needs to be visible and present, which indeed it is not everywhere. I mean, just from a business practice, but also diversity, inclusion. I mean, to create inclusive environments for our clients, for our advisors. Talk about retention, so if we hire women in, it needs to be an inclusive environment so that they'll stay.

Amber Stitt [00:14:08]:
Well, and I'm also thinking about grandchildren, too, because you mentioned websites. So if someone's been working with one advisor for years, but then the website's just really not in place, the younger gen is going to be like, "Where's this person at? I can't find the digital footprint." So there's some of that, too, that could be more legacy and keeping that community alive as time goes on.

Daralee Barbera [00:14:29]:
Absolutely. Think about the beneficiaries. We know what the statistics are, that 70% of widows leave their advisor.

Daralee Barbera [00:14:37]:
Well, that is just so sad. What a disruption. First of all, you lose your spouse and now you're going to lose your advisor. The advisor relationship should be one that is not just for the couple, but is familial. And I have another individual that I coach. It's a four woman practice. They know every beneficiary, that is their business model. And they always have at least 2 of them on every appointment.

Daralee Barbera [00:15:07]:
So that the clients know what the succession plan is.

Daralee Barbera [00:15:11]:
And they're very out in the open about that, that this is for a succession plan.

Amber Stitt [00:15:16]:
I think from like the legality of future issues, too, then everyone knows who's on the team.

Daralee Barbera [00:15:20]:
Absolutely, so those are such important things and as we think about advisors looking at succession planning, it is never too early to put things like that in place. It's so important for retention of clients.

Amber Stitt [00:15:33]:
Typically we wrap up with a little takeaway nugget. But I actually want to talk about your "C's" that you talk about.

Daralee Barbera [00:15:39]:
Oh.

Amber Stitt [00:15:40]:
Because if the listener is not able to come here, but they're trying to get some nuggets of wisdom from you, I think these could be tangible in a sense of like, we could take one of the "C's" and apply it to our lives today. Would that be helpful to wrap up with the 3 "C's"? Is that what you call it?

Daralee Barbera [00:15:54]:
Yes, and it really goes hand in hand with the website. So just to ask yourself, am I checking the box of the 3 "C's"? So, one is creating "Community". I mean, it's about community. And then the other one is about the "Connectivity". And then the 3rd one is "Communication". And communication is just huge for us. And I don't think we can ever stop being a student of it. And particularly now because the awareness is up about communication.

Daralee Barbera [00:16:27]:
It's kind of interesting, I work with advisors who we'd spend time looking at when they're preparing for an appointment, how are they going to allocate their 50 minutes? Well, most advisors are thinking about, "Okay, here's all the things I need to present." And I say, "The most important thing is to know what questions do you need to ask." Because what answers do you need to get before you lose those clients right there in front of you? So it's not always about the answers. It's about the questions. And then it's about certainly being a sender of a message, but also about being the listener, the receiver of the message. And then how do you package that message? I mean, so really communication can be this 1, 2, 3. And it matters.

Daralee Barbera [00:17:11]:
And we need to be able to identify what are the components, and we need to practice it and just be as good as we can be at communication because the clients are counting on us.

Amber Stitt [00:17:20]:
Yeah, well, and I was saying in different entrepreneurial conversations, how I would say communication is the currency of life. And I think about the younger generation and our distractions and technologies and things that we're doing. We have to really work on our communication skills because that's going to make us stand out, build trust, but really take care of the people that we love and care about. And that's an ever, ongoing process in our families and our relationships.

Daralee Barbera [00:17:44]:
I was just gonna say on a personal note, of course we wanna work on communication.

Amber Stitt [00:17:48]:
Well, I am so happy that everyone got to meet you through the podcast, if they don't already know you, yet.

Daralee Barbera [00:17:53]:
Well, thank you so much for inviting me.

Amber Stitt [00:17:55]:
Thanks for making the time. We're gonna go hang.

Daralee Barbera [00:17:57]:
Yeah, let's go do that.

Amber Stitt [00:17:58]:
All right, thanks everybody for listening.

Amber Stitt [00:18:01]:
Thank you for joining us for this special edition of Pathways e3 recorded at the NAIFA e3 conference in Newport Beach, California. Join us for more insightful conversations with the experts and leaders of their industries. Until next time, keep taking action on your unique path!