Kristen Oliveri, Head of Private Wealth Content at
Markets Group, sits down with Carina Diamond, the chief experience officer of
Dakota Wealth Management, to discuss how Diamond has cultivated a unique firm
culture within her RIA, helping both clients and employees flourish in a time
of great change.

Markets Group: Your background as an advisor has led
you to the role you currently have: chief experience officer. What exactly is
that?

Carina Diamond: Quite honestly, I made it up when I
was joining Dakota. Then I found out that there were other people with that
title. Basically, it means that I’m in charge of organic growth and I oversee
the other advisors as well as the client experience, so what’s it like to be an
advisor at our firm and how we support the advisors. And then also what’s it
like to be a client at Dakota.

MG: I’d imagine part of that is creating a dynamic firm
culture because that’s part of what you do and your description of chief experience
officer. Where does one even begin to evaluate a firm’s culture, let alone
curating one like you are?

CD: Well, in our case, we were building it. Dakota
has only been around for four years, and I’ve been there for three of [those].
We’ve been helping to create the culture, but it really starts at the most
basic level, like what does it feel like to be a part of this firm, whether
you’re working there or whether you’re a client. How are you greeted every day?
What’s the tone coming from executive management? How do you feel? Do you feel
appreciated? Do you feel heard?

It really trickles down to the clients as well because they
can tell right away if they’re dealing with people that are happy and feeling
nourished and feeling cared for, or if they’re people that are just answering
the phone for the heck of it.

I think that culture is made up of lots of little things
like that. Like how does our CEO thank people for something? Our CEO is
actually extremely sincere and will personally do it. I wrote personal notes to
everybody at the company several times during the pandemic, which my wrist is
still recovering from. But to get a personal note, even just a couple lines,
shows you that you’re really valued and that you’re cared about.

MG: And when you’re establishing a firm culture, I think
something that comes to my mind is this concept of diversity. How do you see
that fitting into the idea of a firm’s culture?

CD: To me, diversity is so all encompassing. One of
the biggest things in the ways that I look at diversity is that it is really
critical to the succession of any firm. So, what’s diversity? Diversity could
mean race, gender, but it could be, do you have anybody under 30 working at
your firm? I think age is also a big part of diversity. And the fact of the
matter is we’ve all seen these statistics about more people are over 60 than under
30 in this business and if we don’t expand the pool of people that might be
working here, you’re going to be out of business.

Some other things are bringing diversity of thought, whether
it’s again from age, from background, religion, LGBTQ, just all these different
things. What’s going to happen is our client base is getting more diverse and
so if we don’t have the diversity of thought, we’re not going to be able to
relate to clients as things continue to progress – and they’re only progressing
faster and faster.

MG: Where do you see the women in wealth piece coming
into play? Can you talk a little bit about how you’re seeing women enter this
industry, if you are at all?

CD: It’s a fact that more and more clients are female
just because of demographics and longevity. Most of the women that I know want
an advisor that’s going to be a great advisor and going to be respectful and
educational and not use a lot of jargon. A lot of women I know would be happy
with a man who did that, but also the fact of the matter is that I think women
traditionally have connected better with other women and are not condescending
and are going to ask questions and make eye contact and understand. It’s also
about personal goals, not just about beating the S&P 500. The rise of the
female as a client is part of what’s driving this.

There are lots of misconceptions about wealth management and
financial services, one being that it’s all about math. It’s all about numbers.
It’s all hard sales. In reality, you have to be decent at some of those things,
but it’s really a helping profession, which is something that tends to come
naturally to many women. I think that’s what we are as a profession and we need
to just continue to articulate that, not just to the public, but also to very
targeted groups like, for example, guidance counselors, teachers,
superintendents. We are a profession that is just starving for talent.

MG:  How else do
you see the industry bringing in the next generation of talent into wealth
management, whether it be women or men?

CD: One program that I’m very involved with at the University
of Akron is called Diversitas,
which is Latin for diversity. We started it over five years ago in Northeastern
Ohio having programs where we invited teachers and gave them continuing education
credit. We also invited high school students and college students to try to
show them what this profession is all about.

Then the pandemic hit. We weren’t sure if we should just
shut down, and instead we exploded and we went virtual and now we have over 30
other universities. Some of the top universities in the country, including
historically black institutions, Hispanic serving institutions, some of the
biggest programs in financial planning, are now part of Diversitas.

We have amazing speakers of all different backgrounds so
that anyone who’s viewing this can see that there’s someone who looks like me
who’s doing this. I led a panel at last year’s program that had a lesbian, two
African American men and a Hispanic man, all 30 or under. And they were talking
about their experiences and kind of showing employers: ‘Hey, we might need a
little extra help to make sure that we fit in, and we might need a little bit
of extra coaching, but we’re hungry. We may not look like the broker that your
mom or dad had. But we have the skill set as well.’

MG: Managing teams is never easy, regardless of the time.
Then you mix in a pandemic and people coming back to a remote/hybrid world.
What are some lessons learned leading through all of that?

CD: It’s reminded me very much of becoming a parent
for the first time and thinking there’s no playbook. We’re all in this. We’re
all in the same boat. What do we do? A lot of it, I would say, was instinct,
but driven by caring for people as individuals.

I think the biggest lesson is that regular communication is
so essential. I think we communicated a lot with our staff as well as our
clients beforehand. But we just ramped it up even more during the pandemic and
it was hard because we ourselves, the leadership team, were suffering too. I
mean everybody was suffering and whether they were sick or affected by someone
who was sick or just completely freaked out by this craziness that was
happening in the world.

So, we just tried all sorts of things and did different
kinds of campaigns internally. Some people liked my crazy hat day. Some people
thought it was really dumb. We did contests and games and we sent little gifts
to people and one of our most successful things we did was a virtual cooking
class. We invited our employees, but we invited their families to join as well.

MG: You’re obviously a leader within your own management
team at Dakota and you’re a leader, in my opinion, in the RIA/ wealth
management space. How do you view leadership from your perspective and what
would you say your approach is to it?

CD: It’s kind of like sales; people fail. I’m not a
salesman; I’m behind the scenes. I think leadership is the same way. People
think they’re not a leader, but everybody is a leader of something, and
everybody has a role. What I’ve really learned about leadership is that it
really needs to be fluid and responsive to what’s happening. We did not lose a
single employee during the pandemic, which is amazing considering everything
that was going on, and we had a very low client attrition rate as well. Being
fluid and responsive has become such a part of my leadership style.

I was asked to speak at a local university recently to a
group of female chemical engineers, a really rough field for women to be in, given
that there’s huge attrition. I was asked to present to this class and I got
there and looked around and I read the room and I just said, ‘Would you all
mind just pulling your chairs up front and let’s just make a circle and have a
conversation like people rather than me lecturing you on all that?’

I could just see everyone exhaled and was in the moment with
me. We ended up having this amazing conversation about first jobs and employee
benefits and what to look for, what HR isn’t going to tell you.

You just have to keep evolving and listening to what people
are saying. And if you don’t, you’re just going to be left behind. No one will
follow you.

MG: In your estimation, how is today’s leadership better
than in past generations?

CD: I think the workplace and today’s effective
leadership is a lot more flexible. I’m not sure I would even say that it’s
necessarily better than it used to be, but I just think that’s what fits the
needs of today. Leaders have to realize, when you show up, it’s showtime. Just
like when you go into a client meeting, it’s showtime. You’re nothing without
the team behind you and in front of you. I always say I’m just steering a
little bit, trying to communicate. I’m always trying to be a better leader. I’m
always trying to communicate better. I’m always striving for better clarity.

I think the best leaders don’t take themselves too seriously
and are always willing to keep morphing and growing and learning and being.
It’s the most humbling, sometimes humiliating, experience, maybe next to parenting.

MG: Where do you think mentorship falls into the broad
theme of leadership? How do you approach that?

CD: I started a leadership program for graduate school
women and what I learned was that those women are actually the loneliest
because they have the least support, and they have the most personal conflicts
and families. Other things I found was that there’s so many people out there
that could be good mentors.

More and more people are willing to be a mentor. For one
thing, I would say is that sometimes mentoring isn’t enough. So like, what’s a
mentor? What’s a guide? What’s an advocate?

We talked about diversity earlier and what I’m finding more
and more is that what diverse people need is not always just mentoring, but
advocacy. It’s great that behind the scenes you told me that I need to get a
manicure and I need to wear this kind of clothing every day. But are you
advocating me when an opening comes? There’s a fine line between the two. I’m
trying to get people to focus in on it because sometimes all the best advice in
the world behind the scenes doesn’t necessarily help somebody navigate an
actual work environment.

MG: What are some overarching trends that maybe we
haven’t touched upon that you think are really shaping the future of wealth management?

CD: I think of two things. One is, of course, the
impact of fintech. There’s just so much to learn when it comes to technology, and
there’s so many new tools coming out. If you can’t get on board, you better
have someone close to you who is on board because you’ll be left behind. But
the good news about all of that is that relationships still matter.

So even with all this technology, I think more than ever
people are seeking community and personal connections, whether it’s a client
connection, whether it’s a coworker or a boss. Personal connections are not
incompatible with the rise of fintech. And there may be people who’ve gotten
super used to working from home and maybe haven’t kept up with their connections.
I think that those people and their careers are going to get affected
negatively if they have not been able to do that.

The other thing is mentoring and being an advocate and all
that diversity. What I would love to see is more help given to the people doing
the mentoring and the guiding. A perfect example would be so many wonderful men
in the profession and they’re a little lost because they’re hearing about all
this diversity stuff. They know it’s a good idea, but they aren’t quite sure
what to do without stepping in it. My heart goes out to these men, so I would
love to see more support for them as a group and teaching them to be the best
mentors and advocates that they can be for others. I think that’s part of this
equation of us all growing together and all rising together.

MG: My final question to you today, Carina, is one that I
love asking people in wealth management because everyone seems to be a
renaissance person. Tell me about your personal background and how you got into
the wealth management space.

CD: If there’s any Star Trek fans out there, everyone
knows Mr. Spock. But when I was growing up, there was a Dr. Spock that my
parents read. He was a psychologist, and so I was this dorky kid in the late 1960s,
and I was sneaking them [from] my parents’ bookcase and I was reading
psychology books. As I grew up, I was pretty sure I wanted to be a child
psychologist.

As time went on, I found out that I was good at math and
good at numbers, so it was sort of like a melding of those two skills and really
wanting to help people. I like to joke around that I wanted to be a child
psychologist and when dealing with many people in their money, I have become
one.

My first job out of college, I was an investment analyst at
a bank and because of my creative side, I would be given a company to research
and then to present, I would try to buy some of their products or just be able
to show something. I think I was the first person that brought props to an
investment meeting.

MG: Any final thoughts?

CD: I would just say to everyone: remember that
relationships matter. Remember that you probably are a leader, whether you
think you are or not. And for anyone in this business, it is such a great, broad
profession, there’s so many ways to go about it. It’s not all about math and
sales. And do us all a favor—try to bring a younger person into the business.