Episode 1: Building Inclusive Teams In A Virtual World With Derek Thomas

Running a business in a virtual world means dealing with various cultures, viewpoints, and time zones. Leaders in remote setups must be flexible and versatile enough to cultivate interconnectedness and build inclusive teams. Derek Thomas, Chief Strategy Officer for Galway Holdings, shares with Megan Martin how they bring employees together from around the world by meeting them where they are at – despite not seeing each other physically. He breaks down strategies for empowering diversity within the team, especially when working with introverts and people from different generations. Derek also opens up about using the same inclusion strategies in making his son, who is diagnosed with Asperger's syndrome, always feel accepted and loved.

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Building Inclusive Teams In A Virtual World With Derek Thomas

We are very blessed to have Derek Thomas joining us all the way from Atlanta. Derek, welcome.

Thank you very much. Nice to meet you.

Tell us a little bit about you and what you do. What does the day-to-day look like for you?

I am the Chief Strategy Officer for Galway Holdings. Galway Holdings is the holding company for a number of intermediaries. We have our EPIC Insurance Brokers & Consultants, which is our retail insurance brokerage business. We have Gen Cap and Paragon that fall into Galway specialty wholesale. That's a wholesale business, as well as managing general agent and general underwriter-related business. We also made an acquisition of a company called AMI in the wealth management space.

My responsibility as a Chief Strategy Officer is to work for our Chairman, Jon Hunt. I work on a number of major strategic initiatives, from digital transformation to business transformation and things around what the world knows as ESG, DEI, and other things that are important to driving enterprise value within the organization. I'm also the President of Galway Strategic Solutions. I work with an internal consulting team that supports me on all of the initiatives we're trying to drive strategically.

It's quite the responsibility and quite the diverse industries that you find yourself in. Do you think being in those very different sectors of the economy of the world helps you think differently when it comes to diversity and inclusion?

Absolutely. I happen to be in an industry that is not extremely diverse in terms of senior levels throughout the industry. In my career, I've been very fortunate. I've had a lot of great mentors of Black, White, Latino, Asian, straight, and gay that have been great sponsors and mentors for me. Having that happen to me earlier in my career is something that I advance. I happened to work for a gentleman that firmly believes in diversity and inclusion and creating a culture that is available for people to join our organization and thrive within the organization.

Whether I was at publicly traded companies or privately held companies in this industry, diversity has always been front and center as something important to me to make sure that we have great representation on behalf of our clients and great thought process within our organization as we brainstorm and innovate on behalf of our organization and our clients.

Some of the things that resonated when I was preparing for our conversation were some of the things that you've talked about over your career as far as diversity, like sexual orientation as diversity, gender, and racial diversity. One of the things that you've touched on is generational diversity. How does that play into your strategy? Is that helpful when you have people coming from different backgrounds and generations when you're thinking about innovation?

It's interesting, and it's a great question. I have been fortunate. As a strategy officer, I get involved in a lot of things that start with a blank piece of paper, from the conceptualization of the idea or the establishment of the vision and going to what is our mission goals and objectives. It's all about the team. I use a simple formula of strategy, structure, process, people, and alignment. Once the strategy is clear, when we have a perspective on the structure and what we need to accomplish, it's a matter of pulling the team together.

I manage a major strategic initiative now that's in the area of digital and business transformation. I have individuals that are older than me on my team and significantly younger on my team. It's a diverse representation from a generational standpoint, as you stated. It's the ability to bring those folks together to innovate, brainstorm, and bring their collective experiences, or in some cases, lack of experience, which is thinking blue ocean.

We are able to get to a whole another level of dialogue and, in some cases, discourse, but the output is something that is well thought out. We're looking at things from multiple angles. We're leveraging the strengths of everybody on the team to bring a collective voice to a solution either organizationally or on behalf of our clients. That, for me, is seeing diversity in action on a daily basis. Our client base is changing. Our client base is becoming more diverse.

Younger entrepreneurs, you have to be able to speak to people and meet them where they are. We still have a number of clients that are older clients. You can't say, "We're going to focus on everything being high tech, low touch." We have to have balance. The diverse representation in our organization has an impact on how we engage with our clients and business partners internally and externally.

Diverse representation impacts how an organization engages with clients and business partners internally and externally.

That's a great point. Thinking about the workforce in general, we have four different generations all participating in full-time work now. I'm not sure the last time that's probably happened with such, and then thinking about the technological advancements that have happened from the Baby Boomers to the Gen Zs that are now entering the workforce, and how differently the world has been for those polar generations that are entering. That speaks to a lot of the diversity that you talked about.

You bring up a great point. You then add a pandemic and everybody working differently. I think about the power of technology and how it has connected people or kept people connected and formulated some teams that would not traditionally have been formed. You don't have the social elements, which is a challenge around esprit de corps like, "What are we doing after work? How do we get to know each other beyond Zoom?"

That's a bit of a leadership challenge now, but what it has done is said, "Who's the best person for the position, irrespective of anything other than their capability, skillset, passion, desire, and will?" If you can bring those people together, the generational impact, which in a traditional social situation may not always jive. We've been able to do some amazing things. My team has been 100% virtual since before the pandemic and is a diverse representation of the talent in our organization.

That was going to be my next question. Here's a great segue. What did that team look like? Is everyone in Atlanta with you? Are you geographically dispersed? Where does that look?

We have people on the East Coast, West Coast, and Midwest. I have folks in Philadelphia, Northern California, and Florida. I'm here in Atlanta. There are folks in Michigan and also Southern California. Because of what I do, we're also interacting with project teams all over the country that are not even within our organization. We have underwriting partners who are all over the country. We have technology partners that are based in Boston and Dallas.

As I mentioned on another podcast, we probably have 90 to 100 people working on a project. A lot of them, we've not even met in person because a project started at the beginning of the pandemic. It's been interesting to see how we've been able to leverage technology to manage our community and ecosystem around driving towards aligned goals and objectives.

Have you found your team being so geographically dispersed that some of that inclusivity became harder or easier because of technology? Because we have the tech now, is it easier to engage with those people who maybe aren't down the hallway from you or in the office next to you? How have you found that balance of including everybody when they're not necessarily physically together?

You need a great cadence of meetings, but not over-meetings. We have regular meetings on a weekly basis, biweekly basis, monthly check-ins, quarterly planning, and review sessions. We try to get the team together at least once a quarter or three times a year in person because you have to have those points of relationship development and connectivity and talking about family and things that matter beyond the project.

Virtual World: Remote workplaces need a great cadence of meetings but not over meetings. You need those the relationship development and connectivity points, talking about family and thing that matter beyond projects.

It has been a leadership challenge to figure out how you manage and build a team virtually. A lot of it is how we run and facilitate our meetings. We even have rotational facilitation because, through Zoom, you see how critical facilitation skills are. You may have a great team that can come in and bounces things off, but to keep the ball moving, you have to have facilitation, operate with project management discipline, and communicate.

Whether it's formal meetings or one on ones that I have with people on my team, you have to meet people where they are. Some people like that formal structure. Some people like a little looser. For a leader, it's constantly saying, "How can I be as effective as possible and efficient with people's time to make sure that we drive all the right outputs?" You can't yield on face-to-face in general. You have to try to build those touch points in.

Do you find that having a fully remote team has allowed you to be a little more inclusive and diverse because you're able to include people that are outside of your geographic network?

On the one hand, it's the challenge of our current state. That is, people are either choosing to come back or not to come back into the office, but because we were 100% virtual, it meant I could find the right person, and it didn't matter where they were. It doesn't matter. It opened up the talent pool of people I knew, connected with, or had unique skillsets. Because we are doing a lot of work throughout the United States, having people in different ZIP codes has been incredibly helpful. We turn lemons into lemonade and have found a way to say, "This is the way the world is now. Let's utilize this expanded reach to identify talent and put the best team on the field every day."

Now that you're able to expand that reach and ZIP code doesn't matter, where it's not the qualification for the job entry, how do you attract and empower diversity then? Now that the world is your oyster, what are some of the tactics you use to find that right fit?

The good news is I work for a very large organization. The goal is not just myself, but what type of culture we are creating and how we are supporting and resourcing our leaders. One of the things that I talk about is people want to see people that look like themselves in organizations. It creates a comfort level. I had a conversation with a diverse team in Naples, California. We were talking about this issue. What's the first thing people do? They go to look at an organization. They go to the website. They look at the leadership team. They look at, "What are the values of the organization? Are they supportive of climate-related issues? Are they supportive of diversity and inclusion? Are they involved in their community?" All of those are ways in which we can send a message around our brand as to what matters to us.

What we want to be able to do is create a culture and have values that are attractive to diverse talent. It also means having diverse leadership and the ability to have sponsoring and mentoring when you join an organization because that is a big part of how you navigate an organization. We're constantly looking to diversify at multiple levels within the organization. We have a chief diversity officer in our largest entity, which is EPIC Insurance Brokers & Consultants. From a Galway Holdings level, we want to constantly reinforce the things that matter to the overall ecosystem and support the execution within the operating companies to power and empower our companies around things like diversity and inclusion.

Virtual World: Aside from creating a culture that has attractive values for diverse talent, you must also have diverse relationships and the ability to have sponsorship and mentoring.

What are some of the obstacles that you've overcome in building that community, ecosystem, and trust across your culture? JUNO is a fully remote company, so I fully understand and live that every day. We practice our culture and values at the beginning of every single meeting that we have internally and externally. When you're this geographically dispersed, that matters more than when you're down the hallway and can have those informal hallway chats, cubicle chats, whatever it might be. What are some of the obstacles that you had to overcome in this geographically diverse team to keep that culture and trust going?

There are a couple of things that you hit on. We have a chairman who believes in culture. We have CEOs of our different operating companies that believe in diverse cultures. They have to build in and have had to build elements of systemic processes. You have to be purposeful, which means that if you don't have it as part of your recruiting strategy, you're not going to recruit diverse talent. If you don't have an environment where people feel comfortable and be themselves at work, you're going to lose diverse talent, and you won't be able to attract diverse talent. The word I would use as to what we are doing in our organization is we are being very purposeful.

Our industry is historically an apprenticeship industry. It's a who-you-know industry. It has been largely led by White males. If there is no introduction or break from a traditional community relationship structure, which is, "These are the people in my neighborhood. This is who I know. These are the people I hire," it's hard to diversify if you do not live in a diverse community or diverse area or have a diverse thought process. If you don't put processes in place, whether it's hiring, retention, promotions, and sponsorship, it doesn't happen. Step number one, as an organization, we are being very purposeful. I do that as an individual leader.

If you do not live in a diverse community or an area with thought processes, diversification will never happen.

With the leaders that I work with, this is top of mind. These are conversations, our all-hands calls that are happening, our HR-related updates, and our business updates. It has to be front and center. You've got to recruit and train younger people. We also have to become an organization that attracts mid-level and senior-level diverse talent. We have to realize that we're competing for talent every day. Since we are in professional services and what we do for a living is provide service to people, and it's a people business, all these things matter.

The people business part of it has lost and also accelerated during the pandemic. At the end of the day, we can't forget that there's always a human on the other side of the phone, text messages, and the computer. That human connection piece becomes so important when talking about inclusivity, meeting people where they are, and embracing differences. Something you said in your last point was about diverse thought.

I don't know if that gets discussed enough when we talk about inclusivity and diversity. I hope it's okay if I talk about your son. The story of your son resonated with me a lot. I also have family members on the spectrum as well. Our family took a similar approach to immersion and not allowing that to make them different. They think differently doesn't mean they're different. Talk to me a little bit about how you guys embraced diverse thought as part of your inclusion strategy.

I appreciate you bringing that up. My middle son is on a spectrum. Early in his career, he was originally identified with general anxiety disorder. Before, there was an Asperger's label that was in second grade. Thank goodness my wife was a teacher. We had access to resources. For parents, that's the most important thing. Can you identify the resources that can help you navigate challenges, especially around learning disabilities or social challenges?

We made the decision to keep him in a mainstream program with IEPs throughout his elementary, middle school, and high school career. Even though he struggled on the social side, he went on to a program at Kennesaw State University for students with disabilities, then went on to Ryan Hart and got his Associate's degree. In keeping him in the mainstream and keeping him included in the process versus set aside from the process, you don't realize until your kids get older that they hear what you say and that they are influenced by all of those things.

It has led him to be an incredibly independent, wonderful young man who's got an amazing heart and is working hard through challenges every day, but has the coping skills and the mechanisms to do so and bring something unique. I use that as an example of what it feels like joining an organization and not being integrated into the organization. You can be in the company, set aside, and not feel like you are part of the culture. As I mentioned, you don't have to be an extrovert. This isn't a slam against introverts that want their space. It is about what it is that you are thinking about in that space, so when you have the opportunity to communicate or show your work or value, it becomes part of the overall advancement of the organization.

That's inclusion. It's not just social inclusion. That is one part of it, but it is thought process and perspective. Sometimes the quietest people in the room, when they finally say something, it's incredibly powerful. We have to be conditioned as an extrovert to listen, ask questions, learn, integrate, and figure out how we show our appreciation for the diversity of thought. Not just that extroverted person that is always upfront speaking, but we talk about the power of teams that no one person does anything alone and that there's a spot for different types of personalities.

I love that. As an introvert myself, I struggled with that a lot early in my career of feeling included in the process because I wasn't always going to be the first one to speak up. I have a sign hanging in my home office that said, "Weird is a side effect of awesome," to remind myself and embrace my quirkiness and weirdness because it is my superpower and has made me a very empathetic person.

A lot of that had to do with great mentors and leaders in my life who embraced that part of it and brought me into the conversation. As a leader, how do you approach the person sitting quietly in the corner where you know their wheels are spinning and something's going on there? How do you bring them into the conversation and make them feel included?

You can go to leadership training programs. You can study leadership in college. Those are all important things for folks that choose to double down on reading and self-help books. All those things are great, but mentoring, coaching, and sponsorship are mission critical to success. That means that you have the ability back to what I stated before about meeting people where they are.

I've got a young, bright gentleman on my team who is extroverted in some ways but introverted in other ways. He is a strategic thinker and is into technology. I've got people on my team that are smart but don't say a lot. I've got a diverse group. My job as a leader is to meet each of them where they are and to understand what their goals are, understand what their objectives are, and what elements they perceive as either a strength that they want to enhance or a weakness that they want to eliminate, and finding a way to partner them with people.

I always say this in sales. You go into a sales meeting with two people. There's a chance a client's going to like one of you. You go in by yourself. They're either going to like you or not like you, and the deals are on or off. I believe partnering with people that have different and unique personality types and skillsets is important. We use the example of ham and egg. What is that Batman and Robin type duo in any given situation and also being able to have one on one and talk to people about where they're going? I say it all the time. I can't have anybody on my team who doesn't want to be successful, and I don't want anybody on my team who doesn't want to be on my team.

That's not fair to anybody. If you are on my team, my goal is success, which means I have to do the work to figure out what success means to you and help you achieve that. If I'm doing that, that means you are waking up every day, realizing we have aligned goals, and then you are operating with, "I have your back." One of the things I say to the people on my team all the time and the people I partner with is, "I have your back." What that means is whatever challenges we run into, we run into together. Whatever victories we have, we celebrate together. That is part of how we drive esprit de corps.

Are you finding better business successes with that approach? Are your projects hitting it out of the park because of the approach that you take?

Hitting it out of the park is a relative term when you are in a strategy role. I say this all the time. Our job is to see what other people don't see, build it, show them, and they go, "When did that happen?" but never say, "I told you so." That's always the hardest part. Humility is a big part of what we do. When I look back at my career, I've either done R&D on opportunities that we did the analysis and decided not to advance, did the analysis and decided to advance differently, or did the analysis of the vision where it was spot on and has helped to drive millions or hundreds of millions of dollars of value.

Our organization has gone from $50 million several years from $0 to $1.3 billion in revenue. I joined a few years ago. When I joined, we went from $50 million to $1.3 billion. That's a lot of ideas, a lot of trial and error. What I will tell you is it all came down to the people that were pulled together to drive the build-out of this organization. Because we've grown rapidly, we're constantly tinkering and enhancing. That has been helped by a diverse pool of talent, either people that were organic to the company, people that were recruited into the company, or acquisitions that we've made.

Those acquisitions that operated one way for twenty years or a legacy business also have to be integrated. They come from different cultures. We can slice and dice culture, diversity, and inclusion. There's a core element of what it means, but there's a more macro or broad perspective, which is people that think differently or have different backgrounds and experiences or different thought processes, can you bring them together around a common goal and have them be the best of human beings, which is to excel, create, and innovate?

Virtual World: In a diverse and inclusive workplace, you must unite everyone around a common goal and make them the best human beings who can excel, create and innovate.

There are two things that you said that resonated. One is projects you didn't advance. Sometimes doing all of that work just to come to a no that this isn't the direction or isn't the project is hard. It's admirable to embrace that. Failure is not even the right word, but you go through the process to say, "This maybe isn't working and maybe not the direction we want to take." The other point I want to close out is tinkering. This is an evolution. There are going to be people coming on and off the teams that change the dynamic of how people work together.

That's why being inclusive is such a moving target because it's always can be better. You can always bring in new voices and embrace new people on the team. Why don't you leave us with the final thought? If someone was starting out to change their culture, be more inclusive, building community internally and externally in their organizations, where's one place that they could start, knowing that it's an evolution, and they might be tinkering with it for a while?

The first move is always strategy. Bring together a diverse group of people in your organization. If your organization isn't diverse, bring together a group of diverse thought leaders or people with diverse perspectives. If the perspective is, "We're not diverse. We don't know how to do this," the first thing you can do is bring together people that are open-minded and who want to advance a strategy around diversity and inclusion. There are so many third-party resources that can be tapped into. That's why consultants are so huge around the world.

That is bringing an outsource partner that can help you with what you don't have internally. The first step is to have a big, bold vision and strategy. Think about what your desired state is, be honest about what your current state is, figure out what the gaps are, and turn those gaps into an action plan, an action plan where you hold people accountable and have timelines, deadlines, and measurements. If you do not build the infrastructure around purposeful activity, it usually does not happen. It becomes a meeting that leads to another meeting. Step number one is to be bold enough to say it matters, pull the right team together, and empower them to build and do something great.

Turn your gaps into an action plan and hold people accountable. If you do not build a team around purposeful activity, everything becomes a meeting that leads to another meeting.

What a mic drop moment. We're going to leave it there. I want to thank you so much. This conversation went all over the map, and I very much enjoyed it. There are a lot of takeaways from our conversation on how to get started, and where to think about diversity and not just some of the geographic, gender, or racial diversity that we generally think about with that term, but building inclusive teams and how that plays into a bigger organizational impact. I want to thank you so much. Make sure you guys are subscribing. We will see you next episode. Thanks for joining us, Derek.

I appreciate it. Have a great day.

You too.

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About Derek Thomas

I am the President of Galway Strategic Solutions (GSS), EVP of Galway Holdings LP and Galway Ventures, and Former Chief Strategy Officer of EPIC. As President of Galway Strategic Solutions, I lead a team of seasoned executives experienced in strategic consulting and advisory; digital platform, program, and channel development; and supply-side and distribution enhancement solutions. We bring real-world expertise to the Galway portfolio companies, including EPIC Brokers and Consultants, working closely with leadership on the critical issues they face, while remaining focused on value creation.

By aligning the GSS team with partner companies and select technology solutions, we implement business and digital transformation strategies through a holistic approach. Core components of our business and digital transformation engagements include investment analysis, strategic planning, operational process improvement, technology, underwriting and product development, sales and marketing plans.