Most CPA firm owners spend their improvement season updating software or tweaking processes. Rachel and Marcus Dillon are doing something different. They’re taking their entire 26-person remote team to Mexico for four days of relationship-building, goal-checking, and some serious fun in the sun.
The husband-and-wife team behind Dillon Business Advisors just shared their complete retreat strategy on their latest “Who’s Really the Boss?” podcast episode. Their approach reveals how treating team culture as business infrastructure—not just a nice-to-have—creates competitive advantages no software upgrade can match.
From Monthly Breakfasts to International Retreats
The Dillons didn’t always plan elaborate team getaways. When everyone worked in the same office, they kept things simple: bringing in lunch, organizing breakfast meetings, or grabbing dinner together. Even after going remote with a local team, monthly breakfast meetups worked well.
But as their team spread nationwide, those frequent touchpoints became impossible. Instead of giving up on team building, they made a strategic shift that many firm owners would never consider: two high-impact retreats per year.
The economics work better than you’d expect. Their domestic beach trip to Destin, Florida, last year cost significantly more than this year’s all-inclusive Mexico resort.
“The international all-inclusive option is actually a little more budget-friendly,” Marcus explains. Plus, team members won’t face surprise expenses for drinks and meals like they did in Florida.
This shift is about more than cost savings; it’s about recognizing that relationship building requires concentrated investment to generate meaningful returns.
Using Data to Build Better Relationships
The Dillons don’t plan retreats based on gut feelings. They treat team dynamics with the same analytical rigor they apply to financial planning.
Before finalizing their Mexico agenda, they surveyed their leadership team using Patrick Lencioni’s “Five Dysfunctions of a Team” assessment. The results revealed something important about high-performing teams: excellence in some areas can make weaker spots stand out more clearly.
Their team scored well across all five dysfunction categories—absence of trust, fear of conflict, lack of commitment, avoidance of accountability, and inattention to results. However, the assessment identified their two lowest-scoring areas: conflict avoidance and peer accountability. These weren’t crisis-level problems, just the next areas for improvement.
“When you refine something and it becomes really good, then the next friction point stands out just a little more because now the other areas are running so smoothly,” Rachel explains.
The assessment also came with ready-made solutions. “One really cool thing with that assessment, when it came back, they actually sent activities to try to help build the areas of weakness,” Rachel says. “We did not have to go out and search. We didn’t have to call our friend, ChatGPT, to help us come up with ideas.”
This systematic approach beats generic team building every time. But it requires a crucial commitment: following through on what you learn.
“The worst thing you can do is survey somebody or ask somebody their opinion and not do anything with it,” Marcus emphasizes.
The Mexico Agenda: Four Hours That Shape Six Months
The Dillons arrived in Isla Mujeres on a Thursday, then dedicated Friday morning to formal meetings. The rest of the trip focuses on culture, relationships, and fun. Still, those four hours of structured time drove real business improvements.
They started with celebrations and goal reviews. Marcus shared revenue numbers, client acquisition progress, and team updates. “We share revenue. We share where we’re at on track as far as the goals we’ve set,” he explains.
This transparency creates collective ownership of business outcomes. When team members understand exactly how their work contributes to the firm’s success, they make different decisions about client service and efficiency.
Next came “Turning Conflict into Connections,” their targeted response to the assessment results. Instead of hoping team members will naturally become more assertive, they created explicit permission for difficult conversations.
“Team meetings aren’t only for the leadership team to talk,” Rachel explains.
Angel, their director of technology, covered cell phone security protocols. Then they tackled something that could transform their client service: categorizing clients based on team experience rather than leadership assumptions.
“There are simple clients and complex clients, but there are also good complex clients,” Rachel says. The hypothesis: responsiveness matters more than technical complexity. “The complex clients who are responsive, who implement the advice and the strategies we give them, they’re not as hard to manage.”
They wrapped up with peer accountability training, moving beyond traditional top-down management to distribute leadership responsibility across the entire team.
Beyond the Meeting Room
The non-meeting activities included relationship-building exercises that translate into better workplace collaboration: water activities with paddleboarding and snorkeling, Mexican bingo (Loteria), and a team dinner where Marcus recognized each team member in front of their spouse or guest.
“It’s nice for families and friends to see the impact you have for all of the hours you spend away from them working,” Rachel says.
The trip concluded with karaoke, something they missed at their last retreat when the karaoke spot was too far from the hotel. This time, they brought karaoke to the team.
The Numbers Game
Taking 26 people across international borders, coordinating planes and boats to reach an island resort, and budgeting tens of thousands of dollars is a big investment, and it sends a clear message about how the Dillons value their team.
But the real return shows up in compound effects: reduced turnover, faster problem resolution, better client satisfaction, and the competitive advantage of having a team that genuinely enjoys working together.
While competitors debate software features or chase marketing trends, the Dillons are building human infrastructure that’s much harder to replicate. You can’t download better team communication or purchase improved conflict resolution skills.
Your Next Move
The Dillons prove that systematic investment in team relationships creates business advantages that technology alone cannot provide. Their transparent approach offers a roadmap for any firm owner ready to treat culture as seriously as revenue. The question isn’t whether you can afford to invest in team relationships; it’s whether you can afford not to.
Ready to hear their complete strategy? Listen to the full episode for their detailed retreat agenda, specific dysfunction-busting activities, and the real numbers behind their cultural investment approach. You’ll discover how they handle team transitions, their client categorization exercise, and why peer accountability might be the missing piece in your team dynamics.
Rachel and Marcus Dillon, CPA, own a Texas-based, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 15 professionals. Their latest organization, Collective by DBA, supports and guides accounting firm owners and leaders with firm resources, education, and operational strategy through community, groups, and one-on-one advisory.