Team retreats can easily become forgettable obligations. People spend a few hours in a conference room, have some general discussion about “next year,” and everyone returns to their desks unchanged. But Marcus and Rachel Dillon have spent nearly a decade figuring out how to make their twice-yearly retreats count for something more.
In this episode of Who’s Really the Boss?, recorded just after a successful year-end team retreat, the Dillons share exactly how they plan and execute gatherings that keep their remote team aligned all year long. This retreat was particularly significant, as it was the first time their entire team came together after two acquisitions that grew their firm from $3 million to $6.5 million in revenue.
Starting with Leadership Alignment
The work that made this retreat effective started in late September. Their leadership team, including Marcus, Rachel, Director of Operations Amy McCarthy, and Director of Accounting and Advisory Lezlie Reeves, met in Saint Louis, Missouri.
They were already there for a meet-and-greet related to their recent acquisition, so they carved out a full day specifically for 2026 planning. The change of location helped them focus beyond daily operations.
“We were out of our normal element, which was great because it changed the pace and place and allowed us to focus better,” Marcus explains.
The team uses a framework originally developed by C12, an organization of Christian business owners, which they’ve adapted for their accounting firm. The framework breaks planning into five key areas:
- Revenue Generation. Setting targets and monitoring progress, with flexibility to adjust client onboarding based on team capacity
- Operations Management. The steady force that keeps the firm grounded when new opportunities arise
- Organizational Development. Team structure, hiring, roles, and succession planning three to five years out
- Financial Management. KPIs and reporting—the self-accountability accountants sometimes neglect for their own firms
- Ministry. How the firm gives back and serves as good stewards
What emerges is a one-page document with a matrix showing each goal area, the strategic objective, success metrics, who’s responsible (including first and second chair assignments), and deadlines.
“If there’s no timeline, you just keep kicking the can down the road,” Marcus notes. “And those goals never get touched again.”
The leadership conversations extend beyond immediate goals. They discuss where each person sees themselves in three to five years, and what they want to see happen. These discussions require openness from everyone involved.
“As a leader, you have to be prepared for whatever your fellow leaders’ answers may be,” Marcus says. “You have to be open to hearing that.”
Finding the Right Time
The Dillons learned through trial and error that when you hold a retreat matters as much as what you cover. Their timing has evolved over the years.
Initially, they held retreats in January, capturing the new year, fresh goals energy. But that created immediate conflicts. “Taking a day and a half or two days right when you come back from the holidays is tough,” Rachel explains, especially with year-end financials due by the 15th and 1099 work piling up.
They tried pushing it to after January 20th, but that still felt rushed with the January 31st deadline approaching. Moving it any later meant they were already more than a month into the year before rolling out goals.
Their current approach places the retreat in mid-November, the week before Thanksgiving. This timing works because teams have just finished the November 15th deadline for month-end financials. Leadership has ten and a half months of data to review, enough to project year-end performance and celebrate achievements without waiting for perfect December numbers.
“If people are busy and have deadlines and clients waiting and asking for things, they cannot be fully focused and engaged in the retreat,” Rachel emphasizes.
For a remote firm where more than half the team flies in, the schedule runs Sunday arrival, full day Monday, half day Tuesday, with people heading home Tuesday afternoon. This prevents taking up too much of people’s weekend and avoids the stress of same-day travel.
The Logistics That Matter
Every detail either helps team members focus or creates distraction. The Dillons have learned which investments pay off.
They provide hotel rooms for everyone who needs one, including local team members. “Some people took us up on that because they didn’t want to wake up super early, commute, and get ready. That’s just not their normal routine,” Marcus explains.
Food is available throughout both days. Hotel catering costs more than bringing things in, but it simplifies coordination dramatically. The team eats lunch off-site both days, providing mental breaks from the meeting room.
When everyone’s together, they maximize the opportunity. A photographer comes in for professional headshots, and team members cycle through during sessions without disrupting the flow. Only Monday requires professional dress; Tuesday is comfortable.
The Monday evening Christmas party happens at a nearby Brazilian steakhouse, with spouses invited. But first, the team went to Great Big Game Show, a venue where groups compete in TV-style game show formats.
“It was less than $40 per person. It was an hour and a half event,” Rachel notes. “So it was fairly cost effective but very memorable for the team.”
“It doesn’t have to be expensive to be memorable,” Marcus says.
Building Trust Through Transparency
What happens in the room determines whether the retreat creates lasting change or fades by the following week. The Dillons’ approach centers on transparency about the firm’s actual performance.
They share real revenue data, including year-to-date numbers, projections, where the firm stands against goals. Many firm owners hesitate at this level of openness, but the Dillons have only seen positive results.
“There has never been an instance where someone has come to us and said that we are unfair based on a revenue number,” Rachel says. “The only things that have come from us sharing more has been positive response and feedback.”
This transparency extends to the firm’s direction. In 2021, during their pivot to remote work, they created “Future Direction” statements, which are clear commitments:
- Monitor, monetize, or refer annual tax clients outside core services
- Operate within a fully connected tech stack
- Share industry best practices with peers
- Be the model firm in small business accounting
- Attract highly qualified, highly motivated team members
- Implement travel retreats
- Create initiatives to give back locally and abroad
Four years later, they still reference these statements at every retreat. “We can go through and put a check mark next to every single one and point back directly to exactly how we achieved those things,” Rachel explains.
The continuity matters when firms undergo major changes. “When they look back at this, they see it’s not any different than what we said we were going to do,” she notes. “Maybe how we get there or what we use to do it changes, but the overall direction definitely aligns.”
Celebrating Before Charging Forward
The Dillons organize both achievements and initiatives into four categories: Growth (clients and team), Process (procedures and technology), Team Development, and Collective by DBA (their peer network offering). This structure ensures nothing gets forgotten between retreats.
For 2025, there was plenty to celebrate:
- Securing 12 out of 15 targeted new organic clients
- Two successful firm acquisitions
- Multiple director-level additions including Operations, Accounting and Advisory, Technology, and Tax and Financial Planning
- Implementing of Double for improved client reporting
- Launching monthly role-specific training programs
- Growing the team from 15 to 25 people
“I don’t do a great job of stopping to celebrate,” Marcus admits. “So I made sure that it was built in.”
Each year gets a theme. For 2025, it was “Growth, not comfort.” For 2026, they’ve chosen “Lead change, create impact,” reflecting their shift from a growth phase to refinement as they integrate everything they built.
The firm also shares specific quarterly goals and hiring plans. “When we started opening up more transparently with the financials and the overall plan of the business, we could actually invite people who are smarter and better than us in given areas,” Marcus explains.
Even the closing gifts reflect practical thinking. The Dillons receive quite a bit of vendor swag throughout the year, including high-end items from Canopy, Intuit, QuickBooks, ADP, and Double. Rather than letting these accumulate, they share them with the team.
“If you don’t have stuff like that laying around, I’m sure you can reach out to your partners, your technology partners, and they’ll send you some stuff to share with your team,” Marcus suggests.
Making It Work for Your Firm
The difference between retreats that drain resources and those that create momentum is intentional planning that starts months ahead, timing that respects your team’s reality, logistics that remove friction rather than create it, and transparency that turns information sharing into trust building.
Listen to the full episode of Who’s Really the Boss? for more advice for running a successful team retreat. Plus, Rachel offers to share DBA’s actual retreat agendas and planning templates with any firm owner or team member who reaches out. “Don’t feel like you have to reinvent the wheel,” she says. Email her at rachel@collective.com or use the contact form on their website.
As the Dillons have learned through nearly a decade of refinement, when you invest in getting retreats right, a two-day gathering can align and energize your team for the entire year ahead.
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.
