The Four R's That Make Every Tax Season Better Than the Last

Every April 16th, accounting firm owners collapse into their chairs thinking "never again." Yet come January, they're trapped in the same exhausting cycle. In a recent episode of the "Who's Really the Boss?" podcast, Marcus Dillon and I share how our firm broke this pattern by transforming summer into structured "Improvement Season."

Fresh off dropping both daughters at college (and officially empty nesters except for our high-maintenance dog, Cash), we shared our Four R's framework to ensure each tax season at Dillon Business Advisors actually gets better than the last. 

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The Problem With Traditional Post-Tax Season Approaches

Most accounting firms treat the months after April 15th in one of two ways. Either they completely disconnect for an extended break, losing all momentum and forgetting the specific pain points that made tax season difficult. Or they immediately dive into new projects without rest, burning out their teams before the next busy season even arrives.

Both approaches guarantee one outcome: next tax season will be just as painful as the last.

If you wait too long to address problems, everyone within the firm forgets how painful things were or what didn't work. Those brilliant solutions that seemed obvious at 11 PM on April 14th? They disappear if you wait until June (or beyond) to capture them.

The Four R's Framework

Instead of the typical summer drift, at Dillon Business Advisors, we designate April 16th through August 15th as official "Improvement Season" with four distinct phases:

Recharge: Strategic Rest Without Losing Momentum

The first breakthrough challenges conventional wisdom about recovery. Marcus frames it perfectly: "It's recharge, not retire."

We recommend just three to five days off (seven maximum) immediately after the deadline. This tight timeframe preserves team energy and the sharp memory of what needs fixing. For example, when tax season ended mid-week in 2025 with Easter weekend following, we gave the team an extra day off to allow a long weekend of rest and recovery.

But before anyone left, the tax season survey was already in team members' hands. People could complete it during quiet moments or while waiting for final returns to process. By Tuesday after Easter, our leadership team had compiled feedback ready to analyze, while the pain points still stung and victories still glowed.

 Review: Systematic Feedback Collection

The review phase transforms scattered observations into actionable initiatives. We use a dual approach at DBA: team surveys capture ground-level experiences while leadership analyzes key performance indicators (KPIs) and metrics.

This year's review uncovered an oversight from our January 31 acquisition. We hadn't immediately obtained 7216 disclosures (allowing external contractors to work on tax files) from acquired clients. "Not having that limited the available team members that could help with some of those projects," Marcus explained. "If we had the whole team available to help, it would have gone a lot smoother."

I take a practical approach to review meetings. "Put it on the calendar." I no longer wait until everything is figured out. Instead, I block time first, creating "accountability to continue moving forward." Perfect preparation is the enemy of progress.

Refocus: Aligning Improvements With Core Values

All that feedback gets filtered through our accounting firm's mission, vision, and values. This isn't corporate buzzword compliance; it's strategic alignment that prevents initiatives from pulling the firm in conflicting directions.

During Dillon Business Advisors’ mid-year team retreat in Mexico, we revisited these foundational elements, asking whether planned improvements still aligned with "what everyone knows to be true” about the firm.

Some conversations work better in person. For example, when implementing new cell phone security measures that could feel invasive, we waited for the retreat to explain face-to-face. You can have more conversations, especially for team members who have reservations, and really understand where both parties are coming from.

Refine: Sustained Execution Through Summer

The longest phase, Refine, is where most accounting firms fail. As team members rotate through vacations, initiatives tend to stall. DBA maintains momentum through structured accountability.

We talk about goals and initiatives weekly at lead team meetings. If it's something that's more the responsibility of one or two people, then those check-ins happen in our one-on-ones every other week.

Marcus acknowledges the challenge. "You look up on any given week during the summer and you've got team members out, you've got lead team members out." But by maintaining visibility across the team, work continues even when individuals are absent.

He also admits, "The refinement season is where I get bored, and I want to go start something new or break something just to fix it." This self-awareness is crucial. It recognizes that steady implementation isn't as exciting as planning but is infinitely more valuable.

Real Results From Improvement Season 2025

The concrete improvements from this year's Improvement Season demonstrate the framework's effectiveness:

Technology Transformation

Our Director of Technology, Angel Sabino (hired in January), rebuilt our entire tech stack, moving from a basic hosted solution to Microsoft Azure. Single sign-on now works across all platforms, including UltraTax. New team member onboarding, which previously took two days just for IT setup, now takes 30-60 minutes. Dell ships pre-configured laptops directly to new hires' homes.

Enhanced Security

Dillon Business Advisors implemented cell phone security thoughtfully. Rather than forcing compliance, leadership explained the reasons for the policy change during their Mexico retreat. Team members could choose to bring personal devices into the security bubble or use them solely for authentication. "We treated people like adults," Marcus explained.

Team Dynamics

Sessions on healthy conflict and peer accountability (complete with role-playing) transformed meeting culture. There is more discussion and conversation in team meetings. People don't feel like they have to stay on mute and have permission to share ideas and ask questions that could differ from the group.

Client Integration

Our firm gradually transitions acquired clients to DBA's team-of-three model with monthly service. Rather than forcing immediate conversion, the team "consistently shows them why constant, proactive communication is a better option versus retroactive."

Grading Our Own Performance

When asked to grade our improvement season, I give the team an A+. We didn't let momentum stop no matter who was out of office, no matter what challenges came up. The team learned to step in when others were absent and developed discipline around calendar blocking.

Marcus, grading himself a modest A-, captures essential wisdom: "Improvement season is more a marathon than a sprint. Definitely keeping a good, consistent pace is what's going to win the race."

Your Next Tax Season Starts Now

The 4 Rs Improvement Season framework proves that summer doesn't have to be a choice between exhausted recovery or aimless drift. Small improvements compound over time. That technology upgrade saving each person 15 minutes daily? Over busy season, that's hours of recovered productivity. Communication protocols that prevent misunderstandings? They eliminate fire drills that derail entire days. 

Perhaps most importantly, Improvement Season sends a powerful message to your team: their pain points matter, their ideas have value, and the firm is committed to getting better.

You don't have to wait until next April to start. Even after October 15th, there's still plenty of time in the year to begin your own improvement season.

Listen to the full episode to hear more tips from Marcus and I on implementing your own Improvement Season. The question isn't whether you can afford to invest time in improvement. It's whether you can afford another year of the same painful patterns.