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Who's Really the Boss

Uncover the Strategy That Turns Extended Leave into an Innovation Opportunity

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When two team members announce overlapping maternity leaves, many firms would anticipate a major disruption. But when that scenario played out at Dillon Business Advisors, something remarkable happened: team efficiency improved, profitability rose, and the firm discovered innovative ways to serve its clients.

In a recent episode of the Who’s Really the Boss podcast, Lezlie Reeves, Fractional CFO at Dillon Business Advisors, discussed with hosts Rachel and Marcus Dillon how the firm transformed what could have been a significant operational challenge into a catalyst for growth. With a team of 15 employees serving numerous clients, extended employee leaves often spell strained client relationships and overwhelmed staff—issues many CPA firm owners know all too well.

Yet through methodical documentation, systematic training, and strategic role delegation, Dillon Business Advisors didn’t just maintain their service levels—they raised them. Their experience offers valuable lessons for any firm looking to build more resilient teams and sustainable growth.

Building the Foundation: Systematic Documentation

Before team members announced their leaves, Dillon Business Advisors had already laid the essential groundwork. They recognized a common issue in accounting firms: too much vital knowledge residing in employees’ heads.

“Many of our CSMs do such a great job, but a lot of things would live in their head,” explains Lezlie. “If they needed to be out or someone left unexpectedly, they were not covered.”

Their solution was straightforward: using Excel templates and Vimeo recordings, the team documented every client’s comprehensive workflow—from daily tasks and weekly responsibilities to monthly financial preparation and client contact details. Rather than creating more administrative burdens, they integrated documentation into normal processes: recording videos during actual client work and updating Excel templates in real-time.

The team had previously solved for  password management by implementing Practice Protect, ensuring secure access to client systems wouldn’t become a bottleneck during employee absences and exits.

This foundation of systematic documentation paid off when employees announced their leaves. Instead of scrambling to capture processes and procedures, the firm focused on strategic preparation and training. It’s a powerful reminder that the best time to document critical workflows is before you need them.

Methodical Training: The Key to Seamless Transitions

With documentation in place, Dillon Business Advisors turned their attention to training team members over six to eight months.

The training began with basic daily tasks before progressing to specific client work. To avoid overwhelming both the trainers and the trainee, they introduced five clients at a time. This paced approach allowed the CSM Assistants to gain confidence with one cluster of clients before moving on.

 “If you’ve ever trained someone, you know it is exhausting to train while you’re working,” Lezlie says. 

To address this, the firm distributed training responsibilities across multiple team members instead of burdening a single trainer with 40 hours of instruction. Each group of clients followed a three-month progression:

1. Month One: The CSM Assistant shadowed the CSM.  

2. Month Two: The CSM Assistant handled the work with the CSM shadowing.  

3. Month Three: The CSM Assistant worked independently with support available.  

By the time employees went on leave, their replacements were fully prepared and confident—a stark contrast to common last-minute handovers.

From Disruption to Opportunity: Strategic Role Distribution and Unexpected Benefits

Rather than assigning all responsibilities to controllers, Dillon Business Advisors strategically divided tasks. The CSM Assistant handled bank feeds, reconciliations, journal entries, and financial preparation, while controllers managed client communication, tax filings, and payroll. This balance prevented any team member from becoming overloaded and ensured critical deadlines were met.

An unexpected bonus soon emerged. 

“One added benefit we’ve had is with the client service manager assistant and the controller stepping in on different tasks—they’re just putting a different set of eyes on things,” Lezlie notes. “They can reevaluate, maybe trying new ways of doing things.”

These fresh perspectives resulted in process improvements across multiple clients. Team efficiency grew, and rather than seeing a dip in profits during the leave periods, the firm saw an increase in profitability. When the team members returned from leave, they even requested to continue assistant support because it had enhanced their ability to serve clients effectively.

What began as a workaround for extended leave transformed into a sustainable model for growth, enabling the firm to create capacity without hiring more full-time CSMs. This led to more efficient workflows and improved profitability overall.

Turning Challenge into Opportunity

What started as leave preparation became a catalyst for enduring change at Dillon Business Advisors. Through systematic documentation, methodical training, and strategic role delegation, they not only maintained client service—but improved it.

By viewing extended leave not as an unavoidable disruption but as an opportunity for growth, accounting firms can build more resilient teams, streamline workflows, and create new paths for expansion.

Want to learn more about how Dillon Business Advisors transformed their approach to employee leave management? Listen to the full episode of the Who’s Really the Boss podcast for deeper insights and practical tips you can implement in your firm.  

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.

Breaking Free From the Tax Return Trap: Building an Advisory-First Accounting Practice

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Tax revenue can be addictive. Each $1,000 return during tax season feels like security, building a predictable revenue stream that’s hard to walk away from. But what if there was a way to transform those same clients into relationships worth $15,000 per month?

In a recent episode of the Who’s Really the BOSS? podcast, hosts Rachel and Marcus Dillon shared how their firm broke free from the trap of transactional relationships. While many accounting firms remain caught in the cycle of seasonal tax work and basic compliance services, their story shows there is a different path forward.

Through strategic patience and value-focused communication, Dillon Business Advisors evolved from processing tax returns to providing comprehensive advisory services. This transformation wasn’t just about offering new services – it required fundamentally changing how they engaged with clients and demonstrated value.

Setting the Stage for Transformation

“In the early years, we were just taking numbers and plugging them into a program to get people compliant,” Marcus admits. “That’s what a tax return does.” This transactional approach defines many accounting firms’ early stages, but technology and changing client needs have opened the door to something more valuable: true advisory relationships.

This evolution requires a shift in the mindset around client relationships. Rather than trying to retain every client and any revenue, successful firms learn to approach client conversations with clear outcomes in mind: either clients opt into expanded services, or they’re referred elsewhere. This takes both confidence and a strategic vision.

“Go into the conversation assuming they’re no longer going to be a client,” Marcus advises. “Just assume they’re going to tell you no, and you’re going to have to refer them out.” This means having referral options ready before crucial conversations. It might seem counterintuitive, but this mindset builds stronger client relationships.

Many firms fall into the trap of accepting less than ideal arrangements that stretch into years of suboptimal relationships. “You kind of give in and it’s like any revenue is good revenue,” Marcus reflects. ” Yeah, we’ll keep doing your return for one more year, but that turns into two more years and three more years.” Instead, the Dillons recommend focusing time and energy on clients who demonstrate they value advisory relationships while confidently referring others to firms that better match their needs.

This selective approach sets the stage for transforming transactional relationships into something more valuable.

From Annual Tax Client to Monthly Advisory: A Case Study

To demonstrate how value-focused communication can transform client relationships, the Dillons shared a client story. Initially, this client, a large family group, paid the firm roughly $60,000 per year to prepare multiple tax returns. Today, that client is a $15,000 monthly advisory engagement – but this didn’t happen through aggressive selling or rushing the relationship.

As part of a client acquisition years ago, this client demonstrated they valued the firm’s expertise long before expanding services. Throughout the year, they would seek opinions and book additional consultations, showing they viewed the firm as more than just tax preparers. When business changes created new needs – including the departure of key team members – DBA laid the groundwork for expansion through years of trust-building.

The transition succeeded through what Rachel Dillon calls “reverse selling.” Rather than pushing services, they explained their standard processes and let the client discover how these services could address their needs. “By communicating what we do for other people, he found the ways it could work in his business,” Rachel explains. “We didn’t have to convince him.”

Clear communication about service structure proved crucial. When discussing delivery timelines, they were upfront about monthly financials being ready by the 15th rather than the 5th – a change from the client’s internal team. This transparency about service parameters allowed the client to make informed decisions about the transition.

The client even readily accepted onboarding fees, noting he didn’t have a problem paying for onboarding because he knew any conversion would have a cost with it.” This willingness stemmed from understanding the value proposition and having experienced the firm’s advisory capabilities over time.

While this transformation showcases what’s possible, many firm owners wonder how to begin their own evolution. The key is taking practical steps toward change.

Practical Steps Toward Transformation

For firm owners feeling overwhelmed by the prospect of transformation, Marcus suggests starting with a simple question: “If I were to invest $10 million in your business today, what would we do differently?” This thought experiment helps identify priorities and possibilities without the immediate pressure of financial constraints.

Often, the changes needed don’t require millions – they require strategic thinking and incremental steps. For example, rather than transforming 5,000 tax clients into advisory relationships at once, consider transitioning just 150 clients to create initial capacity. This selective approach aligns with the strategic patience needed for successful transformation.

“Your business does not look the way it does because you had a crappy tax season,” Marcus explains. “It is all the days of every year. That’s why your business looks like it does. And so to change that, you just have to take action.” This perspective helps overcome what Marcus calls the “addiction” to tax revenue – the comfort of seeing those annual returns stack up.

The key is breaking down barriers into manageable steps. Major costs, like hiring key team members, can be spread over time rather than needed upfront. A $150,000 annual salary becomes manageable when viewed as a monthly investment in growth. This same principle applies to transforming client relationships – progress happens through consistent, strategic actions rather than overnight change.

Moving Forward with Confidence

The journey from transactional relationships to trusted advisors isn’t just about changing service offerings – it’s about transforming how you engage with clients and demonstrate value. As the Dillons’ experience shows, success requires strategy, clear communication, and the confidence to pursue ideal client relationships.

The potential financial impact of transforming annual tax clients into monthly advisory relationships is significant. But equally important is the shift from seasonal stress to sustainable, year-round client partnerships that deliver value for both sides.

Listen to the full episode of the Who’s Really the BOSS? podcast to learn more about pricing structures, service delivery models, and specific client communication approaches that lead to successful transitions. Your evolution from tax preparer to trusted advisor awaits.

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.

Facing Growth Challenges Alone? Discover How Structured Peer Support Can Change Everything

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For many accounting firm owners, success is a lonely path. Even as revenue grows, teams expand, and client bases strengthen, the weight of daily decisions—capacity planning, strategic pivots, team management—rests squarely on their shoulders. Casual networking and brief connections rarely offer the deep support needed to navigate these unique challenges.

In a recent episode of Who’s Really the BOSS?, hosts Rachel and Marcus Dillon interviewed Ben Gabriel, a former technology consultant and current mastermind group facilitator with over 20 years in the accounting industry. Ben shared a compelling alternative: structured peer support. Unlike traditional networking, these groups foster ongoing, committed relationships where firm owners share their struggles, celebrate successes, and access the wisdom of peers who truly understand their journey. These groups transform professional growth from a solitary pursuit into a collaborative journey, providing a framework for achieving sustainable success without sacrificing values or vision.

Moving Beyond Networking to Structured Support

Professional growth requires more than occasional networking. As Marcus reflects, “These groups were the highlight of my week, my months, sometimes just a season of life—to be surrounded by peers who, while not going through the exact same thing, are facing similar challenges.”

Collective by DBA offers structured peer support at three distinct levels of engagement. The first level, Collective Community, involves self-guided improvement, where firm owners work through challenges independently using resources within the online community. The second level introduces peer groups, Collective Forums, fostering monthly interaction and shared experiences. The third and highest level, Collective Advisory,  involves one-on-one advisory relationships that provide focused guidance and accountability.

Unlike casual meetups or networking events, structured peer groups prioritize consistent, in-depth engagement. Each session opens with members sharing a recent success and a pressing challenge, creating a supportive environment where members can reflect on progress and receive constructive input. As Ben explains, the power of these groups comes from the continuous nature of the relationship, which extends beyond monthly meetings to include group chats, direct messaging, and online forums for real-time feedback and support.

Creating Safe Spaces for Honest Conversations

Structured peer groups excel at fostering psychological safety, allowing members to share personal and professional challenges openly. Rachel highlights the importance of this, admitting, “I get nervous to share things that are personal or that carry a lot of value for me.” This sentiment likely resonates with many firm owners, who may hesitate to share financial or operational details.

Marcus agrees, “For accountants, sharing financials is intimate. To others, it may seem mundane, but for us, it’s deeply personal.” 

However, over time, members build a foundation of trust. Unlike traditional gatherings where vulnerability may feel risky, the recurring nature of structured peer groups allows members to form meaningful bonds, knowing their peers understand the nuanced challenges of running an accounting firm. This creates a space where members receive not just quick fixes but thoughtful, experience-based insights.

Leveraging Collective Wisdom for Complex Problems

One significant benefit of structured peer support is the collective problem-solving that arises, especially when dealing with complex issues like capacity planning or burnout.

Marcus describes burnout as “a misalignment between work and passion. If your work involves tax returns but you dislike tax, you’ll feel burnout no matter your workload.” Structured groups encourage firm owners to explore deeper causes of burnout, like misaligned values or unfulfilling tasks, rather than just focusing on time management.

Rachel echoes this, suggesting a practical approach: “Start by identifying what you don’t like and remove those elements. Whether that’s exiting non-ideal clients or delegating tasks, it creates space for alignment with your goals.” These discussions lead to actionable strategies that members can adapt based on real-world experiences, transforming burnout from an isolated issue into a shared learning opportunity.

Structured groups also allow members to benefit from the experience of peers. Members may exchange insights on hiring virtual assistants, implementing new technologies, or refining service offerings. By learning from others who’ve already navigated similar transitions, firm owners can make more confident, informed decisions, reducing the trial-and-error burden.

Transforming the Professional Journey with Peer Support

Running an accounting firm doesn’t have to be a solo endeavor. Structured peer groups provide more than solutions—they foster community, creating a network of peers who celebrate each other’s successes and offer support through challenges. Whether addressing burnout, capacity planning, or strategic shifts, these groups provide a blend of practical insight and emotional encouragement, empowering members to pursue sustainable growth.

Ben shared the advice his grandmother gave him: “Keep on moving and don’t shuffle your feet.” To Ben, that advice means there’s no better way to keep moving forward than with the support of peers who truly understand your journey.

To explore how structured peer support enhances your professional growth, listen to the full Who’s Really the BOSS? podcast episode featuring Ben Gabriel. Discover how other firm owners leverage peer groups’ power to build sustainable practices while staying true to their values and vision.

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.

Why This Modern Firm Still Tracks Time—and How It’s Boosting Their Success

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What if the secret to modern accounting success isn’t abandoning time tracking but reimagining it? Dillon Business Advisors (DBA) discovered that time tracking—separated from billing—is a powerful strategic tool for managing their subscription-based practice.

In a recent episode of the “Who’s Really the BOSS?” podcast, firm leaders Marcus and Rachel Dillon discussed how this traditional practice transformed their modern firm. While many industry thought leaders suggest firms discard time tracking and hourly billing, DBA found that maintaining it—with a crucial twist—provided valuable insights into team management and business growth.

Time Tracking as a Strategic Tool in a Virtual Firm

Traditional firms primarily use time tracking for billing. However, in DBA’s virtual environment, it’s a crucial window into team performance and client profitability.

Marcus explains, “In a virtual environment, it’s hard to wrap my mind around what’s going on. Not that I care how much time is being spent, but it weaves into our project management. It highlights an abnormal month, and then we can discuss what happened.”

Rather than using time data for invoicing, DBA leverages it to gain operational insights—which are especially vital when managing a remote team across multiple client engagements.

When team members feel stressed about particular clients or workloads, time data provides objective evidence to evaluate the situation. Rachel notes, “Often, when there are outside stressors and client requests pulling on you, you may perceive one as your biggest problem over the other, without data to support that.”

Tracking time is also valuable for managing their subscription-based services. The firm regularly compares historical time data against current trends. For instance, “If two months ago it took our team eight hours to complete the engaged work, and now it’s taking 14 hours, is it still the same work, or are there out-of-scope tasks? Has the business increased in volume or complexity?” Data from time logs allows DBA to proactively address scope creep, adjust pricing when necessary, and ensure their team isn’t overwhelmed by expanding client demands.

Combining Manual Oversight with Data Analysis

While many firms aim to fully automate their time data oversight, DBA prefers a manual approach, especially in a virtual environment.

Their monthly review process, which takes Marcus and Rachel around three to four hours, combines tools like Excel pivot tables with human analysis. DBA finds that manual review provides strategic insights that automation might miss.

Rachel explains, “I see it not as invoicing but as clearing out time for write-ups and write-downs. It gives us extra accountability to address issues sooner rather than later. If you’re busy, you might not address out-of-scope issues or potential team burnout as promptly.”

 Marcus agrees, “I need to be looking at this data monthly.”

This intentional review helps the firm quickly identify patterns, recognize potential team burnout, and spot clients needing pricing adjustments—crucial insights they might miss with a fully automated process.

Leveraging Time Data for Strategic Decisions

Time tracking’s strategic value extends beyond daily operations, influencing growth, staffing, and firm valuation decisions.

DBA finds that understanding team capacity through time data helps them manage part-time staff and plan for growth.

For part-time remote team members, time tracking ensures workload balance without compromising quality. Marcus explains, “If a part-time person doesn’t have billable work, they’ll log off, and it’s hard to know—are you willing to give DBA more time, or were you really done?” This led to committing to consistent hours for part-time staff while optimizing their workload using time data.

Time data is also valuable for firm valuation and succession planning. Marcus notes, “Allan Koltin says the most valuable firm is the one with team members and no clients.” He describes a recent M&A event in which “because they had excess capacity, they were more valuable to the buyer—nobody wants to buy overworked and burned-out employees.”

This shifts excess capacity from a cost to a valuable asset, enabling strategic marketing, growth, and succession planning decisions. Whether determining when to “turn on a little bit more marketing” or evaluating pricing for new engagements, time data provides insights for informed decisions on firm growth and future value.

Transforming Traditional Metrics into Strategic Assets

As firms evolve toward value-based pricing, DBA’s experience shows firms can reimagine traditional tools like time tracking for modern practice management.

Viewing time data as a strategic tool rather than a billing metric allows firms to gain essential insights and maintain oversight of team members in a virtual or hybrid environment.

To learn more about transforming traditional metrics into strategic assets, listen to the full episode of the “Who’s Really the BOSS?” podcast. Marcus and Rachel share additional insights about managing virtual teams, optimizing processes, and building a modern accounting practice that thrives beyond the billable hour.

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.

Beyond EOS: A Better Path Forward for Accounting Firm Growth

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What if the very business system you’ve implemented to streamline operations is stifling your firm’s growth? While popular frameworks like EOS (Entrepreneurial Operating System) promise efficiency and scalability, many accounting firm owners discover that these generic solutions fail to address their unique challenges—from managing seasonal workflows to optimizing tax preparation processes.

In a recent episode of the “Who’s Really the BOSS?” podcast, hosts Rachel and Marcus Dillon sat down with industry consultant Christine Nietzke to dig into operating systems for accounting firms. Drawing from decades of experience working with accounting firms, Christine shared why traditional business systems often constrain rather than enhance firm performance, especially when implementing specialized workflows and managing industry-specific demands.

The Promise and Limitations of Generic Business Systems

The appeal of systems like EOS is clear: they provide a structured approach to running your business through quarterly meetings, defined priorities (called “rocks”), and regular check-ins to maintain momentum. As Christine explains, “It’s a great process. It helps business owners keep at the forefront the things they’re trying to achieve.” There’s even science behind the system’s 90-day check-ins, aligning with natural human motivation cycles.

However, implementing EOS comes with significant commitments and crucial limitations many firm owners don’t initially recognize. EOS requires a “purity” commitment from its implementers that prevents them from providing industry-specific guidance or operational advice outside the system’s framework.

Christine discovered this limitation while exploring becoming an EOS implementer herself. “I would have been prohibited from helping an accounting firm specifically with an operational issue or workflow,” she explains. “That was the deciding factor for me—a deal breaker.” This restriction reveals a fundamental challenge with generic business systems: they prioritize standardization over specialization, potentially leaving accounting firms without the specific guidance they need to address their unique operational challenges.

For accounting firm owners, this means choosing between maintaining system purity and accessing the specialized expertise needed to optimize their practice. Christine shared an example of how this choice can significantly impact firm efficiency and growth.

When Generic Systems Meet Real-world Challenges

Christine worked with a firm owner who inherited his practice from his father—a common scenario in the accounting industry. Along with client relationships came embedded inefficiencies in workflows and processes holding the firm back. Notably, every tax preparer handled each return from start to finish, creating unnecessary complexity and reducing productivity—a challenge that generic business systems can’t address.

“Working with him, I helped reimagine what his tax process looks like in his firm,” Christine explains. By understanding the nuances of tax preparation workflows, she implemented a tax administrative professional role to handle front-end and back-end processes—a change that would have been impossible under the constraints of a generic system focused solely on high-level business practices.

The results were immediate and measurable: fewer tax extensions, improved efficiency, and better workflow management. They didn’t achieve this transformation through general business principles or quarterly goal-setting but by applying specialized industry knowledge of the challenges and proven solutions specific to accounting firms.

As the profession continues to evolve and new challenges arise, firms will continue to need specialized solutions. Forward-thinking firms are discovering that the path to sustainable growth is approaches explicitly tailored to their unique needs.

The Power of Industry-Specific Solutions: GRIP in Action

Enter GRIP (Goal Ready Implementation Plan), a solution that exemplifies the move toward industry-specific approaches. Unlike generic systems that apply the same framework to every business, GRIP was designed specifically for accounting firms, with a built-in understanding of tax seasons, industry workflows, and practice management challenges.

“While EOS is a process and a system, GRIP is actually a blueprint,” Christine explains. “It’s going to get you exactly where you want to be. And you have consultants and advisors ready to help you when things aren’t progressing the way you wanted.” This distinction is crucial: rather than just providing a framework, GRIP offers a concrete roadmap tailored to accounting firm success.

The program’s effectiveness comes from its deep integration of industry knowledge. Implementation timelines account for tax seasons, preventing the chaos that can result from instituting significant changes during peak periods. Documentation and delegation strategies are designed specifically for accounting firm dynamics, and ongoing advisory support comes from professionals with direct industry experience.

Firms implementing GRIP bring their blueprint to every leadership team meeting, using it to guide decision-making and track progress. This practical application demonstrates how industry-specific solutions transform high-level goals into actionable improvements—proving that specialized knowledge matters when it comes to accounting firm success.

Embracing Tailored Solutions for Firm Growth

Accounting firms face unique challenges that generic business systems often fail to address. By adopting industry-specific solutions like GRIP, firms can implement strategies that account for the nuances of their operations, leading to sustainable growth and operational excellence.

Ready to transform your firm’s operations with specialized approaches? Listen to the discussion on the “Who’s Really the BOSS?” podcast, where Christine shares additional insights and real-world examples of accounting firms achieving breakthrough results.

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.