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Archives for September 2025

Why Most Accounting AI Will Hit an Auditability Wall

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Every day, another AI agent promises to revolutionize accounting. But there’s a fundamental problem most tech companies don’t understand: AI accounting will hit what FloQast CEO Mike Whitmire calls “the auditability wall.”

While Silicon Valley churns out press releases about AI agents that can handle complex accounting tasks, a reality check awaits. In this episode of the Earmark Podcast, host Blake Oliver sits down with Mike Whitmire, founder and CEO of FloQast, to explore why accounting AI is fundamentally different from AI in other business functions. Rather than getting swept up in the AI marketing frenzy, FloQast stepped back to solve the core problem: how to harness AI’s power while maintaining complete audit trails and human oversight.

As Whitmire warns, “A series of companies will come out with AI agents that can do a lot of this work fairly accurately. Then they hit this auditability wall, and it creates a big problem for companies trying to scale.”

The Auditability Problem That’s Breaking Accounting AI

Unlike other business functions where AI mistakes can be shrugged off, accounting operates under rules most tech companies don’t understand. When a sales AI messes up a lead, the stakes are minimal. But in accounting, every transaction must be traceable, every decision documented, and every process capable of withstanding regulatory scrutiny.

This creates a fundamental conflict between how most AI systems work and what accounting requires. “AI is really about automating work, and agents are doing non-deterministic work,” Whitmire explains. “So that becomes a little scary when you’re thinking about auditability.” Most AI systems function as “black boxes.” They can produce results, but they can’t explain their decision-making process in the detailed, step-by-step manner that auditors and regulators demand.

The problem is about to hit the industry hard. When AI systems can’t provide proper documentation and audit trails, auditors are forced to recreate all the work, defeating the entire purpose of automation.

Rather than getting swept up in the AI marketing that dominates press releases from major ERP vendors, FloQast took a different approach. “We tried to avoid the noise and think about how AI should be applied to accounting,” Whitmire says. They started with their experience as former auditors and accountants, asking: How do you combine AI automation with traditional software code and human oversight to create something that actually works?

The answer required rethinking the entire approach to accounting AI, leading to a solution that preserves audit trails and human oversight while still delivering efficiency gains.

FloQast Transform: Building AI Auditors Can Actually Trust

Rather than chase the latest AI trends, FloQast built something different: an AI system that auditors can actually work with. The FloQast Transform product harnesses AI’s power while maintaining the audit trails financial reporting demands.

The approach is simple: let accountants describe their processes in plain English, then use that narrative to generate automated scripts and complete audit documentation. “You build your agents,” Whitmire explains. “You chat with the product and explain your process in pretty extreme detail.”

As accountants describe their workflow step by step, the system populates what looks like a familiar Excel workbook. “This Excel workbook will ultimately be the audit evidence,” Whitmire notes. This isn’t just a user interface choice. It’s a deliberate design decision to ensure every AI-driven process produces the documentation auditors expect to see.

Take FloQast’s benefit allocation journal entry example. The process starts with integrating with UKG Payroll to pull down employee data. The accountant describes each step: “integrate with UKG,” then “pull down information around names, dollar amounts, state,” then “populate column A with this, populate column B with this, and bold and make the header gray because that’s the format I like.”

The system combines different types of automation. For routine tasks, it generates deterministic code that produces consistent results every time. But when the AI encounters something new, like when FloQast hired its first Kentucky employee, it doesn’t guess. Instead, “it surfaces the question to the reviewer of that work,” Whitmire explains. The accountant can approve the change, and going forward, Kentucky will be handled properly.

This approach changes the accountant’s role. Instead of being the preparer who manually processes transactions, they become the reviewer who oversees AI agents and approves exceptions. “Our goal is to empower accountants to automate the really repetitive, rote part of this job. Elevate them into the reviewer of the more complicated work that the agent’s now doing,” Whitmire says.

The system preserves every prompt sent to the AI, every output generated, and every decision made. When auditors come knocking, they can trace exactly how each transaction was processed and where humans intervened. It’s the kind of comprehensive audit trail that makes regulatory compliance possible while still delivering efficiency gains.

Beyond transaction processing, FloQast applies AI to other areas like variance analysis. When account balances trigger materiality thresholds, the system analyzes the biggest transactions causing the change and drafts explanations. “It’s like balance went up because of boom, boom, boom, boom, boom,” Whitmire says. “It’s not these wonderful essays on how things change. It’s like a list of transactions.”

The Future of Accounting: Cyborgs, Not Replacements

The auditability challenge yields a surprising conclusion: rather than replacing accountants, AI will transform their role in ways that could solve the profession’s biggest problems. But this transformation requires rethinking what it means to be an accountant.

Whitmire envisions accountants becoming “accounting transformation information managers,” professionals who combine accounting knowledge with software engineering capabilities. “It will be much more like the merging of an accountant with a software engineer,” he explains. “So you have the accounting knowledge, supplemented by software engineering tools like FloQast, where they can take their accounting knowledge, use our product, and automate their work.”

This isn’t just about learning new software. It’s about fundamentally changing the structure of accounting work. Instead of spending hours manually processing transactions, accountants would deploy AI agents to handle routine work so they can focus on reviewing exceptions, making judgment calls, and ensuring compliance.

The career implications depend on where you are professionally. For younger professionals, Whitmire recommends “Get really good at technology, learn these tools as they come out, and continue to learn about accounting. You’re going to be a very, very valuable employee going forward.” For experienced professionals, “You need to be really great at reviewing the work. Continue to be really great leaders, and run great organizations.”

This evolution could address the profession’s talent shortage. By making accountants more productive and the work more intellectually engaging, AI could help attract and retain talent. “My hope is that it does a really good job of plugging the talent gap we talk about so much,” Whitmire notes.

But there’s a learning concern. Whitmire worries about newer professionals who might skip foundational manual work and jump straight to reviewing AI-generated results. “I feel like the old man saying this, but I did learn a lot doing the work manually and struggling through it,” he admits. He recalls learning about jet lease accounting by struggling through contracts and GAAP guidance—work that an AI could now handle instantly.

The solution may require restructuring how accountants learn their craft. Perhaps starting in accounting roles where they do manual work before moving into audit, rather than the current model, where most start as auditors reviewing work they’ve never performed.

As Oliver puts it, “I would rather manage AIs than manage people.” It reflects both the appeal and reality of this AI-augmented future. Managing AI agents eliminates many interpersonal challenges while allowing professionals to focus on technical and analytical work.

The accounting profession is heading toward becoming a hybrid of human judgment and AI automation. The question is whether professionals and firms will adapt quickly enough to thrive.

Regulatory Changes on the Horizon

The discussion also touched on significant regulatory changes that could reshape the profession. There are efforts in Congress to eliminate the Public Company Accounting Oversight Board (PCAOB) and transfer its responsibilities back to the SEC without additional funding, effectively ending independent audit oversight.

“When I was at EY, we were always scared of a PCAOB audit. So it was a thing that drove behavior,” Whitmire reflects. The fear-based incentive improved audit quality, even if the overall effectiveness is debatable.

Without the PCAOB, the industry would likely return to peer review, where accounting firms review each other’s work. As Oliver notes, “You’re not so afraid of your buddies reviewing your work.” That’s the same dynamic that led to audit failures before the Sarbanes-Oxley Act.

This regulatory uncertainty adds another layer of complexity to the AI transformation. Firms implementing AI systems need to consider current audit requirements and how oversight might change in the coming years.

The Path Forward: Auditability as Competitive Advantage

The accounting profession’s rigid requirement for auditability is often seen as a weakness. But it may become its greatest competitive advantage in the AI revolution. While tech companies rush to market with AI agents that promise to automate everything, firms that understand and embrace the auditability challenge will build sustainable, scalable solutions.

FloQast Transform demonstrates that the future isn’t about choosing between human judgment and AI automation. It’s about creating systems where they work together seamlessly. By preserving audit trails, maintaining human oversight for exceptions, and generating documentation that auditors can use, they’ve solved the fundamental problem that will likely sink many AI accounting startups.

For accounting professionals, this is a career evolution opportunity. The future belongs to those who combine accounting expertise with technology capabilities. These professionals will be empowered by AI to focus on higher-level analysis, judgment calls, and strategic work. The professionals who master these systems now will find themselves in increasingly valuable positions as the technology matures.

To hear the complete conversation about FloQast’s approach to accounting AI, including detailed technical examples and Whitmire’s predictions for the profession’s future, listen to the full episode above.

How Smart Small Businesses Turn Economic Headwinds into Competitive Advantages

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Small businesses are navigating a unique economic moment in 2025. They’re still serving customers and meeting market demands, but they’re doing it while managing changing costs and ongoing policy uncertainty. Despite these challenges, they’re not shutting down or laying people off. Instead, they’re finding creative ways to adapt.

Nicholas Tremper, senior economist at Gusto, shared this insight in a recent Earmark Podcast episode. Tremper tracks data from hundreds of thousands of small businesses through Gusto’s platform, so he has a unique view into how small businesses respond to today’s economic challenges.

The picture Tremper paints is more complex than the headlines suggest. While businesses face real pressures from tariffs, labor shortages, and economic uncertainty, many thrive by combining two essential strategies: utilizing AI to boost productivity and offering more appealing benefits to attract workers. For accounting professionals, this creates new opportunities to become strategic advisors rather than just compliance providers.

Economic Headwinds Create Planning Challenges

In the current economic environment, several interconnected challenges reshape how small businesses operate. Tariffs have reached a weighted average of about 18% across all imports—a significant jump from single digits in previous years. While this level is manageable for most businesses, the bigger problem is uncertainty.

“Small businesses don’t necessarily know how to think about what their costs will be three or six months from now,” Tremper explains. This uncertainty affects everything from inventory planning to contract bidding. For example, if you’re a retailer trying to stock up for the holidays or a contractor giving price estimates months in advance, not knowing future costs makes planning nearly impossible.

The labor market adds another layer of complexity. Unemployment sits at a relatively low 4.3%, but the July jobs report showed weakness with only 73,000 jobs added versus 100,000 expected. More concerning was the massive downward revision of 258,000 jobs from previous estimates for May and June. (Updated numbers released after the show was recorded are +22,000 jobs for August.)

This reflects what Tremper calls an economy that’s “idling”—staying in place rather than growing or contracting. Businesses aren’t laying people off, but they’re not hiring aggressively either. The combination of an aging population and tighter immigration policies creates structural labor shortages, especially in construction and hospitality sectors that traditionally relied on both groups.

These pressures force businesses to delay growth plans. As Tremper puts it, “You may not be able to work on that fourth development. You may have to stop at the three.” When you can’t reliably access more labor, expansion is much more complicated.

Entrepreneurship Boom Continues Despite Challenges

Despite these headwinds, there’s been an entrepreneurship renaissance in the United States. The number of new business applications skyrocketed during the summer of 2020, and as of June 2025, new businesses were still 57% higher than June 2019 levels.

The resilience of small business formation helps explain why the economy has remained relatively stable. “One of the reasons that the economy has been so resilient is because these new businesses have been bringing creative ideas to market,” Tremper notes.

What’s particularly interesting is who’s starting these businesses. For the first time, almost half of new businesses were started by women, compared to 30% in 2019. There’s also been an increase in businesses started by nonwhite entrepreneurs, showing entrepreneurship is spreading across demographics.

These new business owners face similar challenges regardless of their background. When asked about their top three challenges, they consistently mention cash flow, time management, and acquiring customers and employees. At least two of these are areas where accountants can provide significant value.

AI Boosts Productivity Without Replacing Workers

Here’s a statistic that might surprise you: 95% of small businesses using AI aren’t cutting their workforce. Instead, they’re making their existing employees more productive. This contradicts the common narrative that AI inevitably leads to job losses.

The productivity gains are substantial. According to Gusto’s research, 80% of small businesses using AI report productivity increases of 20% or more. But the key insight isn’t just that AI works; it’s how it works.

“Rather than an AI doing somebody’s job, what the person’s doing is they’re like, I’m the expert and you’re going to be a teammate to help me accomplish this quickly,” Tremper explains.

Businesses use AI for routine tasks like summarizing information and conducting market research—the necessary work that doesn’t require deep expertise. Meanwhile, humans focus on applying their knowledge, making judgment calls, and building client relationships.

This approach creates an unexpected benefit in hiring. Businesses that allow employees to use AI report 45% less difficulty finding new workers. It turns out people want to work for companies that give them tools to focus on meaningful work instead of tedious tasks.

The most successful AI implementations happen when businesses develop clear plans about when to use human expertise versus when to leverage AI for efficiency. This strategic approach creates a cycle where better tools lead to more satisfied employees, which makes companies more attractive to potential hires.

Benefits Become Essential for Talent Competition

While AI tackles productivity, smart businesses simultaneously invest in benefits to attract and retain workers. In today’s tight labor market, benefits are competitive necessities.

Offering healthcare benefits increases employee retention by 40% in the first year. Retirement plans show similar effects. What’s interesting is that half of the businesses offering retirement benefits don’t do any company matching. They get significant retention benefits just by offering the benefit.

This creates opportunities for businesses willing to think strategically about their total compensation packages. While competitors focus solely on wages—an expensive and difficult race to win—smart businesses create comprehensive value propositions that extend beyond the paycheck.

For accountants, a communication gap represents a missed opportunity. Fifty percent of small businesses don’t know if their accountant offers benefits guidance, and two-thirds of those simply never thought to ask. When small businesses receive benefits guidance from their accountants, 60% say it influences their benefit decisions. For businesses under two years old, that number jumps to 85%.

Accountants as Strategic Partners

This economic environment creates new opportunities for accounting professionals to evolve beyond traditional compliance work. The share of businesses reporting productivity gains from their accountants has jumped dramatically—from 52% in 2021 to two-thirds in 2025.

“Small businesses view their accountants as business partners. These aren’t number crunchers. These are people who are actively helping me figure out what I’m going to do next,” Tremper explains.

Businesses navigating today’s challenges need more than bookkeeping and tax prep. They need guidance on cash flow analysis, scenario planning, and strategic decision-making. When small businesses can’t predict their costs or easily access more labor, having an advisor who can help them model different scenarios is invaluable.

Cash flow, time management, and hiring are all areas where accountants can provide significant value. Whether it’s helping a client switch to upfront billing to improve cash flow or advising on benefits strategies to attract workers, these services directly address the problems keeping business owners up at night.

Interest rates remaining higher than business owners would like make this financial guidance even more critical. As Tremper notes, “It’s so important to really understand the return on investment on those borrowing costs.” Businesses need help evaluating whether investments will generate enough return to justify higher borrowing costs.

Cautious Optimism for Small Business Future

Despite the challenges, Tremper remains optimistic about small businesses’ prospects based on their track record of resilience. Over the past five years, small businesses have navigated a pandemic, an inflation crisis with rates hitting 8-9%, a major labor market reshuffling, and now uncertain tariff policies. Through it all, more people keep choosing to start businesses.

“They’ve got this grit, this creativity,” Tremper observes. “These things make me most optimistic about small businesses.”

The economic fundamentals, while softening, aren’t collapsing. Consumer spending continues to increase, albeit more slowly. People are choosier about purchases, but demand hasn’t fallen off a cliff. This provides a foundation for businesses that can adapt to changing conditions.

The businesses succeeding in this environment understand that sustainable competitive advantage comes from combining cutting-edge tools with meaningful employee value propositions. They’re not choosing between technology and people; they’re investing in both simultaneously and strategically to create resilience against future uncertainty. By maximizing productivity per employee and creating strong retention through benefits and culture, these businesses position themselves to weather whatever economic storms may come.

For accounting professionals, this transformation represents a challenge and an opportunity. Clients need more strategic guidance than ever, and they’re willing to pay for and value that guidance in ways they haven’t before. The firms that master this new approach can build sustainable competitive advantages that compound over time.

Listen to the full conversation with Nich Tremper to discover specific strategies for advising your clients through this period of transformation and learn how to position your practice as an indispensable strategic partner in their success.

This Forbes Top 200 CPA Says Sponsors Matter More Than Mentors

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Picture this: You’re sitting across from a potential client—an older gentleman who seems kind and polite. Your expertise fills the room, your credentials speak for themselves, but throughout the entire meeting, he keeps calling you “darling.” Not your name. Just “darling.”

This experience happened to Nicole Davis, founder of Conscious Accounting (formerly Butler Davis) and a Forbes Top 200 CPA. For Davis, who’s originally from Georgia, where terms like “honey” and “sweetheart” are common, it wasn’t about being offended. It was about something deeper.

“Since we’re in a professional setting, I’m like, ‘you need to call me by my name,’” Davis explains. “When some men see a pretty face or just women in general, they kind of tend to sidestep our expertise.”

Sound familiar? If you’ve worked in accounting, tax, or bookkeeping for any length of time, you’ve probably been there. That moment when your face is seen, but your capabilities somehow become invisible. It’s why a recent episode of the She Counts podcast bears the title “Don’t Call Me Darling,” and why Nicole’s response to these moments is a masterclass in redefining professional power.

When Power Looks Different Than Expected

Davis’s journey to commanding respect didn’t happen overnight. Despite her current reputation for dominating whatever room she enters, she admits something that might surprise you: “I am highly introverted. People think I’m not because I can turn on. But as quickly as I turn it on, I can turn it off.”

Early in her corporate career, Davis bought into traditional definitions of power. “Early in my career when I worked in corporate America, I thought power meant title, power meant that corner office, power meant I’m calling the shots and I’m telling people what to do.”

But when she started her own firm, that facade crumbled. What emerged was something far more powerful. “Real power isn’t in a title. Real power isn’t in how much money you have. Real power is when you own who you are, and you make everyone else also accept that person.”

The catalyst for this shift? Representation. Davis’s boss at the Federal Home Loan Bank, Michelle, was the first Black woman she’d ever worked for. “When I started working for her, my eyes started to open. I started to see myself like a boss, but I didn’t see the path to get there as a Black woman, because all I saw was white men.”

This speaks to something we don’t talk about enough in our profession. When you don’t see people who look like you in positions of power, it’s hard to imagine yourself there. As co-host Nancy McClelland admits, “When I hear the word ‘doctor,’ I presume it’s a white male. Now, that is just absolutely ridiculous. It’s these deep-seated institutional societal biases we all have.”

For Davis, seeing Michelle changed everything. It showed her there was a path and more importantly, she could define what that path looked like.

Redefining What Domination Really Means

When Davis talks about “dominating” spaces, she’s not talking about aggression or making others small. “Dominating means agency. It means I am calling the shots. I’m writing my own tickets, I’m making the rules. I am doing things my way.”

But here’s the part that gave podcast co-host McClelland chills: “Dominating is not about making men small, right? Dominating is about making the space honest enough for all of us to fit into it.”

This isn’t about rejecting collaboration or building walls. It’s about what Davis calls “owning your story so completely that the room moves to your rhythm. I’m not moving to theirs.”

Learning to do this required Davis to develop boundaries that she calls “non-negotiables.” “I set boundaries and I set them fast with people,” she says. The key is being “warm but firm.”

As Davis explains, “People think you have to walk into a room and be the loudest person there to show you’re significant. No, you don’t. You walk into a room and you’re just there. Your presence says way more than words you could ever speak or say.”

This kind of presence requires something many women in accounting struggle with: refusing to shrink ourselves to make others comfortable. But when you do it right, something magical happens. Davis describes authenticity as working “a lot like Wi-Fi” because “people in range of you being who you are get that signal and they log into theirs.”

In other words, when you show up authentically, you give others permission to do the same.

Technology: The Great Equalizer

One area where Davis sees a massive opportunity for women is technology, specifically AI. Her philosophy? “Buddy up with the bots.”

“AI is making a grand stand in our profession, and so many people still have not latched on to it yet,” Davis observes. But here’s where women have an advantage. “Women have mastered efficiency out of necessity. Women are perfectly positioned to make a big major splash in the tech industry.”

Davis describes AI as acting like “a tireless junior associate” that “never needs to take a vacation. They never get tired. They can do all the things you really don’t want to do from an administrative standpoint, possibly from an analytical standpoint.”

This is about layering technology with relationship-building, and it’s something women excel at.

This approach has allowed Davis to build her firm primarily through relationships rather than traditional sales tactics. “I built my firm strictly on relationships,” she says. “I just kept taking care of my current clients and adding more services to what they needed.”

The result? A practice designed around her values rather than traditional expectations, what she calls achieving true freedom through strategic use of technology.

The Power of Sponsorship vs. Mentorship

While many people focus on finding mentors, Davis believes sponsorship is more critical. “Mentors guide, but sponsors vouch.” This concept was a key inspiration to co-host Questian Telka in her initial creation of the She Counts podcast.

Davis’ own story illustrates this perfectly. In 2020, Jeff Drew from the AICPA reached out about the practitioners planning committee. “I had no idea this committee existed,” Davis admits. But Drew’s sponsorship opened doors she didn’t know were there, eventually leading to her current role as committee chair.

“Sponsors rewrite the guest list for you so your name is on it,” Davis explains. “And when you’re on the list, your mentors help you stay on the list and guide you as you go through your journey.”

This distinction matters because it shows sometimes the biggest barrier isn’t our capability; it’s visibility. Sponsors help solve that problem by putting your name in rooms where decisions are made.

From Spaces Not Built for Us

When asked about spaces traditionally dominated by men, Davis counters, “What space was ever built for me?”

It’s a powerful question that reframes the entire conversation. Rather than trying to fit into existing structures, Davis has consistently created her own path, from starting her accounting firm to launching a construction company.

“Who said women can’t wear heels and then put on some steel-toed boots in the same week?” she asks with characteristic wit.

This mindset shift, from asking for permission to creating opportunities, separates true leaders from those still waiting for someone else to open doors.

Getting Out of Your Own Head

Davis’s advice for women wanting to take up more space is, “Take it. I know we haven’t touched on this a lot, but stamp out imposter syndrome. You’re not an imposter.”

Her approach involves speaking life into your goals. “Say it out-loud. Say it to yourself in the mirror. Say, ‘I am a badass speaker. I am an exceptional accountant. I know how to do this, this, and this.’ Even if you don’t know how to do it, say it anyway. Because eventually your mind is going to start believing it, and eventually your actions start following what your mind believes.”

It’s about recognizing that you’ve already proven yourself. “You wouldn’t have gotten this far without knowing anything. You know something. Use that to level you up.”

The Ripple Effect

Davis’s journey from being called “darling” to being recognized as a Forbes Top 200 CPA represents something bigger than individual success: cultural transformation.

When women refuse to shrink themselves, when they set boundaries while maintaining warmth, when they leverage technology to create more inclusive practices, they create ripple effects that extend far beyond their immediate sphere.

As Davis puts it, authenticity becomes “a permission slip” for everyone around you. Refusing to apologize for taking up space permits others to do the same.

In the accounting profession, technology is challenging traditional power structures and changing client expectations. There’s a new generation of professionals who refuse to accept “that’s how it’s always been done” as an answer.

Women like Davis are leading this transformation, not by playing by the old rules, but by writing new ones. They prove you don’t need to adopt masculine models of authority to command respect, and you don’t need to diminish others to demonstrate your strength.

Every boundary you set, every authentic moment you choose over conformity, every time you refuse to make yourself small, you give the next generation permission to thrive.

Because the world needs more women who understand that true domination isn’t about making others small. It’s about being so genuinely powerful that everyone around you gets permission to thrive.

Ready to transform how you show up in your professional spaces? Listen to the full She Counts episode to hear more of Davis’s insights and discover specific strategies you can implement immediately. 

The Lookback Period Mistake That Turns Valid Refunds Into Permanent Losses

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Lenora Hamilton thought she had everything figured out. She filed her 2017 tax return in November 2021—late, but still claiming a $2,070 refund she believed was rightfully hers. The IRS immediately rejected her claim. She appealed, lost, and spent nearly a year fighting in federal court.

The final verdict in early 2025 delivered a crushing blow: the court ruled her claim was “timely filed,” but she couldn’t recover a single dollar. Not because the refund was wrong, but because she missed something called the “lookback period.” A technical timing rule had permanently erased her entire refund.

In a recent episode of the Tax in Action podcast, host Jeremy Wells used Hamilton’s story to explain the refund statute of limitations—a subject most tax professionals think they understand but actually don’t. The stakes are enormous: once these deadlines pass, Wells warns, “there’s virtually no going back.”

The Two-Step Framework That Trips Up Even Experienced Practitioners

Most tax professionals think the refund statute of limitations is straightforward. File within three years, get your refund. But Wells explains it’s a complex two-step process where each step has different rules and different consequences.

Step One: Can You File at All?

The first step determines whether you can file a refund claim. This “limitation period” is the later of either three years after the return was filed or two years after the tax was paid if no return was filed. Wells calls this the “refund statute end date,” and it’s your final deadline to file any claim.

Here’s the key detail that trips up practitioners: “The filing of an original return, not an amended return, begins the period of limitation,” Wells explains. This means if you amend a return filed years ago, you’re still working within the timeline set by that original filing date.

Step Two: How Much Can You Actually Get?

Even if you file a timely claim, step two determines how much you can recover through the “lookback period.” The rules change dramatically based on when you file:

  • File within three years: You can look back at the full three years
  • File after three years: Your lookback period shrinks to just two years

This is where Hamilton got trapped. The court found she filed a timely claim, satisfying step one. But because she filed her 2017 return so late—November 2021—her lookback period couldn’t reach back to her 2017 tax payments, which were deemed made on April 15, 2018.

As Wells puts it, “The court said she filed a timely claim for refund. However, for that timely claim, there was no refund available. What does that mean? How can that be?” To understand the answer, you have to know when the IRS considers payments “made” under tax law.

The Payment Timing Trap That Caught COVID-Era Taxpayers

The lookback period depends on when payments are “deemed made,” not when they actually happened. This creates counterintuitive situations that can permanently cost taxpayers money.

The Withholding Rule

Under IRC section 6513, all tax withheld from your paychecks during the year is deemed paid on April 15th of the following year. It doesn’t matter if the money was withheld in January or December—it’s all considered paid on April 15th.

For Hamilton, “Her 2018 withholding is deemed paid on April 15th, 2019, which is the 15th day of the fourth month following the close of that tax year.”

The COVID-19 Disaster

These timing rules created a perfect storm during the pandemic. The IRS postponed filing deadlines—2019 returns were due on July 15, 2020, and 2020 returns were due on May 17, 2021. But payments were still deemed made on April 15th of each year.

This trapped taxpayers who filed during the postponement periods. Someone who filed their 2019 return on July 15, 2020 (perfectly timely) might wait until July 15, 2023, to file a refund claim. Their three-year lookback would run from July 15, 202,3 back to July 15, 2020. But their 2019 payments were deemed made on April 15, 2020, which falls outside their lookback window.

Wells explains: “This left taxpayers who didn’t file extensions for those tax years stuck with potentially valid refund claims, yet they didn’t have any periods within the lookback period because those payments were still deemed filed as of April 15th.”

The IRS eventually provided relief through Notice 2021-21, but only after recognizing that its own timing rules created harsh consequences for taxpayers who did nothing wrong.

The Dangerous “Due Date” Myth Costing Taxpayers Money

A destructive misconception in refund statute law sounds perfectly reasonable: “You have three years from the due date to claim a refund.” 

But Wells makes it crystal clear that this perception isn’t accurate. “The end date is actually three years from the filing date or possibly two years from the payment date.” The due date might coincide with these periods for taxpayers who file on time, but it’s not what controls the deadline.

Why the Due Date Myth Fails

The due date myth crumbles in the exact situations where practitioners need precision most:

  • Late-filed returns: A taxpayer who files their 2020 return in September 2023 doesn’t have until April 15, 2024 to claim refunds. Their three-year period starts from September 2023.
  • Amended returns with post-deadline payments: Wells explains these create situations where “a valid refund claim made more than three years after the due date, could look back into those payments made after the deadline.”

The Hamilton case perfectly illustrates this. If you applied the due date myth, you’d think she was too late filing in November 2021 for a 2017 return. But the court found her claim was timely because the real rules don’t work that way.

The Professional Liability Risk

For tax professionals, relying on the due date myth creates serious liability exposure. When practitioners give advice based on this oversimplified rule, they risk costing clients money they can never recover.

Wells emphasizes the finality built into these rules: “Once that statute of limitations is up, once you have passed that refund statute end date, there is no going back with some very, very limited exceptions.”

Why These Rules Are So Unforgiving

The refund statute of limitations operates with mechanical precision, regardless of hardship or apparent unfairness. Courts consistently rule that these deadlines are clear and unambiguous, so there’s no room for equitable exceptions or reasonable cause relief.

The Finality Principle

Congress built finality into the tax code intentionally. As Wells explains: “There’s an implicit concept in the tax code that Congress has written into it. I tend to call it finality.” At some point, taxpayers should feel confident that old tax years are truly closed.

But this finality only works if practitioners understand the real rules. The Hamilton case, with its modest $2,070 refund that became a years-long legal battle, shows how even small amounts trigger the same unforgiving rules that govern million-dollar refunds.

The Stakes for Tax Professionals

These rules affect every practitioner who works with amended returns, late filers, or clients with potential refund claims. Understanding when the IRS deems payments made, how postponements interact with lookback periods, and when the due date myth doesn’t apply isn’t just technical knowledge—it’s client protection. And it can be the difference between recovering thousands of dollars and losing them forever.

When Time Runs Out, Money Disappears Forever

The refund statute of limitations represents tax law at its most technically demanding and unforgiving. The two-step framework of limitation periods and lookback periods creates a system where understanding timing rules can mean the difference between financial recovery and permanent loss.

For tax professionals, these rules represent the intersection of expertise and fiduciary responsibility. Relying on oversimplified rules or misunderstand the distinction between filing dates and due dates means risking giving advice that permanently costs clients money.

This finality places enormous responsibility on practitioners to understand and navigate these rules correctly.

Don’t let technical complexity cost your clients money they can never recover. Listen to Wells’ complete Tax in Action episode to master these critical timing rules and protect your clients’ interests and your professional reputation.

Why Your Audit Fails Before Fieldwork Even Starts

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“Some audits are doomed before the fieldwork even begins.”

In Episode 2 of Audit Smarter, Sam Mansour cuts to the heart of a problem many audit professionals face but don’t fully understand. You’ve been there: an experienced team, solid procedures, and a reasonable budget. Yet somehow, the engagement still feels like constantly playing catch-up. Testing seems disconnected. Risks surface at the worst possible moment. Partners ask questions during review that should have been answered weeks ago.

The culprit? Poor risk assessment that undermines everything that follows.

Most audit professionals understand risk assessment is important, but few realize how dramatically it shapes their engagement. Mansour explains, “The risk assessment drives the entire audit approach. And if we misidentify or overlook specific audit risks, your testing could be misaligned, and you could waste time. But even more concerning, you might miss material misstatements.”

Here’s what’s happening across the profession and, more importantly, what you can do about it.

Why Risk Assessment Gets the Short End of the Stick

The problem isn’t that auditors don’t know how to assess risk. It’s that firms have systematically devalued this critical phase, treating it as administrative overhead rather than the strategic foundation it actually is.

“Many teams view planning just as a compliance step and not as a strategic one,” Mansour observes. Budget pressures and efficiency demands create an environment where teams feel pushed to rush through risk assessment. “We devalue the risk assessment phase. We think of it as a textbook thing. Let’s just check some boxes and move on.”

This leads to what Mansour calls “pencil whipping,” mechanically completing checklists without genuine thought or analysis. The evidence shows up everywhere in audit files: work paper references that don’t make sense, incorrect years, or references to people who no longer work at the organization.

“It’s pretty clear it’s been rolled forward,” Mansour notes. “And it’s also very clear no one read through it.”

When external reviewers, whether peer reviewers or regulators, see this kind of documentation, it immediately raises red flags. “As a peer reviewer, you look at some of these risk assessments, and it’s crystal clear they just rolled this from last year and they didn’t even look at it,” he explains. “You’re probably going to be pretty strict when you’re looking at the rest of that file because clearly these guys are just rolling from the prior year.”

The pressure to be “efficient” in planning creates a dangerous cycle where the foundation of the audit becomes weaker, making it much harder to execute proper testing throughout the engagement.

5 Common Mistakes That Derail Audits

Understanding where things typically go wrong helps you avoid these pitfalls in your own engagements. Mansour identifies several patterns that consistently create problems.

Generic, Template-Driven Approaches

When risk assessments are generic and not customized to the specific client, the walkthroughs and procedures that follow suffer. “If we are general or vague in our identification of risks, it results in generic audit procedures,” Mansour explains.

Copying Prior Year Without Thinking

Using prior-year documentation as a starting point makes sense, but many teams go too far. They simply copy everything over with minor adjustments, becoming “a little complacent, a little lazy” in the rollover process. A better approach is to use prior-year information as a guide but take a fresh perspective on the current year.

Failing to Link Risks to Procedures

One “gut-wrenching” moment in an audit review happens when the audit team identifies risks in checklists, but no corresponding procedures address them. “You identified this risk, but what did you do about it?” This mistake exposes fundamental gaps in audit logic.

Superficial Inquiries

Take related party transactions, for example. Many auditors accept a simple “we have none” from the client and move on. But as Mansour points out, “that’s not sufficient.” Instead, “auditors should dig into board minutes, vendor relationships, and ownership records” to understand whether related parties exist and what transactions might occur.

Misusing Junior Staff

Sending inexperienced team members to conduct walkthroughs without proper guidance is a recipe for problems. Junior staff might identify three issues out of ten while missing critical problems that experienced auditors would catch immediately. “Sometimes you need experience to tell you, you’re looking at ten different things and eight of them are going to be a problem and two of them are not,” Mansour explains.

The solution isn’t to avoid using junior staff. It’s to pair them with experienced team members who can provide real-time guidance and fill in the gaps.

Practical Tools to Strengthen Your Risk Assessment

The good news is that these problems are entirely fixable with the right approach and tools. Here’s what works:

  • Dynamic checklists. Move beyond simple checkbox exercises to checklists that challenge teams to collect new information and think deeply about what they find. Ask different types of questions that force auditors to go beyond surface-level inquiries.
  • Structured brainstorming sessions. Don’t just conduct one brainstorming session and call it done. Mansour recommends peppering collaborative discussions throughout the engagement. “Have the engagement team go out to lunch and consider that part of your brainstorming activity,” he suggests. These sessions force teams to share knowledge and often uncover overlooked areas.
  • Early data analytics. Instead of treating analytics as nice-to-have add-ons, deploy them “immediately after engagement acceptance,” Mansour advises. His approach: “Give me your trial balance, and I will do some data analytics on it right from the get-go.” This generates specific issues to investigate before client meetings, allowing you to connect numbers to client stories strategically.
  • Simple intelligence gathering. Something as basic as Googling your client’s name can reveal critical information, yet “a lot of auditors won’t even do that,” Mansour observes. “You’d be shocked at some of the stuff” these searches uncover. Review prior audit findings, look for industry changes, and stay current on client updates.
  • Collaborative team approach. Instead of having one person update risk assessment documentation alone, assign different sections to different team members. This ensures multiple people read through and think about the content, rather than having it all flow through one person who might miss important details.

What Separates Top Performers

Firms that consistently execute superior risk assessments share several key characteristics that set them apart.

They Treat Risk Assessment as a Mindset

“Top performers treat risk assessment as a mindset, not just a task,” Mansour explains. “They understand that there’s value in risk assessments. It’s not just a checkbox on their list.” Their teams are intellectually curious rather than robotic, but this requires giving people adequate time and breathing room to think deeply.

They Create Collaborative Environments

These firms don’t silo team members into individual sections. Instead, they “connect the dots between client goals, internal controls, and audit processes with purpose.” Team members actively consider how discoveries in one area impact testing in others, creating a comprehensive understanding that reduces risk while improving efficiency.

They Invest in Proper Mentorship

Rather than throwing junior staff into complex situations alone, top performers create systematic mentorship structures. They pair junior staff with experienced seniors who provide real-time guidance, immediate field discussions, and progressive responsibility increases.

They Focus on Custom Solutions

Elite performers avoid generic approaches entirely. They tailor audit plans to each client and engagement year. Their team members can explain their logic clearly without defaulting to “it’s what we were told” or “it’s what we did last year.”

Three Changes to Make Right Now

If your firm wants to improve immediately, Mansour recommends focusing on these three foundational changes:

  1. Slow down in the planning process and allow for deeper team discussions. Invest upfront time that prevents downstream scrambling and quality issues.
  2. Ensure walkthroughs include a formal evaluation of control effectiveness with documentation customized to the specific client and current year rather than generic templates.
  3. Critically assess each risk and match it to custom procedures designed to address it, eliminating the disconnect between identified risks and actual testing approaches.

How You Know You Got It Right

Success in risk assessment is measurable through specific indicators. Your audit plan should be tailored, not generic. This demonstrates genuine client-specific thinking rather than template dependency. Your team members should be able to explain their logic clearly and provide substantive reasoning for their approaches.

Most importantly, when partners or regulators review your documentation, they should be able to “read your risk assessment and understand the rationale,” as Mansour puts it. They should see a clear narrative and strategic thinking rather than dry, templated responses.

If your team can’t explain their logic, or if external reviewers see obvious evidence of rolling forward prior year templates, you’re still in checkbox mode rather than strategic thinking mode.

The Foundation Makes the Difference

Risk assessment isn’t preliminary work that happens before the “real” audit begins. It’s the foundation that determines whether your entire engagement succeeds or struggles. As Mansour explains using a gardening analogy, if the risk assessment seed “doesn’t get planted properly, if it’s not cared for properly, it sets you up for failure.”

Firms that recognize this and invest accordingly create sustainable competitive advantages through systematically superior approaches to this critical phase.

The strategies and tools we’ve covered are proven approaches to transform your risk assessment process from liability into a strategic advantage. However, implementation requires commitment to changing how your firm approaches and uses its resources for this foundational work.

Ready to dive deeper into these risk assessment strategies and discover the specific frameworks top performers use? Listen to the full episode of Audit Smarter for Sam Mansour’s complete insights on transforming your approach to risk assessment and elevating your audit practice.