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Your Crypto Loss Might Not Be Deductible (Even Though Your Neighbor’s Is)

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When someone loses $100,000 to a cryptocurrency scammer, the financial blow is devastating. But finding out whether that loss is tax-deductible means navigating rules written decades before anyone imagined digital theft.

In this episode of Tax in Action, host Jeremy Wells, EA, CPA, tackles a confusing area of tax practice: theft losses. While theft has existed forever, the digital age creates entirely new ways for criminals to steal—from “pig butchering” scams to romance frauds—that challenge how we apply old tax laws to new crimes.

The Three Categories That Determine Everything

Before helping clients who’ve been scammed, tax professionals need to understand which of three categories their loss falls into. This distinction can mean the difference between a valuable deduction and no tax relief at all.

Under IRC Section 165, losses fall into three buckets. Losses from a trade or business and losses from transactions entered into for profit—even outside a business—are generally deductible. However, personal losses not connected to business or profit-seeking are the problem area.

The Tax Cuts and Jobs Act eliminated personal casualty and theft losses for 2018 through 2025. The only exception is losses from federally declared disasters. As Wells explains, this even includes theft during disasters, like the looting that happened after Hurricane Katrina when “there was just a general lack of any sort of law enforcement.”

This means two neighbors could lose the same amount to the same scammer, but only the one who was investing for profit gets a deduction. The retiree who sent money for personal reasons? They’re out of luck.

The Three-Part Test Every Practitioner Must Know

Beyond figuring out the category of the loss, Wells explains that courts have developed three essential criteria for any theft loss claim.

First, the theft must have occurred under state law where the loss happened. This requirement isn’t in the tax code or regulations; it comes from court cases trying to define “theft” when the IRS never did. The 1956 Edwards v. Bromberg case said federal courts must look to state law, but as Wells notes, that creates “probably about 50 different definitions, one for each state.”

Second, you must be able to determine the amount lost. For cash or stocks, this is straightforward. But for jewelry or collectibles? You’ll need insurance records, appraisals, or reasonable estimates. Proving value becomes nearly impossible without documentation from before the theft..

Third, you need to know when the taxpayer discovered the loss. This is crucial because it’s not when the theft happened, but when the victim realized it. Wells emphasizes: “That could be the same day, maybe a few hours later. It could be a few days later. It could be weeks, months, or even years later.”

The courts are clear about one thing: simple disappearance isn’t theft. Wells shares the Allen v. Commissioner case, where someone lost jewelry in a museum. Despite searching everywhere, publishing newspaper ads, and filing police reports, the court denied the deduction. Why? The taxpayer couldn’t prove someone actually stole it rather than it just being lost.

Timing Is Everything (And It’s Complicated)

The timing of theft losses works differently than most people expect, especially with digital assets and cryptocurrency.

A theft loss is deductible in the year you discover it; not when it actually happened. But Wells stresses a major catch: if you have a “reasonable prospect of recovery” through insurance or lawsuits, you can’t claim the loss yet. You must wait until you know with “reasonable certainty” whether you’ll be reimbursed.

“It’s not that you go ahead and claim it, and then wait until you receive the reimbursement,” Wells clarifies. “You have to wait until the outcome of that process is actually either known or within a reasonable certainty.”

With cryptocurrency scams, you might have three different dates spread over years: when the theft occurred, when you discovered it, and when you know recovery is impossible. Each delay pushes your potential deduction further into the future.

When Corporate Fraud Doesn’t Count as Theft

Surprisingly, even massive corporate fraud doesn’t create theft losses for shareholders. Wells uses Enron as an example. Investors lost everything due to “fraudulent and illegal activity,” but for tax purposes, these remain capital losses, not theft losses.

The 1975 Payne v. Commissioner case established this rule. Corporate executives don’t have “specific intent to deprive that particular shareholder” of their money. Even when executives commit crimes that destroy your portfolio, you haven’t been “robbed” in the tax law sense.

This distinction matters enormously for crypto investors. When an exchange halts withdrawals or a platform gets “hacked,” you need to determine whether it’s actual theft (potentially deductible if for profit) or platform failure (capital loss at best).

Five Modern Scams and the Profit Motive Test

In 2025, the IRS Chief Counsel addressed five common scams that don’t fit the traditional Ponzi scheme mold. The key factor? Whether victims had a profit motive.

Deductible scams (entered into for profit) include:

  • Pig butchering scams work by “fattening up” victims. Scammers start with small investments that show big returns. Victims invest more and more until the scammer disappears with everything. Because victims expected investment returns, the loss is deductible.
  • Compromised account scams involve criminals convincing victims their accounts need securing. Since victims move investment funds expecting to preserve them, the profit motive remains intact.
  • Phishing scams use fake websites to steal login credentials for investment accounts. Again, the investment nature preserves deductibility.

Non-deductible scams (personal losses) include:

  • Romance scams create fake relationships before asking for funds, often for medical emergencies. There’s no profit expectation; just personal generosity. As Wells emphasizes, “There’s no expectation of profit here. So that makes the theft loss nondeductible.”
  • Kidnapping scams involve fake ransom or bail demands. These are fear-motivated, not profit-motivated, making them personal and nondeductible.

The cruel irony? Two victims could withdraw the same amount from identical IRAs and send it to the same overseas account. But only the one expecting investment returns gets a deduction. The one motivated by love or fear gets nothing—plus they owe tax on the IRA withdrawal.

Lessons from the Experts Who Got It Wrong

Wells ends with a humbling case: Booth v. Commissioner. The taxpayer bought Civil War-era land rights that turned out to be invalid, then got sued after selling them to someone else.

Eighteen Tax Court judges split 10-8 on whether this was theft loss or capital loss. The Ninth Circuit reversed them, saying it was both. When Wells polled tax professionals, only 13% got it right.

“There are a lot of smart tax people out there and they can disagree and they can even be wrong,” Wells reflects. “The important part is that we keep thinking about these issues.”

What This Means for Your Practice

For tax professionals dealing with theft losses, three things matter most:

  1. Document profit motive upfront—not after the loss. The client’s intention when entering the transaction determines deductibility.
  1. Track timing carefully. Discovery dates and recovery efforts affect when (or if) clients can claim losses. This might mean waiting years.
  1. Know the current guidance. The IRS issues new interpretations as scams evolve. What wasn’t deductible yesterday might be tomorrow.

The collision between 1950s legal precedents and 2020s digital crimes creates daily challenges. While the basic rules haven’t changed in 70 years, applying them to cryptocurrency scams and online fraud requires both historical knowledge and modern insight.

For clients devastated by digital-age theft, understanding these rules helps you identify opportunities where they exist and provide clarity where they don’t.

Ready to master these distinctions? Listen to Jeremy Wells’ complete analysis in this episode of Tax in Action, where he breaks down additional examples, Form 4684 reporting details, and why even seasoned professionals struggle with these issues.

Navigating QuickBooks Online’s Interface Changes: From Frustration to Opportunity

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QuickBooks Online’s latest interface changes have left many accounting professionals feeling like the ground is shifting beneath them. Just when you get the hang of one workflow, the layout moves, the buttons change, and suddenly everything takes twice as long. 

In episode 106 of The Unofficial QuickBooks Accountants Podcast, titled “Cha-Cha-Cha-Changes: Navigating QuickBooks Online’s New Interface,” host Alicia Katz Pollock, MAT, dives into what these updates mean in practice. She acknowledges the frustration many users feel without brushing it aside.

Understanding the Real Disruption

“I am not minimizing your experience when I’m talking about this stuff. I am not discounting your turmoil in any way,” Katz Pollock emphasizes early in the episode. What she’s trying to do is provide perspective and practical solutions.

The productivity hit is real. Two weeks before recording, Katz Pollock’s screens were loading so slowly, she’d “literally click to open a sales receipt and the framework would come up and literally nothing would load.” She’d start chugging water and get “six or eight sips in” before the transaction appeared. While performance has improved since then, the delays remind us we’re not just learning new workflows. We’re doing it while the platform struggles with its own growing pains.

Katz Pollock frames this challenge through a lens every accountant understands: onboarding time. “When I bring on a new hire, I don’t actually expect them to be productive out of the gate,” she explains. The same applies here. Build in grace periods over the next month or two. Communicate with clients about timeline adjustments if needed. This isn’t making excuses, it’s acknowledging reality.

Practical Solutions You Can Use Today

Instead of dwelling on what’s changed, Katz Pollock offers concrete navigation solutions that work right now.

First, she shares a few helpful navigation tricks:

  • Right-click links to open them in new tabs (two clicks instead of hunting for the missing “New Window” option)
  • Drag menu items up to your tab bar to create new tabs instantly
  • Bookmark frequently used pages like the Reminders list (which requires three clicks to reach otherwise)
  • Customize your menu using the pinned section in the bottom left corner

Katz Pollock strongly recommends RightTool by Hector Garcia and Mark Corum. “For me, it’s essential equipment,” she says. This browser extension adds shortcuts and automations, like copying classes down entire journal entry columns with one click.

Other interface changes accountants need to know about include:

  • The Transactions menu is now called Accounting
  • Sales is now Sales and Get Paid (highlighting the underused payment links feature)
  • Apps moved to Integrations in the upper right corner
  • Accountant Tools briefcase became My Menu in the upper left

The new sticky second-tier menus actually improve navigation once you get used to them. When doing customer work, all the customer links stay accessible without constant back-and-forth clicking.

Hidden Features Worth Exploring

While everyone’s focused on what’s different, Katz Pollock discovered several improvements that solve long-standing problems.

The Tasks feature (clipboard icon in upper right) now lets you link directly to specific transactions. “When you click “link a record,” you can actually pick an invoice or a bill or almost any kind of transaction,” Katz Pollock explains. You can attach backup documents, assign priorities, and even create recurring tasks in QBO Advanced to outline your entire workflow.

Inventory improvements are coming. New QBO files now offer FIFO or Moving Cost Average valuation methods. The development team is working on assemblies and units of measure—features that previously required third-party apps.

The Sales Tax Center has its own menu section with a product grid where you can assign tax settings to all products at once, instead of editing each individually. You can even turn sales tax off now, which wasn’t possible before.

For bookkeepers managing client billing, you can now transfer wholesale billing rates directly to another accountant user without losing discounts. This means no more calling Intuit support.

The AI Reality Check

Here’s where Katz Pollock puts the tough realities on the table. While we complain about AI pop-ups in QuickBooks, the entire industry is racing in a different direction.

“The new general ledgers that are generating all the buzz are like Digits and Puzzle,” she notes. “Their entire general ledger is built on AI first. The manual work is the secondary thought.”

This is a fundamental change rather than a gentle evolution. The choice isn’t whether to accept AI in accounting software. It’s whether to work with AI that still respects manual oversight (like QuickBooks) or jump to platforms where human input is treated as an afterthought.

Turning Disruption into Opportunity

Rather than just updating her QuickBooks courses piecemeal, Katz Pollock is seizing this moment for a complete overhaul. Starting September, she’s teaching her entire Royalwise OWLS curriculum in sequence, all in the new interface, at an accelerated pace: one class per week through June,  progressing from basics through advanced features

Annual membership is $1,500. This includes more than 35 classes, 81 hours of CPE credit, plus monthly Q&A sessions. There’s also a business membership option covering fundamentals through December—perfect for clients who need training. Her “Great QBO Refresh” opportunity can be found at http://royl.ws/QBO-Refresh?affiliate=5393907.

“Investing a little bit of time in direct education,” Katz Pollock explains, “means you don’t have to spend all that time spinning your wheels down the road.”

Making Your Voice Heard

Throughout the interface, you’ll find feedback links specific to each feature. “Don’t just say, I don’t like that the pane takes up too much room,” Katz Pollock advises. “Say, ‘I would like an option to have this pane open up or not’.”

Be specific and actionable. The more people who communicate similar needs, the more likely changes will happen. Remember, Intuit uses MVP (Minimum Viable Product) philosophy. They release features to gauge interest, then develop or abandon based on user engagement. The more people who comment about a feature, the quicker the feedback will be implemented.

Looking Ahead

Katz Pollock will be at several conferences this fall, including Women Who Count in Mesa, Intuit Connect in Las Vegas, and Hector Garcia’s Reframe conference in Miami. These events offer opportunities to learn more about upcoming changes and connect with other professionals navigating the same challenges.

The bottom line? Yes, these changes are disruptive. Yes, they cost us time and cause frustration. But they also push us to evolve. As Katz Pollock reminds us, the choice isn’t whether to adapt; it’s whether to approach change strategically or reactively.

Listen to episode 106 for Katz Pollock’s complete analysis, more navigation tips, and a healthy dose of perspective on thriving in a profession where the only constant is change. Whether you’re drowning in the new interface or ready to master it, this episode provides both the validation and practical strategies you need.

Visit royalwise.com/qbo-refresh to learn more about the Great QuickBooks Refresh training program, or find the podcast at uqb.show/106.

Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

Your Team Actually Wants You Less Involved in Daily Operations—Here’s How to Give Them What They Need

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For an accounting firm owner, days can feel like an endless stream of Slack notifications and “quick questions” from your team. You’ve become your company’s “internal Wikipedia”—the go-to source for every operational decision, client question, and process clarification. Sound familiar?

Chase Damiano, founder of Human at Scale and recent guest on the Earmark Podcast, has a name for this trap: the bottleneck.

Damiano brings a unique perspective to the accounting world. After scaling Commonwealth Joe Coffee Roasters from zero to $5 million in revenue and earning a spot on Forbes’ 30 Under 30 list in 2018, he experienced burnout so severe it drove him to take a 12-week sabbatical that included two weeks of silent meditation. This radical reset transformed his understanding of leadership and delegation. Now, he shares those insights with accounting firm leaders trapped in similar operational quicksand.

In his conversation with host Blake Oliver on the Earmark Podcast, Damiano challenges a fundamental assumption plaguing firm owners: the belief that hiring more people will solve their capacity problems. The reality is far more complex. Breaking free requires a systematic approach to delegation that transforms how you communicate expectations and how you measure success.

Every overwhelmed firm owner needs to understand three critical transformations. First, why the traits that make you successful—perfectionism and desire to serve—become the quicksand that traps you. Second, how a six-part delegation framework frees you from daily firefighting. And third, why building a “team responsibility inventory” provides the roadmap for extracting yourself from workflows while actually increasing your team’s autonomy.

The Psychology of Being Stuck: Why Good Intentions Create Bad Systems

Before you can implement systematic delegation, you need to recognize that the very traits that made you successful now hold your firm hostage.

Damiano knows this pattern intimately. After scaling his coffee company to $5 million in revenue, he found himself addicted to the productivity habit. It took three full weeks of his sabbatical just to stop compulsively “figuring things out.”

“Even the act of ‘figuring out your life’ can now look more like a job,” he explained to Oliver. “Wake up, have breakfast, go to a coffee shop to figure things out. Then it’s time for lunch, more figuring out, dinner—and suddenly another day has vanished.”

This addiction to busyness hits accounting firm owners particularly hard. Your perfectionism, your genuine desire to serve clients, and your technical expertise aren’t character flaws. They’re the foundation of your professional success. But when it comes to scaling a firm, they become quicksand.

Oliver admits he fell into this exact trap with his own firm. “I said yes to everything,” he reflected during the conversation, “and then I’ve got too much to do and I’m busy all the time, working 60 hour weeks.”

The desire to help everyone feels noble in the moment. But it creates a system where your brain becomes the firm’s operating system. Every decision, every quality check, every client question routes through you.

The perfectionism problem runs deeper than just workload. Oliver shared an example from his time at a Big Four firm. The nonprofit team was performing full compilation engagements for clients who didn’t need them. “Most of these nonprofits did not need compilations, but we were doing it anyway with a huge added cost,” he observed. The team could have delivered a simpler service at better margins while still meeting client needs.

Damiano challenges firm owners to examine their “inner data”—not financial metrics, but the intuitive signals about energy and alignment. When he asks bottlenecked CEOs how they feel day-to-day, the answer is always the same: “incredibly draining,” “incredibly stressed,” “I don’t want to do this.”

Yet the pattern continues. They know they’re stuck, they can articulate the problem, but they take no action to change it.

This paralysis stems from a fundamental identity crisis. As Damiano discovered after exiting his coffee company, entrepreneurs often don’t know who they are without their business. “Everyone asked me what I’m going to get into next.” he recalled. “People assume you’re going to go on to an even greater thing, but you might not be clear about that internally, and that’s okay.”

The reality check comes when you realize your team actually wants you less involved. Teams see your pain from being overwhelmed. But more importantly, they experience frustration when you inject yourself into processes and “muck things up,” as Damiano puts it.

Your team craves autonomy over their roles. They want to make decisions without running everything by you. But first, you need to accept that your five-minute solution might be worth sacrificing for their two-hour learning experience.

Damiano’s perspective on one-on-ones captures the mindset shift required: “Your one-on-ones should not be about status updates. It’s an opportunity to develop them as leaders in every role, in every position. They should do 80 plus percent of the talking.”

Understanding these psychological barriers is crucial, but awareness alone won’t free you from the trap. You need a concrete system for transferring responsibilities that addresses both your need for quality and your team’s need for clarity.

The Six-Part Delegation Framework: From Chaos to Clarity

The breakthrough moment in Oliver and Damiano’s conversation came when Oliver realized effective delegation to humans uses the exact same structure as prompt engineering for AI.

“What you just described is a well-written prompt,” Oliver exclaimed as Damiano outlined his delegation system. “It’s the same thing.”

This revelation transforms delegation from an art into a science. The framework emerged from Damiano’s observation of countless delegation failures. One particularly instructive disaster involved a chief operating officer who attempted to delegate a billing process. She wrote just seven words on a piece of paper: “Manage billing process while I’m out on vacation.”

The predictable result? Complete failure. Without context, success criteria, or clear boundaries, the delegation was doomed from the start.

During the podcast, Damiano and Oliver worked through a real example: delegating the management of weekly team meetings. Here’s how the framework transformed this common bottleneck into a clear, delegatable responsibility:

1. Name the responsibility: “Manage and coordinate weekly team sync.” Just two to three sentences that start with action verbs.

2. Define the purpose: As Oliver articulated: “Our weekly team sync is what keeps everyone organized and makes sure nothing falls through the cracks. It helps us prioritize.” Damiano added, “This is our command center for what is happening for the week, but also a place for us to come together as a culture.”

3. Establish success metrics: “Everybody leaves the meeting with their top three to five priorities clearly defined. We’ve addressed any blockers,” Oliver said. Plus the binary metric: Did the meeting happen? Did everyone who could attend actually attend?

4. Document the process: They mapped out everything from sending meeting invites and creating agendas to collecting topics, facilitating discussions, and updating the practice management system.

5. Identify resources: Access to calendars, ability to run reports on upcoming deadlines, time for preparation and follow-up. “In a prompt that would be the tools,” Oliver noted.

6. Clarify decisions: The operations manager can choose meeting times and create agendas autonomously, but needs approval to cancel meetings two weeks in a row.

The elegance of this system lies in its flexibility. “Those first three are perfect delegation opportunities for a more senior individual,” Damiano explains. Junior team members benefit from all six elements as guardrails.

What makes this framework powerful is how it addresses trust issues that sabotage most delegation attempts. When delegation fails using this structure, you can pinpoint exactly what went wrong.

“You can literally look at it and pinpoint exactly where,” Damiano says. “And that is what makes the delegation stick, because you can just fix that one issue.”

The framework also flips the traditional delegation dynamic. Instead of the owner having to document everything, team members can use these six elements as a guide to ask better questions. This transforms delegation from a top-down directive into a collaborative process.

Oliver’s enthusiasm was immediate: “I’m going to start using this. I’m going to do this tomorrow with my team.”

The framework addresses his core challenge: getting his team to take ownership without constantly coming to him for decisions. By clearly defining decision boundaries upfront, team members gain confidence to act autonomously while knowing exactly when to escalate.

But individual delegation is just the beginning. True transformation requires examining every responsibility across the entire firm.

Building Your Delegation Roadmap: The Path to Strategic Leadership

Moving from technician to strategic architect demands a systematic inventory and redistribution of all responsibilities across your firm.

Damiano calls this process building a “Team Responsibility Inventory.” As Oliver discovered with his own 16-person company, you can reach a point where founders are still doing work from when the company was half its size.

“We’re the bottleneck,” he admitted, recognizing how he and his partner had become “functionally critical participants in the workflow” even though they now had a team capable of handling that work.

The Team Responsibility Inventory begins with radical transparency. Every team member completes a seven-day time audit, brain-dumping every task and responsibility they handle. No organization needed, just raw data.

Then comes the revolutionary part: a facilitated session to compile all these responsibilities and review them line by line as a company. For many firms, this marks the first time the team sees exactly what’s on the CEO’s plate.

“Imagine you’re going line by line through these responsibilities and as a team making a decision,” Damiano explains. “Should the CEO still have this responsibility?”

The power of this collective review can’t be overstated. Team members who’ve been frustrated by their CEO’s constant intervention suddenly understand the impossible workload their leader carries. More importantly, they become active participants in solving the problem.

Each responsibility faces one of six possible destinies: hire someone, delegate and train internally, outsource to a service provider, automate through software, consciously eliminate, or keep.

The elimination option deserves special attention. “This is an underused one,” Damiano emphasizes. After years of growth, firms accumulate zombie tasks—reports nobody reads, processes that served a purpose five years ago.

Oliver shared the perfect example: “There’s all these people running weekly, monthly, quarterly reports that were defined five years ago that they’ve been sending out constantly and nobody’s actually reading them.”

The delegation roadmap shows how responsibilities shifts over time. But successful execution requires developing your team’s decision-making capabilities, not just their technical skills.

This is where Damiano’s “Problem-Outcome-Solution Framework” comes in. Instead of bringing problems to leadership, team members learn to present complete proposals. Define the problem and its cost. Articulate the desired outcome. Recommend a solution with clear resource requirements.

Oliver’s current challenge illustrates why this matters: “My team comes to me with a problem and then I have to use my brain space to think about the solution. But it’d be much better if they defined the problem, defined the outcome they want, and gave me a proposed solution.”

This shift transforms every interaction from a drain on the CEO’s cognitive resources into a development opportunity for the team member.

The framework works because it addresses a fundamental misunderstanding about delegation. Firm owners often justify keeping tasks because “I could do this in five minutes. Why delegate something that takes them two hours?”

But this calculation ignores the compound effect. That two-hour learning investment today becomes 90 minutes next week, then 60 minutes, then eventually faster than you could do it yourself—all while freeing you to focus on strategic work only you can do.

Oliver’s ultimate success story proves what’s possible. After five years building his firm with these principles, he achieved the dream: “I was doing no sales, I was doing no client work. We were getting customers. They were getting served. They were happy, they were paying. Money was coming into the bank and I was not involved.”

For anyone trapped in 60-hour weeks, Oliver’s enthusiasm is infectious: “I will tell you that it is the greatest thing in the world to get into that position, because then you’re really just an owner of a business.”

From Bottleneck to Breakthrough: Your Next Strategic Move

The journey from bottleneck to strategic leader is about fundamentally reimagining how knowledge and decision-making flow through your organization.

Damiano’s framework reveals that delegation isn’t a single skill but a system. It requires clear communication, defined success metrics, and the courage to accept “good enough” from others. The same perfectionism that built your reputation can become the cage that limits your growth.

This transformation extends beyond individual firms to the entire accounting profession’s evolution. As AI handles increasingly complex technical work, the firms that thrive will be those where owners have already extracted themselves from technical execution. They’ll focus on strategy, relationships, and innovation instead.

What makes Human at Scale different is, “We don’t just come in as a consultant or advisor or coach,” Damiano explains. “We actually come in and join your team. We are in there, actually running these systems and building that with you.”

Listen to the full conversation between Oliver and Damiano on the Earmark Podcast to discover additional frameworks and tools. Visit Human at Scale to take their operational leadership assessment that can diagnose your firm’s specific bottlenecks.

Your Best Audit Findings Hide Behind the Questions You Never Ask

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Picture this: A controller walks an auditor through their revenue recognition process, casually mentioning a manual journal entry they make at year-end to “true things up.” That offhand comment—captured only because the auditor asked an open-ended question rather than a checklist query—led to uncovering improper revenue recognition that would have otherwise gone undetected.

In this episode of Audit Smarter, host Abdullah Mansour sits down with Sam Mansour, CPA, to explore an often overlooked aspect of auditing: the art of asking effective questions. Through their conversation, they reveal how the most basic tool in an auditor’s toolkit can make the difference between surface-level compliance work and truly understanding a client’s operations.

As Sam points out early in the discussion, “The quality of the answers we get is only as good as the questions we ask.” This principle shapes everything that follows, from why traditional yes-or-no questions fail to practical techniques for creating an environment where clients willingly share critical information.

Why Yes-or-No Questions Sabotage Your Audits

The most common mistake auditors make starts with two simple words: “Did you?” As Sam explains, yes-or-no questions create a trap that undermines the entire purpose of audit inquiries. They push clients toward specific answers and provide almost no insight into actual processes and controls.

Consider the typical scenario Sam describes: an auditor asks, “You reviewed this reconciliation, right?” The client faces an almost impossible choice. “What are they going to say? No?” Abdullah observes during the conversation. Sam agrees. “They almost have to say yes, even if they’re lying.” The phrasing practically forces a “yes” response, but even when that answer is truthful, what has the auditor actually learned?

“Let’s say they did review the reconciliation and the answer is actually yes,” Sam continues. “So you say, ‘You review this reconciliation, right?’ Then they say, ‘Yes, I did.’ It’s like, well, that’s it, right? You’re done.”

Instead of asking whether someone reviewed a reconciliation, Sam suggests a different approach: “Walk me through how you review the reconciliations. What do you look for? What happens if it’s off?” This reframing transforms a binary checkpoint into a window into the client’s actual processes.

The power of this approach became crystal clear in Sam’s story about uncovering improper revenue recognition. During a routine inquiry, he asked a controller to walk him through their revenue recognition process. The open-ended question invited explanation rather than confirmation. “Midway through, they casually mentioned a manual journal entry they made at year end to true things up,” Sam recalls. “That comment led to further testing and uncovered improper revenue recognition. If I hadn’t asked that open-ended question, we would have missed it.”

But there’s an art to crafting these questions. Sam warns against being too broad. For example, asking about “internal controls in general” leaves clients unsure where to start. He also cautions against cramming multiple questions into one. “Sometimes people will ask you like three different questions in one shot,” he notes. “And it’s really hard to remember what was number two or number three.”

The sweet spot? Be specific about the area you’re investigating, but open about how you want it explained. For example: “How do you receive cash in that specific area?”

Moving from yes-or-no questions to open-ended inquiries is just the first step. The real challenge is creating an atmosphere where clients feel comfortable sharing detailed, honest information.

The “New Employee” Technique That Changes Everything

Technical knowledge alone won’t extract meaningful information from clients. As Sam demonstrates through his eight years of field experience, the key lies in how you position yourself during the inquiry.

“When I’m doing these inquiries,” Sam explains, “I’m like, look, I understand how payroll generally works really well, but I don’t understand how you do it here. That’s very new to me. And so I want you to pretend like I know nothing about payroll, pretend like I’m brand new to this, and you’re explaining it to someone for the first time.”

Abdullah immediately grasps the value, “As if you’re a new employee to their firm.” This positioning accomplishes two objectives. First, it prevents clients from assuming the auditor already knows their processes and therefore skipping crucial details. Second, it reduces the threat level of the interaction.

“You don’t want to fill in gaps in the process,” Sam explains. “Maybe they don’t explain specific things to you because it’s like, well, that’s just how it’s done for payroll, right? Of course. But the thing is, what if they don’t actually do it like that?”

The physical and tonal elements matter just as much as the words. Sam paints a vivid picture of what not to do. “If someone walks in and they cross their arms and put on a frowny, unpleasant face, that body language and tone definitely gives you the feeling they’re unapproachable.”

But swinging too far in the other direction creates its own problems. “You don’t want to become their best friend in the whole wide world,” Sam warns, “because then if you have to write them up for a finding or communicate bad news in the future, you might feel uncomfortable doing that.”

The solution is what Sam calls being “professional but approachable.” He starts meetings with simple human touches like asking about their weekend, checking if it’s a good time to meet, and crucially, asking if clients have questions about the audit before diving into his own inquiries. “Giving them the opportunity to  ask why we’re doing certain things makes them feel good.”

One of Sam’s most powerful techniques is the strategic use of silence. “Clients often fill the space with valuable content,” he notes. “If you ask a question and give room for pause, they might feel a little bit uncomfortable and start giving you more information.”

The danger of getting the approach wrong becomes clear in Sam’s cautionary tale about a staff auditor who burst into the conference room declaring, “I know we have a finding in this area. I know there’s a problem here.” The aggressive approach damaged the client relationship and led to an incorrect conclusion. The auditor missed compensating controls that actually addressed the perceived gap.

“When they were doing the inquiries, they came off as a little arrogant and accusatory,” Sam recalls. The client later confided that this approach “kills the conversation really quick.”

Different personality types require different strategies. Some clients barely speak, requiring you to seek information from other sources or approach them with very specific questions. Others flood you with information. “Sometimes you have to rein them in if they’re more on the chatty side,” Sam advises. “Don’t be afraid to control the conversation a little bit.”

These interpersonal skills don’t develop automatically. They require deliberate practice and a commitment to continuous improvement—even for senior professionals.

Practice, Preparation, and the Path to Mastery

The gap between knowing how to ask better questions and actually doing it in the field is larger than most auditors realize. Sam references Neil Rackham’s book “SPIN Selling” to illustrate this point. “If you’re trying to train yourself to sell, don’t use something you’ve just learned on a big deal because it’s not familiar to you. It’s going to be kind of clunky.”

The same principle applies to audit inquiries. Entry-level auditors are unfamiliar with clients and uncomfortable with fieldwork and the expectation to ask potentially invasive questions. “It’s not just potentially uncomfortable for the client,” Sam acknowledges, “it’s probably uncomfortable for you.”

His solution might surprise those used to traditional accounting training: role-playing. Picture a lunch meeting where team members practice asking each other the same questions they’ll pose to clients. The senior auditor observes, catching those yes-or-no questions before they become habits.

“You want to be able to hear yourself saying the question and feel comfortable with those questions coming out of your mouth,” Sam explains. He uses payroll as an example. After ten years, asking for everyone’s pay scale feels routine, but “as an entry-level person, you might think, oh, it’s really strange to ask them to give me the pay scale for everyone that works here.”

Abdullah agrees:, “Role playing is one of the most helpful things I’ve done in certain situations.”

Preparation extends beyond practice sessions. Sam strongly advocates for developing questions in advance, challenging the notion that spontaneous inquiries appear more confident. “If you go into an inquiry and you’re just winging it, it could be very unprofessional.”

His reasoning is practical. When dealing with a difficult or unresponsive client, having prepared questions serves as both a roadmap and a safety net. “At least when you walk away from that inquiry, you have achieved your goal of asking the right questions,” he explains. The alternative—having to return for follow-up questions on the same topic—triggers a cascade of problems, from client complaints to difficult conversations with audit partners.

Active listening requires its own skill development. Sam describes maintaining a notepad during inquiries, jotting down items that need follow-up but resisting the urge to interrupt. “You don’t want to stop them and say, ‘Show me that journal entry.’ You want them to just keep going.”

The learning curve extends throughout an auditor’s career. “For a partner or manager to think they’ve achieved the highest level of skill in this field is somewhat unrealistic,” Sam observes. 

This matters because teams watch their leaders. Sam recalls being an early-career auditor, observing every interaction between partners and clients because those conversations typically involved “more sophisticated or important things.”

Yet formal training in this area is scarce. “Unfortunately, I don’t think there’s a lot of great CPE out there on the skill of strong inquiries,” Sam laments. This gap forces motivated professionals to seek resources outside traditional accounting education, including from books on sales, negotiation, and communication.

The payoff extends far beyond audit quality. “Being able to uncover key details in your personal life, professional life, at the client, in your own organization, it’s just so critical,” Sam reflects. 

Your Next Steps Toward Better Audit Inquiries

The journey from checkbox auditor to strategic advisor doesn’t require mastering new accounting standards. As Sam demonstrates, it requires three fundamental shifts in how we approach asking questions.

First, abandon yes-or-no questions in favor of open-ended inquiries that reveal what clients do and how and why they do it. Second, cultivate an environment of professional approachability—warm enough to encourage dialogue, professional enough to maintain objectivity. Third, treat inquiry skills as a career-long development priority, not a soft skill you’ll somehow absorb over time.

Sam’s final advice brings it all together. “Be approachable, but be professional. If you’re not professional, it derails the inquiries. If you’re not approachable, it also derails the inquiries.”

These aren’t just nice-to-have communication techniques. The controller who mentions those year-end “true-up” entries won’t share that information with someone who makes them feel defensive. The employee who knows where the real control gaps exist won’t confess them to someone asking yes-or-no questions from a checklist.

For audit professionals, the quality of audit findings will never exceed the quality of your questions. Whether you’re preparing for your first solo client inquiry or you’ve been asking the same questions for decades, there’s always another level to achieve.

Ready to transform your audit approach? Listen to the full episode of “The Art of Audit Inquiries: Asking Better Questions” on Audit Smarter to hear Sam’s complete framework for handling difficult clients, managing different personality types, and knowing when to pivot your approach. Your next significant audit finding might be just one well-crafted question away.

The Hidden Tax Trap That Turns Disaster Relief Into Taxable Income

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When Hurricane Ida slammed into Jessica’s print shop in northern Florida, it destroyed equipment worth tens of thousands and left her building damaged. But when she claimed a casualty loss deduction, she discovered that receiving $250,000 in insurance actually created a taxable gain instead of the tax break she expected. Her (fictional) story shows how complex disaster relief provisions have become for tax professionals and their clients.

In this episode of Tax in Action, Jeremy Wells, EA, CPA, begins a three-part series on disaster-related tax provisions. This first installment focuses on casualty losses and how the rules have changed since the Tax Cuts and Jobs Act (TCJA). As Wells notes, “the world’s changing in multiple ways, and one of those ways is that we see more and more frequent big storms, earthquakes, catastrophic events, and those can have serious financial implications.”

The TCJA limited personal casualty loss deductions to federally declared disasters starting in 2018. The documentation requirements are strict. Taxpayers must file insurance claims even when they seem unnecessary. And the calculations, based on the lesser of basis or fair market value changes, can produce unexpected results when insurance enters the picture.

Understanding What Qualifies as a Casualty Loss After 2018

The Tax Cuts and Jobs Act created a two-tier system that treats personal and business casualty losses differently. Starting with the 2018 tax year, personal casualty losses are only deductible if they result from federally declared disasters. This means a house fire, a tree falling on your car, or flood damage from a broken pipe no longer qualify unless FEMA declares your area a disaster zone.

A deductible casualty loss still requires three specific criteria. First, there must be actual damage, destruction, or loss of property. As Wells explains, “theoretical losses or potential losses don’t qualify.” Second, the damage must result from an identifiable event that can be isolated from other occurrences. Third, that event must be sudden, unexpected, and unusual in nature.

The “identifiable event” requirement plays out in interesting ways. Wells shares a Tax Court case where a taxpayer successfully claimed a casualty loss for his home in a Vietnamese village that was destroyed during the war. The court ruled in the taxpayer’s favor because the North Vietnamese invasion of that specific village was an identifiable event, distinct from the broader, years-long conflict.

But not all disasters qualify. When property values drop due to fear of potential mudslides without any actual damage, no casualty loss exists. Wells notes that “even though there’s going to be a significant economic and financial impact on the taxpayer, that doesn’t actually qualify as a deductible casualty loss because there’s been no damage, destruction or loss of property directly to the taxpayer yet.”

Between personal and business losses lies a tricky middle category: activities engaged in for profit but not rising to the level of a trade or business. These might include passive real estate investments or limited partnership interests. Courts consider whether the taxpayer’s main goal was economic profit independent of tax benefits. They also consider factors like the taxpayer’s expertise, reliance on qualified advisors, and success in similar ventures.

The insurance claim requirement often surprises taxpayers. Congress stated that choosing not to file an insurance claim doesn’t create a casualty loss. Instead, it represents “the taxpayer’s personal decision to forgo making a claim against the insurance company.” This means you must file a timely insurance claim to qualify for any casualty loss deduction, even for minor damage where you’d rather not involve your insurance company.

Calculating Losses When Insurance Changes Everything

The basic formula seems simple: take the lesser of your adjusted basis or the change in fair market value, then subtract any insurance or reimbursement received. But each part carries hidden complexities that can dramatically change the outcome.

Jessica’s case shows how insurance can create unexpected results. Her building had a $200,000 adjusted basis, but insurance paid her $250,000. That created a $50,000 gain. Her equipment, with a $50,000 basis but only $30,000 fair market value when destroyed, generated a $30,000 loss. The net result? A $20,000 taxable gain reported on Form 4797, despite her business suffering major damage.

Revenue Procedure 2018-08 provides safe harbors for establishing fair market value when formal appraisals aren’t possible. Wells explains you can use repair costs as evidence if the repairs meet four criteria:

  1. they’re necessary to restore pre-casualty condition,
  2. not excessive,
  3. only fix casualty damage, and
  4. don’t increase value beyond pre-casualty levels.

Getting two qualified repair estimates and using the lower figure offers another safe harbor. But Wells acknowledges the challenge: “It might be difficult to get two different companies or crews to come by and give you estimates” when entire regions need repairs after a disaster.

For personal casualties, the calculation gets even tougher. After determining the basic loss, you reduce it by $100 per event, then reduce the net amount by 10% of adjusted gross income. Wells shares his experience with Florida clients: “It’s entirely possible after the netting of gains and losses, then the reduction by $100, then the reduction by 10% of adjusted gross income, they don’t really see much of any tax effect. And that can be frustrating and disappointing.”

The increased standard deduction under the Tax Cuts and Jobs Act adds another hurdle. Since personal casualty losses become itemized deductions, many taxpayers see no benefit even after suffering significant losses. A couple with $100,000 AGI suffering $20,000 in casualty losses might receive no tax benefit at all after the reductions and standard deduction comparison.

Business casualties avoid these personal loss limitations but face their own issues. Form 4797 captures these transactions and might trigger depreciation recapture, converting expected capital treatment into ordinary income. Mixed-use property requires careful allocation between personal and business portions.

Documentation and Timing: Making the Right Moves

The essential documentation includes several key items. First, you need the cost or adjusted basis for every damaged property. Next, you need fair market value immediately before and after the casualty, although Wells notes “people don’t usually see, for example, a hurricane is about to strike and then go hire an appraiser.” Insurance policies and filed claims are mandatory. For personal losses, you also need the FEMA declaration number.

A valuable option allows taxpayers to claim casualty losses from federally declared disasters on the prior year’s return. For example, if disaster strikes in 2023, you have until October 15, 2024, to elect to claim that loss on your 2022 return, potentially getting a refund much sooner. Wells explains this involves filing an amended return with Form 4684, marking the special election box.

Form 4684 splits casualty losses into two sections. Section A handles personal property with its various reductions and thresholds. The FEMA declaration number goes above line one as proof of deductibility. Section B streamlines business and income-producing property calculations.

Wells emphasizes the importance of cloud storage, especially for firms in disaster-prone areas. “A lot of firms in these disaster prone areas have had to deal with storms hitting and losing their clients’ records.” He strongly recommends digitizing records and backing them up to the cloud.

The timing rules mean casualties are deductible in the year they occur, regardless of when repairs happen. But this creates challenges. How do you prove repair costs for work not yet done? Deadline postponements in disaster areas offer some relief, but you might need to file extensions to gather proper documentation.

Key Takeaways for Tax Professionals

The casualty loss rules have become more restrictive and complex since 2018. Personal losses rarely generate meaningful deductions outside federally declared disasters. Insurance payments can turn apparent losses into taxable gains. And the requirement to file insurance claims even when you don’t plan to pursue them catches many taxpayers off guard.

Preparation is essential for taxpayers and their advisors in disaster-prone areas. Maintain cloud-based records of all property basis and insurance coverage. Document property condition periodically with photos. Understand which events typically qualify for federal disaster declarations in your region. And prepare clients for the possibility that insurance proceeds might create tax liabilities.

Wells, speaking from experience in Florida, observes that hurricanes “don’t happen all the time, but they happen every now and then and they’re becoming more frequent and more powerful.” This reality makes understanding these provisions essential for tax professionals who serve clients in vulnerable regions.

Listen to the full episode to hear Wells explain all the calculations and share details that could save thousands in unexpected tax liabilities. Over the next two episodes, Wells will cover theft losses (including Ponzi schemes and cryptocurrency disasters) and involuntary conversions (which could have helped Jessica defer her unexpected gain entirely). With natural disasters increasing in frequency and severity, this series provides critical knowledge every tax professional needs before the next storm hits.