Blog – Full Posts

Beyond the Policy Binder: Building Workplaces Where Women Actually Feel Safe

Earmark Team · February 5, 2026 ·

“I ended up leaving that company by choice because I did not feel comfortable with him still there,” audience member Kimberly shared, her voice steady but carrying the weight of a difficult decision. “I didn’t want to go to court. But if I prevented this from happening to anyone else, that was enough for me to speak up so I could prevent some other young woman from ever going through that again.”

This powerful moment came during Part Two of a special She Counts podcast episode, recorded live on the main stage at the Accounting & Financial Women’s Alliance (AFWA) Women Who Count conference. Hosts Nancy McClelland and Questian Telka called it their best episode yet, bringing together employment attorney Kami Hoskins and HR expert Julie Thiel for an unfiltered two-hour CPE session about sexual harassment in accounting.

“Seeing all those faces in the audience and hearing from women who’ve been directly impacted by sexual harassment, it was everything I hoped it would be,” Nancy reflected. The discussion tackled the issue from multiple angles, including employees facing uncomfortable situations, employers trying to build better cultures, and small business owners managing client relationships.

The Real Goal is to Stop the Behavior, Not Destroy Careers

One revelation from the session was understanding what actually happens when somebody reports harassment. Many women fear reporting because they don’t want to destroy someone’s career or face retaliation.

“The goal of a good investigation is for the behavior to stop,” Kami explained. “It’s not to put the person in the public square and flog them. It’s not to cause them physical harm or to embarrass or shame them. It’s to stop the behavior.”

Sometimes extreme behavior requires termination. But often, intervention works, behavior stops, and everyone moves forward. This reframing matters because reporting helps create a workplace where everyone can do their jobs.

Harassment from clients and vendors matters just as much as harassment from coworkers. Julie emphasized that protection extends beyond your own company walls. “You are protected both within your company and in how you’re interacting with others as well,” she said. The investigation process and standards don’t change because the harasser works elsewhere.

When Nancy asked how many audience members were managers or supervisors, about 80% raised their hands. This matters because supervisors are legally obligated to report harassment they witness or hear about, even if the affected employee hasn’t complained.

“The supervisor can get the message to the Human Resources department,” Kami noted. “It doesn’t have to be the employees themselves. It’s on all of us to make sure that information gets to this function.”

Simple Words That Stop Bad Behavior

The experts shared surprisingly simple strategies for interrupting inappropriate behavior before it escalates. You don’t need a confrontational script or perfect comeback.

“It’s always easier to interrupt bad behaviors when they’re sort of lower level,” Kami explained. When someone makes a weird comment or inappropriate joke, small responses like “What?,” “That was weird,” “Awkward,” or even a pointed look can work.

Julie’s favorite intervention might be the most powerful: “What did you mean by that?”

“Often, people aren’t really thinking deeply about what they’re saying,” Julie explained. “That question gives them a pause to reflect again.”

Nancy shared a story that showed exactly why these tools matter. At an accounting conference earlier in the year, a woman made an extremely inappropriate sexual comment to a man in front of a group. The comment was so explicit Nancy wouldn’t repeat it on air.

“We were all just stunned,” Nancy recalled. “If a man had said that to a woman, there is just no way they would have gotten away with it. But we were just all so stunned because it was a woman saying it to a man. None of us knew what to say.”

Looking back, “What did you mean by that?” would have been perfect. Instead, Nancy managed only “Awkward,” which, the experts agreed, also works.

Julie noted that conferences pose particular risks. “When people are relaxed and in informal settings, those are often the situations where they make bad decisions.” Her advice is to stay self-aware. Check in with yourself about how you feel and whether anyone seems uncomfortable.

Culture Beats Policy Every Time

The most powerful moment came when another audience member, Katie, shared her experience at a nonprofit healthcare company. Despite being almost all women with male leadership, everyone felt comfortable because of one consistent practice.

“They called it the tone from the top,” Katie explained. “Every single meeting started with a tone at the top, coming from the board members and from the executive leadership.”

Even during days with 13 budget meetings, each one began with acknowledging company values and recognizing someone who exemplified them. This wasn’t performative; it was how the organization operated.

Kami shared why this works. “I don’t think leaders understand how often employees need to hear the message. It’s not something that you can hear once a year or twice a year. Employees need repetition.”

The discussion revealed a critical gap in leadership training in most organizations. “Most leaders get put into leadership positions without any training,” Julie observed. “It’s like, ‘Good luck in the deep end of the pool!’”

Nancy illustrated this with a story from her husband’s job at Microsoft. A colleague discovered he’d been promoted to manager when someone said, “I guess I report to you now.” An email had announced it to his new team, but nobody had told him first.

“You’re taking somebody who’s an introverted software developer who’s very good at technical work, and now he is managing people,” Nancy said. These preparation gaps contribute to cultures where harassment can flourish.

Real Questions, Real Challenges

The audience Q&A highlighted the complex realities women face. An anonymous question asked about an executive who had asked if her “boobs were fake.” She never reported him because of his position.

“Any comments about anyone’s body for any reason are not cool,” Julie responded firmly. Kami added that while a judge or jury determines if something legally constitutes harassment, it’s clearly “problematic behavior that should not have happened.”

For those fearing powerful harassers, Kami noted many employers have anonymous ethics helplines. “Having been on the inside of a legal department, I can tell you a lot of work goes into maintaining anonymity.”

Michelle, a volunteer firefighter, raised another challenge: inadequate investigations in volunteer organizations. She described a situation where someone was falsely accused, and the accused faced immediate threats of expulsion before any investigation.

“That’s why that investigation is so critical,” Kami responded. “We want to do good fact-gathering before we make decisions about what to do next.”

Kimberly asked about the “he said, she said” problem, when harassment happens privately with no witnesses or proof. “How do you prove that?” she asked, describing her own experience reporting someone in power.

“If there’s no reason for me not to believe you, I would still address it,” Julie reassured her. She explained that HR’s job is to remain neutral and hold everyone accountable. Even without proof, strategies exist to ensure behavior doesn’t continue, such as never being alone with that person again, check-ins, and accountability measures.

“If there’s no proof, it’s hard to win in court,” Kami acknowledged. “But that doesn’t mean there aren’t a whole other universe of resolutions available to ensure the behavior stops.”

Resources for Every Organization Size

When Nancy asked about resources for small firms that don’t have an HR department, Julie recommended fractional and outsourced support. Just as firms use fractional CFOs, they can access fractional HR and legal expertise. “Building that relationship can be important,” Julie advised. “This isn’t the kind of stuff you want to guess about.”

For those needing to escalate beyond their employer, resources include:

The Equal Employment Opportunity Commission (EEOC) at the federal level
State civil rights divisions
Anonymous ethics helplines within larger companies
Employment attorneys for serious cases

Kami emphasized starting with your employer when possible, but “there’s always opportunities to go outside of the organization.”

Measuring What Matters

For an audience of accounting professionals, Kami offered data-driven accountability. “You can actually look at the data and see if your culture is working for you.”

Key metrics include:

Retention rates
Efficiency metrics
Promotion patterns across genders
Pay equity (“same role, same experience, different comp?”)

“In addition to all the warm and fuzzy stuff,” Kami said, “there are really tactical, measurable metrics organizations can look at to make sure they’re keeping themselves honest.”

Your Voice Is Your Power

The session closed with Questian sharing a quote from Melinda Gates. “Women speaking up for themselves is the strongest force we have to change the world.”

Julie’s admission resonated throughout the room. “I was 50 learning how to find my voice, and I am still finding my voice at 55.” Finding your voice is an ongoing practice that gets stronger with use.

For women in accounting firms, corporations, or running their own practices, these insights offer a path forward. Not just policies on paper, but real cultural change that makes speaking up safe and normal.

Listen to both parts of this special She Counts episode to hear the full conversation, including more audience questions and expert guidance. Follow She Counts on LinkedIn to join the conversation about creating workplaces where women don’t have to choose between their safety and their careers.

Because as Kimberly’s story reminds us, no woman should have to leave a job she loves to escape harassment. It’s time to change the culture, not just the policy.

The Accounting Profession Has AI Completely Backwards

Earmark Team · February 5, 2026 ·

When Accounting Today surveyed industry thought leaders about AI’s impact on the profession, every expert agreed that AI would automate the boring stuff like bank reconciliations, data entry, and transaction matching while humans would rise to strategic advisory work. Not one thought their own job was at risk.

On a recent episode of The Accounting Podcast, hosts Blake Oliver and David Leary did something clever. They fed the same questions to ChatGPT, asking it to respond as an accounting thought leader. The AI’s answers were just as good as the human experts’.

“None of the accounting thought leaders think their job could be replaced,” David said, “which is crazy because essentially AI can at least do the thought leader job.”

Blake and David argue that the profession has AI’s impact exactly backwards. While everyone confidently predicts automation will eliminate mundane bookkeeping tasks, the technology actually excels at synthesis, narrative-building, and strategic analysis—the very work that defines “thought leadership.”

What AI Actually Does Well

The standard story about AI in accounting is machines will handle the boring, repetitive tasks while humans ascend to strategic advisory work. It’s comforting and logical. But according to Blake and David, it’s completely wrong.

“AI can take financial statement information and turn it into a narrative better than I can, better than almost anyone can at this point,” Blake states. “That’s what we should be using it for.”

Consider Mike Salvatore, a Chicago business owner with two cafes, two bars, and a bike shop. He used to analyze his cost of goods once or twice a year, spending hours crunching numbers. Now he does it every three weeks by feeding data from QuickBooks and his point-of-sale system into Google’s NotebookLM, which creates a podcast-style summary of his business performance. He sends these AI-generated recordings to his managers.

“It’s essentially my CFO,” Salvatore told The Wall Street Journal.

This isn’t AI doing mundane bookkeeping; it’s performing executive-level analysis and communication.

Blake’s own experience drives the point home. He built an AI system that turns news articles into detailed research notes and social media posts. That work used to eat up hours each week. He also trained an AI ghost writer on hundreds of his past writings. Now he can dictate a voice memo and get back a polished article in his own style.

“Basically, it has made it so, as ‘thought leader,’ I don’t do any of that anymore,” he admits. “It’s like I have a team that does that for me. I started working out and I’m just enjoying life.”

Meanwhile, the supposedly “easy” transactional work is stubbornly resistant to automation. David, who spent years taking QuickBooks support calls before co-founding the podcast, gets fired up about this misconception.

“Matching bank feeds is not bookkeeping. That’s just matching,” he argues. “Accounting is sending an invoice to somebody so they’ll pay me.”

He describes his recent struggle trying to upload an invoice to a client portal. It’s a “mundane” task that should be simple but isn’t. The process requires navigating confusing interfaces, making contextual decisions, and handling exceptions that don’t fit predetermined patterns. AI can’t do this reliably because it lacks the real-world context that humans take for granted.

The disconnect is striking. Thought leaders keep repeating the same message they’ve preached about cloud accounting for a decade: technology will free you up for advisory work. But as David points out, “I don’t think AI is freeing up your time to do that work yourself.” Instead, AI is doing the advisory work directly.

Are You Willing to See the Opportunity?

Where things get interesting is the same AI capabilities that threaten thought leaders create a massive opportunity for regular practitioners if they’re willing to see it.

Mike Salvatore, the Chicago business owner interviewed by the Wall Street Journal, wasn’t working with an accountant before. His AI “CFO” didn’t displace a human. He simply started getting insights he’d never received.

“Very few accountants serving Main Street businesses will actually do that kind of work for a price these business owners want to pay,” Blake explains. “So they do it themselves, but they don’t do it often and they don’t do it well.”

AI is filling a vacuum, not replacing existing services. And that vacuum is huge.

If a business owner can get advisory insights that are even 50-80% accurate from AI, that’s better than the nothing they’re getting now. The question for accounting firms is whether to let clients figure this out themselves or to offer AI-powered advisory services with professional oversight.

“Firms can feed data from clients’ QuickBooks files and their point of sale systems into these tools to generate AI analysis,” Blake suggests. “You can charge for it, because you’re adding the oversight—checking the numbers, making sure it actually makes sense.”

David connects this to a decade-old challenge. He remembers when LivePlan tried to train bookkeepers to offer business planning services. “They really struggled with it because they’re good at bookkeeping. But it’s hard to teach somebody to tell a story and create the narrative around the numbers.”

Now, “all those bookkeepers can basically offer that with AI out of the box and charge for that additional service.”

When ChatGPT (playing the role of thought leader) was asked what would make it worry about being replaced, it gave a revealing answer: clients accepting “AI-generated advice as good enough, even in ambiguous scenarios.”

Blake’s interpretation is blunt. “That’s what AI will fill—the gap in the market where accountants aren’t providing the service. There’s a big gap and there aren’t enough of us.”

Why Billable Hours Kill Innovation

One survey question asked about the “AI premium.” How much more should an AI-savvy accountant earn compared to an identical colleague who doesn’t use AI? The thought leaders said these employees should obviously be paid more.

Blake laughed at this. “How can you pay them more if you’re looking at them in terms of billable hours? AI is going to actually reduce their billable hours, not add more.”

If an employee uses AI to finish work in half the time, they bill half the hours. Under the traditional model, they look less productive, not more. Under the traditional model, “you should pay the AI employees less because they’re working less,” Blake points out.

This creates a ridiculous situation where your most innovative, efficient employees appear to be your worst performers.

Ryan Lazanis, who built and sold an accounting firm and now coaches other firm owners, has a different approach. He focuses on just two numbers: bottom-line profit and monthly recurring revenue. Not billable hours, utilization rates, or time per client.

“He is not breaking it down by client. He’s not looking at individual job profitability,” Blake explains. The only thing that matters is whether the firm made money over the year.

This makes sense because staff costs are fixed. “The amount of hours they spend has no impact on your profitability,” Blake notes. You only need to worry if one client is so demanding they prevent you from taking on others.

“You don’t have to track hours for months to figure out which clients are eating up your profits,” David adds. “You just go to your team and say, ‘Who’s the biggest pain in the ass client?’ And they’re going to tell you.”

There’s also a technical angle to consider. Blake cites research showing AI is nearly 100% accurate on tasks that take humans 4-5 minutes. That accuracy drops for longer tasks, but the threshold is “doubling every seven months.” By the end of 2026, AI might handle 10- to 20-minute tasks reliably.

But this only matters if firms can capture the productivity gains. Under billable hours, faster work just means more hours to fill. Under outcome-based metrics, faster work means more capacity for growth.

Is the AI Accounting Influencer Coming?

As the episode wraps up, Blake and David float an idea that captures the absurdity of the current moment. They’re considering creating an AI accounting influencer—a completely artificial thought leader to see if it can build a following comparable to real industry voices.

“Let’s make an AI accounting influencer and see if we can build its following to eclipse that of those real influencers,” Blake suggests. They could have it write newsletters, create content, maybe even land sponsorship deals.

It’s partly a joke, but it makes a serious point. If an AI can answer thought leadership survey questions as well as humans, write articles, and provide strategic insights, what exactly makes human thought leaders irreplaceable?

The answer might be less comfortable than the profession wants to admit.

Looking Ahead

The Accounting Today survey offered some important insights, though probably not what it intended. The people most confident about AI’s limited impact are those whose work AI does best. When ChatGPT generated answers indistinguishable from human experts, it demonstrated the very vulnerability those experts deny.

The real story is that AI excels at synthesis and narrative, which are the heart of advisory work, but struggles with the contextual, exception-filled world of everyday bookkeeping.

Firm owners should rethink their services to capture the advisory opportunity AI makes possible, and abandon billable hours before they strangle your ability to innovate.

For individual practitioners doing transactional work, the news is actually good. Your skills remain valuable precisely because your work requires the messy, contextual judgment that AI lacks.

And for thought leaders? As David observed with obvious frustration, the elitist attitude that “I’m better than you” has been in accounting for 30 years. “The reality is completely opposite. People are completely missing what’s really going to be replaced by AI.”

The race isn’t between humans and machines. It’s between practitioners who recognize AI’s true capabilities and those who cling to comfortable narratives while missing the transformation happening around them.

To hear more about Blake’s AI-powered lifestyle, David’s thoughts on what bookkeeping really is, and their plan to create an AI influencer that might outperform the human ones, listen to episode 469 of The Accounting Podcast.

How to File 1099s Without the January Scramble

Earmark Team · February 2, 2026 ·

Alicia Katz Pollock, host of The Unofficial QuickBooks Accountants Podcast, just spent a week in what she calls “1099 Heaven,” teaching her comprehensive 1099 class and attending Nancy McClelland’s Ask a CPA workshop. She came away from that week ready to share a concentrated breakdown of everything accounting professionals need to know about 1099 filing.

“I’ve been watching the socials and people are asking, ‘Which report do I run so to filter out payments under $600 and payment processors?’ and, ‘How do I export to Excel?’” Alicia observes. “And the truth is, you don’t need to.”

QuickBooks Online has built-in tools that handle most of the filtering and analysis automatically. Yet every January, accounting forums light up with practitioners frantically exporting data to Excel, second-guessing payment methods, and chasing down W-9 forms as the deadline approaches.

In episode 125, Alicia breaks down what you actually need to know, including who qualifies for a 1099 (and why small errors won’t hurt you), which payment methods trigger reporting in our fintech-heavy world, and the QuickBooks tools that eliminate hours of manual work.

Understanding 1099 Compliance

Before diving into QuickBooks tricks and automation, you need to understand what these forms actually accomplish, and what’s changing in 2026.

Essentially, the 1099 system exists because the IRS wants to verify that contractors report their income. When you pay another business for services, you’re telling the IRS about that payment. They match your report against what the contractor claims on their taxes, making sure nobody’s working under the table.

“Literally millions of dollars, if not billions of dollars, is wasted in lost productivity while we chase down W-9 forms and file all these forms and do all of our research just to make sure that everybody is on the up and up,” Alicia says, not holding back her frustration. “So it’s kind of a vicious cycle.”

What’s New for 2026

This year brings a significant addition with Form 1099-DA for digital asset transactions. The IRS is finally tracking cryptocurrency sales and income, attempting to bring crypto economics into the traditional tax framework.

The $600 threshold that’s been in place for decades stays the same this year, but relief is coming. The One Big Beautiful Bill raises this to $2,000 starting in 2027. As Alicia notes, “The vast majority of my small businesses and micro businesses probably wouldn’t even qualify and won’t need to do this at all next year.”

Who Gets a 1099?

The rules are simpler than many make them:

Send 1099s to:

Self-employed individuals
LLCs filing as sole proprietors
Partnerships
Attorneys (even if incorporated)
Independent landlords (not property management companies)

Don’t send 1099s to:

S Corps
C Corps
Property management companies

Remember to check beyond your expense accounts. Balance sheet items like prepaid expenses, leasehold improvements, and due to/from accounts might contain qualifying payments. And if one company pays on behalf of another, the company that received the service files the 1099.

The Accuracy Question

Fear of making small mistakes keeps practitioners up at night unnecessarily.

“If your 1099 is off by $100 or $200, nobody’s going to come knocking on your door,” Alicia says reassuringly. “The IRS is short staffed. They’re really not looking for $600 in revenue. But if you’re talking hundreds of thousands of dollars, then it’s a bigger concern.”

The IRS primarily cares whether contractors report income lower than their total 1099s. If someone receives $200,000 in 1099s but reports $250,000 in income, no red flags appear. Problems only arise when reported income falls below documented payments.

Alicia shares a cautionary tale about a cleaning service client who paid cleaners as contractors for 15 years despite warnings. “Sure enough, she got audited after 15 years. And it turns out that the IRS agreed with me that they really are employees, so she now has some fines to pay.”

W-9 Best Practices

The key to avoiding January panic is to collect W-9s immediately when hiring someone. Don’t wait to see if they’ll hit the threshold; just send it. And don’t pay until you receive it back.

If contractors ignore your requests, you have leverage. Threaten to withhold 24% of their payment for backup withholding. “That warning is usually enough to get them to reply,” notes Alicia. If they still won’t cooperate, file the 1099 anyway with a blank EIN. “Unfortunately that might trigger an audit for them, but if they’re not sending you a W-9, well, what are they hiding?”

One persistent problem is W-9 forms often come back filled incorrectly, especially from LLCs. The form should show information for the entity actually paying taxes, not a pass-through or disregarded entity. Many people put their personal name on line one and business name on line two backwards, creating confusion about their tax status.

Navigating the Payment Method Maze

Much of the 1099 confusion stems from uncertainty about which payments count. With the explosion of fintech platforms, determining what triggers reporting has become increasingly complicated.

The Foundation Rule

You send 1099s for payments from your bank account, including:

Cash and checks
Online bill pay
ACH transfers
Wire transfers
Zelle

You don’t send them for credit or debit card payments. The merchant processors handle their own 1099-K forms.

The Fintech Gray Zone

PayPal, Venmo, and similar platforms create confusion. The determining factors are whether you use the business or personal version and whether you’re paying “friends and family” or for “goods and services.”

Alicia recommends asking two key questions:

Does it charge a transaction fee? If yes, you likely don’t need a 1099
Does it have its own bank balance? PayPal and Venmo do, so that’s another sign you’re off the hook.

Business versions of these platforms send their own 1099-K forms. However, merchant services use different thresholds: $20,000 and 200 transactions, maintained by the One Big Beautiful Bill. This creates a gap where payments between $600 and $20,000 via credit card aren’t reported by anyone, and that’s perfectly fine from a compliance standpoint.

For navigating the infinite fintech combinations, Alicia strongly recommends Jennifer Diamond’s 1099Problems website.

Material Reimbursements

How contractors invoice determines the treatment:

When materials are wrapped into the service invoice, you include everything.
When materials are itemized separately, you exclude materials and report services only.
When materials are invoiced separately, you ignore them entirely.

“The IRS knows you’re paying them the full price for the whole service, and it’s up to the contractor to do their own deductions for their own material costs,” Alicia explains.

The Reference Number Secret

Alicia shares a “hot tip” most practitioners don’t know. QuickBooks expense forms have a reference number field that automatically excludes transactions from 1099 processing.

“You would think the payment method would be the thing that allows you to do the exclusion, but no. It doesn’t work that way,” she notes. Instead, enter “debit,” “card,” “Visa,” “MC,” “Chase,” “Discover,” “PayPal,” or “Amex” in the ref number field. The wizard recognizes these and excludes the transactions—a feature carried over from QuickBooks Desktop.

Mastering QuickBooks Online’s 1099 Tools

Despite QBO’s built-in capabilities, Alicia observes practitioners still asking which report to run in order to filter out for the $600 and for the payment processors. The tools exist, but many don’t know where to find them.

The Contractors Center Hub

The Contractors Center, located under Expenses and Bills (and under Payroll, if enabled), manages 1099-eligible vendors from start to finish. Any vendor with “track 1099” checked appears here automatically.

The standout feature is self-onboarding. Invite vendors via email to complete a digital W-9 through their QuickBooks account or the free QuickBooks Money app. The system captures everything, including their name, address, tax ID, entity type, and qualification status.

“Tell them to look for it because it looks like spam,” Alicia warns. “It just says QuickBooks needs your W-9 and bank info and who is going to click that?”

Payment Processing Options

The Contractors Center offers multiple payment methods, including:

QBO Payroll subscribers: Contractors treated as employees at your per-employee rate
Contractor-specific plan: $10.50 monthly for up to 20 contractors, $1.70 each additional
QBO Bill Pay: Standard functionality

The 1099 Preparation Wizard

Access the wizard via “Prepare 1099” in the Contractors Center or the dedicated 1099 section under Expenses and Bills in the new navigation.

There are two approaches available: “Try Autofilled Forms,” which is an AI-powered automation, or “Prep My Own” for manual step-by-step control.

“I tried it this year and honestly they came up with the same information,” reports Alicia. Choose based on comfort level—automation for hands-off clients, manual for those wanting verification.

Custom Reports for Analysis

The wizard includes two reports: Accounts to Pay Vendors and Vendor Transactions. “I turn on the track 1099 status and then filter it so the status is on and the amount is greater than $600 instead of looking at the big list of all the payments for all the vendors,” Alicia says, explaining her workflow.

State Filing Complications

Some states participate in the Combined Federal and State Filing Program, and QBO handles both simultaneously. Others require separate filing through state websites.

Alicia’s particular frustration is that she’s located in Oregon. “it stinks for me because QuickBooks doesn’t export any kind of report that I can import into Oregon’s filing system. So I wind up having to type them all in by hand.”

Corrections After Filing

If you make an error, QBO allows corrections after IRS acceptance. Replace incorrect forms with $0, add forgotten contractors, or submit corrected amounts. Third-party platforms offer similar capabilities.

Your 1099 Action Plan

As Alicia emphasizes throughout the episode, the tools exist to make this process manageable. Stop exporting to Excel. Stop manually filtering. Use the automation that’s already there.

Looking ahead, the 2027 threshold increase to $2,000 will eliminate this requirement for many small businesses entirely. Until then, master these tools and workflows to transform 1099 season from a compliance nightmare into a streamlined process.

For an even deeper dive into 1099 filing, check out Alicia’s Payroll Perfection bundle, which includes QBO Payroll, QuickBooks Time, and payroll compliance training. And be sure to listen to the full episode for additional insights from Alicia’s week in “1099 Heaven.”

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!

Leading with Empathy: Building Accounting Teams That Thrive

Earmark Team · February 2, 2026 ·

Earn free NASBA-approved CPE for listening to this episode. Visit Earmarkcpe.com, take a short quiz, and get your certificate.

“Star performers aren’t immune from accountability,” says Lisa Gilreath, Managing Partner at Acuity. “Often they perform really high. But you’re going to see the other half of your team suffer in terms of their performance.”

This frank observation cuts to the heart of one of accounting’s toughest leadership challenges—dealing with talented but toxic employees. It’s just one of many practical insights shared during this episode of the Earmark Podcast, recorded live in Atlanta during the Advisory Amplified tour.

Host Blake Oliver sits down with Lisa Gilreath and Valerie Heckman, Accountant Community Manager at OnPay, to explore what empathetic leadership really looks like in accounting firms. Their conversation goes well beyond feel-good management theories to address the real challenges firms face when deadlines hit and pressure mounts.

Why Empathy Makes Business Sense

When Blake asks Lisa why firms shouldn’t burn out their people, her answer is refreshingly honest: “They’re really hard to replace right now.”

This practical reality drives home why empathetic leadership isn’t just nice to have—it’s essential for survival in today’s talent market. Lisa explains that with staffing shortages and people tired of 60-80 hour work weeks, firms have to build healthier workplaces to succeed.

But deadlines don’t disappear. Tax seasons still come. Clients still have needs. The key is finding ways to meet those demands without destroying your team in the process.

Building Breathing Room Into Your Firm

Traditional firms plan for 100% utilization, assuming everyone will be productive every single day. Lisa takes a different approach at Acuity, planning for 75-80% capacity instead.

“You can’t run the people to the absolute end and expect not to be in a crisis situation if somebody has an issue,” she explains. This isn’t about accepting lower productivity. It’s about building resilience into your workflows.

Personal crises illustrate why this matters. “Personal crises, tragedy or challenges never check your calendar to see if you have time to deal with them,” Lisa notes. Over 20 years at Acuity, she’s seen it all—employees who unexpectedly passed away, team members losing spouses, medical emergencies that required immediate attention.

These aren’t rare events. They’re the reality of managing people over time. The question is whether your firm can handle them without falling apart.

Lisa recommends having your “phone a friend on speed dial”—an HR expert or advisor who can provide objective guidance when emotions run high. Small firms especially struggle when close relationships make it hard to separate business needs from personal loyalty.

How Systems Create Space for Humanity

Many firms see standardization as rigid and impersonal. Lisa flips this completely, showing how standard processes actually enable empathy.

“If you do have a standard scope of services for your transactional stuff, you can plug and play people,” she explains. “Paying bills is paying bills. Doing payroll is doing payroll. It’s just a matter of where you get that source data.”

When every client engagement follows similar patterns, any qualified team member can step in during an emergency. This protects both the employee who needs support and the client who needs continuity.

Acuity spreads work throughout the year using recurring CAS engagements rather than accepting the traditional feast-or-famine cycle. “We’re focused on being proactive in those interactions all year long,” Lisa says. This creates predictable workflows that allow for coverage when life happens.

The approach helps team members too. Lisa tells her people: “Build our workflows and build our communication patterns so that if you need to leave unexpectedly, we’ve got your back. Help us help you.”

Reading the Warning Signs

Technology provides new ways to spot problems before they become crises. But Lisa doesn’t just watch productivity metrics. She pays attention to communication patterns.

“I’m noticing when people are no longer engaging in Slack conversations at the same pace that they once were,” she explains. “They’re not showing up in meetings and being as talkative as they once were.”

These changes signal that something’s wrong before performance completely deteriorates. A normally responsive team member whose emails slow down. A strong performer whose deliverables lag. These whispers often matter more than what people explicitly say.

Valerie adds another important metric: PTO usage. “If people aren’t using it, that’s a sign,” she notes. “Are they afraid to use it? Do they feel like if they use it, they’re not contributing enough to the team?”

Her own mother exemplifies this problem, going years without taking vacation because she worried about work piling up. “She would never, ever take a day that payroll needed to be run or the day after in case there were mistakes,” Valerie recalls.

The flip side matters too. Excessive PTO usage might signal disengagement or job hunting. These patterns hide in payroll data most firms already collect but rarely analyze for team health insights.

The Toxic High Performer Problem

Every firm faces this dilemma eventually: what do you do with someone who delivers great results but poisons team culture?

“Toxic workers will take you down,” Lisa states plainly. While star performers deliver individually, the rest of the team suffers. The math is clear—protecting one toxic high performer often means losing multiple good employees.

But Lisa doesn’t jump straight to termination. “I start from a place of curiosity,” she says. “How did we get here? What’s going on with them?”

Sometimes it’s a personal crisis. Sometimes they don’t understand expectations. Sometimes they genuinely don’t realize they need to collaborate. Starting with curiosity creates space for course correction.

The same principle applies to clients. When Blake asks about unreasonable client demands on her team, Lisa’s response is swift: “They’re probably not going to be a client for much longer.”

Acuity holds both team members and clients to their values. “This is how we intend to operate,” Lisa explains. They regularly review their client base to ensure alignment, not just to cull unprofitable work but to protect team wellbeing.

Navigating Industry Change With Compassion

The pace of change creates another empathy challenge. Many experienced accountants built careers on consistency and process. Now they’re asked to develop entirely new skills.

“We liked that about them for a really long time—that they followed the process and they didn’t question the process,” Lisa observes. “Now we’re asking them to talk to clients, and they’ve never had to talk to clients. They just had to fill out the form.”

With AI transforming the profession, these changes feel overwhelming to some team members. The empathetic response isn’t to abandon these people but to “bring those people along at their pace as well as the pace of the industry.”

This is where hiring for adaptability becomes crucial. Lisa looks to new graduates who see AI as normal, not threatening. “They’re unafraid. They will just try anything,” she says. These digital natives may help bridge the gap for more experienced team members struggling with change.

Taking Action This Week

Valerie offers practical advice for leaders wanting to be more empathetic: pause.

“Taking that time when something happens, when there’s an experience with a worker or team dynamic and saying, okay, we’re going to sleep on it,” she suggests. This fights the instinct to immediately jump in and solve problems.

Pausing allows you to ask better questions rather than make assumptions. It could be personal challenges, professional struggles, or something else entirely. Without that pause, you might treat symptoms instead of root causes.

Lisa adds another suggestion: engage your team in discussing a problem and just listen. “They will often lead with things that are coming from a place of fear or concern,” she notes. Understanding these underlying worries helps you address real issues, not just surface problems.

Your Role as an Advocate

Perhaps the most important mindset shift involves how leaders see their role. “I am their number one advocate,” Lisa says about her team. “My role is not just to drive them to production, it’s really to advocate for their needs.”

This means creating multiple channels for support, recognizing not everyone feels comfortable approaching their direct supervisor. “If I’m not the person that you can reach out to, I promise you, I have paths for you to go raise your concern,” Lisa tells her team.

The business case remains clear throughout the conversation. In today’s environment where good people are “really hard to replace,” protecting team culture isn’t charity—it’s strategy. Firms that recognize their people as “the engine” and act accordingly will outlast those clinging to the burnout model.

Listen to the full episode to hear more practical strategies for implementing these changes in your firm. Lisa and Valerie share specific tips on creating buddy systems for coverage, working with HR consultants, and building workflows that respect both deadlines and humanity. Their insights offer a realistic path forward for firms ready to lead with empathy while maintaining business success.

From Data Entry Nightmare to Automated Workflow in One Demo Session

Earmark Team · February 2, 2026 ·

You’re ten days away from the 1099 and W-2 deadline, and you’re still wrestling with QuickBooks, fielding a flood of W-9 request emails, and dreading the inevitable data entry marathon. Sound familiar?

You’re not the only one. As David Leary admitted during a recent Earmark Expo webinar, “I’ve been procrastinating on issuing 1099s. It’s just not a great experience.” He described the dual frustration that many accountants know all too well. “It’s annoying work on both sides. I need to do my 1099s, but then, as a business that receives them, I get a slew of emails from other companies asking for a W-9.”

In the webinar, David and co-host Blake Oliver took TaxBandits for a test drive with Nikita Sullivent, the company’s Support Specialist, to explore how this IRS-authorized e-file platform handles over 70 tax forms. The live demo included the authentic technical hiccups we all face with real-world software and shared practical solutions for the compliance challenges that hit every January.

Getting your data in: from hours to minutes

Manual data entry for hundreds of 1099s is a bottleneck that keeps you from serving more clients. TaxBandits tackles this with multiple import options that meet you where your data lives.

The platform offers three main paths for getting data in. You can:

Enter forms manually one at a time (perfect for that forgotten contractor),
Use bulk upload templates for larger volumes, or
Connect directly with accounting software (current integrations include QuickBooks Online, Xero, Sage Intacct, and Zoho, with Karbon integration coming soon).

The bulk upload process stands out for its simplicity. As Nikita demonstrated, “You’re reviewing the columns at the top and inputting the data beneath them. Once we have all of that data input, we’ll just download it as a CSV and drag and drop it in.”

David particularly appreciated one detail. “I like how on your templates, in the header of each column, you give the instructions for the values you accept in that field.” No more guessing whether to use “CA” or “California,” or whether TINs need dashes.

The workflow breaks down like this:

Download the Excel template with clear column headers
Fill in your data following the built-in instructions for each field
Drag and drop the file into TaxBandits
Review the automatic error check that flags issues like missing digits in EINs or duplicate records
Fix any problems by either editing in the app or exporting just the error records for correction

For QuickBooks users wondering about the process, David confirmed you can export your vendor list, filter for 1099 vendors, and use the “upload your own file” feature. The first time requires mapping your fields to TaxBandits’ fields, but that mapping saves for future uploads.

One webinar attendee asked whether they needed to re-enter last year’s payees. “Absolutely not,” Nikita answered. “Everything stays in your account and rolls over year after year.” When you import this year’s data and the system finds a duplicate, you can either delete it or update the existing record with any changes.

The platform also distinguishes between importing only recipient data and importing both payer and recipient data. If you maintain TaxBandits throughout the year, importing just recipients during filing season works best since you’ve already set up your payers. But if you’re adding everything at once, the combined import saves steps.

With data flowing smoothly into the system, the next challenge is ensuring that data won’t bounce back from the IRS.

TIN verification: the new compliance reality

Getting data into the system efficiently matters only if it passes IRS validation. The agency’s transition from the FIRE system to IRIS (Information Returns Intake System) brings stricter requirements that every accountant needs to understand.

“The IRIS system is going to be far stricter on TIN matching than the FIRE system was,” Nikita warns. “Which means if the SSN, the EIN, the TIN, and the recipient name don’t identically match the IRS database, it’s going to kick the form back to you as accepted with errors, and you have to file a correction.”

The keyword is “identically.” A contractor who goes by “Mike” but whose Social Security card reads “Michael” could trigger a rejection. Even punctuation differences in business names can cause problems.

TaxBandits builds TIN verification into multiple touchpoints:

When collecting W-9s throughout the year
When adding recipients to your address book
During the 1099 workflow as a final check

The smart approach starts early. “When you get a W-9, when you get a new employee or contractor, you go ahead and do the TIN matching on that prior to the filing season,” Nikita advised. This prevents last-minute surprises when deadlines loom.

Verification typically returns within two to four hours during normal periods. But during peak season “it can be up to 24 hours,” Nikita warned. If you’re verifying TINs within the 1099 workflow itself, the system waits for results before transmitting, which is potentially problematic if you’re filing on January 31st.

For those worried about the cost of corrections, TaxBandits offers some protection. Their “TaxBandits Commitment” covers correction filings at no additional charge. But even free corrections cost you time and stress.

The platform also streamlines W-9 collection. Instead of chasing paperwork, you can send electronic W-9 requests. Recipients complete them online, and the data flows directly into your TaxBandits account, ready for immediate TIN verification if desired.

Once your forms are prepared and verified, you still need to get them into recipients’ hands compliantly.

Distribution flexibility that actually works

The old choice between hours at the post office or forcing everyone into electronic delivery is over. Modern distribution needs flexibility, and TaxBandits delivers exactly that.

“Everything is very customizable to your needs,” Nikita explained when asked about mixing delivery methods. “You can choose some postal mail, some online access, and some want both.”

The three distribution paths each serve different needs:

USPS postal mailing handled entirely by TaxBandits
Electronic recipient portal requiring just an email address
Both options for recipients who want backup

The electronic portal solves a critical compliance issue. The IRS requires formal consent for electronic delivery, so you can’t just email a PDF. TaxBandits automates this. Recipients receive a secure link, enter a PIN for verification, and provide documented consent.

If someone ignores that email, the system tracks everything. You can see who consented, who declined, and who never responded and then handle postal delivery for the holdouts.

For returning recipients, the portal builds value over time. “If you file for that same recipient next year, they’ll use the same link, and they’ll access all of the documents from the same portal,” Nikita noted. Recipients get their own organized tax document archive without any extra work from you.

State filing adds another compliance layer, but TaxBandits simplifies this, too. The platform tells you exactly what each state requires:

States requiring direct filing (you handle separately)
Combined Federal/State Filing participants (automatic forwarding)
States requiring no 1099 filing

Throughout the process, you get real-time status updates so you can see which forms were transmitted to, received by, and accepted by the agency. For postal mail, statuses are submitted to USPS and en route to the recipient. When a client claims they never received their form, you have documentation. After transmission, watermarks disappear from your copies, and you can reprint professional versions anytime.

For firms with multiple preparers, the platform offers even more control through team management features.

Scaling with teams and support

Larger firms need more than just bulk upload; they need workflow management. TaxBandits’ team management features let you maintain control while delegating the actual work.

The system offers three permission levels:

No roles: Any team member can prepare, approve, and transmit
Two roles: Preparers create forms, approvers review and transmit
Three roles: Preparers create, approvers review, transmitters handle payment and filing

You can also create location-based groups. Nikita shared an example. “Say you have a group in Indiana and a group in Tennessee. Anytime you add a new payer and assign them to the Tennessee group, then all of the team members included in the Tennessee group have access to that payer.”

Support is critical when things get complex. During busy season, TaxBandits extends hours to 8 a.m. to 8 p.m. Eastern. They offer phone, email, and chat support, plus an AI assistant that pulls from both their knowledge base and IRS guidelines.

The platform’s YouTube channel provides step-by-step videos for specific workflows. For Sage Intacct users who asked about integration, Nikita recommended checking their channel for detailed walkthroughs showing the complete process from Sage to TaxBandits.

Pricing works on a credits system with bulk discounts. Buy more credits upfront, pay less per form—and credits never expire. As Nikita confirmed when asked about rollover, “Your credits will never expire. So if you want to purchase for the next five years now and get the best price we can give you, go for it.”

Making next year easier starts now

The strategies demonstrated in this webinar show a fundamentally different approach to information returns. TaxBandits treats compliance as a year-round process rather than a January panic.

The IRS’s push toward e-filing mandates and stricter validation isn’t slowing down. The IRIS system is just the beginning of modernization efforts that will continue tightening requirements. But the webinar demonstrated real workflows you can adopt immediately, from template imports to electronic W-9 collection to role-based team permissions.

Ready to transform your 1099 and W-2 workflow? Watch the full Earmark Expo webinar to see TaxBandits in action, including the complete demo of bulk uploads, error checking, and team management features. The platform offers over 70 tax forms beyond just 1099s and W-2s, making it a comprehensive solution for year-round compliance needs.