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Blake Oliver

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.

From Vanishing Jobs to Work Slop: Inside Accounting’s AI Reality Check

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The accounting profession faces a stark reality-check as entry-level auditor positions have declined by 43% since January, and a third of accountants admit they cannot identify AI-generated fake receipts. 

In episode 455 of The Accounting Podcast, hosts Blake Oliver and David Leary address the growing evidence that AI is disrupting accounting more rapidly than most firms can keep up with. From vanishing entry-level jobs to the rise of “work slop” (low-quality AI output that wastes time and money), the profession is struggling with changes that are both promising and perilous.

The Tech Stack Problem Nobody Wants to Talk About

Before diving into AI’s disruption, Oliver shared a surprising statistic: only 37% of accounting firms require their clients to use their technology stack. That means 63% let clients choose their own tools, creating a mess of incompatible systems and inefficient workflows.

“It’s one of the things we did in my firm that was a differentiator and allowed us to scale quickly,” Oliver explained. “It reduced training time. It increased the speed at which we worked.”

The reluctance to standardize reveals a deeper problem in the profession: firms are so afraid of losing clients that they sacrifice efficiency and scalability. Yet Oliver found the opposite: “The ones that were willing to make that shift ended up listening to us about other things, too. So you might want to consider requiring clients to switch as, like a testing mechanism to see if they’re actually going to be a good fit.”

This standardization challenge becomes even more critical as firms try to implement AI. Without consistent data inputs and workflows, automation becomes nearly impossible.

The Vanishing Entry Level: A 43% Wake-Up Call

The most alarming news Oliver shared was the 43% drop in entry-level auditor job postings since January, based on a study of 126 million job postings. Meanwhile, senior positions requiring ten or more years of experience increased by 6%.

“These firms are extremely shortsighted,” Oliver argued. “They are just trying to juice profits and revenue in the short term. And the easiest way to do that is to replace your entry-level people with AI.”

The vulnerability of these positions is clear. As Oliver explained, “The stuff an entry level auditor does is so basic, like cash confirmations. You can have an AI agent doing cash confirmations all day long. It’s not complicated.”

The fear extends beyond auditing. Nearly half (45%) of accounts payable professionals now fear layoffs in 2025, up from 27% last year. These workers see AI agents matching invoices, approving bills, and processing expense reports—tasks that once required human oversight.

Leary raised an important question: Are firms actually succeeding with AI, or are they cutting staff first and hoping to automate later? In Oliver’s view, the automation is working well enough to justify the cuts. But this creates a long-term problem. Without entry-level positions to train tomorrow’s senior accountants, where will future leaders come from?

Work Slop: The $200 Hidden Cost of Bad AI

A new Harvard Business Review study coined a term for low-quality AI output: “work slop.” And work slop is expensive. Each incident wastes nearly two hours and costs about $186 per worker per month.

Forty percent of workers report receiving work slop in the past month. More than half feel annoyed when they get it, and 42% view the senders as less trustworthy.

“Every time one coworker gives another coworker slop, it costs your company 200 bucks,” Leary emphasized. But, “Employees who turn out work slop probably already did work slop before. They just did it at a much slower volume.”

The hosts shared their own experiences with work slop. Job applicants submit unedited ChatGPT responses. Guest pitches reference the wrong podcast. Some candidates even feed interview questions into AI during live video calls.

“It looks good,” Oliver said about typical work slop. “Like if you look at the email, it’s nicely formatted and it looks good and then you actually read it and you realize that it’s garbage.”

The paradox is striking: 97% of firms admit they’re not using technology efficiently, yet 86% believe AI-using firms have a competitive advantage. The gap between aspiration and execution means firms produce more low-quality work faster rather than better work more efficiently.

The Fraud Detection Crisis

Perhaps most concerning is accountants’ declining ability to spot fraud. Thirty-two percent admit they can’t recognize AI-generated fake receipts. Another 30% are seeing more fraudulent receipts than last year, and 42% suspect colleagues have submitted fake or altered receipts.

“If you want to see just how difficult it is or how easy it is to make one, just go and ask ChatGPT to make you a receipt,” Oliver challenged listeners.

Leary noted that expense fraud isn’t new. After all, people used to pick a receipt up off the ground at McDonald’s. But AI changed the game. Now anyone can generate perfect forgeries on demand.

Oliver explained that current AI models don’t understand physics, so shadows and lighting in fake images often don’t match reality. But detecting these requires expertise most accountants don’t have.

“When nothing is physical anymore, how do you, as an auditor or an accountant, rely on a scanned document?” Oliver asked, highlighting a fundamental challenge for the profession.

Solutions Emerging from the Chaos

Despite the challenges, practical solutions are emerging. Zapier announced a “human in the loop” feature that pauses automated workflows for human review at critical points. “Don’t try to automate the whole workflow,” Oliver advised. “Try to automate one task in the workflow.”

Keeper launched a new AI product that converts payroll reports and settlement statements into journal entries—a task that previously required complex spreadsheets and manual work. At $50 per client per month, it represents the kind of targeted automation that actually works.

Even Drake Software, long criticized for being behind the times, launched cloud-based tax software. While limited to certain forms, it signals that even legacy providers recognize the need to modernize.

These tools show that successful AI implementation isn’t replacing humans entirely. Instead, it augments specific tasks while maintaining human oversight for quality and judgment.

Looking Ahead: A Profession at a Crossroads

The accounting profession faces interconnected challenges that require more than technological solutions. The 43% drop in entry-level positions poses a threat to the talent pipeline. Work slop erodes trust and efficiency. Fraud detection capabilities are falling behind those of fraudsters.

Yet there are opportunities within these challenges. Firms that thoughtfully integrate AI, maintain human oversight, and invest in training the next generation will have an advantage over those who chase short-term profits by cutting entry-level positions and blindly implementing AI.

As Oliver noted about his own firm’s success, standardizing technology, requiring client buy-in, and focusing on quality over quantity created real competitive advantages. The same principles apply to AI adoption. Success requires strategy, not just software.

To hear Oliver and Leary’s complete analysis of these shifts in accounting, including their discussion of H-1B visa changes, Trump’s latest tariff threats, and more practical insights for navigating AI’s impact, listen to the full episode of The Accounting Podcast. Their unfiltered weekly discussions provide essential perspective for anyone trying to understand where the profession is heading and how to thrive despite the uncertainty.

Stop Pricing the Deliverable and Start Pricing the Relationship

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Marie Greene once spent more than 20 hours on a client she was charging just $12. But she only realized how little she was charging for her time when her firm started tracking time. While extreme, Greene’s story highlights a problem that plagues accounting firms everywhere: chronic underpricing that leaves practitioners exhausted and struggling to grow.

In this episode of the Earmark Podcast, recorded live in Los Angeles during the Advisory Amplified tour, host Blake Oliver explores the pricing puzzle with Greene, a CPA and founder and CEO of Connected Accounting, and Ryan Embree, Director of Partnerships at Ignition. Together, they tackle one of the profession’s toughest challenges: how to charge what you’re worth without losing clients.

The Time-Tracking Wake-Up Call

Greene’s journey to better pricing started with tears of frustration. “I literally cried, but I didn’t know it was so bad. My pricing was so bad until we started tracking time,” she admits. Even though Connected Accounting had always used fixed fees instead of hourly billing, they had no real grasp on whether their pricing made sense.

The problem got worse when Greene hired her first team member. She’d been pricing based on how quickly she could complete tasks, not realizing she was “super mega efficient” compared to most people. “When it takes someone a normal amount of time, I was destroying my budgets and I couldn’t delegate fast enough. And then I was just buried in work,” she explains.

This pattern isn’t unique to Greene’s firm. Embree sees it repeated across hundreds of firms he works with at Ignition. The problem often hides in compliance services, where firms fall into the trap of charging “the same as last year.”

“If you quoted someone X amount of dollars seven years ago and they’re still paying that fee, that is the biggest opportunity,” Embree points out. Many firms hesitated to raise prices during COVID when clients were struggling. But as Embree notes, “price increases are normal. They’re a part of business.”

Eventually, Greene’s managers staged an intervention. They took over pricing and told her to stop selling certain services at unsustainable rates. Six years later, the firm has a much more realistic pricing model. But it all started with that uncomfortable first step of tracking where time actually goes.

Pricing the Whole Relationship, Not Just the Deliverable

The real breakthrough came when Greene realized she was charging two clients the same amount for identical services, but one required far more time and attention than the other.

“You can’t just price the deliverable, which is a P&L at the end of each month,” Greene discovered. “You have to also price the number of touchpoints. You have to price how often they have ad hoc random questions that are not part of the scope.”

Connected Accounting now looks at multiple factors when setting prices:

  • Number of bank accounts (17 credit cards vs. one checking account makes a difference)
  • Transaction volume (one account with 1,000 transactions can be more work than multiple quiet accounts)
  • Number of bills and invoices processed monthly
  • Meeting frequency (weekly touchpoints vs. monthly check-ins)
  • Communication style and expectations

This approach also creates natural price escalators. “We’ve always been very clear up front that we grow with you,” Greene explains. “As you add employees, as you add bank accounts, as your transaction volume increases, our fees increase.”

Embree adds that this reframing helps clients understand price changes. “They know they’re growing. They know they’ve exceeded scope. So they know they’re just kind of leveling up to a new level of service.”

Beyond pricing existing services correctly, firms often miss revenue by not telling clients about everything they offer. Greene discovered this after creating a comprehensive list of which clients used which services. “I was like, oh, we only have six accrual clients, or we only have three that use X.”

This led to casual conversations during client meetings. “We’d say, hey, by the way, we notice you do this. Who does your payroll?” Greene recalls. “We’re not saying we sell payroll and you should buy it, but it was just planting a seed.” Often, clients would respond enthusiastically, not even knowing Connected Accounting offered that service.

Having the Conversation: A Live Repricing Role-Play

During the discussion, Greene demonstrated her approach to repricing conversations in a role-play with Embree acting as the client. She showed how her strategy turns a potentially awkward discussion into a collaborative planning session.

Greene starts with enthusiasm, not numbers: “Hey, Ryan, how excited are you about next year? What are you looking forward to doing with the business?”

When Embree shares his growth plans, she follows with genuine concern: “And with the growth, what are some of the things that keep you up at night?”

Only after understanding his challenges does she pivot to solutions: “Would you be interested if we can find a way to help you lower some of your costs by not having to hire one more admin, and we can take on some of the grunt work?”

The conversation naturally flows into discussing additional services like benefits renewal and talent retention strategies—services Embree’s character didn’t even know Connected Accounting offered.

After these discovery conversations, Greene presents three-tier proposals. “I was no longer trying to force a single price. I showed three and then they could choose. And that was the relief,” she explains. This approach gives clients control while removing the pressure of “selling” a single option.

Despite common fears, clients rarely leave over price increases. Embree observes, “A lot of firms that want to cut clients think raising fees is the way to go. And the short answer is no, they actually still stick around.”

In fact, the worst clients often prove surprisingly price-insensitive. “Whatever the fee is, you can’t actually price them out,” Embree notes.

Technology makes these conversations easier. Connected Accounting now automates annual increases using opt-out language in engagement letters. “Every year in December, we send a notice saying, hey, you have 30 days to cancel your services. But just so you know, effective January 1, all pricing across the firm is going up 3%,” Greene explains.

This mirrors how services like Amazon Prime handle increases: making them expected rather than exceptional. As Oliver points out, “That fee just goes up every year. And we get the email and we look at it and we accept it.”

Your Pricing Transformation Starts Now

Greene’s journey from charging $12 for 20-plus hours of work to running a profitable firm with systematic pricing shows that transformation is possible, even if it takes time. The lessons are: track your time to understand true costs, price the entire client relationship rather than just deliverables, and reframe price discussions around growth and value.

The fear of losing clients to price increases is largely unfounded. When one client left Connected Accounting for a competitor offering a deal, they returned after 12 months and started paying the competitor’s higher rate, which Greene then maintained. “The market often values accounting expertise far more than practitioners themselves realize,” she discovered.

Greene admits she still gets nervous before pricing calls. But she’s learned that authenticity matters more than perfection. “They see how excited I get. They know I’m a huge nerd, I love technology, I love accounting,” she says. “Eventually, they’re like, okay, cool. She sounds like fun to work with.”

Embree emphasizes that positioning yourself as an expert dramatically increases what clients will pay. “People’s willingness to pay is infinite for that piece of mind,” he notes. “To know that you have an expert in your corner that has done this with other clients and knows everything about you and your business.”

The profession’s chronic underpricing doesn’t just hurt firm owners; it limits the entire industry’s ability to innovate and serve clients well. When accounting professionals charge appropriately, they can invest in better tools, training, and talent.

Ready to stop leaving money on the table? Start by tracking where your time really goes. Then look at your client list and identify who’s grown beyond their current service tier. Finally, practice having value-focused conversations that celebrate client success rather than apologizing for price increases.

The full episode includes the complete repricing role-play, detailed pricing metrics, and specific strategies you can implement this week. Because as Greene’s story proves, the biggest barrier to profitable pricing isn’t your clients’ willingness to pay. It’s your own reluctance to ask.

The Real Cost of Being Everyone’s Favorite Boss

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Madeline Reeves thought she’d hit rock bottom when she found herself face-down in a parking lot. She was wrong. That was before her million-dollar agency lost half its revenue in 30 days while she scrambled to save a monthly payroll costing anywhere from $88,000 to $102,000.

Meanwhile, Lynnette Oss Connell had engineered what she calls “a life of overfunctioning”—using technology and systems to layer on more and more responsibility instead of freeing up her time. When Oss Connell told her assistant she planned to add overnight Thursday shifts to handle overflow work, she expected pushback. Instead, her assistant asked how she could support the plan. That’s when Oss Connell realized, “Nobody’s coming to rescue me.”

In this episode of the Earmark Podcast, recorded at the Advisory Amplified Tour in Seattle, host Blake Oliver sits down with these two leaders who rebuilt their careers after burnout. Reeves, founder of Fearless Foundry and host of the Finding Fearless podcast, and Oss Connell, a CPA turned burnout prevention coach and founder of Burnout Bestie, share raw stories about what happens when professional success comes at the cost of personal destruction.

The Accounting Burnout Trap

The accounting profession doesn’t just attract service-oriented people. It rewards behaviors that lead to burnout. During one marketing event Reeves attended, personality testing matched attendees with unique drinks based on their personality types. The result? Out of 100 accountants, 97 received the same drink.

“This profession attracts a certain type of person,” Reeves observed. “For most accountants, their primary love language is acts of service. You live to serve. And that’s why I love accounting professionals.”

But that service mentality became destructive during the pandemic. Reeves led two firm communities during that period—one for female firm founders and another for advisory firms. For two years, she held space for leaders to “just cry privately together on Zoom because they were holding it together for their families and their staff.”

These professionals delayed their own compensation to maintain cash flow. They were filing PPP loans, figuring out EIDL requirements, and watching clients’ businesses collapse, all while absorbing the emotional and financial aftershocks.

“We went back to conferences and nobody was talking about what happened,” Reeves noted. “Doing that work for your clients was incredible, but it has a real impact on people.”

When Rock Bottom Has a Basement

Both Reeves and Oss Connell discovered that what feels like rock bottom often isn’t. “We all think we know what the burnout bottom feels like,” Reeves explained. “And then you’re like, oh wait, it can go even deeper.”

For Oss Connell, 15 years of building and rebuilding her CAS practice meant multiple burnout cycles. She had all the right support systems: a nanny, her mother as backup for her children, workflow software, and backup systems for clients.

“I had all the things you’re supposed to have,” she reflected. “But I didn’t put solutions in place that freed me up. I put solutions in place so that I could just layer more on.”

Her rainbow-blocked calendar, once a source of pride, actually represented something darker. “I was where the buck stopped and started, both at work and at home,” she explained. Even though work sometimes felt like a respite from personal stress, she wasn’t setting any real boundaries.

Reeves’s journey from that parking lot to losing half her revenue revealed similar patterns. As a service-oriented leader who loved building teams and culture, she initially got energy from mentoring her growing team. But soon she was coaching 12 employees while simultaneously mentoring all their clients, with two young children at home, a new marriage, and a recent move during the pandemic.

When four major clients, each worth over $100,000, canceled within 30 days through no fault of her team’s work, she scrambled to save everyone. She closed a $100,000 funding round in 30 days to save payroll. “That money was gone within a couple of months,” she admitted. “I was in the red for anyone who’s doing that math.”

The Three Warning Signs You Can’t Ignore

According to Oss Connell, burnout shows up in three distinct ways that serve as critical warnings.

First is emotional exhaustion. This can manifest in various ways, as seen with accountants, teachers, and healthcare workers during the pandemic.

Second is cynicism. It’s “that feeling of being jaded, the feeling that something you love doing, you now no longer find joy in. That is a big red flag,” Oss Connell says.

Third is a lack of accomplishment. You feel like “you’re on a hamster wheel, and no matter what you’re doing, you’re not getting ahead,” Oss Connell explains.

“Burnout isn’t the end of something,” she emphasizes. “It’s an indicator that you need to adjust something to be your most successful self.”

But recognizing these symptoms intellectually is different from acknowledging them emotionally. Both Reeves and Oss Connell waited for someone else to give them permission to stop.

“I was very conditioned, as I think most women are, to be a people pleaser,” Reeves admitted. She lived off the feedback of being told she did a good job, taking on clients from very large accounting firms despite values misalignment, because they represented good money and validation.

Oss Connell’s breaking point came when nobody challenged her plan to work overnight. “I desperately wanted somebody to intervene and say, ‘Hey, you’re doing too much.’ And nobody did.”

Rebuilding on Your Own Terms

Recovery required dismantling old structures and rebuilding with new boundaries. For Reeves, the first step was radical. “I stopped trying to be so likable.”

She audited every client in the firm’s history, dividing them into two categories: “love them or hate them.” Using this data, she analyzed patterns across services, timelines, and engagement types. This informed a complete overhaul of their service offerings.

“We redid our brand strategy, which clarified our ideal client. And that quickly kicked some people off the menu,” she explained. They productized all services, implemented annual repricing, and built documented processes so no single person was “the glue.”

“If I went on vacation for a week or two, people need to know how to onboard clients,” Reeves said. “If I’m the only person who can tell you how to do those things, that’s not very scalable.”

The firm now operates by a simple mantra: “Life is too short to work with people and projects you hate, so don’t do it.”

For Oss Connell, the solution involved honest conversations with her husband about their different visions for their co-owned firm. He wanted to grow and scale; she wanted to keep it lifestyle-oriented and small. They ultimately decided to sell the firm so neither had to compromise their vision.

These changes weren’t overnight. “It took us well over a year or two,” Reeves said, “but we stacked them one on top of the other and they unlocked.”

Community as Life Support

Strategic changes created the framework, but emotional support proved equally critical. Reeves and Oss Connell emphasize that isolation accelerates burnout.

“We need to have smaller spaces where we can talk candidly about what we’re going through,” Reeves said. This means being vulnerable—not in a performative way, but simply admitting “this is a part that I’m still working on” or “this part I haven’t figured out yet.”

The challenge is that many professional communities create pressure to present a polished image. “We’re all like A-plus students around here,” Reeves observed. “That pressure to show up and just show your shiny, polished ‘I have it figured out’ self is really high.”

But community requires effort to find. “Nobody’s going to come and be like, join our community, you really need this,” Reeves emphasized. “A lot of people who are like, ‘Well, I’m all alone.’ And I’m like, but are you seeking it?”

For Oss Connell, losing her entire support system during divorce while building her firm was devastating. “When I was struggling with my personal life and my firm, I had no support system, and I did not go out and search for it. That is probably the number one problem when I look back.”

Being in a community helps clarify identity. “I can see other people have these skills, and then I begin to see who I am better because I see who you are,” Oss Connell explained.

This extends to leadership transparency. Reeves now openly expresses stress to her team, clarifying, “This is not about you, this is just me getting it out of my body.” She’s learned to show anger or disappointment directly rather than always being the “nice boss.”

Oliver confirmed this approach works. “I talk to my employees when I feel stressed out, and it’s okay. You don’t have to be the perfect boss who has it all figured out. They really appreciate it when I’m honest.”

Breaking the Cycle for Good

The path forward requires accepting that sustainable success doesn’t require self-destruction. As Oss Connell frames it, burnout is an indication that you need to change something,” and that adjustment is ongoing. “As life moves on, your firm evolves. Society evolves. Your clients evolve. You’re going to need to continually recalibrate.”

The accounting profession faces a choice: continue celebrating martyrdom or recognize that sustainable success requires energized, not exhausted, practitioners. The pandemic showed us the incredible resilience of accounting professionals and the devastating personal cost of that resilience.

“When we set good examples of reducing stress for the organization, we equip our employees to be more sustainable as well,” Oss Connell noted. It’s about creating firms where everyone can thrive.

Listen to this episode to hear the full stories from Reeves and Oss Connell. Whether you’re experiencing warning signs or rebuilding from your own rock bottom, the conversation provides validation that you’re not alone and strategies for creating a practice that doesn’t require your destruction to achieve success.

Why Most Accounting AI Will Hit an Auditability Wall

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

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

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

The Auditability Problem That’s Breaking Accounting AI

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

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

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

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

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

FloQast Transform: Building AI Auditors Can Actually Trust

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

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

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

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

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

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

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

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

The Future of Accounting: Cyborgs, Not Replacements

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

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

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

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

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

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

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

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

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

Regulatory Changes on the Horizon

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

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

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

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

The Path Forward: Auditability as Competitive Advantage

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

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

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

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