Podcasts

The Remote Team Retreat Strategy That Beats Software Upgrades Every Time

Earmark Team · August 6, 2025 ·

Most CPA firm owners spend their improvement season updating software or tweaking processes. Rachel and Marcus Dillon are doing something different. They’re taking their entire 26-person remote team to Mexico for four days of relationship-building, goal-checking, and some serious fun in the sun.

The husband-and-wife team behind Dillon Business Advisors just shared their complete retreat strategy on their latest “Who’s Really the Boss?” podcast episode. Their approach reveals how treating team culture as business infrastructure—not just a nice-to-have—creates competitive advantages no software upgrade can match.

From Monthly Breakfasts to International Retreats

The Dillons didn’t always plan elaborate team getaways. When everyone worked in the same office, they kept things simple: bringing in lunch, organizing breakfast meetings, or grabbing dinner together. Even after going remote with a local team, monthly breakfast meetups worked well.

But as their team spread nationwide, those frequent touchpoints became impossible. Instead of giving up on team building, they made a strategic shift that many firm owners would never consider: two high-impact retreats per year.

The economics work better than you’d expect. Their domestic beach trip to Destin, Florida, last year cost significantly more than this year’s all-inclusive Mexico resort.

“The international all-inclusive option is actually a little more budget-friendly,” Marcus explains. Plus, team members won’t face surprise expenses for drinks and meals like they did in Florida.

This shift is about more than cost savings; it’s about recognizing that relationship building requires concentrated investment to generate meaningful returns.

Using Data to Build Better Relationships

The Dillons don’t plan retreats based on gut feelings. They treat team dynamics with the same analytical rigor they apply to financial planning.

Before finalizing their Mexico agenda, they surveyed their leadership team using Patrick Lencioni’s “Five Dysfunctions of a Team” assessment. The results revealed something important about high-performing teams: excellence in some areas can make weaker spots stand out more clearly.

Their team scored well across all five dysfunction categories—absence of trust, fear of conflict, lack of commitment, avoidance of accountability, and inattention to results. However, the assessment identified their two lowest-scoring areas: conflict avoidance and peer accountability. These weren’t crisis-level problems, just the next areas for improvement.

“When you refine something and it becomes really good, then the next friction point stands out just a little more because now the other areas are running so smoothly,” Rachel explains.

The assessment also came with ready-made solutions. “One really cool thing with that assessment, when it came back, they actually sent activities to try to help build the areas of weakness,” Rachel says. “We did not have to go out and search. We didn’t have to call our friend, ChatGPT, to help us come up with ideas.”

This systematic approach beats generic team building every time. But it requires a crucial commitment: following through on what you learn.

“The worst thing you can do is survey somebody or ask somebody their opinion and not do anything with it,” Marcus emphasizes.

The Mexico Agenda: Four Hours That Shape Six Months

The Dillons arrived in Isla Mujeres on a Thursday, then dedicated Friday morning to formal meetings. The rest of the trip focuses on culture, relationships, and fun. Still, those four hours of structured time drove real business improvements.

They started with celebrations and goal reviews. Marcus shared revenue numbers, client acquisition progress, and team updates. “We share revenue. We share where we’re at on track as far as the goals we’ve set,” he explains.

This transparency creates collective ownership of business outcomes. When team members understand exactly how their work contributes to the firm’s success, they make different decisions about client service and efficiency.

Next came “Turning Conflict into Connections,” their targeted response to the assessment results. Instead of hoping team members will naturally become more assertive, they created explicit permission for difficult conversations.

“Team meetings aren’t only for the leadership team to talk,” Rachel explains.

Angel, their director of technology, covered cell phone security protocols. Then they tackled something that could transform their client service: categorizing clients based on team experience rather than leadership assumptions.

“There are simple clients and complex clients, but there are also good complex clients,” Rachel says. The hypothesis: responsiveness matters more than technical complexity. “The complex clients who are responsive, who implement the advice and the strategies we give them, they’re not as hard to manage.”

They wrapped up with peer accountability training, moving beyond traditional top-down management to distribute leadership responsibility across the entire team.

Beyond the Meeting Room

The non-meeting activities included relationship-building exercises that translate into better workplace collaboration: water activities with paddleboarding and snorkeling, Mexican bingo (Loteria), and a team dinner where Marcus recognized each team member in front of their spouse or guest.

“It’s nice for families and friends to see the impact you have for all of the hours you spend away from them working,” Rachel says.

The trip concluded with karaoke, something they missed at their last retreat when the karaoke spot was too far from the hotel. This time, they brought karaoke to the team.

The Numbers Game

Taking 26 people across international borders, coordinating planes and boats to reach an island resort, and budgeting tens of thousands of dollars is a big investment, and it sends a clear message about how the Dillons value their team.

But the real return shows up in compound effects: reduced turnover, faster problem resolution, better client satisfaction, and the competitive advantage of having a team that genuinely enjoys working together.

While competitors debate software features or chase marketing trends, the Dillons are building human infrastructure that’s much harder to replicate. You can’t download better team communication or purchase improved conflict resolution skills.

Your Next Move

The Dillons prove that systematic investment in team relationships creates business advantages that technology alone cannot provide. Their transparent approach offers a roadmap for any firm owner ready to treat culture as seriously as revenue. The question isn’t whether you can afford to invest in team relationships; it’s whether you can afford not to.

Ready to hear their complete strategy? Listen to the full episode for their detailed retreat agenda, specific dysfunction-busting activities, and the real numbers behind their cultural investment approach. You’ll discover how they handle team transitions, their client categorization exercise, and why peer accountability might be the missing piece in your team dynamics.

Rachel and Marcus Dillon, CPA, own a Texas-based, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 15 professionals. Their latest organization, Collective by DBA, supports and guides accounting firm owners and leaders with firm resources, education, and operational strategy through community, groups, and one-on-one advisory.

June 2025 QuickBooks Updates: Inventory, Square Integration, and What’s Coming

Earmark Team · August 6, 2025 ·

Picture this: You’re an accounting professional starting your Tuesday morning routine, coffee in hand, ready to tackle your client’s monthly reconciliation. But when you log into QuickBooks Online, something’s different. The familiar black navigation bar that’s guided your workflows for years has vanished, replaced by sleek gray buttons and flyout menus. Your muscle memory falters for a moment as you hover over unfamiliar icons, wondering if this change will derail your carefully orchestrated productivity schedule.

This scenario is the reality facing thousands of accounting professionals as QuickBooks Online undergoes its most significant transformation in years. In this episode of The Unofficial QuickBooks Accountants Podcast, host Alicia Katz Pollock and guest host Matthew “Spot” Fulton from Parkway Business Solutions broke down the latest “Now You Know” updates, revealing what’s new and why these changes matter for the future of accounting technology.

The Big News: Inventory Module Goes Standalone

The most significant announcement buried deep in a Firm of the Future article is a complete restructuring of how QuickBooks Online offers inventory features. After years of forcing users into QuickBooks Plus for inventory capabilities, Intuit is finally separating the inventory module into a standalone $40-per-month add-on.

“Until now, if you wanted inventory, you would subscribe to Plus,” Katz Pollock explains. “But they had users who were using Simple Start or Essentials, where they have their inventory in other places. They don’t need everything in Plus, but they do need QuickBooks inventory.”

This change eliminates a long-standing barrier for businesses running Simple Start ($30/month) or Essentials ($65/month) who needed inventory capabilities but couldn’t justify the cost of jumping to Plus. Instead of making that expensive leap, they can add inventory functionality for $40 monthly.

The thinking behind this move connects to QuickBooks’ broader Commerce Center strategy. “They’re doing this because of the commerce tools they’re building out,” Katz Pollock notes. “They have the Commerce Center, which is designed to be a one-stop shop, your single point of truth for integrations with shopping carts like Shopify, or your own website, or eBay or Etsy.”

But there’s a catch. Intuit is also wrapping the shipping label feature into the inventory module, sunsetting it as a standalone option. This means if you currently use shipping labels without inventory, you’ll need to either upgrade to Plus or add the inventory module to maintain that functionality.

The shipping integration actually works quite well, according to Katz Pollock’s testing. “The shipping module adds tracking right inside the invoice,” she explains. “You have those fields for the shipping address and then the tracking number. This auto-populates the tracking for you.”

Square Connector Gets a Major Upgrade

While inventory restructuring grabbed headlines, the Square connector improvements might have a more immediate impact on many practices. The previous “Connect to Square” integration had limitations that frustrated accountants and clients.

“The transactions were slow to appear. There was not a lot of transaction detail. The matching was limited,” Katz Pollock summarizes. “The way Square manages its holds and its adjustments, kind of like PayPal, it can be really confusing.”

The new Square connector addresses these pain points systematically:

Faster transaction processing. Sales now appear within hours instead of days, dramatically improving cash flow visibility.
Better transaction detail. You can now see net amounts, fees, tips, and taxes all broken out separately within each payout batch.
Improved matching. The system better recognizes and matches transactions, reducing manual reconciliation work.
Sales tax integration. Perhaps most importantly, the connector now imports and tracks sales tax automatically.

However, the new system imports individual transactions rather than daily batch summaries, which could create challenges for high-volume businesses. Katz Pollock shared concerns about a cornfield maze client who processes hundreds of daily transactions. “This integration right now looks like it’s individual sales. So that would import all hundreds of them every day, which is not going to be ideal for us.”

Intuit acknowledges this limitation, with batch summary imports planned for “version two” of the connector. The new system supports classes and locations, works with all QuickBooks Online versions, and remains free to use.

Interface Revolution: The New Dashboard Arrives

The most visible change coming to QuickBooks Online is the complete interface redesign, and it’s closer than you might think. The new dashboard represents QuickBooks’ most significant user experience transformation in years, but it’s designed to minimize disruption to existing workflows.

“Intuit has done a really good job of not making something so drastically different that we have to start over again,” Katz Pollock observes from her beta testing experience. “All of the windows, all of the transaction screens they’ve already been updating over the last two years. And so once you go into a transaction, there’s literally nothing different.”

The visual transformation is dramatic. The familiar black navigation bar disappears, replaced by a two-level system with light gray buttons and flyout menus. But beneath this aesthetic change, all core functionality remains intact.

Fulton, also beta-testing the interface, emphasizes this continuity: “Nothing’s actually changing behind it. You have pretty little icons on the far left instead of just words. And then those pretty little icons fly out to more menus, and then guess what? It’s exactly the same when you’re in that.”

QuickBooks carefully orchestrated the rollout timeline:

July 1st: Manual opt-in becomes available (with opt-out option)
August 1-30: Automatic enrollment begins (opt-out still available)
September: Mandatory transition (no opt-out option)
September 22nd: Final cutover date

This phased approach gives users multiple opportunities to adapt while providing safety nets for those who need more time. The timing also ensures completion before the next QuickBooks Connect conference, where QuickBooks will likely showcase new features built for the updated interface.

Key improvements in the new interface include:

Enhanced bookmarks. Favorite reports and frequently used screens are now accessible at the main level, eliminating menu navigation for common tasks.
Customizable dashboard. Users can hide or rearrange dashboard components to match their workflow preferences.
Intuitive navigation. The “silo buttons” (accounting, expenses, sales, customers, payroll) are actually easier to understand than the previous system.
Hover menus. Flyout menus respond to cursor hover, eliminating unnecessary clicks.

Supporting the Transition: Training and Resources

Recognizing that interface changes require comprehensive support, training providers are mobilizing resources to help professionals maintain productivity during the transition.

Royalwise is undertaking a massive curriculum overhaul. “Everything I have has to be rerecorded,” Katz Pollock explains, referring to her library of over 50 QuickBooks classes. “So, you’ve got me here for the next 15 years.”

Starting in September, Royalwise will re-teach its entire curriculum in the new interface through bi-weekly sessions. Silver and Gold members get automatic enrollment at no additional cost—a commitment that demonstrates the scale of change management required.

The training approach extends beyond just explaining new buttons and menus. They’re developing a new book series specifically for the new interface, with comprehensive volumes and specialized guides for daily workflows, inventory, project management, and payroll. A practice set with real business scenarios will help users gain hands-on experience. Preorder your copy at https://www.amazon.com/dp/B0FDX859WD

Fulton’s ongoing QB Power Hour sessions with Dan DeLong provide another support pillar. These live streams every other Tuesday (9 AM Pacific, 12 PM Eastern) offer continuing education that adapts to current challenges and allows real-time interaction with experts.

What’s Coming Next: AI Agents and Beyond

July’s “In the Know” session will focus heavily on AI agents—automated assistants designed to handle routine tasks like sending invoices, tracking payments, reconciling books, and managing customer leads.

Intuit is developing four types of AI agents:

Accounting agents to handle routine bookkeeping tasks
Payments agents to manage payment processing and tracking
Customer agents to oversee customer relationship management
Finance agents to provide financial analysis and insights

These agents will integrate with the new dashboard and existing workflows, representing the next phase of QuickBooks’ evolution toward more automated, intelligent accounting processes.

Other developments on the horizon include expanded CRM tools, deeper MailChimp integration, and enhanced mineral HR features for payroll Premium and Elite users. The Mineral HR platform, available since 2019, includes law alert libraries, wage calculators, employee handbook builders, and safety training courses—resources many users don’t realize they already have access to.

The Path Forward

QuickBooks understands the critical balance between innovation and disruption in professional environments. The modular approach to inventory, careful interface preservation, and comprehensive training support show enterprise software evolution can enhance rather than disrupt existing workflows.

For accounting professionals, this blueprint suggests future changes will follow similar patterns: gradual, well-supported, and designed to amplify rather than replace professional expertise. The phased rollout timelines, preserved functionality, and extensive educational resources show a commitment to maintaining productivity during technological transformation.

As these changes roll out over the coming months, they’ll provide valuable insights into how the accounting profession adapts to technological evolution. The strategies demonstrated here offer a roadmap for future innovations that prioritize professional continuity alongside technological advancement.

Ready to dive deeper into these game-changing updates? Listen to the complete episode of The Unofficial QuickBooks Accountants Podcast where Alicia Katz Pollock and Matthew “Spot” Fulton provide their full analysis of these developments and discuss how these changes will affect your practice and your clients’ businesses.

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!

From Homeless to $20 Billion Deals: An Accountant’s Journey Through Automation

Blake Oliver · August 4, 2025 ·

Fifteen years ago, Devon Coombs was sleeping in his car. Skip ahead, and he’s helping negotiate $20 billion AI deals at Google Cloud. His story isn’t just another rags-to-riches tale—it’s a preview of accounting’s future.

I interviewed Devon on the Earmark Podcast, and what struck me wasn’t his remarkable turnaround. It was his pattern recognition. Devon lived through technology’s destruction of the music industry. Now he’s watching the same forces reshape accounting. The difference? This time, he’s riding the wave instead of getting crushed.

The Recording Studio That Technology Killed

At 18, Devon owned Antipop Records in North Hollywood. He’d grown up in foster care. His mother died when he was 15, and he never met his father. But he had talent and a passion for music, so he did what passionate people do: invested everything in professional recording equipment.

Then Logic Pro happened.

“My rates went from $50-100 an hour to competing with guys charging ten bucks,” Devon told me. “Musicians could record in their kitchen and get 90% of my quality.”

The 2007 recession started the bleeding. Technology finished it. Devon’s $100,000 studio became worthless overnight. He ended up homeless, sleeping in his car, trying to figure out what went wrong.

Here’s what he learned: Technology doesn’t destroy industries. It destroys intermediaries. Musicians who could compose, produce, and distribute music thrived with infinite digital instruments at their fingertips. Recording engineers and session musicians who only executed other people’s visions? They became extinct.

The Community College Revelation

While living in his car, Devon started taking business classes at Pierce College, a community college in the San Fernando Valley. He planned to become a music attorney. But accounting grabbed him instead.

“I was surprised by how much I liked doing the work,” he says. The profession also offered something Devon had never experienced: predictable career progression and financial security.

His first internship taught him an unexpected lesson. The CPA who hired him was successful despite being disorganized and barely keeping clients happy. “If this guy could make bank being this scattered,” Devon thought, “imagine what I could do if I actually tried.”

1,000 Cold Calls and One Big Bet

At Deloitte, first-year associates reconcile bank statements. Devon had other plans. He made 1,000 cold calls and emails to controllers across Los Angeles.

His pitch was brilliant in its honesty: “I’m new at Deloitte. I want to learn. Give me your time, and I promise you’ll get more attention from me than from any partner here.”

It worked. He landed GoGuardian as a client—one of the first ASC 606 implementations in the country. The partner told him it would never work. Nobody wins clients as a first-year associate.

Deloitte gave Devon a $100 bonus for bringing in a $100,000 client. That’s when he knew the Big Four model wasn’t for him. When Effectus Group offered to double his salary plus commission, he jumped.

Becoming the 606 Expert

ASC 606 was rolling out, and nobody understood it. The guidance ran thousands of pages. Most accountants waited for CPE courses to explain it.

Devon printed every page.

“I’d read 30 pages every night, then figure out how to apply it,” he explained. In two years, he completed over ten implementations across industries—software companies, call centers, and even nonprofits.

Six months into his new job, he won Automation Anywhere as a client. A multibillion-dollar unicorn choosing a boutique firm over the Big Four. Why? Because Devon knew 606 better than anyone.

“Put in six months of deep work on any technical topic,” he told me, “and you’ll blow everyone else out of the water.”

The AI Orchestrator Revolution

Today, at Google Cloud, Devon helps negotiate billion-dollar AI deals. But here’s what matters: He’s not just selling AI. He’s living the future of professional services.

“Agentic workflows,” he calls them. AI bots handle routine tasks while humans orchestrate the work. “You’ll have bots calling companies, and no one will know they’re bots. All those little tasks in between? Just bots talking to each other.”

It’s the music industry all over again. Technology eliminates executors and elevates orchestrators. The accountants who only know how to follow procedures? They’re the session musicians of the 2010s. The ones who can design systems, manage AI workflows, and apply judgment? They’re the producers.

Devon is now leaving Google for PCG (Principal Consulting Group), where he’ll build a practice around this orchestrator model. His goal: “better quality work with higher judgment applied with all my expertise and one-tenth the cost.”

Your Window Is Closing

Recording studios were given years of warning, but they ignored it. By the time musicians started canceling sessions, the game was over.

Accounting firms today are experiencing the same warning signs: clients questioning fees, staff leaving for tech companies, and AI tools handling basic bookkeeping. The script is playing out again.

But unlike Devon’s recording studio, we can see it coming. We can choose to be orchestrators instead of executors. We can build practices around AI enhancement instead of human grinding.

The transformation isn’t some distant future. Devon’s already building it. He’s creating an entirely new service model where CPAs orchestrate AI agents to deliver superior results at a fraction of traditional costs.

“The AI movement is our chance to add real value,” Devon insists. “But only if we lean in now.”

Listen to the full episode to understand how to position yourself for this shift. Because Devon’s journey proves one thing: Those who embrace disruption don’t just survive. They discover possibilities they never imagined existed.

The question isn’t whether AI will transform accounting. It’s whether you’ll be the orchestrator or become obsolete. Devon made his choice. What’s yours?

Women in Accounting Need Mentors Who See Their Potential Before They Do

Earmark Team · July 30, 2025 ·

“We see in others what we fail to see in ourselves.”

This simple but powerful insight came from a coffee conversation between two accounting colleagues. One was sharing her frustrations about advancing in a male-dominated leadership environment. The other pointed out strengths that were completely invisible to their owner: clear communication, authentic presence, and natural insight.

This conversation sparked a recent episode of the She Counts podcast, where hosts Questian Telka and Nancy McClelland dive into why mentorship is critical for women in accounting.

The Hidden Crisis in Accounting Leadership

The numbers tell a troubling story. Men and women enter the accounting profession at roughly equal rates: about 50/50. But women hold only 19% of partner positions in CPA firms nationwide.

As Nancy points out, some major accounting firms are completely scrapping their diversity, equity, and inclusion programs (while others are doubling down on them). “Think about what the future of leadership in those companies is going to look like,” she says.

The reality is that this leadership gap isn’t about qualifications. When Questian worked at a Big Four firm early in her career, seeing a female chairperson of the board felt “unbelievable,” not because the woman wasn’t qualified, but because such representation was so rare.

Even more troubling are the explicit barriers that still exist. One colleague shared how she was promised a partner position when she joined a firm. After years of working toward that goal, the position went to a male colleague instead. When she had her first child, firm leadership told her she “wouldn’t want to be in a leadership role now anyway, because she was a mom.”

This kind of thinking—illegal as it is—shows the deeper assumptions that still limit women’s advancement.

Civil rights leader Marian Wright Edelman said it best: “You can’t be what you can’t see.” When leadership representation is so skewed, it creates a visibility problem. Women entering the profession may limit their own ambitions simply because they haven’t seen enough examples of women successfully reaching senior leadership roles.

The Science Behind Seeing Potential

The power of mentorship isn’t mysterious; it’s grounded in neuroscience that explains why outside perspective can literally change how we see ourselves.

As women, we’re often taught to fixate on our shortcomings rather than our strengths. “It is so common for us to focus on looking at our negatives,” Questian explains, “that we are often not paying enough attention to what our good traits are, and all of the positives that we bring to the table.”

Nancy admits she struggles with this, too. “If I’m naturally good at something, I don’t really take credit for it. I don’t think there’s anything impressive about this. It just is.”

This is where the science gets fascinating. Mirror neurons make it possible for us to learn something without doing it ourselves. When we watch someone teaching on stage or demonstrating a skill, “the audience can actually learn that thing as if they were doing it themselves,” Nancy explains.

In mentorship relationships, this means we can observe behaviors in our mentors and begin to see those possibilities for ourselves. When Nancy saw women like Claudia Hill speaking at accounting conferences, her immediate reaction was “me too. That’s a thing I’d like to do.”

When we receive positive feedback from someone we trust, our brains release dopamine. This reinforces the behavior that created the praise in the first place. “Getting a positive affirmation from it makes you much more inclined to continue to repeat it,” Questian says.

This creates a positive cycle where confidence builds on itself, leading to more confident behaviors that generate more positive responses.

This science helps explain Questian’s remarkable transformation. She went from someone who “could hardly get on a zoom call” to confidently delivering webinars and speaking at conferences. When Nancy pushed her to take a Theater of Public Speaking class, she wasn’t just suggesting skill-building; she was recommending a way to rewire her brain around public speaking anxiety.

Even today, Nancy provides the outside perspective that catches limiting thoughts before they take hold. When Questian says something like, “I’m going to submit this topic to Intuit Connect, but I’m sure they won’t take it,” Nancy immediately calls it out: “Is that your lizard-brain trying to protect you from rejection?”

Finding Your Mentors

Understanding the science is one thing. Actually building these relationships is another. The good news is that mentorship opportunities exist everywhere… if you know where to look.

But first, you need to get clear about what you actually need. As mentor Gaynor Meilke told Nancy, “How are you going to get to where you want to be if you don’t know what that is?”

Sometimes you need technical guidance. Sometimes confidence building. Sometimes a roadmap for advancement. Sometimes just someone who understands your challenges.

Questian never had a formal mentorship program. Instead, she’s found value in informal relationships with people who share similar values and communication styles.

Conferences are gold mines for mentorship connections. Both hosts trace pivotal moments to conference encounters. LinkedIn, Facebook groups, mastermind communities, and even your current workplace all offer potential mentor relationships.

The step that stops many people is actually asking for help. “You have to ask them,” Questian emphasizes. “What’s the worst they can say? No.”

Questian learned this when she persistently pursued Nancy as a mentor, even after initial hesitation. Sometimes the answer is no. But often, people who seem unreachable are willing to help if you show genuine interest.

Mentorship doesn’t depend on traditional hierarchies either. Nancy’s relationship with Melissa Miller Furgeson shows peer mentorship in action. “I feel so comfortable being able to go to her and say, I have no clue what I’m doing, and she’ll be like, here’s a Loom.”

Questian notes that mentors can even be younger than you. She considers Krista Marina Apardian from Theater of Public Speaking a mentor despite Apardian being younger, recognizing her as “an incredible speaker” with valuable expertise.

Different life phases need different types of mentorship. When Nancy needed encouragement to pursue tax preparation, Theresa Briggs saw potential Nancy couldn’t recognize. She gave Nancy a CCH Master Tax Guide with an inspirational inscription Nancy still treasures.

When Nancy needed business operation skills, Clare Karchmar taught her to “come to me with solutions, not problems.” This lesson fundamentally changed how Nancy approached professional challenges. Karchmar even gave Nancy a name badge that said “Hello, I’m: Shocked” to help break the habit of expressing surprise instead of focusing on solutions.

Recognizing Bad Mentorship

Not all mentorship relationships are helpful. Recognizing warning signs protects you from relationships that could harm your career.

Nancy shares a cautionary tale about approaching a leader for help with overwhelming work challenges. The leader’s solution was to make herbal tea and suggested yoga. “That would not have happened to a man.”

Warning signs include mentors who seem more interested in making themselves look good than developing you; those who take credit for your work; or anyone whose treatment feels patronizing.

Nancy advises, “If something happens that would never happen to a man… this is not your person.”

Being a Mentor Yourself

The mentorship relationship works both ways. Even as Nancy mentors Questian, she continues seeking mentorship for her own challenges.

“I am going to be turning 53 years old in a couple of days, and I am still in need of mentorship,” Nancy says. “We need to both have and be mentors at every stage of our lives.”

This eliminates the pressure to wait until you’re “qualified enough” to help others. Your current struggles and experiences are valuable to someone a few steps behind you in that area of life.

Some women hesitate to mentor because of imposter syndrome. “What do I have to offer?” is a common thought. But as Nancy points out, “Sometimes it’s your mistakes and your failures and your experiences that make you a more valuable mentor.”

When women support each other through mentorship, they create visibility that makes ambition feel achievable for the next generation. This gradually shifts from initially seeing a female leader as “unbelievable” to it eventually feeling normal.

Moving Forward

The accounting profession’s leadership gender gap at least partially stems from the absence of mentors who can see and nurture potential before women recognize it themselves.

As Marianne Williamson reminds us, “When you let your light shine, you unconsciously give others permission to do the same.”

Building mentorship relationships is about creating the visibility and support systems that will help other women recognize and develop their potential, too.

Listen to the full episode and join the conversation on the She Counts Podcast LinkedIn page. The hosts want to know how firms and businesses can build good mentorship cultures and what mentorship experiences have worked for you. Share your thoughts and experiences to help build a stronger community of women supporting women in accounting.

Whether you’re seeking mentorship or stepping up to mentor someone else, remember that these relationships have the power to transform the profession. The accounting industry’s future depends on women supporting women, and that future starts with the mentorship relationships we build today.

When Two Accounting Apps Listen to Their Customers (And Actually Do Something About It)

Earmark Team · July 22, 2025 ·

Picture this: It’s 2021 at ‘Appy Camp, and Ben Stein from Keeper is standing at a bar, drink ticket in hand, ready to exchange it for a well-deserved cocktail after a long day of conference sessions. But when Alicia Katz Pollock rushes past—bass guitar case slung over her shoulder, racing to join the evening’s music circle around the fire—and tosses him her drink ticket with a hurried “Can you get me my drink?”, Ben doesn’t hesitate. He heads to the bar, discovers they’re not accepting drink tickets, and simply buys her a drink anyway.

That spirit of going above and beyond would prove fitting. Three years later, Ben’s company, Keeper, just launched an integration with Anchor that’s making accounting professionals everywhere take notice. When Katz Pollock brought together Stein and Tal Ben Bassat from Anchor for a special episode of The Unofficial QuickBooks Accountants Podcast, the conversation revealed how real software partnerships actually happen.

The story isn’t about corporate strategy meetings or market research. It’s about two companies that actually listened when their customers said, “We want these apps to work together.” And then they did something most software companies don’t: they made it happen…

…like chocolate and peanut butter…better together!

When Customers Become Your Product Team

Here’s what most software companies get wrong: they build features based on internal roadmaps instead of user requests. But when Stein’s team at Keeper and Ben Bassat’s team at Anchor started getting the same message from customers, both companies did something simple. They listened.

“Really, the idea came from our mutual customers,” Ben explains. “This is something that our customers asked for and Anchor’s customers asked for. We have a lot of overlapping customers and we want to keep them happy.”

Ben Bassat’s approach at Anchor takes this customer focus even further. “Everything we do on Anchor comes from our clients. Every feature, every development we have,” he says. “Our product team spends full days speaking to customers about what they need.”

The proof came after they launched. Stein admits it “caught my team off guard” with the response. “We go live with the integration, and all of a sudden, our support team was just inundated with dozens of tickets from Anchor customers and Keeper customers that were super excited about getting this up and running.”

This customer-driven approach creates a simple but powerful advantage: when your users tell you exactly what they need to work more efficiently, you don’t have to guess what to build next.

How the Integration Actually Works

For those not familiar with these tools, here’s what they do.

Anchor handles contracting and billing. Accountants can create proposals with multiple pricing tiers, get electronic signatures, and automatically invoice clients monthly. The invoices sync to QuickBooks Online. Keeper manages your bookkeeping workflows and checklists. It integrates with QBO so you can review transactions, ask client questions, and track your monthly procedures without jumping between systems.

Now here’s where the integration gets useful. When a client receives a proposal in Anchor, they can choose from different service packages and even agree to automatic annual price increases. Once they sign and connect payment information, the integration takes over automatically.

Based on your Anchor settings, the system auto-configures a client in Keeper, applying templates, creating tasks, and setting properties—all without manual work. “Once the client signs the agreement, Anchor will take the upfront payments. So you’re already clear on that. And then your team gets a notification and they start to work on Keeper immediately,” Ben Bassat explains.

This eliminates what Ben Bassat calls the traditional approach: “someone in your back office who starts organizing the onboarding process.” No more Excel spreadsheets tracking tasks. No more manual emails. No more wondering where each client stands in the pipeline.

Future updates will include amendment management. When you add services in Anchor, it will automatically trigger new workflows in Keeper. The integration keeps evolving based on what users really need.

Why Specialized Tools Beat All-in-One Platforms

Both companies made a conscious choice to focus on what they do best rather than trying to build everything. “No one can do everything perfectly. It’s not possible,” Ben Bassat explains.

His philosophy is clear: master your core function, then integrate with others who’ve mastered theirs. “Our approach on Anchor is not to give people a half-baked CRM experience or half-baked project management or practice management experience because it will not be as good. Keeper spent years developing their product.”

Stein agrees, recognizing that building billing software is “enormously complex.” Meanwhile, Keeper has spent years perfecting practice management and client communications that are “so deeply coupled to each other” that splitting them across multiple systems would create problems.

As Katz Pollock puts it, QuickBooks Online is like “a multifunction printer where it can print and it can copy and it can fax, but it doesn’t do any of them really, really well.” That’s why we have an entire ecosystem of specialized apps that excel at their one thing, and then connect to create something more powerful than any single platform.

Building the Integration Right

This wasn’t just two companies slapping together a quick connection. It was Keeper’s first major integration, and both teams approached it with their full attention.

“It surprised me how involved it was,” Stein reflects. “Anchor sort of took the whole process very seriously.” Keeper had to modify their API and release new endpoints specifically to support what Anchor needed.

Ben Bassat’s team matched that commitment. “Our approach is to deliver the best we can.” The development included extensive customer research, with Anchor’s product team speaking directly to Keeper users to understand their expectations.

The mutual respect between companies is evident in how they talk about each other. Stein praises Anchor’s authentic customer approach, while Ben Bassat marvels at Keeper’s user loyalty: “Clients are in love with the company, with the product. It’s something you don’t see a lot.”

When both companies share the same standards for quality, the collaboration works better.

The Bigger Picture

The Keeper-Anchor integration is a model for how accounting technology should evolve. When specialized companies listen to their customers and collaborate instead of competing, they create something more powerful than bloated platforms trying to do everything poorly.

The overwhelming user response—support teams flooded with excited customers wanting immediate access—shows that accountants recognize good tools that work together seamlessly. You don’t need another platform that does everything adequately. You need best-in-class solutions that communicate perfectly.

As these founders envision a future with universal bank APIs and seamless connectivity between all accounting apps, they’re describing an ecosystem where your software works as hard as you do. Where signing a proposal automatically sets up workflows, amendments in one system update tasks in another, and tools anticipate needs instead of creating more work.

When software companies prioritize partnership over competition and specialization over generalization, everyone wins. Your clients get better service. Your team gets better tools. And you get back to what you do best: serving clients instead of wrestling with software.

Want to hear the full conversation? Listen to this episode to discover how customer feedback drove this integration, what’s coming next, and why the future of accounting technology is specialized, connected, and customer-driven.