The Soundtrack of Stagnation

The fluorescent lights in Conference Room B always hum at a low C sharp, vibrating somewhere deep in the temples until the sound becomes an ache. It’s a sensory scene I know too well, and it was the soundtrack for the third time this quarter that we tried to discuss the Great Accounting Software Upgrade of 2025.

We had the proposal, detailed line by line, demonstrating a projected efficiency gain of 235 working hours annually. We had the consultant who promised painless migration. We had everything, except the required signature from Beatrice. Beatrice, who has been here for 45 years. Beatrice, who installed the current system herself using five floppy disks back when dinosaurs roamed the data center.

She leaned back, her face a mask of tired patience, and dismissed the entire six-month project with three words: “That won’t work.” Not “That’s too expensive.” Not “We lack the manpower.” But the ultimate organizational shut-down: *That won’t work.* When pressed on why, specifically, it wouldn’t work, her explanation was a fog bank of procedural necessity and tacit institutional knowledge. “The way we handle accruals-you need this specific nested report structure. No modern system understands it. We tried this in 2015.”

The Expert Beginner Paradox

And that’s the moment you realize you aren’t fighting technical debt; you are fighting organizational debt that has ossified into organizational sovereignty. We talk about competitors, market disruption, and black swans, but the most dangerous person in your company is almost always someone who believes they have earned the right to stop learning.

They are the Expert Beginner. They know just enough about the legacy architecture-because they built it-to identify exactly how any proposed change *might* fail, but they lack the modern perspective to understand how that change *must* succeed.

The veto power of the Expert Beginner is rarely malicious; it is almost always self-preservation disguised as corporate guardianship. Their entire value proposition relies on the complexity of the current, inefficient system. If the system becomes intuitive, integrated, and simple-if, say, a modern platform like OneBusiness ERP can automate those ‘unique’ accrual reports-their unique knowledge base, the thing that secures their employment and status, dissolves.

It’s a peculiar kind of entrapment. We unintentionally reward tenure by creating information silos. These silos aren’t designed to protect secrets; they’re designed to preserve inefficiency. Because inefficiency ensures only one person can navigate the maze.

Organizational Aikido

I often think about Oscar J.-M., a friend of mine, who teaches complex modular origami. He spends his weeks demonstrating how to fold a single sheet of paper into incredible, interlocking structures that look structurally impossible. He once told me that the difference between an amateur mistake and an expert mistake is that the expert’s error is always based on historical success. The amateur messes up a fold; the expert insists on using a paper stock that worked great in 1985 but tears immediately with modern glues and complexity. Oscar constantly has to unlearn the precise tolerances he mastered 20 years ago.

Beatrice, and those like her, are operating on 45 years of historically successful tolerances. They see the new system not as a pathway to 235 hours of efficiency, but as the erasure of their hard-won mastery.

The real failure isn’t that Beatrice resists; the failure is that we designed a corporate structure that allows 45 years of accumulated, uncataloged expertise to become a single, catastrophic point of failure. If Beatrice retires tomorrow-or, God forbid, is hit by a meteor-$575 million in annual revenue sits unsecured on tribal knowledge. The problem isn’t her attachment to the system; the problem is our reliance on her attachment.

This system, the one she defends so fiercely, the one she knows intimately, is costing us more than $5,000 in monthly maintenance fees. It’s costing us momentum.

Rewarding Extraction, Not Hoarding

I’ve heard the argument that we must respect the institutional knowledge, and I do. But respect doesn’t mean granting a permanent veto. Respect means documenting, extracting, and formalizing that knowledge so it can live outside of a single individual’s head. This requires a shift in leadership focus: rewarding documentation, rewarding teaching, and rewarding the successful sunsetting of legacy tasks.

We need to treat organizational debt like the financial debt it mirrors. The longer we carry it, the higher the interest rate (measured in stagnation and lost opportunities). That original configuration that Beatrice designed 45 years ago was brilliant for its time, truly. But a brilliant configuration from 1985 is a dangerous liability in 2025.

It’s like designing an ornate, complex bridge structure and then refusing to update the structural integrity reports because the original engineer is still alive and says, “It hasn’t fallen yet.”

The Question That Corrodes

We need to change the conversation from *”How do we get Beatrice to adopt the new system?”* to *”How do we restructure our information flow so that no single employee, no matter how valuable, possesses the unilateral power to halt critical business evolution?”*

This requires recognizing that the veto power is not granted by their job title, but by the sheer volume of undocumented process knowledge they possess. To neutralize the threat, you don’t fire the person; you dissolve the silo.

And that means prioritizing systems built for shared visibility and agility, rather than bespoke customization that simply mimics the inefficient processes of the past. The goal is not just a technology upgrade, but a power transition-from the expert who masters complexity to the organization that masters simplicity.