The Office Obstructionist

The company was not technically broke.

This distinction mattered deeply to the people who were staring at the bank account and wondering how they were going to make payroll.

There was no mountain of debt. Vendors were paid. Subscriptions were current. Employees received their checks. Creditors were not circling the building, partly because there was no building. The entire company worked remotely, which meant even the vultures would have needed a Zoom link.

On paper, this small international coaching company appeared responsible, organized, and remarkably punctual.

In reality, it was quietly bleeding to death.

Revenue had fallen from roughly $3 million in 2024 to about $2 million in 2025. By the time I was brought in during 2026, the company was tracking below $1 million. Leads were down. Sales were down. Cash was tight. Optimism was being rationed.

Eight months earlier, the company had replaced its CEO.

The new CEO was not entirely new to the business. He had previously served as an executive and understood the company’s mission, clients, and general operations. What he had not seen were the daily financial decisions, the operating habits, the internal politics, or the strange little ecosystem that had developed beneath the surface.

He thought he was taking over a troubled company.

He soon discovered he had inherited an archaeological dig.

Every layer revealed another platform, another subscription, another consultant, another approval process, and occasionally what appeared to be a complete duplicate of the layer directly beneath it.

The first question was simple: Where was the money going?

The answer was less simple because the money had gone everywhere.

Using The RYAN Method™, I reviewed the financial statements, recurring expenses, employees, subscriptions, workflows, vendor agreements, and operating systems. This was not a six-month expedition requiring matching polo shirts and a consulting team that referred to everything as a “transformation journey.”

It did not take long to see the problem.

For a small company, they had an astonishing number of tools.

They had HubSpot. They had Notion. They had GoHighLevel. They had Slack. They had GoDaddy, WP Engine, Pantheon, Stripe, QuickBooks Payments, multiple AI products, project-management platforms, scheduling systems, file-storage services, and enough digital infrastructure to suggest they were preparing to launch a moderately sized nation.

Some employees had basic subscriptions. Others had premium accounts. A few had several versions of similar tools. Nobody seemed entirely sure which platform was the official platform, which naturally meant all of them were official until someone needed information.

The company had more than one customer relationship management system, which is generally helpful when your goal is to ensure that no one knows where the customer relationship is being managed.

One department used one system. Another preferred something else. Leadership had its own favorite tools. Marketing had additional platforms. Data lived in several places and occasionally, as far as I could tell, nowhere at all.

The company was not large, but it was spending as though an initial public offering might occur by Friday.

It also had a rare and admirable quality: It paid its bills.

In fact, it paid them too well.

Whenever an annual payment option was available, the company took it. If a vendor offered a discount for paying twelve months in advance, someone apparently reached for the corporate card before reading the second half of the sentence.

Paying annually can be sensible when a company knows it will use the service. It becomes less sensible when the company is experimenting, switching platforms, duplicating systems, or buying software because someone attended a webinar.

This company had prepaid for tools that did not work, tools that were no longer used, and tools that had been replaced by newer tools that were also paid in advance.

Unused software is the office equivalent of exercise equipment in a spare bedroom. It was purchased during a moment of optimism, used briefly, and then ignored while continuing to occupy space and inspire guilt. Trust me, I walk by an Echelon rowing machine many times a day that has become a collector of dust more than a method for me to reduce weight or shed some sweat.

The company had also accumulated a team of virtual assistants.

There was a VA supporting the CEO. A VA supporting the person serving as both chief financial officer and chief operating officer. A VA supporting the outside marketing company. There may have been a VA who needed a VA, although we stopped before confirming it.

These services were purchased in large prepaid blocks of hours.

Again, the reasoning initially sounded responsible. Buying hours in bulk lowered the hourly rate. The problem was that the company often could not use the hours before they expired. Carryover was limited. Work was delayed. Assignments were unclear. Hundreds of prepaid hours sat unused while payroll became a weekly suspense thriller.

The CEO had asked why the company was scraping together cash to pay employees.

Imagine his surprise when we found that a meaningful amount of that cash had already been handed to software companies, service providers, contractors, and virtual assistant firms for work and access the company might never use.

The financial waste was significant, but it was not the most damaging problem.

The deeper issue appeared when we examined how work moved through the company.

We reviewed emails, approvals, project histories, employee responsibilities, and decision-making patterns. We interviewed team members. We watched what happened when someone proposed an idea, requested an expense, needed approval, or simply tried to complete the job for which they had been hired.

Nearly every road led to one person.

The CFO/COO had become the central point of control for the entire business.

She was considered indispensable.

All important decisions ran through her. Financial questions, operational choices, vendor approvals, employee actions, marketing requests, technology decisions, and routine matters all found their way into the same inbox.

This arrangement might have worked if decisions moved quickly and consistently.

They did not.

Approximately 90 percent of the requests reaching her were rejected, revised, redirected, delayed, or returned in a form that bore only a distant resemblance to the original request.

If an employee recommended red, she preferred yellow.

If marketing requested a landing page, she approved a brochure.

If someone found a tool that solved a problem, she insisted on a different tool she already believed in, even if that tool had caused the problem.

She did not merely want visibility into the company’s work. She wanted jurisdiction over it.

Every employee interview contained some version of the same complaint: She would not allow people to do their jobs.

Capable employees had been reduced to order takers, except the orders changed frequently and were often issued after the work had already begun. Managers were responsible for outcomes but lacked authority. Vendors were hired and then prevented from implementing the work they had been hired to perform. Marketing could not market without operational approval. Operations could not operate without financial approval. Finance, unfortunately, was also operations.

The result was a company with plenty of movement and very little progress.

Micromanagement is often defended as attention to detail.

Sometimes it is.

Other times it is anxiety wearing a name badge.

There is an important difference between oversight and obstruction. Oversight makes sure the right work happens. Obstruction makes sure no work happens without the obstructer receiving credit, control, or an opportunity to change it.

This executive had accumulated enough authority that the organization could no longer function without her. She had also designed the organization so that it could barely function with her.

That is not job security.

That is organizational hostage-taking.

The financial contradictions were equally strange. She would challenge small expenses, delay modest purchases, and debate relatively minor charges while approving larger commitments that made little operational sense.

The company would spend hours discussing a small monthly fee and then pay thousands of dollars in advance for a platform that duplicated one it already owned.

This is how companies become penny-wise, pound-foolish, and eventually payroll-nervous.

Then we discovered something that explained much of the behavior.

The CFO/COO had another full-time job.

Because the company was remote, the arrangement had gone largely unnoticed. She was being paid for a full Monday-through-Friday workweek while simultaneously working elsewhere.

The coaching company was not receiving her full attention. It was receiving the time left over after her other job, personal schedule, and competing obligations.

Suddenly, the constant delays made sense.

The bottleneck was not merely controlling. It was unavailable.

She could not delegate because delegation would reduce her control. She could not move faster because she did not have the time. She could not allow others to make decisions because the entire structure depended on the belief that every decision required her involvement.

She had built a sandbox, appointed herself lifeguard, and then spent much of the day at another beach.

This discovery did not make the final recommendation easy.

It made it unavoidable.

The CEO had two choices.

He could keep one powerful employee and continue losing the company, or he could remove the obstruction and give the company a chance to recover.

These decisions are rarely comfortable, particularly when the person involved has institutional knowledge, control of systems, access to finances, and years of history with the organization.

Leaders often mistake dependency for value.

The fact that one employee knows where everything is, approves everything, and controls everything does not necessarily mean that employee is highly valuable. It may mean the company has allowed a serious governance failure to develop.

A healthy company does not require one person’s permission to breathe.

The numbers supported the recommendation. The interviews supported it. The workflow analysis supported it. The conflicts of interest made the decision even clearer.

The employee was terminated.

She returned to her other full-time position, now presumably with the benefit of only having one full-time position.

Then something remarkable happened.

The company began moving again.

Decisions that had been stalled were made. Employees were allowed to perform the work they had been hired to do. Systems were consolidated. Duplicate subscriptions were canceled. Prepaid waste was identified. Responsibilities were clarified. Approval authority was redistributed.

Within thirty days, the company secured two new contracts.

It would be satisfying to say this happened because of a dazzling new sales strategy, a revolutionary marketing funnel, or a proprietary artificial-intelligence platform featuring twelve dashboards and a holographic consultant.

It did not.

The company simply removed the person preventing the company from functioning.

That is the uncomfortable lesson.

Not every struggling business needs more people, more software, more meetings, more consultants, or more ideas.

Some need fewer obstacles.

Business owners are often taught to look for weak performers. They search for employees who miss deadlines, make mistakes, lose customers, or fail to produce.

The office obstructionist is harder to identify because this person often appears extremely busy.

She is copied on every email. Invited to every meeting. Consulted on every purchase. Required for every approval. Her calendar is full, her inbox is overflowing, and everyone is waiting for her.

From a distance, she looks essential.

From inside the company, she is the traffic jam.

The obstructionist does not always refuse to work. Often, she works constantly. The problem is that much of her work consists of reviewing, changing, delaying, correcting, questioning, or reclaiming work that should have been owned by someone else.

She becomes the human tollbooth through which every idea must pass.

Eventually, employees stop proposing ideas. Managers stop making decisions. Vendors stop taking initiative. Good people learn that the safest course is to wait for instructions, document everything, and avoid being blamed.

The business loses speed, creativity, accountability, and morale.

Then leadership wonders why nobody takes ownership.

Nobody takes ownership because ownership has been outlawed.

This case was more dramatic because of the second job, but the broader problem is common. Companies frequently allow one person to accumulate control because it feels efficient at first.

She knows the books.

She understands the systems.

She has been here the longest.

She catches mistakes.

She keeps everyone organized.

Perhaps she does all of those things.

The question is whether she also allows the company to function without her constant intervention.

A valuable leader creates clarity, builds capable people, documents systems, and distributes authority. A dangerous leader collects information, centralizes decisions, withholds access, and ensures that no one else can operate independently.

One makes the organization stronger.

The other makes herself harder to remove.

The coaching company still has work ahead. Two contracts do not erase two years of declining revenue. Canceling subscriptions does not automatically restore a sales pipeline. Improved morale does not appear immediately on the income statement.

But the company now has something it did not have before.

A fair chance.

The money is no longer disappearing into as many redundant systems and prepaid experiments. Employees can act. Leadership can lead. The business can make decisions at something closer to the speed of commerce rather than the speed of one executive’s overloaded inbox.

The CEO originally asked where the cash was going.

The more important discovery was where the company’s momentum had gone.

It had been waiting for approval.

Ryan Gartrell is a business operations consultant, author, and founder of Ryan Gartrell, P.A. He helps companies uncover waste, remove operational bottlenecks, and build systems that allow good people to do their jobs without waiting for permission.