The Hidden Costs of Technical Debt: Are Your Best People Masking Bad Processes?

Every organization has them. The people who just know how to get things done.

They know which spreadsheet is really the right one. They know the workaround nobody documented. They know which system needs special attention, who to call when something breaks or even how to fix it themselves.

We value these people. We should.

But sometimes their ability to make things work hides a bigger problem.

“It’s Working” Doesn’t Mean It’s Working Well

Give good people an aging system they know, a security gap, an inefficient process or an infrastructure problem and they’ll usually find a way around it.

That’s a great quality in an employee. I want them on that wall. I need them on that wall.

But it’s not necessarily a great operating model for a company.

Because eventually the workaround becomes the process.

• A legacy application can’t be replaced this year, so your people keep it running.
• Two systems don’t communicate well, so somebody manually moves information between them.
• Access rights aren’t quite right, so exceptions accumulate.
• An infrastructure problem keeps recurring, but somebody knows how to fix it.
• A Microsoft 365 environment grows for years, but its security and governance don’t necessarily grow with it.

And everything keeps working.

Sort of.

There Is a Hidden Cost to “Making It Work”

This is the part I think we often miss.

Inefficiency doesn’t always show up on a bill, and we don’t budget for it.

When talented people spend hours reconciling spreadsheets, troubleshooting recurring problems, managing manual processes or compensating for technology that doesn’t work the way it should, that “line item” is hidden. Because it’s hidden, we can ignore it for a time.

But it’s there.

It’s buried in payroll. It’s buried in overtime. It’s buried in slower decisions and delayed projects.

And it’s buried in the opportunity cost of what your best people aren’t doing.

A workaround can look inexpensive because nobody submitted a purchase order for it.

That doesn’t make it free.

As a CIO, I learned to ask a different question.

Not simply: Is it working?

But: Why is it working?

If the answer is because the technology is current, secure, monitored and well managed, great.

If the answer is, “Because Bob knows how to keep it running,” you may have both a business risk and a hidden cost.

Technical Debt Charges Interest

I’ve always liked the term technical debt because the financial analogy works.

Taking on some debt can be perfectly rational. Maybe replacing a system isn’t the priority this year. Maybe there are better places to invest the capital. Maybe the workaround really is the right answer for now.

I’ve made those decisions too.

The problem comes when “for now” becomes five years.

• The aging system requires another workaround.
• The workaround requires another exception.
• The exception creates another security concern.
• Another application gets added.
• More time is spent maintaining all of it.

Eventually, you’re not just paying the original debt.

You’re paying compounding interest on the interest.

Technical debt compounds and compounds again.

And the bill isn’t just the eventual cost of replacing the technology. It’s all the money, time, complexity and risk you accumulated while you waited.

Your Best People Can Hide the Bill

Here’s the irony.

The better your people are, the longer this can continue.

They know the shortcuts. They know what breaks. They know the infrastructure. They know where the security gaps are. They know how to get things done despite the technology.

Leadership sees positive outcomes. Things are working.

What we don’t always see is what it takes behind the scenes to keep them working.

That’s when it’s worth asking your people some very simple questions:

• Where are you spending time working around our technology?
• What keeps breaking?
• What worries you?
• What are we doing manually that we shouldn’t be?
• What have we learned to live with simply because we’ve gotten good at living with it?

You may be surprised by the answers. Your people may be surprised you asked.

Eventually, You Need to Stop Accepting the Interest as a Cost of Delivery

Not every workaround needs a technology project. Not every old system needs to be replaced tomorrow.

Good technology leadership is about knowing the difference.

But there comes a point when maintaining the status quo costs more than fixing it.

• Maybe that’s replacing a key application that is well-liked but no longer meeting the organization’s needs.
• Maybe it’s time to modernize aging infrastructure or move more workloads to Azure.
• Maybe it’s tightening identity, access and security across Microsoft 365.
• Maybe it’s addressing cybersecurity gaps that have accumulated over time and may be leaving you exposed.
• Or maybe it’s simply getting an outside view of an environment that has become so familiar that nobody sees the complexity anymore.

These are conversations I’m increasingly having with clients at PSM.

And I don’t think the starting point should be, “What technology should we buy?”

The better questions are:

• Where are we carrying unnecessary risk?
• Where are we spending money we can’t see?
• And where are our best people compensating for technology that should be working harder for them?

Your best people should be creating value for the business. They shouldn’t be paying the interest on your technical debt.

What Is Your Technical Debt Really Costing You?

When workarounds become part of everyday operations, it can be difficult to see how much time, money and risk they have created.

PSM Partners can provide an outside perspective on your technology environment, helping you identify recurring inefficiencies, aging infrastructure, security gaps and opportunities for modernization. Together, we can prioritize what needs attention now and build a practical roadmap for what comes next.

Start a conversation with PSM Partners to uncover where your people may be compensating for technology that should be working harder for them.

Thanks for reading,
Dave