Most organizations don’t wake up one morning and realize their software is holding them back.
The systems still run. The reports still get pulled. The work still gets done.
But over time, something subtle shifts. What once felt supportive begins to feel heavy. Tasks take longer to complete, not because they’re more complex, but because moving through the systems requires more effort, more checking, more mental overhead.
This is the moment when “working” quietly stops meaning “working well.”
The cost isn’t visible on a balance sheet. It shows up elsewhere — in slower decisions, in extra steps no one remembers choosing, in the constant low-grade friction that teams absorb without complaint. It’s a hidden tax, paid not in dollars, but in focus, energy, and momentum.
And it’s important to say this clearly: “good enough” software is not a failure. It’s often the result of success. Systems that once fit perfectly can fall out of alignment simply because the organization outgrew the version of itself they were built for.
This isn’t about broken tools. It’s about software that stopped evolving while the business kept moving.
Capable teams are remarkably good at adapting.When a system doesn’t quite support the way work needs to happen, people find a workaround. They export data. They track edge cases in spreadsheets. They add a manual check “just to be safe.” None of this feels dramatic in the moment — it feels responsible.
Over time, those workarounds become routine. The spreadsheet gets shared. The extra step becomes part of the onboarding process. The manual handoff turns into an assumed role.
Eventually, friction stops registering as friction. It becomes “how we do things.”From a leadership perspective, this is almost invisible. Outcomes are still delivered. Deadlines are still met. Teams appear busy and responsive. The system, technically, works.
What’s harder to see is how much effort is spent navigating the software rather than being supported by it — and how much organizational knowledge now lives in people’s heads rather than in the systems meant to carry it.
Most organizations evaluate software functionally, even when they think they’re being strategic.
Functional software answers a simple question: Can we do this?
Can we process requests? Can we track data? Can we move work from one stage to another?Strategic software answers a different question: Should this be easy, repeatable, and scalable?
Should this require human memory? Should this depend on a specific person knowing a workaround? Should this slow us down as volume increases?
The difference isn’t technical — it’s behavioral. Functional software enables tasks. Strategic software shapes how an organization operates, decides, and grows.
Many teams never pause to ask whether their systems are merely allowing work to happen or actively helping the organization work better. The distinction feels subtle — until it isn’t.
The challenge with “good enough” software isn’t the inefficiency itself. It’s how quietly that inefficiency compounds.
As teams grow, coordination requires more structure. As data increases, clarity becomes more important. As decisions carry more weight, leaders need faster, more reliable signals.Small frictions that once felt manageable begin to slow execution. Decision-making requires more context gathering. Oversight becomes more hands-on, not because leaders want control, but because the systems don’t provide confidence.
This creates a subtle but powerful feedback loop. Leaders rely more on intuition and check-ins. Teams hesitate to change processes because the risk feels high. Momentum slows — not dramatically, but persistently.Nothing is “wrong.” And yet, everything feels harder than it should.
There are signs that the success phase of “good enough” software has passed — and they rarely show up as urgent problems.
You may notice leaders spending more time manually reviewing work that systems were meant to handle.
You may find that critical knowledge resides with specific people rather than in shared tools.
You may hear resistance to change, not because teams dislike improvement, but because any change feels risky in a fragile system.
These aren’t alarms. They’re signals.They point to a growing gap between how the organization operates today and what its systems were designed to support.
This isn’t a call to rebuild everything. It’s not a mandate to modernize for the sake of modernization.It’s an invitation to notice.
Before asking whether software is broken, it’s worth asking a quieter, more revealing question:
Is this still serving who we are now?
For many organizations, simply naming the hidden tax is the first step toward clarity. And clarity — not urgency — is where strategic change actually begins.