Why Companies Keep Failing at Software (And Never Learn)

Software engineering has been around for decades, yet many companies still manage to do it badly. Fred Brooks wrote The Mythical Man-Month nearly 50 years ago, warning of the pitfalls of software development—yet the same mistakes he outlined are repeated daily in companies across the world.

Why? Why do organisations that rely on software for their very survival continue to ignore decades of wisdom, making the same catastrophic errors over and over again? Why do they believe they are somehow different, that they will succeed where others have failed, despite following the same doomed path?

The answer is a mix of arrogance, short-term thinking, and a fundamental misunderstanding of what makes software development work. Let’s explore why so many companies keep getting it wrong.

1. Short-Term Thinking and Executive Arrogance

Many software failures stem from decisions made at the executive level. Leaders often prioritise short-term gains over long-term sustainability, despite the overwhelming evidence that rushing software development leads to disaster.

“We’ll just add more people to speed it up.”
Brooks debunked this in The Mythical Man-Month—adding more people to a late project makes it later. Yet, this lesson is ignored by executives convinced they can “scale” their way out of delays.
“We don’t need proper planning or architecture.”
Many leaders treat software development like factory work—just assign people tasks and they’ll get it done. They underestimate the complexity of software systems, leading to spaghetti code, technical debt, and inevitable failure.
“We’re different. The usual rules don’t apply to us.”
There’s a persistent belief that this company, this project, this time will be different. Hubris blinds decision-makers to historical lessons, ensuring they repeat the same errors others have made before them.

2. The Cult of Agile (Without Understanding Agile)

Agile was supposed to fix software development. Instead, it has been mangled into something unrecognisable, turned into an excuse for chaos, and a cover for bad management.

Scrum Theatre – Many teams claim to be Agile, but they just do stand-ups and sprints while still following waterfall thinking. They prioritise deadlines over adaptability, and they cut corners under the illusion of “moving fast.”
No Documentation, No Architecture – Agile does not mean “don’t plan.” Yet many teams abandon architecture, proper design, and technical documentation, believing that constant iteration alone will lead to a well-structured system. Spoiler: It doesn’t.
Velocity Over Quality – Teams are pushed to maximise story points rather than build reliable software. This results in feature bloat, unsustainable tech debt, and a system that collapses under its own weight.

Agile isn’t the problem—the way companies misinterpret and misuse it is.

3. Ignoring Technical Debt Until It’s Too Late

Every company swears they care about quality. Few actually invest in it.

“We’ll fix it later.” Later never comes. Every shortcut, every hack, and every postponed refactor adds up. Eventually, the software becomes unmaintainable, releases slow down, and entire systems need to be rewritten.
Legacy Systems Rot in the Background – Old, unstable code remains critical to the business, yet nobody dares to touch it. Companies pour resources into building new features on top of broken foundations, rather than fixing the core issues.
Developers Burn Out Trying to Fix the Unfixable – Teams are stuck maintaining impossible systems with mounting bugs, endless firefighting, and unrealistic deadlines. Eventually, they quit, taking valuable knowledge with them.

Ignoring technical debt isn’t just a bad habit—it’s a ticking time bomb.

4. Software Projects Are Managed Like Construction Projects

Executives love to compare software development to building bridges or skyscrapers. They demand fixed timelines, predictable costs, and clear deliverables—despite decades of evidence that software doesn’t work that way.

Software is not predictable. Unlike a bridge, which follows a well-defined process, software is a complex, evolving system. New requirements emerge, unknowns appear, and rigid plans quickly become obsolete.
You can’t estimate the unknown. Yet, companies keep demanding accurate estimates for projects that involve new technology, shifting requirements, and unpredictable challenges. When teams inevitably miss deadlines, management blames the engineers rather than the flawed approach.
Change is inevitable—but companies resist it. Businesses demand adaptability, yet they cling to rigid roadmaps and outdated plans. Instead of embracing change, they fight it, leading to unrealistic expectations and failed projects.

Software is not a factory process—it’s an evolving, creative discipline that requires a fundamentally different approach.

5. The Wrong People Make the Decisions

One of the biggest reasons companies fail at software is that non-technical people make technical decisions.

MBAs and middle managers dictate architecture. People with no coding experience decide which programming languages, frameworks, and tools should be used—often based on buzzwords rather than technical merit.
Engineers are ignored. Developers warn about bad decisions, but their voices are drowned out by managers obsessed with deadlines and “deliverables.” When things go wrong, the same managers wonder why nobody spoke up.
Consultants and vendors sell snake oil. Companies waste millions on consultants who promise “magic solutions” but leave behind a mess. Vendors lock businesses into expensive, bloated platforms that cause more problems than they solve.

Good software decisions come from experienced engineers—not executives chasing trends.

6. Failure Is Hidden, Not Learned From

Unlike industries where failures are studied and learned from, software failures are often buried, forgotten, or blamed on the wrong factors.

Failed projects are rebranded. Instead of admitting mistakes, companies rename projects and keep throwing money at them. The same flawed ideas get repackaged under different names, doomed to fail again.
Nobody does proper post-mortems. Rather than analysing why things went wrong, failures are brushed aside, and teams move on to the next doomed initiative.
Engineers leave, and history repeats. The people who understand past failures quit or get laid off. New teams come in, unaware of past mistakes, and repeat them.

If companies actually studied their failures, they might stop making the same mistakes. But they don’t.

Conclusion: The Cycle Continues

Despite decades of hard-earned lessons in software engineering, companies still fail at software because they:

Prioritise short-term gains over long-term stability.
Misuse Agile as an excuse for chaos.
Accumulate technical debt until systems collapse.
Treat software like a construction project.
Let non-technical people make technical decisions.
Hide failures instead of learning from them.

Until businesses start treating software as a complex, evolving discipline—led by experienced engineers rather than executives chasing quarterly goals—the same mistakes will continue for another 50 years.

Software development isn’t broken. The way companies approach it is.