The CTO's Dilemma (or The Unintended Consequence of Initiative): A Workplace Parable

The Story

A talented software developer, let's call him Timmy, had just started a new job. Very soon after starting, Timmy learned that the company's CTO had recently signed a costly provisional contract, worth tens of thousands of pounds, with a third-party software vendor for software to automate a specific business task.

Wanting to demonstrate initiative and keen to impress his new boss, Timmy examined the business problem that the purchased software was to solve and reasoned that he could build software of his own to fulfil that purpose. He told the CTO of his findings and said that he would build the needed software in his own time over the weekend, thus saving the company a significant amount of money.

And he did. By Monday, Timmy had a fully-functional, production-ready solution. When he proudly presented his cost-saving alternative, the CTO's response was swift and harsh: take it away, forget it ever happened and never speak of it again.

Timmy was confused. His solution clearly met the needs of the business to automate the necessary task and would obviously save the company significant money. However, eventually, Timmy's confusion turned to understanding. While his solution was technically superior and financially prudent, it had created a political problem. The CTO had already secured executive buy-in for the vendor software, convincing them that the expensive purchase was necessary. Accepting Timmy's well-intentioned solution now would expose the CTO as having made a costly mistake, undermining their prior decision, and by extension, their credibility with their peers.

The Lesson

In organisational life, doing the "right thing" for efficiency or cost savings isn't always the "right thing" politically, especially if it threatens someone's ego, reputation or political standing. Solutions that make decision makers look foolish, even inadvertently, will often be rejected regardless of their merit, and doing the "right thing" also requires understanding and respecting existing decisions, human dynamics, and individual reputations.

Epilogue

This parable perfectly captures one of the most frustrating yet common dynamics in corporate life. Timmy's story illustrates how organisational politics can override logic, efficiency, and good intentions. The lesson extends beyond just protecting egos, it's about understanding that every decision exists within a web of relationships, commitments, and reputations that may not be immediately apparent. The tragedy is that Timmy's impulse was exactly what most organizations claim to want: initiative, problem-solving, and cost consciousness. But the reality is that timing, context, and political awareness often matter far more than the quality of the solution itself.