IT leadership lessons from ‘Leroy Jenkins’

In 2005, Leroy Jenkins gained notoriety in the gaming world as a hapless World of Warcraft player immortalized in a viral video. Leroy single-handedly wrecked a carefully planned mission by charging headfirst into danger, shouting his name in a spur-of-the-moment battle cry. His impulsiveness left his team scrambling in chaos, and the carefully strategized mission ended in complete failure.As humorous as his antics were, Leroy Jenkins is a cautionary tale. His mindset bears an eerily similar resemblance to how many IT leaders operate today. Good intentions collide with impulsive actions. Leaders charge ahead with little concern for strategy and careful planning. The result? Their IT initiatives often fail to deliver value and meet business objectives.

The Leroy Jenkins in IT

Over the years, enterprise IT leadership has rushed into various technology trends as though they were shouting “Leroy Jenkins!” rather than carefully assessing fit, strategy, or long-term value. Numerous enterprises adopted cloud computing, for example, without fully grasping the complexities of cost governance, architectural consistency, or operational oversight. Some companies achieved revolutionary transformation, but others experienced ballooning costs, fragmented architectures, or underperforming systems.Trends such as service-oriented architecture in the 2000s and now generative AI and agentic AI highlight the same pattern. Eager to stay ahead of the curve, IT decision-makers often dive headfirst into buzzworthy technologies, deploying them as knee-jerk experiments without aligning them with organizational needs or measurable outcomes. Over time, this results in complex sprawl and a weak return on investment (ROI).Leadership later wonders why IT initiatives fail to hit their intended targets. The answer consistently lies in the failure to prioritize planning, strategy, and governance before entering the implementation battlefield.

The root of the problem

A combination of factors drives the impulse to chase the latest technology trends. Executives feel pressured to innovate quickly and avoid being seen as laggards. Vendors take advantage of this urgency, promising game-changing results with flashy marketing and unrealistic timelines. Meanwhile, IT leaders sometimes prioritize speed over smart delivery, mistakenly believing that rapid adoption translates to long-term relevance.What’s missing is a strong emphasis on connecting IT innovations to broader strategic business goals. Too often, IT operates in a silo, optimizing for technology rather than outcomes. This creates a pattern where new technologies are initiated through tactical trial-and-error cycles instead of as intentional tools designed for meaningful returns.This lack of strategic planning leads to predictable challenges. Solutions either fail to meet actual business needs, become redundant within a year, or create technical debt that hampers agility. This is the IT equivalent of a haphazard charge into battle when what’s truly needed is a thoughtful, coordinated advance.

Avoiding the Leroy Jenkins trap

The solution to this chaotic approach lies in a renewed focus on creating disciplined, long-term strategies for adopting enterprise technology. Each initiative should be anchored in business objectives and a clear understanding of what technologies such as generative AI, cloud computing, or service-oriented architecture aim to achieve. Goals should focus on measurable terms, not buzzwords.Enterprise architecture is the foundation for this transformation. With a robust framework in place, organizations can grow their IT systems in a way that consistently aligns with business needs, scales predictably, and reduces inefficiency. Enterprise architecture promotes interconnected systems, effective life-cycle management, and deliberate scaling. In short, it emphasizes strategy over impulse.Adopting a deliberate approach allows organizations to test new technologies on a manageable scale, establish governance early, and assess performance against clear ROI metrics. Starting small and scaling thoughtfully ensures that early wins build trust with decision-makers while minimizing waste and risk. The meaningful adoption of technology hinges on its alignment with key performance indicators related to revenue growth, cost efficiency, or improvements in customer experience. By continuously measuring success and course-correcting as needed, organizations can avoid the kind of haphazard experimentation that puts entire IT budgets at risk.

A better way forward

Successful organizations treat IT investments as long-term endeavors rooted in strategic goals. Instead of chasing trends for the sake of being innovative, they enable transformation by merging technology opportunities with strong governance, ongoing life-cycle management, and clear success metrics. As a result, these organizations experience fewer failures and higher ROI from their IT initiatives. They don’t lose trust with executives or stakeholders, and they don’t waste time digging themselves out of technical debt caused by ill-planned systems. Most importantly, they demonstrate that IT’s role is not just to implement technology, but to drive consistent value.Leroy Jenkins may be a memorable piece of internet culture, and apparently a spoof, but his approach is no model for IT leadership. Charging ahead unprepared—whether into a battle or the next big IT trend—leads to chaos, missed opportunities, and failure. IT leaders must shed this mindset and commit to disciplined strategic planning, guided by enterprise architecture frameworks and a focus on achieving measurable business outcomes. Success in IT is rarely about speed; it’s about alignment, execution, and the ability to deliver lasting value. Please do take a look at the video—it’s hilarious—but don’t be a Leroy Jenkins.