The screen, a cold blue beacon in the pre-dawn quiet, taunted me. “Two-factor authentication required.” My work phone, the device entrusted with the precious verification code, sat in its usual cradle on my office desk, a good 45 miles away. I was, as company policy dictated for the last 5 months, working from home. A familiar, almost visceral sigh escaped me. It’s the same frustration that bubbles up when I consider the ludicrous hoops to jump through just to reset my password-a form that demands my manager’s signature, then her manager’s, before it even reaches IT. And yet, just last week, our CEO, a man whose decisions shape a sprawling enterprise, clicked on a rudimentary phishing link, compromising his inbox with a casual indifference that defied every one of those onerous policies.

The Contextual Drift of Rules

I’ve watched Kai L., a conflict resolution mediator who specializes in corporate quagmires, navigate these exact waters for over 25 years. Kai often says that organizational rules, like old recipes, frequently lose their context over time. You keep adding a pinch of salt because the recipe says so, not because you remember why it’s needed or if it even still applies to today’s ingredients.

I’ll admit, I’ve been part of the problem. Years ago, I spearheaded a project to automate a reporting system. We added five layers of approval, each with a timestamp, a digital signature, and an audit log. On paper, it was bulletproof. Accountability was etched into every byte. What I missed, in my zeal for comprehensive oversight, was that the critical data entry step was still manual, and the five layers of approval had created a three-day delay, making the reports almost useless for real-time decision-making. We had built a perfect tracking system for irrelevant data. It was like carefully polishing a tarnished spoon while the entire kitchen was burning. Eventually, like expired condiments I recently cleared from my fridge, those superfluous layers were thrown out, but not before a year of wasted effort and frustrated users.

The Human Element: Circumvention as Logic

This obsession with documented compliance over practical security stems from a fundamental misunderstanding of human behavior. People, when faced with an impenetrable wall of bureaucracy to do their job, will find a way around it. They’ll share passwords (if only physically), use personal devices, or simply avoid the ‘secure’ pathway if it means they can actually get work done.

These aren’t malicious actors; they’re employees trying to meet deadlines, driven by a logic far more primal than any compliance manual: the need to deliver. Every rule that makes a necessary task 25% harder is an invitation for circumvention. And when that circumvention inevitably leads to an incident, the compliance team points to the meticulously crafted paper trail, absolving themselves, while the ‘irresponsible’ employee (who was just trying to work) takes the fall.

Bridging the Canyon: Enabling Security

So, how do we bridge this canyon between the ideal and the actual? How do we build systems that protect without punishing? It requires a fundamental shift in perspective. Instead of starting with ‘how do we cover our asses,’ we must ask, ‘how do we genuinely secure this, while enabling our people?’

Kai often brings teams together, not to argue about who broke which rule, but to map the actual flow of work against the existing rules. In 95% of cases, simply visualizing the disconnect is enough to initiate change. It’s about finding the critical 5% of rules that truly mitigate risk and stripping away the 95% that merely create busywork and frustration.

The Goal: Evolved Compliance

Imagine a world where accessing a crucial document doesn’t involve a 35-minute detour, where securing data doesn’t feel like navigating a minefield, and where the processes empower rather than impede. That’s not just a pipe dream; it’s a strategic imperative.

The goal isn’t to abolish compliance, but to evolve it. To transform it from a punitive, blame-focused exercise into a proactive, enabling force. We need to look at our rulebooks with the same critical eye we apply to our software: constantly updating, refining, and removing anything that no longer serves its original, practical purpose. Because until we do, the war on common sense will continue, and the true cost will be paid not just in lost productivity, but in eroded trust, stifled innovation, and ultimately, a less secure future for everyone involved.