Why Leaders Are Paid to Break the Rules, Not Follow Them

by: David R. Freedman, MBA

In business, rules provide structure and predictability, laying the foundation for organizations to function. But when it comes to leadership, adherence to every rule is not a virtue—it’s a liability. Great leaders are not celebrated for coloring inside the lines; they are paid to challenge the status quo, rewrite the playbook, and break the rules that no longer serve the organization.

?Here’s why.

Rules Preserve the Past, Leaders Build the Future

Rules are typically designed to maintain order and repeat proven successes. However, in today’s fast-paced, disruptive world, yesterday’s strategies often fail to address tomorrow’s challenges. Leaders are tasked with identifying where those rules create bottlenecks instead of breakthroughs. For instance, Steve Jobs famously ignored conventional product development timelines to produce the first iPhone—an act of defiance that changed the world.

Leadership isn’t about preserving traditions; it’s about crafting visions that disrupt and redefine industries. This requires the courage to dismantle norms and the foresight to establish new ones.

Breaking Rules Sparks Innovation

If every leader simply followed the rules, innovation would stagnate. Rules often reflect assumptions that no longer hold true. Think about the rise of remote work. Before the pandemic, traditional wisdom dictated that productivity required physical offices. Leaders who broke that rule—like Brian Chesky of Airbnb, who embraced permanent flexibility—unlocked new opportunities for both employees and businesses.

Rule-breaking leaders cultivate cultures that encourage experimentation and risk-taking. They know that progress depends on questioning “the way we’ve always done things.” This doesn’t mean anarchy; it means selectively dismantling rules that stifle creativity.

Leaders Solve Problems Rules Can’t Address

Rules are designed for predictability, but the biggest problems leaders face are often unprecedented. During crises, such as the COVID-19 pandemic, leaders had to act decisively in the absence of clear protocols. Companies pivoted to produce masks, ventilators, and vaccines—not because of established guidelines but because leaders dared to step into uncharted territory.

Leaders earn their pay by navigating ambiguity, making tough calls, and finding solutions that don’t exist in the rulebook. They understand that clinging to the rules can mean inaction, and inaction is often the greatest risk of all.

Rule-Breaking Requires Responsibility

It’s important to note that breaking rules doesn’t mean abandoning ethics or compliance. Reckless rule-breaking leads to disaster (as seen in cases like Enron or FTX). Responsible leaders challenge rules thoughtfully, balancing innovation with accountability.

When Satya Nadella became CEO of Microsoft, he broke the company’s inward-focused culture by fostering collaboration with competitors like Apple and Google. This wasn’t about defying logic—it was about reimagining Microsoft’s place in a rapidly evolving tech ecosystem.

The Bottom Line

Leaders are paid to break the rules not out of rebellion but out of necessity. They question assumptions, dismantle barriers, and chart bold paths forward. In a world that demands adaptability and innovation, rule-followers maintain the present; rule-breakers create the future.

If you aspire to lead, ask yourself: which rules are you ready to challenge to unlock the next breakthrough? Because real leadership begins where the rulebook ends.

Copyright 2024 David R. Freedman