How to Turn Rule-Breakers Into Your Best Asset
Break rules with a purpose, not just because you want
Your employee broke a company rule to help a customer. Should you praise them or punish them?
That’s a tricky one, right? You want to recognize their good intentions, but you also worry others might start breaking rules, too. If you’re stuck in this dilemma, you’re not alone.
Many leaders punish the wrong people. They crack down on rule-breakers without asking why they broke the rule. Meanwhile, they reward employees who hide behind rules and say things like “That’s not in my job” to avoid responsibility.
The real problem isn’t rule-breakers. It’s that most leaders can’t tell the difference between an asset and a liability.
This post shows how to position rule-breakers to work in your favor. You’ll learn how to help good rule-breakers break rules for the right reasons, not their own benefit.
Why Good Rebels Break the Rules
“The first rule of breaking a rule is to know everything about the rule.” —Nuno Roque
Sometimes, you have to break the rules to start a fire.
“Fire-starters“ are those who drive change. They don’t just start fires—they choose when and where to light them. They do it with a purpose.
Breaking the rules feels good. Rebels don’t just enjoy the experience; they also feel free because they’re not following the crowd. However, this motivation could bring trouble.
Some people break rules to help, others to cause havoc.
A study found that employees with positive intent break the rules to better serve customers or make their organizations more effective. For example, a bank employee might approve a loan for someone who doesn’t meet the requirements but has a strong business plan. Healthcare sometimes bends bureaucratic rules to put patient care first.
Bad rebels, however, break rules to benefit themselves or hurt others. This includes fraud, theft, and unethical behaviors. The same study found that these employees often have a Machiavellian personality—they care only about themselves and manipulate others to get what they want.
Breaking rules is a form of rebellion. “In its modest form, rule-breaking is actually healthy,” says Zhen Zhang of Arizona State University. His research found that people who broke minor rules as teenagers were more likely to become entrepreneurs.
Rebels challenge the status quo and push for change. But not all rebels are the same. Lois Kelly and Carmen Medina identify two types: good and bad.
In Rebels at Work, the authors describe “good rebels” as those who step up to fix problems. They want recognition or a bonus. They’re simply about implementing solutions that help everyone.
Good rebels break the rules to make things better. They challenge the status quo with a positive mindset. They’re passionate, purpose-driven, and committed to their company’s success.
Good rebels want to do great work. They’re creative, adaptable, and resourceful. Their colleagues respect them because of their ideas. Good rebels are an asset to your team.
Bad rebels feel entitled, are disengaged, and hold grudges against others. They break the rules to hurt the organization.
Bad rebels don’t care about improving things around them. They rebel for the wrong reasons. Bad rebels are often disrespectful and hard to deal with. They ignore policies, cross ethical lines, and harm team morale.
So how can your organization encourage the right kind of rule-breaking? The goal is to spark creativity, not burn the place down.
A Three-Step Approach to Breaking Rules
“By all means, break the rules, and break them beautifully, deliberately, and well.” —Robert Bringhurst
Breaking rules isn’t an act of random rebellion. It needs to be purposeful. Focus on what you want to achieve, not just on the obstacle. Good rebels break rules like an artist.
To know when and how to break the rules, you need a method. Here’s a three-step process I teach my clients to help them break rules the right way. The goal is to encourage employees to become good rebels.
Each step uses an even/over statement—a deliberate choice between two good things. It’s not about rules being bad or outcomes being good. It’s about what matters more when they conflict with one another. When you can’t have both, which one will you choose?
Think of these three steps as a complete system, where each complements the other. Use them together, not separately. Share this with your team.
1. Outcome Even Over Rules
Does the outcome justify breaking the rules?
Rules should protect your organization. However, when rules stop people from making things better or doing what’s right, they cause more harm than good.
Before breaking a rule, ask yourself: Is the outcome worth it? Simply put, will the benefit be greater than the consequences?
Southwest Airlines is famous for putting employees first. This is partly due to its culture of encouraging employees to break the rules when needed.
Once, a passenger needed oxygen during a medical emergency. Southwest’s policy said only licensed medical staff could administer oxygen. But a flight attendant decided to break the rules and gave the oxygen herself. She saved the passenger’s life.
When the stakes are high, would you stick to the rules or do what’s right?
Good rebels break the rules when they know the result is worth it.
2. Core Values Even Over Outcome
Does this decision align with your team’s values?
Results alone aren’t enough reason to justify breaking rules. That kind of thinking often leads to unethical behavior. People start using it as an excuse to break not just rules, but even the law.
Before deciding to break the rules, reflect on whether the decision is aligned with your company values—and your personal ones.
Zappos has a tradition of doing this really well. Zappos’ purpose (and one of its values) is to “WOW customers” through great service. Call center employees don’t follow scripts and have no limits on call times. The longest call reported is 10 hours and 43 minutes.
Zappos employees can make any decision to wow a customer. No need to transfer the call to the supervisor.
For example, a woman called Zappos to return a pair of boots she had bought for her husband, who died in a car accident. The next day, she got a flower arrangement. The customer service employee sent them using company money without asking for permission first.
When the opportunity is tempting, would you take it or follow your values?
For good rebels, values and outcomes go hand in hand.
3. Collective Gain Even Over Personal Gain
Are you serving the team or yourself?
Good rebels are courageous. They do what’s right, not what’s easy or convenient. Breaking the rules is often risky; you need to take responsibility for the consequences.
Most importantly, good rebels don’t break rules for personal gain. They do it to help the collective good.
Years ago, Toyota had a massive recall because of faulty accelerator pedals. A quality engineer named Denny Gioia initially told his superior about this issue—who repeatedly ignored him and even punished him for challenging the chain of command. Gioia faced a choice: Stay quiet and protect his career, or break the rules and risk everything to protect customers. He chose collective gain. He went over his bosses’ heads to report the problem to senior executives. Because of his actions, Toyota issued a recall and removed the dangerous vehicles from the road.
When the opportunity comes, will you take the safe path that benefits you, or will you break the rules to help the team?
Good rebels choose collective gain over what’s best for themselves.
Make Rule-Breakers Work for You
Rule-breakers aren’t problems to solve—they’re assets to develop. They notice things others miss. They question rules others accept. They’re willing to take chances to do the right thing.
Good rebels don’t break rules for personal gain. They do it to help the organization better serve employees and customers. They’re intentional about both the motives and consequences.
To turn rule-breakers into assets, use the three-step process: prioritize outcome, values, and collective gain. Consider all three together, not just one. This helps your company encourage new ideas while maintaining a healthy workplace culture. It motivates people to challenge old ways for good reasons, not selfish ones.
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