Following the rules has never been my “thing.” Rules, in my mind, are for people who haven’t yet written their own. Don’t get me wrong, there certainly needs to be boundaries and structure because without order there would be complete disorder. At the same time, however, rules can be stifling.

Consider the latest United Airlines fiasco. According to one Wall Street Journal article, the company “follows strict rules on every aspect of handling its passengers, from how to care for unaccompanied minors to whether someone gets a whole can of Coke.”

Seriously? A Coke? If United Airlines hired five year olds to disseminate soda drinks then I can see how those kids might argue over who gets a full can. But they’re not. Employees are grown adults who can think for themselves—ideally.

The problem with an abundance of rules is that they stifle the creative thinking that enables autonomy, and by limiting autonomy “down there” at the lower echelons of the bureaucracy, organisational leaders “up there” become bogged down with silly, nit-noid decisions that limit their impact. If they—leaders at the “top”—are making decisions that somebody one, two or even three levels below them can make, then not only are those leaders not operating optimally, but neither is the company.

How to Know Which Rules to Break

Knowing which rules to break and when is simple in concept, but not easy to do because fearing the consequences is human. However, ask yourself these questions the next time a silly rule stands in your way between you and your company’s mission:

1. Who or what does breaking this rule serve?

There’s a simple order of priority you can use to test the purpose of breaking a rule, and it looks like this:

1. Mission
2. Team
3. Me

If you break a rule to serve the company’s mission, then doing so should be justified if your intent in doing so is noble. If your intent is noble, then I can’t think of any leader who would impose negative repercussions on your actions. That’s why you hire for character, train for competence, coach for performance and track for success—because you trust your employees to make the right (noble) decision based on their character. You can’t go wrong with character. You just can’t.

However, if you break the rule to serve yourself thereby putting your own self interest ahead of that of the team or mission, then you’re the reason why rules exist in the first place. Always consider the intent behind your next move, who it serves and who it impacts. Had the United Airlines flight attendants increased the incentive to greater than $800, maybe some passengers would’ve volunteered and prevented this PR nightmare.

2. What am I missing that would make this rule make sense?

There’s always a reason for why rules exist despite the fact that you (or I) dislike them. Rules typically cater to the masses, whether it’s people or process. An example of a process where rules are beneficial is a decision making process. One McKinsey study revealed how having a process (i.e. rules) for decision making actually increased the effectiveness of that decision by a factor of six. At the same time, not all decisions have the luxury of slow, deliberate thought. Some demand a more intuitive approach because time is of the essence. So when it comes to why rules make sense, consider the context in which that rule was made in the first place. A few questions to think about when examining context are:

• What are the primary, secondary and tertiary ripple effects of this [rule/decision]?

• What is the goal or objective that would make this [rule/decision/situation] successful?

• Who are the internal and external influences or personalities that I need to make this[rule/decision] a success?

• How does this [rule/decision] still apply and what would make it more relevant?

3. Why does this rule still exist?

If a rule has been in place for a while and it hasn’t evolved, then that’s a sign that perhaps you or your company haven’t either. Ask questions. Challenge assumptions. Routine and process minimise decision making fatigue and provide an emotional safe zone, but if you’re not careful then they can also become unnoticed black holes of complacency. If you want a simple strategy for challenging the status quo, ask why and repeat it five times, or until you get to the root of the problem.

Too much of any one thing is just that—too much—and rules are no different. How about a rule for not upsetting passengers? If that rule were in place, imagine the autonomy United employees would’ve had to enforce it. Sounds like a good rule to me.


This article was written by Jeff Boss from Forbes and was legally licensed through the NewsCred publisher network. Please direct all licensing questions to