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How To Know Which Rules To Break And When

Following the rules has never been my “thing.”

As an entrepreneur, 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. However, at the same time, rules can be stifling.

Rules are for the obedience of fools and the guidance of the wise.
- Group Captain Sir Douglas Robert Steuart Bader, WWII Fighter Pilot, Royal Air Force

Consider that United Airlines fiasco where the passenger was dragged off the plane. According to one Wall Street Journal article, United “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.

Limiting autonomy “down there” at the lower echelons of the bureaucracy, organizational leaders “up there” become bogged down with silly, nit-noid decisions.

Having too many decisions limits that persons impact.

If leaders at the top are making decisions that somebody a couple levels below them can make, those leaders not operating optimally. But, interestingly, 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 seemingly silly rule stands in your way between you and getting the job done:

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. But you have to look at intent in doing so. Is it noble?

If your intent is noble, then most leaders won’t 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 the PR nightmare we all saw unfold.

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 minimize decision making fatigue and provide an emotional safe zone.

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.

So if we mention again what happened clear back when we were all incited and stressed over the United fiasco —

What if there had been a rule that you don’t upset passengers for anything?

If that rule were in place, imagine the autonomy United employees would’ve had to enforce it. The lengths they would have gone to make everything right with all customers.

Sounds like a good rule to me.

Jeff is the author of Navigating Chaos: How To Find Certainty in Uncertain Situations and host of The ChaosCast Podcast: Leadership Lessons from Chaos.

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