Leaders Must Break Some Rules
5 questions to ask when confronting a set of rules
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As a VP at Amazon, I sometimes chose to break rules in ways that could have gotten me fired if I had been caught.
All leaders must choose to break the “rules” at some point, and the challenge is to do so wisely and productively.
I will explain below how all leaders need to evaluate the rules they encounter and decide what to do with them. Sometimes, the correct course of action (in both moral and business terms) is to break the rules.
This is a nuanced topic where there will certainly deep disagreement, and my goal is not to convince everyone of my beliefs. Instead, my goal is to give you a good framework for thinking about when to follow or break rules.
I also want to be clear that I am not advocating for anyone to just do whatever they want and justify it under the guise of “rules are meant to be broken.” Rather, my point is that effective leadership requires deciding when to bend, skirt, or even defy outdated rules.
Judgment: Which Rules to Break
Leadership is about judgment. It is about making the right decisions most of the time and adjusting course when mistakes are made. This applies to products and schedules, but also to rules.
When confronting a set of rules, a leader must ask:
What is the intent of this rule?
What is the benefit of following it? What is the cost or damage of following it?
What is the benefit of breaking it? What are the risks and possible bad outcomes that can come from breaking the rule? What are the odds of those bad outcomes?
Am I willing to face the consequences of being caught breaking this rule?
What is my intent in breaking the rule? Helping someone? Saving lives? Making money? Sparing myself inconvenience?
There are a lot of questions to consider because, while sometimes breaking a rule is the right thing to do, we need to be careful. We need to begin with humility, realizing that the rule was put there by someone for a reason. Good judgment begins with respect and caution, not arrogance.
The amount of consideration that breaking a rule requires also depends on the space you operate in. Do you make something of little true risk or consequence, like iPhone games? Or do you make something with life or death consequences, like medicine or airplanes? It is one thing to break release process rules for your iPhone update and another to skimp on engine testing for a jet.
Rules Cannot Replace Good Judgment
Rules can never replace human judgment, and it is folly to think that they can.
The main reasons for this are:
1) Rule makers cannot anticipate all circumstances
Rules are almost always made to address a recent, specific problem. But, the resulting rule often creates side effects. For example, if a rule is created in response to one foolish or unethical action, that rule then creates overhead and constraints for all the wise and ethical decisions that will be made later on.
2) Rules change too slowly (COVID is a good example)
People are quick to make rules, but they are slow to update them as circumstances change. Rapid change requires all sorts of quick judgments and adaptations, and official rules often struggle to keep up. A good example of this was the pandemic.
The result is that rules accumulate. This is the bureaucracy that slows down governments and larger companies over time. More required reports, more levels of approval, and more mandatory steps all add up to make organizations slower than they were in the past.
3) Often, rule makers have personal agendas themselves
Rules are a form of power. If I can create a rule, I can use it to influence the outcomes I want. This means I have an incentive to create rules that benefit me, my career, my team, and my wallet.
4) There is often no reason to believe that the rule maker is a better decision maker than the rule breaker.
Rule makers usually have the advantage of time (they were there first), but not necessarily any other reason to be seen as more credible or trustworthy.
5) Rules sometimes conflict.
Because rule-making in organizations is distributed, rules are often inconsistent.
In the legal system, we have courts, where people actually called “judges” apply judgment to reconcile conflicting rules. In a workplace, someone else has to do that, and that someone may be you (the leader).
Deciding Which Rules To Follow Is a Moral Right and Duty
All leaders, and in fact all people, face a decision of which rules to follow. As an extreme example, after World War II, many concentration camp guards attempted to justify their crimes by saying that they were "just following orders."
On the other hand, many of the people we venerate as heroes from that horrible time are heroes precisely because they defied immoral rules and orders. This is the case with Otto Schindler (from “Schindler’s List”) and the many other brave people who risked their own lives to help Jews hide and/or escape.
The point here is that the “rules” were the same for everyone. Some people tragically decided to follow them, while a select few heroically decided to disobey.
This example is "life or death," which makes it easy for us to accept that “rule-breaking” was the right thing to do. However, there are other examples in history and popular culture where we almost unanimously accept that defiance of the rules was the correct course of action. For example, the American Revolution against a colonial government and Rosa Parks taking her seat on the bus.
Neither of these situations were “life and death,” but we agree that the revolutionaries and Rosa Parks did the right thing because they were fighting for freedom, equality, and dignity. These examples are all of a “higher order” than most rules and decisions that we face in life or work, but I use them to illustrate that leaders must question orders and decide when and how to defy them. Sometimes it will be publicly like Parks, and other times it will be covertly like Schindler. Knowing how and when to defy the rules is the hallmark of judgment.
All of Us Break Rules
At this point, some people will note that the dramatic examples above are all about “injustices.” They involve cases of “right and wrong” and impact on human lives. They will say that resisting injustice and breaking rules at work are very different.
In many ways, they are right. But now we have established that questioning rules and deciding when to defy them can be natural, moral, and beneficial. The truth is, we all already think that even without these strong examples. We think that because we ourselves do it.
Everyone breaks some rules, and everyone also believes that some rules should be observed.
Here is an example:
If you tell me that you have never once driven over the speed limit or never once told a “white lie,” I simply don’t believe you.
At the same time, I’m going to assume that we all agree that laws against cold-blooded murder should be both observed and enforced.
The subtle hypocrisy here is that “small” rules we are willing to break (like the speed limit) can, in fact, have lethal consequences. But, we don’t think that our driving over the speed limit will lead to someone’s death. To have an honest discussion about rules, we must begin by acknowledging that we often break rules that feel inconvenient when we believe that the associated risk is small.
Most of us are constantly choosing to disobey some rules while feeling that others must be observed. Not all rules are equal in our eyes, which is why judgment is a necessary trait for everyone, especially leaders.
Some Real Examples
A reader debating this topic with me asked me for examples of consequential decisions I made to skirt rules. Here are some examples I gave.
When I was still at Amazon, I had employees who very quickly left the state and worked from other states at the beginning of the pandemic. Technically, this was both illegal (they were not paying appropriate taxes) and against Amazon's policy (they were not authorized to go too far from the offices to commute). I kept my mouth shut, knowingly, and I stand by that decision. I could not easily have gotten them permission to move, but neither could I have easily forced them to return to their listed state. I had no tool to monitor or force their location, so I just ignored the fact that I knew they were somewhere else.
This example makes an important point, which is that one of the most important ways a leader should consider “breaking” rules is by simply not enforcing them. This is how America treats speeding. We could put speed cameras on every road, stopping speeding with a blizzard of tickets, but we do not. The community consensus is that while speed limits are good, they should only be enforced occasionally, on extreme speeders.
As lockdown went on in 2020, I discovered a problem with my team: no one wanted to take vacation time because they could not go anywhere. The result was that the team was working month after month with no breaks. To combat this,I decided to give the entire team the first Friday of every month off as a three-day weekend. I had no authority to remove a work day from the work week, and Amazon later sent out an email explicitly forbidding this practice, but I kept doing it anyway. My team's measured productivity went up as a result, but regardless, I was breaking the rules.
Common Edge Cases and Objections
These are some common arguments against the idea that leaders should make their own decisions about which rules to obey.
1) The Slippery Slope
This argument states that if we start by breaking a few rules, we will inevitably end up ignoring more and more of them, until we find ourselves in chaos where everyone is doing whatever they want.
I offer two rebuttals to this. First, all of us sometimes speed, but (likely) none of us has robbed a bank, a home, or an individual. Clearly, we are all capable of breaking some rules while respecting others.
Second, there is feedback to stop this “slide” into chaos. Workplaces have managers, and if you skirt enough rules, eventually people will notice. I wrote earlier that a leader must use judgment. Your manager and others where you work will step in if your rule-bending goes too far.
2) The Bad Actor
The argument here is that we need everyone strictly adhering to the rules in order to avoid encouraging or enabling “bad actors” (the evil people who intend to exploit others).
The fallacy here is that bad actors don’t follow rules in the first place.
I have firsthand experience with a number of sexual harassment situations. In each case, the person knew the rules; they simply did not care. They were well aware that they were exploiting their position and power to do as they pleased.
Telling such "leaders" to follow rules is meaningless. They didn’t follow a slippery slope from stealing inconsequential office supplies (printer paper, staples) and expensing the odd personal lunch to sexually harassing their employee. Rather, they didn’t respect their employees from the beginning. The bad actors are simply bad actors; stricter rules about other actions will not stop them.
Conclusion
Since sometimes we must break rules, and since all of us do choose to break some rules, the nuance is all about which rules to break and how to decide.
The useful question is not “Should we break rules?” but rather, “How can we make the best decisions about when to break rules and how to do so?”
And, for this question, there simply is no absolute answer.
The best answer I can give is the list of questions I shared above
We will not all agree on when to break the rules, but we should all be able to agree that it is a real, inevitable topic, and that getting good at making these decisions is the best course of action since absolute adherence to rules is neither wise nor practical.
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