The current business climate encourages rule breakers. Not the kind at Enron – those are law breakers. Rule breakers break with convention. Sallie Krawcheck, for example, was a top stock analyst in the 90s. She could have gone to a big investment firm where the heavy-hitters gave stock advice that, in hindsight, seems to have been garbage. Instead, she stayed at a boutique research company, which she made famous for quality. Last year Krawcheck took an enormous career leap to become the CEO of Smith Barney precisely because she had broken with convention years earlier.

All great business people have had to break some rules on their path to huge success. But be careful: people who break all the rules all the time are not innovators or a breath of fresh air, they are sociopaths. Rules create order and process, and no company can operate in a state of anarchy. The key to breaking rules is to know which rules to break.

Break rules that matter.
You always take a risk when you do things differently, so make sure there’s big payoff. Does your company have a dress code? Adhere to it. No one ever made corporate history by wearing torn jeans on casual Friday. If you follow most of the rules, then when you break a rule people will be more willing to let you go with it.

Weigh the risks.
There are a lot of rules that deserve to be ignored, but sometimes breaking rules is more trouble than it’s worth. As a marketing executive in a software firm, I was required to have engineering signoff on every word on the front of the box. The process became an opportunity for code-heads to make illiterate proofreading comments. But I still got signoff every time, because while breaking that rule would save me a day in the box production schedule, it would cost me weeks of assuaging engineers’ egos.

Know the reason for the rule before you break it.
The best example of this is the renegade barrista at Starbucks (if she has not been fired yet). She keeps changing the composition of standardized drinks. Lattes have a little less milk, Frappuchinos have a little more foam. I overheard her declaring that she gives customers what they want even though they don’t know to ask for it. This would be a great idea in another company, but the charm of Starbucks is that wherever you go – Seattle or Milan – the drinks are consistent.

Break rules so that you can be more effective.
Andy Grove broke rules of convention by pioneering the idea of management by walking around. He didn’t necessarily set out to break a rule, he just wanted to manage in a way that felt comfortable to him, and walking around talking to people suited him well.

Break rules that other people would be scared to break.
In 2000, when everyone was still running on Internet adrenaline, stock analyst Jon Joseph announced that the chip sector was in for a big fall. At the time, he received so many death threats that his company hired a bodyguard for him. Recently he was rewarded for going against the grain by receiving a top post at Smith Barney.

Good rule breakers spent part of their life as good rule followers. Jeff Bezos is renown for bucking the conventional wisdom that CEOs shouldn’t micromanage. He does, and it works well for him. But before he was a rule breaker he spent the beginning of his career in consulting and finance positions where he followed the rules for entry-level employees and did what he was told to do.

If you think you’ve got a situation where you should definitely break a rule, remember that good rule breakers are good salespeople. You can’t just break a rule and think it’ll stick. You have to explain to people why your way is better. Get people behind your new way of doing things so that your new direction can have the large impact you hope for. Break a rule and people will gossip; lead down a new path and people will follow.