(Business 2.0) – Q Do I have a better chance of making it to the executive suite as a generalist or as a specialist?

A During the boom, when someone claimed to be a generalist, I would think, "She's trying to justify a salary that's double what it should be." Now when I hear "generalist," I think, "Jack of all trades and master of none." Either way, "generalist" seems to be synonymous with "flawed resume."

Ezra Zuckerman, a professor at MIT's Sloan School of Management, agrees--and has the research to prove it. In his study of typecasting in Hollywood, "Robust Identities or Nonentities?," Zuckerman found that the practice leads to longer, more productive careers, a result he says is echoed in the business world, where the hiring system is also set up to reward those who differentiate themselves. "Headhunters are specialized," he says, "and they look for something they can package and sell."

Indeed, just as successful brands offer specific benefits, successful careerists offer specific talents. Think shampoo: The brand that is everything to everyone is always cheaper than the one that makes a very specific promise, such as fighting dandruff. Or, better yet, think about those who've made it to that corner office on the highest floor: Carly Fiorina landed the top job at Hewlett-Packard because she's extremely good at sales and marketing; Rick Wagoner started his career at General Motors in the treasurer's office, but he soon found his niche overseas, creating an attractive resume for a company increasingly concerned with meshing its global operations.

My advice: Stop trying to convince people that you can do everything--you're annoying those who are talented in areas you're not, and you're failing to distinguish yourself to boot. Figure out what you're best at and stick to it. After all, if you don't even know which of your talents will make you a big-time player, you can't expect anyone else to, either.

Q I keep hearing that it's important to stand out, but I don't want to appear outlandish or get marked as subversive. Is there a rule for when it's appropriate to break the rules?

A It's true that all great businesspeople, at some point in their careers, have had to challenge the status quo. Marcus Buckingham and Curt Coffman, authors of the 1999 management book First, Break All the Rules, discovered that one of the most consistent traits among successful business leaders was that they weren't afraid to fly in the face of conventional wisdom. But this didn't mean that they broke all the rules--no company can operate in a state of anarchy. The key to breaking rules is to know which ones to break. And the ones to break are the ones that really matter.

Whenever you do things differently, you are by definition taking a risk, so make sure the payoff will be big enough. Should you adhere to the company dress code? No one ever made corporate history by wearing torn jeans on casual Friday. This also helps you avoid the "executive who cried wolf" syndrome: If you follow the rules most of the time, people will be more apt to hear you out when you do decide to take a stand.

It also pays to know the reason for a rule before you break it. Upon taking the helm at eBay, Meg Whitman knew full well why CEOs aren't supposed to micromanage--they need to demonstrate big-picture leadership skills. However, she also knew that the company had a reputation for unreliable technology, and that Wall Street was penalizing her for a perceived lack of technological know-how (she had been running Hasbro's preschool division). So Whitman decided to break the rules, rolling up her sleeves and spending days on end in the company's IT department until she was satisfied that the site was bulletproof.

Ultimately, good rule-breakers must be good salespeople: You have to show the skeptics that your way is better. If you can convince people that there's a good reason for you to do what you're doing, as Whitman did with both investors and her own engineers, your new direction will have the impact you're hoping for. If you can't, you're just an anarchist, and corporate America already has plenty of those.

Penelope Trunk is a former New York marketing executive. Submit your career questions to AskPenelope@business2.com.