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Adam Grant, teacher, Wharton School, speaks on stage during Massachusetts Conference For Women at Boston Convention & Exhibition Center on December 10, 2015 in Boston, Massachusetts.
Adam Grant, a professor of management at Wharton School of Business, speaks at a conference in Boston, Mass. in December 2015.
Marla Aufmuth—Getty Images

Imagine you're a thirtyish mid-level employee at one of the world's largest companies, and your billionaire CEO has made a decision you don't support. What do you do?

For most people, the answer is not what sales and distribution manager Donna Dubinsky did in 1985: issue a challenge to the CEO—in this case, Apple's Steve Jobs.

To cut costs, Jobs planned to eliminate Apple's warehouses and inventory and adopt a system of "just in time" computer assembly. But Dubinsky saw big problems with the idea and gave her bosses an ultimatum: She wanted 30 days to develop an alternate plan, or she would quit. Taking a stand paid off for Dubinsky, in large part because she proved she had the company's best interests at heart. Her proposal to revamp distribution was accepted—and she got a promotion.

Dubinsky's is one of many stories about unconventional career moves in Originals, a book out this week from Wharton School of Business management professor Adam Grant. Though Grant focuses mainly on entrepreneurship, the anecdotes and lessons could be valuable to anyone who has struggled against the status quo at work. Originals offers advice that might seem completely counterintuitive at first—but can actually pay off big in a person's career.

Here are some insights that may surprise you.

1. The most original ideas can come from the most ordinary situations.

Grant coins the phrase "vuja de" (a twist on "déjà vu") to describe moments when you spontaneously see an old problem in a new light. In one example, Warby Parker co-founder Dave Gilboa found himself questioning the high cost of his spectacles after a trip to the Apple Store. Why, he wondered, are glasses—which have existed for almost a thousand years—so expensive, while smartphones, a recent innovation, get cheaper year after year? That realization gave him and his co-founders the impetus to start discount spectacle company Warby Parker, valued at $1.2 billion as of April 2015.

2. Being your own critic can be a good thing.

Taking down your own ideas can, weirdly enough, make you look smart. In the right context, doing so displays intellectual honesty and can get your audience to better trust you—and come on board with your plan. When Rufus Griscom approached investors in 2009 to ask for funding for Babble, an online parenting magazine and blog he started with his wife, he led with a slide listing the top five reasons to not invest in the business. That year, he garnered $3.3 million in funding. Negative thinking can make you more prepared for any and all outcomes; "defensive pessimists," as Grant calls them, anticipate what can go wrong in a situation and actively take steps to forestall errors. And studies show they perform just as well as optimists in professional situations.

3. Procrastination can lead to some of your best work.

You've likely been told at some point in your career to always get a head start on major assignments—but there's actually a case for putting them off. Mulling over projects, rather than tackling them early and knocking them off in one sitting, can give you the breathing room necessary to perfect your ideas. It's called the Zeigarnik effect, named after a Russian psychologist who theorized that people have a better memory for incomplete assignments than finished ones. In other words, when you have a task looming over you, you'll keep thinking about it—and ultimately arrive at a more creative solution. Procrastination also leaves you more open to improvisation. Martin Luther King Jr., for example, waited until four days before his “I Have a Dream” speech before composing it. And the speech’s titular line wasn't even originally scripted: King included it after his favorite gospel singer, Mahalia Jackson, yelled “Tell ’em about the dream, Martin!” during the address.

4. If you have a radical plan, it might be best to start small.

The originator of any idea—let alone an unconventional one—risks turning off people who don’t want their long-held convictions challenged. That's why it is safest to present your most radical ideas in a way that will be more appealing to mainstream audiences, even if that means masking what you actually want. For instance, uBeam founder Meredith Perry was shut down repeatedly when she approached engineers and investors with her idea to build a transducer that would transmit power wirelessly. She had more success when she instead approached engineers individually asking if they could build separate parts that together would make up the whole of her system.

5. Lean in to your challenges.

What if your weaknesses could be as valuable to you as your strengths? Grant gives the example of younger children, who are usually at a disadvantage relative to older siblings. “Faced with the intellectual and physical challenges of competing directly with an older sibling, the younger chooses a different way to stand out,” Grant writes. That spirit, he says, can carry over to their professional demeanor. Younger siblings also enjoy the benefit of older siblings' protective instincts, Grant points out, which may be why they tend to take more risks. They’re more likely to choose unconventional jobs—as comedians, for example (Stephen Colbert, Chelsea Handler and Louis C.K. are all youngest siblings).

6. Rules don't work as well as appeals to character.

Research shows people are more affected if you say “don’t be a cheater” than if you tell them simply, “don’t cheat.” Creating rules can tempt people to break them, whereas appealing to your employees' sense of morality can be more effective. A study of children sharing marbles with their peers found that those who received praise for their character were more likely to repeat generous behavior in the future. Focusing on character traits rather than prescriptions “evokes a sense of self, triggering the logic of appropriateness: What kind of person am I, and who do I want to be?” Grant writes.

7. It’s okay to be a little unprofessional—in the right setting.

Professionalism can make or break your career, and its importance can't be overstated: You never want to get caught, for example, bad-mouthing your boss. That said, there will likely be moments in your career when you and your colleagues need to blow off steam—and that can be healthy, when done correctly. Grant writes about a group of surgeons who regularly endured verbal abuse from their attending physicians. So at happy hour (outside of work, of course), they would pick an "Asshole of the Week." It gave them an outlet for their stress and increased their sense of camaraderie. Twenty years later, the surgeons hold positions at the top of their fields, and have vowed to help stop the cycle of abuse by treating residents with more respect than they themselves received.