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From a lowly sales assistant to head of a magazine empire (okay, our magazine empire), Cathie Black has boldly gone where no woman has gone before. Here, in a preview of her forthcoming book, Basic Black, she shares her unorthodox (dare we say daredevil) strategies for getting ahead.
Thousands of years ago, a handful of fortune-tellers roamed ancient China, traveling to the palaces of Mandarins and predicting the future. When they were right, they were showered with riches and praised at lavish banquets. When they were wrong, they were boiled alive.

Taking a risk is scary when you focus on what can go wrong and exciting when you consider the benefits if all goes well. The trick is to think about risk in the right way and use it to your advantage. Most people see taking risks as opening themselves up to unnecessary, even dangerous, chance. But the truth is, avoiding risk won't keep you safe, nor will it guarantee a smooth ride.

In fact, the opposite is often true. It's like the monkey parable: A monkey sees a nut in a hole and reaches in to grab it. Once he's closed his fist around it, he can't get his hand back out of the narrow opening. He can't free himself unless he lets go of the nut, but because he's afraid to lose it, he won't let go.

Trying to avoid risk is like clinging to that nut. You may think you're playing it safe by holding on to what you have, but in reality you're just hindering your own progress.

Rule 1: Take Risks That Are Calculated, Not Crazy

So how can you make risk work for you? The first rule: Take risks that are calculated, not crazy. There's a big difference between rafting in white water with a helmet and an experienced guide and jumping on an inner tube to soar over a waterfall on a whim. When you're considering taking a risk, ask yourself: How can you maximize your chances of success while minimizing the potential downside?

About a year into my first job, as a sales assistant at Holiday magazine, my boss quit. As soon as I heard she was leaving, I wanted her job. I made an appointment with Holiday's publisher, a top executive who'd been in the magazine business about as long as I'd been alive. "I want to talk to you about Phyllis's job," I told him. And although I had a grand total of one year of experience in advertising sales, something about my demeanor, and my aggressive pursuit of the job, must have convinced him I was ready. "Okay," he said after a short interview. "We'll give you a chance. We'll also bump up your salary $3,000 to reflect your new position."

Success! I was thrilled to be moving up—yet there was already a sticking point. I knew how much money Phyllis had been making, and it was considerably more than they were offering me. I could have just thanked the publisher and taken his offer, but I decided to risk asking for more.

"I know what Phyllis was earning," I said. "And I think I ought to be paid the same salary, as I'll be doing the same work with the same responsibilities."

The publisher's face turned the color of a beet. How dare an inexperienced 24-year-old ask for a bigger salary just minutes after getting her first-ever promotion? Didn't I know that moving into a higher position didn't guarantee I'd make the same salary as the person leaving?

Well, no, I didn't. But even if I had known, I probably would have asked for the raise anyway. The upside was obvious: making more money. The downside was...what? That the publisher would think less of me, or even rescind the job offer? Perhaps there was a chance of that, but it was unlikely. Besides, if I didn't take the risk and ask for a higher salary, there was zero chance I'd get it. As ice hockey legend Wayne Gretzky once said, "You miss 100 percent of the shots you never take."

In the end, I didn't get as much money as I asked for, but the publisher did increase my salary above what he'd initially offered. Nothing lost, something gained—it was the ideal outcome for taking a risk.

Which brings us to the second rule for making risk work for you. When assessing the downside of any risk, remember: The worst-case scenario is rarely as bad as you think.

In 1975, after nearly a decade in New York City, I decided to pursue new adventures out West. The draw: a San Francisco–based magazine being published by film director Francis Ford Coppola. It was certainly risky at that point in my career to leave New York, the epicenter of the magazine and advertising businesses, for the West Coast. It was risky to leave Ms. magazine, where I had been the advertising manager for three years and was starting to make a name for myself. And it was risky to leave my friends and colleagues for something unknown, thousands of miles away. But not only was I ready for a change, I fully expected the magazine to take off, and my new life in San Francisco to continue the same upward career trajectory I'd experienced in New York.

Rule 2: The Worst-Case Scenario Is Rarely as Bad as You Think


Within three months of moving to San Francisco, having hauled all my furniture out there and signed a year's lease on an apartment, I could tell the magazine wasn't going to survive. In fact, five months into it, I was so sure the magazine was collapsing that I resigned and went on a skiing vacation. Sure enough, while I was away a colleague called to tell me the magazine had been shut down, with only a note posted at the entrance telling employees that the last issue had been printed and they didn't have jobs anymore.

Talk about a worst-case scenario. Here I was in California with no job, and no real job prospects. It would have been easy to sink into frustration at this turn of events. Instead, I started making calls to reestablish my contacts in New York and to tell people I was on my way back. And as luck would have it, I was able to convince the publisher of Ms. to create a position that would broaden my responsibilities beyond ad sales.

A couple of years later, I had a conversation with Rupert Murdoch. At the time, Murdoch owned just a handful of U.S. media properties, though now he's perhaps the world's biggest media baron. He wanted to know about my decision to go to California. "Would you say that's the biggest mistake you ever made?" he asked.

"No," I told him. "I don't think it was a mistake at all." Murdoch looked at me with surprise. But I really didn't think so—not then and not now. As easy as it would have been to berate myself for pursuing a venture that ultimately failed, I still got a lot out of the experience. I scratched an itch I'd had to move out West and try something new, I made some valuable contacts, and I really enjoyed my six months in San Francisco.

So don't handicap yourself by focusing on the aspects of a gamble you took that didn't work out. Focus instead on what you learned from the things that went wrong, and how you can use that knowledge to your advantage.

Rule 3: Don't Personalize Things That Aren't Personal

Have you ever wanted to suggest something new at work, only to back down for fear people would think it was a dumb idea? Or shied away from offering an opinion or making a decision because you didn't want to rock the boat? Although these are natural reactions, they also show a lack of confidence in your own instincts.

Think of it this way: If you're convinced your idea is a good one—or at least, that it has a high enough potential upside to offset the risks involved—why would you expect others to torpedo it? Believe in your own instincts, and sell your idea. If you don't—who will?

Of course, you have to sell it like you mean it. When you're speaking to someone, do you ever:

  • Insert qualifiers, saying, "I was wondering if we might consider..." as opposed to simply, "Let's try..."?
  • Insert "I think" unnecessarily? I've stopped using that phrase altogether—it only serves to water down your point.
  • Downplay your own ideas with phrases like "I'm probably way off base here, but..." or "This might be a stupid idea, but..."?
  • Talk in circles, trying to head off objections, rather than putting out your ideas as straightforwardly as possible?

It's easy to fall into language traps, most often when you overthink what you want to say rather than just say it. Women in particular are prone to using self-defeating language. But the more clearly you express your ideas, the more seriously they will be taken, putting you a step ahead from the get-go. And don't feel the need to overexplain yourself—have confidence that your ideas are valid on their merits.

In terms of attitudes about their own abilities, people tend to fit into one of four categories. They're good at what they do, and they know it. Or they're good at what they do, but they don't know it or don't believe it. Or they're not very good at what they do, and they know it. Or they're not very good at what they do, but they think they are—or at least present themselves as though they are.

In my experience, more women than men fall into the second category. They're good at what they do, and incredibly valuable to their teams at work—but they continually undervalue themselves. Of the four categories, this is not only the most self-defeating, it's one of the most common. (And by the way, for what it's worth, far more men than women seem to fall into the last category, ascending the corporate ladder on chutzpah rather than talent.) So don't make the mistake of undervaluing yourself and your efforts—you'll only succeed in blocking your own progress.

Rule 4: It's Best In The Long Run To Make Your Life a Grudge-Free Zone

Several years after I became president of Hearst Magazines, a Hearst executive walked into my office with a complaint.

"Cathie," she said, "I just heard there's a meeting this afternoon that I should be in on, and nobody told me about it. I don't know why I'm being shut out, but I should definitely have been included."

"So go to the meeting," I told her. "Assume it was an oversight, and go take your rightful place." She looked surprised, but later in the day she did just that. And as it turned out, she hadn't been intentionally excluded at all—it was an honest mistake. But she'd made a mistake of her own, in forgetting this important rule: Don't personalize things that aren't personal.

Rule 5: Be Generous With Praise—And Careful With Criticism

Offices are kind of like families—you're thrust into close relationships with people you might normally have nothing to do with. And just as with families, this provides all kinds of opportunities for conflict, whether real or imagined.

Yet in my experience, I've found there's actually less real personality conflict than people imagine. All too often, someone takes a stray comment or missed connection as a personal affront, when it wasn't intended that way. And unfortunately, once a degree of friction or mistrust has been established, it often grows into a self-fulfilling prophecy, and problems really do start to develop.

How do you respond when a group of people in the office go out for lunch—and you're not invited? Or when someone interrupts you at a meeting to shoot down your idea? Or when a colleague responds to your e-mail with a sharp critique, cc-ing others in your department?

For many people, the natural response in such situations is to feel not only professionally affronted but personally slighted. Sometimes we're so attached to our own ideas that we can't imagine people having genuine objections to them; we assume it must be a personality thing. And in certain cases it is, of course—but here's a little secret. No matter whether a conflict represents a legitimate criticism, a personality clash, or something in between, you should always treat it as if there's no personal component at all.

Making the choice to view conflict in the office as professional, rather than personal, accomplishes two key things. First, it ensures that you don't accidentally overreact and see a personal component where there is none. Second, it effectively defuses any personality conflict that might really exist. Think of it this way: If someone in the office tries to provoke you personally, what they're really doing is trying to establish dominance or control over you. By choosing not to respond on that level, you deny them that control. There's very little upside to engaging with a colleague in a personal war. It's best in the long run to make your life a grudge-free zone.

Rule 6: Know The Rules So You Know Which Ones To Break

One afternoon at New York magazine, whose publisher I was in the early 1980s, I found myself irritated with the promotions manager. Something she'd done—I don't even remember what it was—set me off, and I went tearing into her office.

I stood in front of her desk, snapping at her, before realizing there was someone else in the office with us, sitting behind me on the couch. I turned to find her husband sitting there, a look of shock on his face. And all of a sudden, I felt incredibly embarrassed. I must have looked like a lunatic, racing in and using that tone with her—something I'd never have done had I known he was there. I took a deep breath, apologized, and walked out of the office.

Rule 7: It's Easier to Ask Forgiveness Than It Is To Get Permission

Over the next few days, I thought about my reaction. If I was embarrassed to be caught speaking like that in front of someone, then why was it okay to do it when no one else was around? Wasn't it better to deal with people in ways you didn't need to hide? Or, more important, in ways you want to be dealt with yourself?

Besides, what had I really expected to gain? Sure, it felt good to let off some steam—but this was a fool's errand. My ultimate goal was not, after all, to make her feel bad or regretful. It wouldn't have helped the team at all if she took my criticism personally, which she was more likely to do considering how I delivered it. The ultimate goal, of course, was to improve her performance, so she wouldn't make such mistakes again. And the more I thought about it, the more I realized there were two ways to help do that: Be generous with praise—and careful with criticism.

When I started at Hearst, I instituted an annual management conference—a chance for executives to get together and talk freely about big issues facing the company and the industry. Because we want people to feel inspired, informed, and energized, we usually hold the conferences at resort locations. We bring in a variety of speakers and encourage our executives to mix, mingle, and share ideas.

A few years ago, as we were planning the event, I wanted to turn up the voltage. I decided to bring in a speaker who would knock everybody's socks off, a man legendary for his speaking skills and personal charisma: Bill Clinton. I knew that having Clinton there would get everyone buzzing, excited about the conference and by extension excited about Hearst. He'd bring the "wow" factor, which employees would carry back to their jobs when the conference was finished.

The only trouble was, Bill Clinton does not come cheap. Because he is one of the most sought-after public speakers in the world, we'd have to be ready to spend considerably more on him than we usually spent on speakers. I was prepared to do that. But I didn't think my boss, Victor Ganzi, would be.

So I went ahead and did it anyway, without asking Vic. Once it was a done deal, I told him we'd gotten Clinton for the event, and his response was what I expected.

"How much did that cost?"

"A lot," I said with a smile. "But it's worth it."

Now, Vic and I know each other very well. I have a track record with him, and we've established an essential layer of trust. The fact is, there are certain bosses I've had over the years who I'd never have responded to in that way. But I knew the rules, I knew Vic, and most important—I knew which rules I could break with Vic. (Remember that lesson: Know the rules, so you know which ones to break.)

After that first inquiry, Vic asked me a couple more times about the cost of hiring Clinton. The final time, he and I were on a plane together. He must have realized there was nowhere I could escape to 30,000 feet in the air, so as we were reviewing some monthly numbers, he looked up and said, "Cathie, you know, you never did tell me how much Bill Clinton's fee was."

I looked right at him and said, "Vic, the truth is, you will never know."

And that, in a nutshell, is one of my favorite rules of all: It's easier to ask forgiveness than it is to get permission.

Cathie Black served as the president of Hearst Magazines, which publishes O, The Oprah Magazine, from 1996 until 2010.

Adapted from Basic Black: The Essential Guide for Getting Ahead at Work (and in Life), by Cathie Black. Copyright © 2007 Cathleen Black. Published by Crown Business, a division of Random House.    

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