A few years ago I attended a party that was broken up by the cops—and when it happened, I was sitting next to my boss. I’ve been invited to a boss’s wedding and gone to dinner with several more. Once, my boss’s boss invited a co-worker and me for drinks at a private social club to which he belonged because I mentioned that I’d always wanted to see it. (Actually, I think I said something like, “Take me to where all the rich people are!” and sent him an appointment reminder through Microsoft Outlook.)
I’ve always gotten along with my bosses and have enjoyed hanging out with many of them outside the office. But not all friendships are created equally, and there’s a distinct line I’ve never felt comfortable enough to cross. There are work friends and after-work friends. There are friends with whom you’ll discuss your love life, friends you approach for favors, friends you drunk dial, and friends you’ll invite into your home even when you haven’t showered and you’re wearing pajamas. Call me old-fashioned, but I just don’t want to watch a Will Ferrell movie and eat Chinese takeout with someone who could fire me.
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To find out if I’m too casual or too rigid with my bosses, I decided to consult some experts. I asked Barbara Patcher, a business etiquette speaker, if bosses and employees can ever be friends. She immediately lectured me about improper relationships. “Are you friends with benefits? Cause that is not O.K.,” she said. (Lord, no. I’d never do that. At least not until Johnny Depp launches a magazine.) “What is the gender balance?” Patcher asked. “Is it male-female? That’s a little tough. What’s the age gap? Is it your immediate boss? If it’s a higher-up boss, they can get in trouble for having friendships with younger underlings. These are all questions that need to be answered.” Talking to Patcher really stressed me out. I’m impressed my boss and I can even have a conversation without a copy of the company harassment policy on hand at all times.
Angie Herbers, a professional HR consultant, told me not to worry, that being friends with a higher-up isn’t that big of a deal. “I actually encourage friendships between bosses and their employees,” she said. “People like to work with people they like, and if you can develop a friendship with your boss, you’ll want to be more productive. You’ll want to worker harder, and you’ll probably want to stay at the company.” Herbers pointed to Zappos Chief Executive Tony Hsieh as someone who develops close relationships with his employees. In the early days of his original company, LinkExchange, Hsieh made a point to hire friends and friends-of-friends, which made the long hours of startup business enjoyable. When he came to Zappos, he cultivated a similar culture and turned the online retailer into a workplace that’s so closely knit its employees now refer to it as the “Zappos family.”
But Zappos’s culture is unusual—so unusual that Hsieh once wrote a book about it—and for every employee who works in a low-key, anti-corporate environment, there are thousands more who toil in Office Space-type cubicles, surrounded by piles of TPS reports. There, befriending the boss might be a little more difficult. Although according to Linsday Cross, a writer in Fort Wayne, Ind., it’s still possible.
When Cross was 23, she worked as an office manager at a beer wholesaler and quickly became friends with a 27-year-old woman named Molly, who just happened to be vice president for sales. They both had children the same age, which meant that they had a lot of conversations about child care. They got along well, so they went out to lunch together, sometimes hung out after work, and quickly developed a regular, nonwork friendship. Then Molly promoted Cross so that she worked directly under her, a move Cross says “bothered some people who had also applied for the job internally. They thought she picked me because I was her favorite.” That made her work harder, which made her a better employee, and surprisingly, her friendship with Molly didn’t suffer for it. “She’s a very straight-forward person, so if she told me something wasn’t right and I had to do it over again, I knew that was something she’d say to me even if she wasn’t my boss,” Cross says.
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Cross and Molly didn’t have many boundaries. But Thomas, 30, who works at a communications company in Dallas, has become friends with his boss’s boss—a relationship that requires definite rules. Thomas says his boss’s boss is significantly older than he is, but because he’s a single man with kids at college, he finds he has more in common with his younger employee than he does the married types who live in the suburbs. “We don’t have families to come home to at night, so we can do other things,” Thomas says. “We play pickup soccer together or go running, sometimes go out to dinner. But I’m not going to invite him to weekend parties.”
The weekend, it turns out, is the most common boundary that people designate in boss-employee friendships. There’s something about a Saturday dinner that’s different from one on a Wednesday. “I talk to my boss about my personal life more than I do some of my real friends,” says Caroline Coykendall, a sales representative for an insurance agency in Las Vegas, who is friends with her immediate manager. “But we’ll never have a ‘Hey, it’s Friday, let’s go get crazy on the Strip’ type of thing.”
O.K., so binge drinking in a casino is out of the question. But what about a lower-key activity, such as inviting someone over for dinner? While Patcher seemed to think anything I did would result in a Monica Lewinsky-style scandal, Herbers said that under the right circumstances, I could have my boss over for dinner. “But do you necessarily want that kind of friendship?” she asked. No, probably not. For one thing, I’d have to clean my apartment first.
Investors are afraid to say the B word, but maybe not for long.