Kim Kardashian's Assistant Got Burned ... So Can You Ever Really Be Friends With Your Boss?

Kim Kardashian's Assistant Got Burned ... So Can You Ever Really Be Friends With Your Boss?

What about when the going gets tough at work?

By Marianne Garvey

Kim Kardashian seemed to be happy with her number one assistant Stephanie Shepherd for so long. The two vacationed together, brunched together ... and even began to look alike. But then Kim canned Steph somewhat abruptly, after the now-ex-assistant complained to Kourtney Kardashian that she wasn’t fulfilled in her job.

This hurts on two levels — one Steph lost a high-profile, likely high-paying job that gave her a platform for her own interests and took her around the world. Two, things got awkward with her boss, also her friend, so when she lost the job, she also lost her pal.

Can you ever really truly be friends with your higher-up? Love each other all you want, the person is still telling you what to do, and that can just get plain weird. How can you be both a good employee and a good friend?

How you met/got the job matters.

In 2009, when Stephanie moved to Los Angeles, she was hired as an assistant to The Real Housewives of Beverly Hills' Erika Girardi, and eventually made her way to Kris Jenner, who introduced her to Kim.

“She had no makeup on and was in her sweats, super pregnant with North. She was just like, 'Look, I need help, Robin loves you and says great things about you; this is what I need. Can you do it?' And I was like, 'OK, sure, I can do that — and if I can’t, I’ll figure it out!' Meanwhile in my head, I was so nervous. Coincidentally we were both wearing French braids... Kim later told me she was thinking 'This girl has good vibes and a braid, I'm into her!’”

The two went on to have a four-year work-friend relationship that worked on both ends until it got a little too cozy.

According to Forbes, where to draw the line on friendship with those you manage — or those who manage you — seems more complicated than ever. “In a recent study, six out of 10 managers admitted that they were uncomfortable being friended on Facebook by their bosses or employees. We’ve all heard stories, or seen personally, how an inappropriate social media photo or post can cause negative professional repercussions,” they report.

Here’s where it gets complicated: while the general rule is that we should avoid building friendships at work that are too close, “current leadership practices embrace connection and openness.”
“In real life, the actual line between personal and professional lives is very thin,” the report says. “After all, we want to work with people we know and like. As for reporting lines, with team-based organizational structures, the term ‘boss’ is relative and shifting.”

And having workplace friendships can have positive effects on both employees and managers. “Our relationships with our co-workers greatly impact our work lives: more than 60 percent of employees who have between six and 25 friends at work admit to loving their companies (compared to the 24 percent who don't have friends at work). In other words, our office relationships have the potential to make us happier and more productive,” says the report.

However, workplace advice site Monster warns that workplace friendships can go sour, and may cost you. 

"Too much socializing impedes productivity; personal or professional information can be revealed to inappropriate people; and cliques may form, leading to favoritism, exclusivity and negativity," they report. "Although clicking with someone on the job can spark a friendship, whether to invest in the relationship may become a deeper issue."

Business owner Kelly Brady, who founded Brandsway Creative, a popular PR firm in New York City which handles celebrity clients, along with hospitality and fashion branding, has a team of 30 she manages — while also managing to be a friendly leader.

"You have to decide between being an authority they respect and caring for your employees. The closer you work together they really do become your friends," Brady tells Personal Space. "It’s finding that balance and making sure they respect you, that they have to follow the rules. Even though they are your friends, if a rule is broken you have to reprimand them. Certain company rules and standards need to be abided by ... As long as everyone is producing results for the company then there’s no reason not to have a friendly relationship. Everyone’s goals need to be aligned."

Brady says it's how you manage your employees, too. No yelling and screaming at her place of business. 

"As a friend it’s a closed door conversation in my office, 'here are the things I feel you're slacking on, here's how it's affecting the company,' and communication is the most important thing. Uncomfortable conversations need to be had, you have to make sure those conversations happen...I pride myself on being a very fair person, I see both sides when I do reprimand an employee."

And she's careful that when she does socialize with her employees, she doesn't go completely bonkers. 

"I go home earlier, I don’t want them to see me in a bad light, I want them to see me as fun, but I know where to draw the line. I learned the balance by having my company for eight years and by growing up myself. It's trial and error." 

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