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Just Friends? What To Consider Before Befriending Your Boss


First Posted: 01/30/2012 6:00 pm Updated: 01/30/2012 6:00 pm

Jennifer Winter | The Daily Muse

One of the first things you realize about professional life is that you're going to be spending the majority of your time in the office - with your colleagues. And if you're lucky, some of those colleagues will become friends.

Bonding with your peers in the office is a no-brainer, but it took a friendship with my boss early on in my career, and relationships with my staff later on, to clue me in about the complicated business of befriending your boss.

If you're fortunate enough to have a manager that you actually want to spend time with after hours, that's fantastic! But, before you start planning dinner parties and introducing her to your significant other, there are a few key things to consider.


What Will People Think?

You may think that your new BFF at work is your business, but the truth is, everyone from senior management to the admin staff will notice your relationship - and they'll have an opinion about it. Make just one mistake, or even get that promotion you've worked so hard for, and the water cooler conspiracy talk begins.

Take a lesson I learned in one of my first positions as an example. I enjoyed my job, did well my first few years, and was even promoted. Over time, I developed a friendship with my boss (one of the few other women in our office) as we navigated the murky waters of the boys' club together. Although my success was in no way tied to my friendship with my boss, the guys I worked with often teased me about being the boss' "favorite."

It was all in good fun, until it was announced our team was being phased out, and that everyone was being laid off. Everyone, that is, except for me.

Those good-natured jabs quickly turned into bitter accusations of favoritism. While I'm sure people would've been upset that I was the only one left standing regardless, had I not been friends with my boss, the fallout would've been much less painful for everyone.


No Secret is Safe

In a standard boss-employee relationship, there are some things you just don't discuss with your boss, and vice versa. But when you become friends, that guard comes down and eventually you'll divulge information you normally wouldn't dream of mentioning at work. As a result, you end up arming the person who has the power to promote or fire you with your dirty little secrets.

Chances are, even if your boss has some skeletons in her closet as well, this will eventually come back to bite you - which is exactly what happened to one of my former employees several years ago. At lunch one day, I asked how she was doing. I'd noticed her performance was slipping, and she was constantly late for work. Because she felt we were friends, she confessed she'd been partying quite a bit, and even admitted to coming in to work while still a little tipsy from the night before!

Naturally, as her manager, I had an obligation to watch her like a hawk after that, which made life miserable for both of us. Understandably, the friendship ended and she eventually resigned.

While this example is a bit extreme, the point is this: Regardless of how close your friendship may be, don't tell your boss anything that could come back to haunt you.


It's Business, It's Not Personal

Managers are tasked with keeping their teams running and performing at optimal levels, which requires giving constant feedback to their employees.

Hearing feedback from anyone is tough, but add a friendship into the equation and the potential for awkwardness and hurt feelings skyrockets. I've experienced this both as an employee and a manager, and it ain't pretty from either side.

As an employee, I tended to waste precious time over-analyzing why my boss would've said "something like that to me" when I should've taken that time to focus on improving my work.

As a manager, I found it so much harder to coach my staff when I knew they viewed me as a friend. Knowing they could take my suggestions personally, I ended up spending a shocking amount of time coming up with ways to sugar-coat my feedback. As a result, my message was often a watered-down version of its former self, and far less effective.


Don't Break Up With Your Boss Just Yet

After considering all these points, you may be contemplating how to end your friendship gently, or how to avoid a boss-friendship altogether.

But while this relationship is a potential minefield, it's in no way impossible. In fact, as my career has progressed, I've had several friendships with my bosses, and one of my most rewarding work relationships grew out of a friendship with one of my employees.

The key to success really stems from one important skill: Can you truly separate what's business from what's personal? If you think you can, and you're aware of the risks - go for it. But if you tend to overshare with your pals, or if you still feel your eyes well up when being corrected on your spreadsheet formatting, it's probably best to keep it professional for now.

Jennifer Winter is a 13-year veteran in financial services, and an aspiring writer and entrepreneur. Originally from Montana, Jennifer has a great appreciation for the outdoors, and takes advantage of all the Bay Area has to offer whenever she gets the chance. Hailing from Oakland, Jennifer is always up for a glass of wine, great conversation and people watching. You can find her on Twitter @fearless_jenn.


This post originally appeared on The Daily Muse.


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