We’ve all seen the boundaries between our personal and business lives all but disintegrate. More and more, we’re becoming friends with coworkers. But what about employees and bosses? Should they be friends?

Over the years I’ve had loads of friends that were also employees. I’ve even called a few CEOs friends. While I’m still on good terms with many of them, there are only a few I would still enjoy hanging out with, and vice versa. And I’m definitely not alone in that regard.

There’s no single reason for the phenomenon, but if I had to boil it down to one sound bite, I’d call it drama. When you work closely with someone there’s always going to be some drama. In time, that adds up to a lot of water under the bridge. And when it’s over, you’d both just as soon put it behind you and move on.

It’s a lot like marriage and divorce. You might stay on good terms for practical reasons. You might even stay friends. But you’re not likely to spend a lot of time together once the dust settles.

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Taking the marriage analogy a little further, I think we’d all agree that it’s better to have loved and lost than to have never loved at all. By that logic, I certainly wouldn’t dissuade anyone from being friends with employees. But in hindsight, there are some tough situations I might have handled differently if I knew then what I know now.

It’s all fun and games until someone gets fired. It’s hard to sit a friend down and tell him he’s screwing up. And it is downright gut-wrenching to have to fire him when he’s not cutting it and really should move on. But when someone you used to call buddy is vindictive and tries to get back at you, that’s when your skin starts to thicken up. It’s happened to me more than once. Be prepared.

When disruption becomes toxic. I cut my teeth in an industry that places enormous value on constructive confrontation. Healthy conflict is critical to making smart business decisions and sometimes it gets heated. But when an employee is consistently disruptive or acts out because he thinks he’s in with the boss – to the point where the team can’t function effectively – he’s got to go.  

When work is like The Real Housewives. I don’t know about you, but my friendships tend to be fun but boring. In other words, there isn’t much drama – certainly not like what you see on your average reality TV show. But work is another story. There are all sorts of pressures, politics and controversies. There’s even the occasional envy and resentment. It can get pretty dramatic and there’s only so much a friendship can take.

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Conflicts of interest. If you’ve never been a corporate officer, let me introduce you to a concept called fiduciary duty. It means you have to act in the best interest of the company. Believe me, there are plenty of situations (compensation and promotions, for example) where personal bias represents a serious conflict of interest. Yes, cronyism is rampant in bureaucracies, but I don’t buy into it and neither should you. 

Boundary issues. A friendship is a partnership. Granted, one often has the upper hand, but that’s behavioral, not organizational. Companies, on the other hand, have hierarchies and there are very good reasons for that. Most of the time, that’s not an issue. But there will always be times – challenging times – when professional boundaries and personal relationships are tested.

If you’re looking for a formula for dealing with this sort of thing, don’t waste your time. While it’s nice to have a little foresight into situations that may very well come to pass, that doesn’t mean you can prevent them from happening. Just be forewarned and prepare as best you can.

One thing’s for sure. Personal relationships are unpredictable. So are business relationships. When you combine the two, you get unpredictable squared. 

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