Let me make it clear up front that I'm not calling anyone a devil. But at what point does your employee become your friend and at what point does your friend become your employee?

This is one of my least favorite questions. And I get it more often than you'd think.

My own work history isn't any different than most. One of my best friends in the world is someone I hired almost 25 years ago. And one of the worst enemies from my past is someone who hired me. I'll probably make a few more enemies by the end of this post.

But that's OK, because we probably weren't friends to begin with. We just worked together.

Friends Versus Employees

A couple of weeks ago, Teaching Startup got a question from an entrepreneur who had just closed his first major B2B deal, and now needed to hire up quickly to meet the terms of that deal. Fortunately, money wasn't an issue, as the customer had already paid, but time was very much of the essence. 

So should he just hire his friends and former co-workers or what?

One of our advisers, Rachel, gave a crisp and thoughtful answer based on her experience hiring friends and family into her many companies, and she went into both the good and the bad. 

But I want to talk specifically about friends versus employees.

The problem with hiring your friends, family, or even just former co-workers is that you're assuming, or even just hoping, that the dynamics from one relationship can translate into the dynamics required by the second relationship. 

This never happens. And the determining factor in whether both relationships survive, personal and professional, depends on how ready you are for that problem to get ugly.

Never Say Never

OK, so as a rule I never hire my friends, but it's a rule I'm ready to break for the right reasons and under extenuating circumstances. In those situations, I know I'm going to get burned, so it's a rule like "Never get on the highway at 5 p.m. on a Friday." You know it's going to happen at some point. You just need to be prepared. 

Let me also make clear that you should never give your friends or family any unfair advantage over otherwise qualified candidates or employees. This isn't about that, and I trust you to be ethical. Even when others are not.

That said, there are always exceptions to any rule. I've worked with my friends before. The friend who started as a hire long ago, I'd hire him again in a heartbeat if he weren't so expensive. And there are probably four or five former hires and co-workers I'd pair up with again, for the same reasons. I hired my teenage kids for one of my side projects, but that's more for their sake than for mine. (Although, to be honest, they don't think that. They think they're saving my company.)  

And before I lose even more friends, don't get me wrong. I'm not saying I don't want to help my friends. I'd do anything to help my friends. Need is one thing, opportunity is another. I'm just saying working for me is no picnic, and I wouldn't do that to them.

So, yeah, if I had a desperate need for talent on a moment's notice, I'd break the rule. You always get that kicker of communicative familiarity and mostly properly set expectations hiring someone you already know or have already worked with. 

You lose out on a lot, though. Including all those things you don't know that you don't know.

Make Friends With Your Co-Workers

Before I went full time into entrepreneurship and technology, I was on a dual career path as a technologist and a working musician. My dad was also a musician who happened to dabble in entrepreneurship on the side.

One of the best pieces of advice he ever gave me was this: Never start a band with your friends, but always make friends with your bandmates. 

It's a good philosophy to take to the workplace. 

There's the devil you know and the devil you don't. And, honestly, the only reason we swing toward the comfort level of hiring people we already know is to not have to deal with the devil we don't know, 

But the devil is still in the details. 

Like I said before, the people I know whom I would hire are never available when I need them. Hell, most everyone I know is working, happily, and not available when I need them. If they were available, and if they really wanted to do whatever I needed them to do, and they really thought they were a fit, they'd raise their hand and slide into the pile of candidates for whatever position I had to offer. 

Why break that logic? And why risk that friendship?

So, yeah, never should probably be never. Hiring friends and family sounds like a quick and easy solution to a difficult problem. But outside of the reasons I mentioned earlier, which are more opportunistic than desperate, I can't think of many good reasons to fall back on familiarity to get a jump on getting the right talent in place.