Should You Work With (or For) Friends?

Should You Work With (or For) Friends?

In college, most of us learned that living with friends can actually be pretty tricky business. So when the question is whether to work with your BFF, the pressure's much higher.

So should you work with a friend? The usual advice goes something like this: 

No. Never. 

And...that's the end of this article.  

Gotcha. If there’s one thing we can agree on, the working world looks a whole lot different than it did when our parents or grandparents were sharing that little piece of wisdom with each other. These days, we’ve traded cubicles for entrepreneurial ventures and office hours for coffee shop meetings. So it’s unsurprising that the whole friends-as-colleagues thing has become something of a trend.

THE SHORT ANSWER: YES

Why? Because embarking on a business venture with a friend might actually improve your chances of success and innovation. The two of you have already built a relationship based on shared experiences, trust, and mutual passions. That’s much harder to do in the workplace than you’d think.

The biggest issue with working with/for friends is pretty much the same one that affects all serious relationships: communication and boundaries.

Recent studies show that we spend less time making friends at work than previous generations. While it’s not entirely clear why (some argue it’s caused by the rise of remote work), there’s no question that we’ve become increasingly dedicated to our computer screens and less enamored with the water cooler breaks and lunch chats required to build strong, lasting relationships. And that lack of personal engagement is not good for anyone.   

In an op-ed piece last year, New York Times columnist, Adam Grant pointed out:

“We may be underestimating the impact of workplace friendships on our happiness — and our effectiveness. Jobs are more satisfying when they provide opportunities to form friendships. Research shows that groups of friends outperform groups of acquaintances in both decision making and effort tasks.”

THE LONGER ANSWER: YES, BUT ONLY IF YOU’RE WILLING TO GET A LITTLE UNCOMFORTABLE

Since Americans are finding it harder and harder to make friends at work, it seems logical that creating work with friends would be a great answer to the personal-yet-professional crisis going on in our offices. But for every success story about friends who work together, there are as tales of total, utter failure. One misstep and you might lose a friendship forever. Bleak. 

The biggest concern when working with/for friends is pretty much the same one that affects all serious relationships: communication and boundaries. 

You may think you and your BFF are great communicators. Maybe you two are so close you finish each other’s sentences. It can still get indescribably complicated.

If you’re unhappy with the work you two are doing, you have to speak up. Early, immediately, often, always.

The Oreo Effect

Remember that roommate who ate all your brand name Oreos but would only buy the stale, off-brand Kroger ones when it was her turn to grab groceries? (Clearly, I'm still stinging from this). 

The Oreo incident (and others like it) demonstrates two major and common communication breakdowns: 

1. You failed to set clear rules for the dynamic, i.e. “Desserts and snacks are not shared groceries. We’ll each buy our own,” and 

2. You probably failed to bring up the issue when it happened the first, second, or even third time, letting it fester until you find yourself writing about it seven years later.

Replace the word “Oreo” with “$50,000 small business loan,” and you’ve got a major disaster on your hands. 

So, work with your friends only if you’re willing to get a little awkward. There’s no room in the dynamic for passive aggressive behavior, letting things slide, or hurt feelings. If you’re unhappy with the work you two are doing, you have to speak up. Early, immediately, often, always.

The Power Play

And that brings us to maybe the most troubling element of all: the power dynamic. If you’re considering working with a friend on a project where you'll assume equal roles, you’ll need to assign clear responsibilities so one friend doesn’t wind up stepping on another’s toes. 

Multiply that process by ten if you agree to work for a friend. You may be on equal footing when you’re out for drinks or splitting a restaurant tab, but if you agree to work for her, that dynamic has no place in the office. In the end, no matter how much she listens to your advice or ideas, she’s the one calling the shots—and making final decisions. If you want to make working with or friends work, you're gonna have to let go of that whole pride thing.

CONCLUSION

The benefits of working with friends are indescribable. You’re walking into an office with a sense of shared purpose and passion, you know that your colleague has your back, and you can push each other in ways that most formal work dynamics don’t allow. Just make sure you make communication your top priority. After all, if you value your friendship, it’s worth putting in the extra work, right?  

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