Is Hiring My Friends Always a Bad Idea?

Q. Can you do business with a friend without damaging the relationship?

A. Years ago, when I wanted to sell my first house, I gave the listing to a friend who had just gone into real estate. The honeymoon didn’t last long. Over several months, we butted heads on how to price, stage, and market the house. Things grew tenser still when the house didn’t sell. Finally we sat down to talk. “It’s not about you,” we blurted out almost simultaneously, then burst into laughter. My friend concluded, “Let’s agree that working together was a failed experiment.” Then we went out to lunch.

We’re still close because we acknowledged our differences without blame, just as we would have if we had disagreed on a personal matter, such as how much we each liked The Hunger Games. At the end of the day, business isn’t as important as a friendship. While you don’t need to shy away from hiring (or working for) a pal, you do need to anticipate possible pitfalls. Before you turn your friendship into a professional relationship, consider the following questions.

Who’s going to be the boss? Pals are on an equal footing. But in a business transaction, one of you is paying the other to perform a job, which creates a power imbalance. If your friend is going to hire you, you need to be prepared to implement her vision and to work harder to make her job easier (which is what any good employee does for the boss). If you’re going to be calling the shots, ask your friend if she will feel comfortable taking orders from you.

How close are you? If this is a dear friend, you may want to think twice before changing or compromising the nature of your relationship. For example, if you are suddenly working for the same company, you may no longer be able to vent about, say, how much you sometimes hate your job.

Do you admire her work? Or do you simply admire her as a person? If it’s the latter, you won’t be doing your friend any favors by putting her in a situation in which you’re unhappy and she’s not able to shine. So, sure, go ahead and hire your brilliant, award-winning decorator friend to redo your living room. However, if your pal’s work is merely adequate, don’t sign on the dotted line.

Do you have similar work styles? Maybe one of you is always scrambling to meet deadlines while the other is organized and detail-oriented. In a professional setting, those differences may drive you crazy. Think about the times that you’ve met for dinner: Is one of you always early and the other always late? If so, before you forge a business connection, discuss how to manage these differences.

Will the relationship be easy to break off? Permanent employees are just that—permanent. Meaning, if your old college roommate makes a lousy sales rep, you may need to fire her. Ouch. It’s easier to risk hiring a friend in a project capacity. That’s because even if it doesn’t work out, there’s already an end date in sight.

—Michelle Slatalla