Hiring friends is a lose-lose situation. Oftentimes, the day that you hire one of your pals will also turn out to be the day that you’re no longer friends. When your title abruptly changes from buddy to boss, it brings with it all of the nuances of being the person in charge, a responsibility that can result in resentment, no matter how well-meaning each person in the relationship is.

On the short but complicated road from weekends at the beach house to Mondays in the boardroom, the lines between comrade and colleague can become muddied. If friends-turned-employees don’t deliver in the workplace, the employer will eventually begrudge them. If the employer has to cut a friend’s pay or is forced to fire him or her, then the friend/employee may be left with hard feelings that will undoubtedly find their way into your personal relationship. This kind of conundrum can result in a painful ultimatum: being forced to choose between a friend and the business that you worked so hard to build.

See also: The 4 Things You Must Do Before You Hire a Friend

Throughout my career, I have experienced the repercussions of hiring a good friend on two occasions. Luckily, at least one of the two relationships survived the turmoil, but that’s not to say that I would recommend this strategy to the next generation of businessmen and women.

In one instance, I hired a close friend who I thought would bring an interesting perspective to the business based on his previous success. When I decided to hire him, my expectation was that he would immerse himself into the business and bring fresh ideas on how to improve it, but that isn’t what ended up happening. In the end, it only caused resentment between the two of us. Inevitably, I needed to let him go and we went our separate ways—both in business and our personal relationship.

I also once worked with a man who was, and still is, one of my best friends. Beyond the confines of the office, our families vacationed together, but our working styles kept us from seeing eye to eye when it came to the business. As time went on, it became increasingly difficult for me to see the value in our business relationship. Eventually, I realized that the only viable solution to keeping our friendship copacetic was to dissolve our business relationship. We ended up selling the company and both moved onto new business opportunities and were able to keep our friendship intact. But I don’t think that situations like this are the norm.

When hiring friends, setting expectations early on is key, otherwise, boundaries will be blurred and lines will be crossed. Oddly enough, in my experience, hiring friends has proven to be frustrating, while working with family has proven to be a success—go figure.