We arrived at the resort after an arduous journey. It was late and we were hungry, so we went straight to the restaurant. GP was sitting at the big table in the middle of the restaurant with about a half-dozen of the waiters and waitresses that report to her. They were eating lobster and drinking wine. Talking and laughing.

We sat down at another table and waited to be served. After a few minutes of being ignored, I cleared my throat to catch GP’s attention. She waved at me, then leaned to the young woman by her side and whispered something. The young woman came over and told us in Spanish, “I’m sorry. The restaurant is closed.”

I was GP’s boss and the GM of the resort. I was there with the principal architect and builder of the entire development. Apparently, that didn’t matter. It was 15 minutes after closing time.

I called GP into my office the next day. “What were you thinking?” I asked. “They’re mis chicas,” she explained. “Mis amigas. We were having so much fun. They really love me!”

Don’t Hire Your Friends… and Don’t Make Friends With Your Employees 

“One of the most important things I’ve learned as an entrepreneur is that the most difficult problems to solve are people problems – and in particular, problems that arise from the personal connections you have with your partners, your colleagues, and your employees.” – Michael Masterson

In 1966, when, at age 16, I started my first “real” business, I hired two of my closest friends to work for me. And it was fine. Between then and 1983, I started and ran a half-dozen other businesses and always hired friends to work for me – with no problems that I can remember.

I began to change my egalitarian view of business relationships in 1983 when, for the first time, I ran a business with more than 100 employees. I hired friends (and even family members) to fill certain job openings. These were hardworking people that for the most part did a very good job. But because of the size of this business, I couldn’t be involved in everything they did. Unlike my earlier businesses, I wasn’t working shoulder-to-shoulder with my worker/friends. I wasn’t able to settle disputes before they began. Nor was I able to resolve personal problems because there were protocols I had to respect.

As a result, I got dragged into some uncomfortable situations. And because I always put my friendships above my loyalty to the business, the outcome was invariably problematic. Feelings were hurt. Productivity was sacrificed. And in two cases (that I’ll never forget), putting friendship first cost me (and my partner) more than a million dollars.

After suffering stubbornly for several years, I made it a rule: I promised my partner – and myself – that I wouldn’t hire friends or family members ever again.

It was a relatively easy rule to follow, and I’ve obeyed it. But I’ve had trouble with the flip side: not allowing myself to befriend employees.

Since I work mostly in publishing and marketing, I have the good fortune to employ lots of very smart and engaging people. Every week, I meet some new employee that has the qualities I seek in a friend: intelligence, good character, and wit. I can’t stop myself from wanting to be friends with these people, even though I know I shouldn’t.

What I do to resist the temptation is tell myself, very consciously, that the desire I have to make friends with them is a sort of mental illness.

I’m serious. I tell myself it’s a morbid combination of narcissism and self-loathing.

And I think, at root, it is. I want to “be there” for these good and interesting people. I want to help them achieve their potential at work. But I also want to help them in every aspect of their lives. In my rational mind, I believe that’s all I want. But in the arrested development of my emotional brain, I want something in return. I want their admiration and everlasting devotion.

It feels to me, as I’m sure it does to you, creepy when I put it that way. And that feeling generally dissuades me.

The Friendship Imperative 

Friendship is a necessary component of a well-lived life.

You can have everything else – wealth, stature, fame, and even power. But if you don’t have friends – true friends – you have a life that is barely worth living.

Yes, friendship matters a great deal. But boss-employee friendships pose problems, all sorts of sticky problems that get stickier as those friendships grow.

Not all of my business partners agree with me on this. Some actually promote work friendships. They say it makes for good company morale and a better work experience for one and all.

Just this morning, I read a loony article in an online business magazine that supported this view. (I will protect the publication and its author out of compassion.)

“Today’s workforce suffers from a lack of work friends,” the writer proclaimed. “Employees need friends to satisfy [their] need for companionship, love, and safety.”

And just in case you didn’t see this coming, he continued with this doozy: “Employees need friendships in dealing with the stress, politics, and hostility that exists in the workplace. They need friends they can turn to when issues arise around sexual harassment, bullying, layoffs, and poor management.”

Really?

I believe it’s impossible to have an opinion like this unless (a) you are an academic specializing in business management, or (b) you’ve never actually employed more than a dozen people.

I am also aware that some CEOs of large businesses promote the idea that “employees matter first” and that if you focus on making your employees happy, everything else will take care of itself and you’ll have lots of happy customers.

This is an equally bad idea. But it’s actually another issue. (We can get to that in another essay.)

A Self-Imposed Dilemma 

I believe in caring about employees.

I believe employers should care about the productivity and potential of their employees and make sure they have the resources to excel at their jobs.

I believe employers should provide their employees with safe and humane working environments.

I believe, too, that employers should care about company morale.

But when business leaders confuse caring about these things with caring about the personal problems or personal happiness of their employees, they put themselves on a slippery, downhill path that eventually involves compromise, favoritism, and all sorts of ancillary problems.

If this philosophy of employer-employee friendship becomes commonplace in the company, the workplace degenerates. The work ethic and, more importantly, the purpose for working become inwardly focused – towards internal relationships and their needs and away from the outwardly focused customer relationships that are the foundation of every healthy business.

Think of it this way: As a business leader, your primary job is not to make your employees happy but to make your customers happy. When you befriend your employees, you are wittingly or unwittingly telling them that customers come second. That is a very damaging and debilitating message.

If you don’t agree with what I’ve said so far, you need to know this: Your employees don’t need your friendship. And if they are smart, they don’t want it. They will see your effort to befriend them for what it is to them – a burden that will one day make their business lives heavier and problematic.

What your employees want from you, and deserve from you, is your support and guidance. They want ideas and mentorship. And the best of them will want you to give them the freedom to work on their own. The fact is, however good it might feel, it is difficult, if not impossible, to provide those things within the boundaries of friendship.

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