Why I regret being a nice boss: Setting boundaries with employees.

Why I Regret Being a Nice Boss

Why I Regret Being a Nice Boss

Small businesses, big ideas
Oct. 2 2014 3:47 PM

Why I Regret Being a Nice Boss

If I could have a do-over, I would set tougher boundaries with my employees.

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The manager of a very nice place should not be very nice.

Photo courtesy Carli Jean Miller/Unsplash

Recently I met a friend at one of my favorite coffeehouses on the Upper East Side in Manhattan. I don’t live in the neighborhood, but I’m willing to go out of my way because the place has good coffee, a tranquil atmosphere, and free Wi-Fi, and there’s always a place to sit. When I arrived, though, I found that the place had changed. There were signs all around in red ink: “You MUST buy something if you are going to be here.” “WIFI is now $10.” A woman whom I presumed to be the owner could be overheard lecturing the staff to keep their breaks short and remarking that disgruntled customers would just have to deal with the new Wi-Fi policy.

As the owner hovered tensely around the tables, my friend and I felt watched and unwelcome. “Our” place was ruined, and it was the owner’s fault! But with my irritation came a pang of recognition. I had been in the owner’s shoes; I knew firsthand that her prickliness was likely masking desperation. This business is struggling, I thought. Perhaps it was even on the precipice of financial ruin.

In 2012, after two years of business in Washington, D.C., I closed my coffeehouse-cum–yogurt shop, Yola. As much as we tried to minimize expenses, we faced one insurmountable obstacle: The rent was too damn high. These days, our failure to foresee that obstacle doesn’t bother me much. But watching the woman on the Upper East Side reminded me of those less obvious failures that still nag at me two years later: the moments when I wasn’t a good manager. I could see parallels with my own mistakes; though she was lashing out at her customers and employees, those people weren’t the problem at all. The problem was structural.

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When you open a small business, you are making a statement about what you expect of customers and employees. This woman had built a cozy place with plenty of seating and free Wi-Fi; therefore, she was sending the signal “Come! Stay all day!” So people did. Presumably she also sent a signal to her employees to take ill-timed or over-leisurely breaks. Almost every “person problem” is really a structure problem—a crack in the system where the rule-makers have failed to effectively communicate with the rule-followers.

Back when I ran Yola, a quotation attributed to George Patton often came into my head: “Never tell people how to do things. Tell them what to do, and they will surprise you with their ingenuity.” Personal ingenuity flourishes when there is a strong structural foundation in place—when people know exactly what is expected of them. Yes, telling grown adults when they can take breaks, exactly how to slice a scone out of a baking sheet, and exactly how many minutes late they can be before getting a “write-up” feels paternalistic. But it eliminates the uncertainty at the root of most management-employee clashes. I hated writing up employees; it felt like the adult equivalent of a time-out, and I resisted it for a long time. When I finally did it, I met with the employee in the basement to discuss the situation. The interaction was surprisingly pleasant; he even looked relieved. And the effects reverberated among the other staff as well, putting an end to what was becoming a tardiness trend.

Not all businesses require that level of micromanagement. But establishing which rules are non-negotiable, and making sure that everyone understands them with crystalline clarity, is a matter of fairness. It’s the thing I wish I could go back and do over—not because it would have saved my business, but because everyone, myself included, would have been so much happier. I allowed my coffee shop to become characterized by permissiveness. Some took advantage of this permissiveness by making up excuses for being late, or by trying to do as little work as possible. Those who didn’t take advantage became resentful of the other employees, and of me. It brought out the worst in everyone.

Recently, I’ve been reading a lot about failed and despotic governments, and I’ve realized that these regimes have some parallels with failing businesses. The most fascinating parts of David Remnick’s account of the fall of the Soviet Union, Lenin’s Tomb, deal with the ways that depraved systems cause ordinary people to behave badly: “The system made beasts of them,” Remnick writes. Most people are only as good as their systems allow them to be. In my case, by trying to give my employees personal freedom—by trying to be nice—I created inadequate systems that didn’t allow them to thrive.

The idea that we must tell adults what to do and exactly how to do it is a hard pill to swallow for most. Writing about it now makes me pleased that I don’t have to do it anymore. But instead of thinking of it as telling people what to do, what if we see it as simply providing people with boundaries? That’s closer to something palatable, although the paternalism still makes me cringe. Since this kind of boundary-setting is what a food-industry boss needs, it seems there’s little hope for me in that line of work.

However, there could be hope for the woman on the Upper East Side. Though she appeared to be behaving badly, she was—in terms of the business, at least—on the right track. She was reassessing her vision for a coffee shop, trying to make it a place where people don’t sit all day and mooch off the Wi-Fi and where employees take well-timed breaks. She’s in the midst of finding the sweet spot between meeting her employees’ needs and doing what it takes for her business to survive. I’ve heard that she’s now reversed her $10 Wi-Fi policy. With a little grace and more thoughtful communication, she may yet turn her place around.