Meet the shadow boss

Behind every boss, you’ll find someone else running the show — the bad ass in the background. They know math. They can actually use programs like Excel. They keep meetings under 30 minutes. They listen and take notes, instead of talking until everyone’s eyes glaze from boredom.

While a boss obsesses over branding and logos, the shadow boss makes sure the printers have toner and paper. They focus on important things like the functionality of your website, keeping the list-servs updated, and editing the weekly schedule. Sound boring? Try running a business where none of the tech works, and nobody knows when they’ll get paid.

A shadow boss may not wear the most expensive suit, and might even show up to the office in jeans and sandals. They remain calm in a crisis, and they value action over speeches. They use as few words as possible to convey their ideas. Above all, they like to empower their employees.

I’ve had plenty of bad bosses. No place suffers from poor management like the restaurant industry. Throughout college, I waited tables and cooked pizzas under the direction of dick heads— overgrown frat boys who showed up hungover and braggadocios about the booze they consumed, only to turn around and fire people for doing the same thing.

One time, a restaurant manager forgot to order bread for the week. We were a deli-style restaurant without hoagie rolls or buns. The manager wouldn’t even accept blame. First he went on a rant about “who let this happen,” until one of us pointed out that nobody else besides him had the authority to make supply orders. Nevertheless he made us tell the patrons ourselves, who sneered at us as they walked out. Luckily, we had a shadow boss — an associate manager. While our dickhead big wig had a meltdown in his office, our shadow boss drove to a supermarket and saved the day.

A shadow boss doesn’t like the spotlight. They melt under it like vampires at sunrise. A shadow boss will never try to give a rousing speech at the start of an 8-hour company retreat. Instead, they get shit done and send out brief email announcements.

Maybe the shadow boss earns less money, and in theory enjoys less prestige. A shadow boss might be younger, quieter, and more internally confident. They don’t need the external affirmation of applause.

Every great boss starts out as a shadow boss. Nothing trains you for leadership like shadowing a bad boss and poor leader.

For a while, I worked at a bar for extra cash. The owner was a huge jerk, and also a bad businessman. He actually looked a lot like The Donald, and acted like him too. He often suspected us of stealing money from him and milking the clock. Once, he even accused some servers of vandalism when someone busted a window and spray-painted the word “Dick” on the front door. He started a fight with a customer once, and got his nose broken.

And yet the bar turned a huge profit for this asshole. Why? He had a shadow boss. The bartender was a seriously cool chick. She made excellent drinks, trained people well, and showed a lot of respect to the wait staff. The bartender managed the day-to-day finances, and even designed the drink menus. Only one or two of us ever knew how much she did to keep the place running, but she didn’t care. She just loved her job.

Eventually, the owner got busted for shady practices with his other businesses. The bar closed for 2 years. But the bartender used the money she’d saved up, got a loan, and used her connections to reopen the place. Now she’s the owner, and business is booming.

I’ve learned a lot from shadow bosses, and so you can you. The person taking all the credit may not be the real deal. Ignore the loud braggart who won’t shut up about brands and logos, the person who seems to talk a lot but says very little. Focus on the quiet associate in the corner. They’re the person to model your career on. Sooner or later, big wig bosses get their comeuppance. Their careers end. The shadow bosses of the world play the long game, and usually come out on top.

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