The Motivating Mark of Humiliation

By | July 23, 2015

I had a friend who used to be amazed that I could start almost any anecdote with “Back when I was a…” and then interject a career path as far flung from my current one as you could think of… over and over again. It doesn’t really speak well for my ongoing search for career satisfaction, but it sure helps add flavor to my anecdotes. That said…

Back when I was an insurance salesman, I had one of the best bad bosses ever. RJ looked a little like Mick Foley after a hard round in the steel cage, minus the blood. His shirts were ill-fitting, he smelled of chronic cigarette abuse, and he gave not one fuck to anyone not deserving a fuck, most especially the slacker agents he had working under him. As far as RJ was concerned, the sad sacks working his desks were just hoping to skip from paycheck to paycheck on the merits of our company’s reputation, and not actually do any selling.

foleyGreat job on the Simmons account, Clary. GET BACK TO WORK!

To be fair, this was true of some people. Most of us, though, worked as hard as we could to make minimum quota (16 policies a week) for fantastic commissions (IF you made quota. Otherwise it was minimum wage for the week). We worked hard for the money, but we also worked hard to avoid the Pineapple.

Before I explain what the pineapple was, let me flash forward 20 years, to the mystical future world of 2014. It’s a different era. People are sensitive toward each other’s feelings. People are more concerned with the well-being of their fellow workers and managers most definitely don’t say mean things about their employees. They certainly don’t ever ridicule an employee who’s done poorly. To do so looks bad, and looks are far more important than actually solving problems through decisive leadership and (gasp!) targeted bullying.

Earlier this year I recommended that — in order to turn a company around that was suffering from massive creative and performance stagnation — we publicly mark employees who’d failed to meet their expected development targets for the week. The company was spinning its wheels and could not get projects done on time, ever, mostly because of an powerful sense of inertia caused by certain employees stonewalling in every way possible.  My recommendation was that we give them something like The Pineapple, but in a good-natured, happy way, so as to not upset the “Good Energy” we all had from working happily, and without conflict.

b72d0139632ace99d8e879dddbec2ace[1]It looked exactly like this, except it was stuffed (like a Teddy Bear)
so RJ could HURL IT FULL FORCE in his wroth


If you didn’t make quota at our agency (a very popular, very well-known high-risk auto insurer in the Los Angeles area), you didn’t make good money. Motivator number one. If you didn’t work late every night until you made quota for the week, RJ would hound your ass every minute of the next day to make sure you did. Motivator number two. If you were 90 seconds late to work (“Doors open at 8:59, you better be on the phones by 9:01, cupcakes!”) you got your ears chewed off and fed to rabid dogs. Motivator number three.

But the Golden Pineapple of Shame was reserved for the worst of the worst. The lowest of the low, the most wretched and villainous of the wretched hive of scum and villainry that was our office. The Golden Pineapple of Shame went to the employee who made a mistake. And if you got the Pineapple, it was yours for the rest of the week or (if you were lucky) someone else messed up worse.

RJ would deliver the Pineapple like a big league closer delivering the last pitch of the game. High, over the plate, and 120 miles an hour. That’s how mine got delivered. “DAN!” he shouted (I, uh, went by Dan when I worked here, for reasons that are, quite possibly, another blog post). “THIS ONE IS YOURS!” You could see the heads of the other agents ducking and know exactly what was coming. The Golden Pineapple of Shame.

See, I had misquoted a guy on his insurance, and not just any guy, but a radio host — on the same radio station as the not-yet-famous Ryan Seacrest. He was a pretty big deal, and if he got mad that he’d been quoted one rate… only to find out after he’d left that the rate was actually substantially higher (it was)… well, that was a huge hit for the company. Pineapple earned.

The secret of the Pineapple was this: the mistake by itself was pretty bad. Most people would go “Crap. I can’t do that again.” Others might not take it so personally. “It’s just a job,” they’d say. “Whatevs.”

But if you had that pineapple on your desk, every day reminding you of your failure. Reminding you of how you utterly screwed up so badly the boss needed to make an example out of you? That stays with you. That haunts your dreams, and if you can help it… you NEVER make that mistake again.

Motivator number four. Bam.

I believe our society is missing its Golden Pineapples of Shame. People are content to go about their business and be mediocre. There’s no shame in doing lousy work, or being a poor citizen, or letting your neighborhood fall apart while you play Xbox and complain about your health care benefits. There’s no one smacking you in the head with a stuffed pineapple, shaming you into doing a better job, taking pride in your work, and focusing on NOT making mistakes.

I learned a lot from those crazy Scientologists. I heard they ran into some problems a few years after I left, but I bet RJ is still there, quietly seething because he’s not allowed to shame his employees into better work. Think you know which insurance company I used to work for? Give you a hint: “I can’t take that bet.”

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