How to deal with a sticky fingered subordinate and a patronizing boss

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I’m currently managing someone who’s 25 years my senior. He’s a good worker with a long track record of competent but unremarkable service to the company. Here’s the thing — he steals all the time. Toilet paper, those Keurig cartridges, pens. Nothing valuable, but it does add up. When I brought it up with a colleague, she told me everyone knows that he’s been doing it for years and it’s kind of a company joke. Should I say something or look the other way and join a long line of apathetic middle managers? I’m not exactly thrilled with the idea of scolding someone who’s old enough to be my dad.

—J.L., Barrington

If there’s one surefire way to earn the respect of your elders, it’s by showing that you get a funny feeling in your tummy when they steal stuff.

You’re young and you’re relatively powerful. That’s awesome. You probably have an MBA and impressive sideburns. But if you start assessing management decisions based on how uncomfortable they’ll make you feel, I don’t know that you’re long for the corporate world. Employees can sense weakness. It smells like fear, which smells like my Aunt Dolores, who smells like potting soil.

I doubt that your employee’s five-fingered discount reaches the level of embezzlement, and I’d be undermedicated if I said that the road to Enron and WorldCom was paved with pilfered office supplies. But I don’t think you want to find yourself on the wrong side of the blurry line between company joke and larceny. Also, if it’s a company joke, everyone who works with you has kind of a bad sense of humor.

As Bill Bratton may or may not have proved in New York City in the early ’90s, broken windows can make criminals feel more comfortable committing crimes. In your particular case, it may sanction other employees to start stealing things that aren’t office supplies. Most folks are honest, but a couple of Harvard profs found that employee theft costs American companies big. $200 billion a year big.

“As a manager, it’s your responsibility to hold employees accountable,” says Stacia Pierce, a career expert with 21 books to her name. “Start with a warning and let him know next time his actions will be documented and reported,” says Pierce. “If the behavior continues, follow through with the proper procedures set in place by your company to handle this kind of situation.”

What if there’s no procedure for dealing with obstinate employees who line their pocket protectors with company pens? Then it might be time to rethink your employee’s affiliation with the company, not because he’s doing irreparable damage, but because he’s blowing you off. Either that or hide the toilet paper.

My boss just had a kid and she now works from home 3 days a week. But when I asked recently if I could work from my folks’ place in Utah during the week in between Christmas and New Year’s, she said that she thinks it’ll be too hard for me to focus with all of my high school friends home. I think that’s patronizing and kind of hypocritical. Should I just drop it or try to reopen the issue? If the latter, how do I broach the subject without getting personal?

— Jana, River North

I don’t doubt that wintertime Utah is chockablock with distractions, what with all of the Tabernacles and ice-cold non-alcoholic beer. But if you’ve managed to get your work done amid the bright lights and Rainforest Cafes of River North, I think you have a strong case that you’re adult enough to put on the blinders and buckle down in God’s country.

This isn’t to say that you’re entitled to work from home for a week, or that it won’t be difficult to concentrate amid the holiday bustle, or that the dispensations your boss has received apply in any way to you. But in today’s work world, remote connectivity cuts both ways. Four in ten managers expect workers to check work email on vacation and more than two thirds of employees do, according to Entrepreneur. If you’re living in a world where you’re never really off the clock, you should be allowed to reap the benefits of universal connectivity.

Now, that argument probably won’t carry much weight with your boss. Nor will gently hinting at her hypocrisy. “Build the business case for working remotely,” says Caroline Ceniza-Levine, who co-founded the career coaching firm Six Figure Start. “Why are you working remotely instead of taking vacation? What will you work on during that week? How do you plan to stay on track with friends and family inviting you all over the place?”

I’m sure you’ve got good answers to each of those questions, and I’d be willing to bet that none of them is, “Because you have a baby and you work from home.”

Got a question about how to act around the water cooler? Tongue planted firmly in cheek, we’ll find an adult to answer it. Email us at

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