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Our vice-president had a laptop stolen from his car, loaded with details of the potential acquisition of a competitor. What should we do?

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Joe McKendry/The Globe and Mail

Cyber nightmares can happen to the best of us, even security expert Terry Cutler. “Years ago, I went for a business dinner and left my computer in my truck,” he says. Cutler had protected himself in advance—encrypted hard drives, strong passwords, multifactor authentication and so forth—but let’s assume your VP is not as security-savvy. “If you’re lucky, the laptop was stolen by some common thief who has no plans but to erase everything on it and sell it,” says Cutler. “But anyone with IT knowledge is going to want to know what’s on it. And if you’re especially unlucky, the theft could be a targeted act that leads to extortion.” However unlikely the latter, this is no time to take chances. “You need to report to the police, and you need to confess to your client,” says Cutler, “because if you don’t tell them and their information gets compromised, you’ll be sued out of existence.” This disastrous worst-case scenario far outweighs the momentary embarrassment of admitting to a breach—not to mention the looming dread of if (or when) the mistake will be discovered. Honesty is the best policy, as it often is, and then you can file this incident under lessons well learned. “Secure your computers and accounts, hire a professional if you don’t know how, and don’t ever leave your laptop in the car,” says Cutler.

Can I make it company policy that we don’t hire smokers?

If it’s your company, you can do whatever you want. But before you make this official policy, stop for a minute to consider all the reasons why you shouldn’t. “This primarily engages human rights legislation,” explains employment lawyer Stephen LeMesurier at Monkhouse Law, “which prohibits discrimination when hiring based on protected grounds.” Don’t recall a citizen’s right to hack butts? “Smoking isn’t a protected ground, but it could be considered an addiction, which is considered a disability,” says LeMesurier. Human rights complaints regarding smoking are rare, though most recently one popped up in Kelowna, B.C. (the employer quietly settled). Unless smoking somehow affects a worker’s ability to do the job—if they’re a nutritionist or a Nicorette salesperson, for example—any official written policy is not worth the legal risk of asking someone if they’re a smoker. If you’re anti-smoking, consider shifting your efforts by offering resources to help smokers kick the habit instead.

Am I out of touch if I don’t think baseball hats should be worn at work, even on casual Friday?

Just as every office is different, says fashion consultant Anja Potkonjak of Alphamale Styling, all baseball hats are not created equal. Potkonjak has been styling men for 14 years, during which time she’s seen a workplace fashion shift that—sometimes, maybe—includes baseball hats. “There’s certainly a particular startup culture of young CEOs like Mark Zuckerberg who wear casual jeans and T-shirts, and there are fashionable men out there who can dress up a hat and make it work, but in general, baseball hats are too casual for corporate,” she says. (Ditto sweatpants and sandals.) That said, know that a staunch no-hat policy directly undermines so-called “casual” Friday, and you don’t get to have it both ways—unless you get creative. “I’d try to make it fun and suggest a monthly Baseball Hat day,” says Potkonjak. Hopefully, cap-wearers will read the subtext and leave that thing at home the other 29 or so days of the month.

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