Illustrations by Ingo Fast
Office pools are fun. Cheap colleagues? Not so much. Here’s how to get those tight-fisted dudes to cough up the dough—and other advice.
Our office is doing a March Madness pool this year, but a couple of the guys haven’t paid up yet. How do I nudge them without causing bad blood? —Alan K., Denver
If possible, avoid singling anyone out, especially in public. Hang the chart you’ve drawn for the pool in a public place, like the break room or office kitchen, so that everyone sees it regularly. There’s a chance the stingy parties have simply forgotten. After that, make a friendly, generalized announcement at your next all-staff meeting, and then give everyone a couple of days to pay up. If that doesn’t work, send a lighthearted email to each of the people who haven’t yet coughed up the dough. Informality, here, is key. Avoid the “Dear so-and-so” format of a business email. After a couple more days of buffer time, you can fall back on your last resort: a face-to-face confrontation. As in all close-quarters relationships (remember, you still have to work with these people), being polite is always your best bet.
My best buddy wants me to invest in his new microbrewery business. How do I say no without ruining the friendship? —Bill M., Highlands Ranch
Take a four-step approach. 1. Start with flattery: “Bob, your idea for an exotic-hops microbrewery business is absolutely brilliant, and I know you’ll make a killing.” Play up the idea of being his biggest cheerleader. 2. Next, tell him you are reluctant to mix business with pleasure, because you value your friendship with him above everything else. If he still pushes, remind him that history is littered with woeful tales of friends who joined forces, only to split unhappily years later: Steve Jobs and Steve Wozniak. Ben and Jerry. The Beatles, for crying out loud. 3. If he still insists, remind him of all the reasons you would not be a good business partner (i.e., take all the blame upon thyself): You are forgetful, always late, a horrible negotiator, whatever. 4. If that still doesn’t work, lie. Tell him you are saving every penny for a.) a new car, b.) your first home, c.) an eight-carat diamond engagement ring for your longtime girlfriend, d.) a yearlong balloon trip around the world.
My boss always invites staffers to hang out after hours, but it just feels like work to me. How can I politely decline without deep-sixing my career? —Nick J., Boulder
This is a tricky one. You have two competing goals here: Staying in the good graces of your boss, and not sacrificing valuable personal time. Let’s start with the bad news: Occasionally, you need to bite the bullet and say yes to him, if only to prove that you are a good sport and don’t find his company boring or distasteful. For those evenings when you do acquiesce, look for ways to make them more palatable: Ask a good friend to join you, and assiduously steer the conversation away from work. It’s a polite way of reminding your boss that a.) this is your time, and b.) you have your own personal life, thank you very much. If he continues to press for nightly get-togethers, find a good excuse (or two or three): You need to put the kiddies to bed by 7; you’re training for a triathlon, and the swimming lanes at your club are open only from 6 to 8; you are taking an Italian class after work two nights a week. Eventually he will get the message that your outings with him are going to be irregular, at best.
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