Dear Urban Diplomat: how do I tell my boss that he’s not welcome in my carpool?

Dear Urban Diplomat: how do I tell my boss that he’s not welcome in my carpool?

Dear Urban Diplomat: how do I tell my boss that he's not welcome in my carpool? (Image: London Permaculture)
 
Dear Urban Diplomat,
Two of my coworkers live near me in the suburbs, so we drive in to work together. Our boss just moved into the neighbourhood and is poking around for a carpool. He hasn’t straight-up asked us yet, but it’s only a matter of time. The problem is, the commute is the only chance we get to vent about him. We can’t swap that cathartic bliss for two hours of awkward silence. What should I say if he asks?

—Shark in the Pool, Too risky to say where I live

If you simply can’t bring yourselves to accommodate the boss, there is a way out. When he asks if you have a spot, lie. For all he knows, you drive someone else who works at a nearby office, so he’s unlikely to press the issue. But I think you’re being myopic about this: you’re forgoing golden ass-kissing opportunities and probably a great parking spot, too.

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