Travels with My Boss
Question: I’m accompanying my boss on a 3- day business trip to visit other companies. It will be a lot meetings but also a lot of traveling to and from - just the two of us. I’ve worked for him about half a year now and we get on perfectly fine - our interactions are all very cordial. He’s pretty stern, though, and a man of few words, so I’m kind of dreading the thought of sitting next to him in silence every flight or cab ride. Should I make small talk when appropriate or just keep my mouth shut? I’m not supposed to entertain him, am I?
Answer: Unless your job description includes “court jester," no, you’re not supposed to entertain him. Business trips can be weird; they put us in close confines with people we may not know that well and normally have some kind of respite from, whether leaving the office at night or escaping for lunch.
You want to keep things professional on a business trip, but it’s also impossible to be in work mode 24/7. Small talk will inevitably be made, stories shared. Have a few amusing but bland stories ready when the right moment for a chuckle comes up. Even if your boss tends to keep to himself, I can’t imagine he won’t at least comment on the weather, or how the coffee at the last meeting nearly burned his tongue off. So, while he might not regale you with stories from his glory days, I doubt you’ll be in a state of constant silence.
The simplest thing to do is let him take the lead: if he feels like chitchatting, then chitchat right back. If he would rather look out the window blankly, then wile away the hours on your smartphone. Or get some actual work done. Silence is golden, after all.