(What Keeps You Up at Night is an annoying business term and is just one of the 212 Most Annoying Business Phrases Managers Effuse, Confuse, and Overuse detailed in the hilarious must-have guide for every workplace: The 30,000-Pound Gorilla in the Room. Available right now on Amazon.)
What Keeps You Up at Night
When you run out of interesting things to say at business gatherings or good questions to ask a potential client, please do yourself a favor and shut up.
Asking, “What keeps you up at night?” will not endear you to the person; it will not make them respect you; and it will certainly not create thoughtful reflection in their brain. It will only make them cringe and want to get as far away from you as possible.
No one – and we do mean no one – truly shares this information with colleagues, coworkers, or potential vendors.
There are only two possibilities that come to mind when you ask someone this: (1) “Nothing keeps me up at night, and I think you’re an idiot for asking such an asinine and contrived question;” or (2) “Something does keep me up at night, and you just made me think of it while looking at your face.”
Instead of being intentionally annoying in these situations, try this: be yourself. Moreover, while it’s good to prepare for most gatherings and meetings, make sure what you intend to speak about or ask doesn’t make you look like a disingenuous jerk.
… Oh, and the answer is you. You and your contrived questions keep us up at night!
Replacement phrases: Most often, there’s no replacement needed. However, if you really do care and you can genuinely provide assistance, try, “Do you face any challenges where you think I can help?”
See also: Keep Me Looped-In
The 30,000-Pound Gorilla in the Room is available on Amazon