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Just thinking about it can make the steeliest executive shudder, but the truth is, it happens: The awkward business lunch, that is.

You take a picky eater to a restaurant that doesn't serve anything that he or she likes, or you end up waiting on the street for a table because you failed to secure a reservation.

Take matters into your own hands, and prevent a blown business opportunity by consulting our no-fail checklist. Here are the questions every business-luncher should ask him or herself before picking up the phone:

  • Are reservations available? In many cities, New York City chief among them, there's no shortage of trendy new restaurants with strict, no-reservations policies. And while your guest might be impressed initially by your cutting-edge restaurant selection, he or she won't be smiling after 45 minutes go by and you still haven't secured a table. Why risk the wait when you can opt instead for a restaurant that takes reservations and is sure to offer you a warm welcome? It's always nice to be expected.
  • Do dietary restrictions need to be considered? Is your guest a vegetarian? Carb-free? Kosher? Or perhaps simply a picky eater? Attempt to do some reconnaissance on your dining companion's likes and dislikes before picking a location.
  • When we say "lunch" are we talking about the same thing? In this working climate, not all offices are amenable to a three-hour lunch. Make sure you are aware of any time constraints your guest may have before ordering a three-course prix fixe.
  • What are we drinking? Some diners are certainly happy to sip a glass of Merlot with their salmon, or to kick off lunchtime conversation with a cocktail. But don't assume that's always the case. Allow your guest to guide drinking decision. If he or she is content with water, don't push; alternately, if wine is ordered don't be the only one at the table without a glass.
  • Is confidential information at stake? If privacy and discretion is required, don't go to that busy corner place where the tables are wedged so close together that you have no chance at a private conversation.