There are small number of people in my life that pop up, every month or so, like clockwork, with the same question:
"My boss wants restaurant recommendations/I'm going to lunch with my boss/My company is taking out clients. Where should we go?"
The whole dining-out-with-superiors situation can be an intimidating one, especially if you're the one suggesting the location. I've answered this question enough to have formed a definitive an opinion on what is and what is certainly NOT okay when it comes to choosing a restaurant.
My DON'T list will hopefully come in handy. Or at least it will alleviate one layer of awkwardness the next time you and the Big Cheese break bread.
DON'T choose a restaurant....
-That offers a too-trendy menu. Assuming that your boss will be into fried, bacon-wrapped hot dogs topped with kimchi is a mistake.
-That does tapas. Sharing may be awkward and ordering one small plate to avoid sharing will leave you both starved and grouchy.
-Whose entire staff either wears skin-tight denim, rocks the bed head, looks too cool to wait tables, or sports disturbing, nature-defying facial hair.
-That's brand new. There are kinks to be worked out, lines to wait in, and music that will have your boss feeling older that he/she is when said boss realizes they can't hear a thing.
-That's too old. If your boss is successful, it's for a reason. They think ahead of the curve, are smart and on their toes. Being surrounded by retired geriatrics at a sleepy, Upper East Side piano bar insults their relevance and hip-to-the-jive sensibility.
-That's too expensive. Unless they say, "I'm looking for a three Michelin star experience," the main course shouldn't cost more than $35. Tops. If it does, it's probably coming out of your bonus, you ingrate.
-Known for it's avant-garde menu. A riff on my first point, your boss may not appreciate being unfamiliar with everything on the menu. Creativity is fine, but sous vide sweetbreads served en croute with confit byaldi and Parmesan foam? I think not.
That said, stick to the classics, take note of the type of food they usually eat, play it safe and throw in a curve ball once in a while. It's just a meal, after all.