Your boss makes a lot of money. Or, as evidenced by their Tesla and once-a-week omakase habits, at least a lot more money than you do. So watching them leave for a crazy restaurant every night before you pick up some Taqueria Cancun on the way home is just the way life is right now. But on the bright side - you can still hit Mauna Loa on a Thursday night, drink too much, and play nine rounds of Buckhunter and not have to worry about catching Caltrain back to the suburbs. It’s the little wins.
Remember that when your boss emails you to set up another fancy dinner. And use this guide to help you nail that perfect restaurant - a place that’s pricey but not over-the-top, mature without giving away how old you think/know they are, and perhaps most importantly, somewhere you can actually get a reservation.
Perfect For: The Pescatarian Boss With Cash To Burn
Leo’s feels like a swanky yacht or small-luxury cruise ship inside. The seafood-heavy menu is both excellent and expensive, and will impress your boss’ spouse/potential investor/whomever they are having an affair with. As long as they’re cool to spend $34 on a lobster roll, they will love it.
Perfect For: The Boss Who Overuses Acronyms
“TL;DR, ICYMI, FTE KPIs for Q3 are looking like a miss. Need updates by EOD.” This is the type of email you regularly receive from your boss, which leads to you immediately fire up LinkedIn and desperately scroll. Try not to respond with IDGAF. Take a deep breath and get on an SPQR reservation. The pasta is excellent and the atmosphere is much more upscale than your boss’ communication style.
Perfect For: The Boss Who Refers To Herself As A “Foodie”
Run by the people behind State Bird, The Progress is a better option for boss-pleasing because dinner there only requires a reservation and not a multi-hour wait on the sidewalk. The interior is very pretty and the food will check all of the boss’s “must look good for my 78 followers” boxes, while avoiding any rehydrated nasturtium blossoms. The whole place is cool without trying too hard, and the lamb tartare is phenomenal.
Perfect For: The Boss Who Is Into Food But Would Never Say “Foodie”
Mister Jiu’s is not the easiest place to get a reservation, but if you’re willing to aggressively stalk the necessary sites, you can do it. Persistence pays off, and while you might not get actual acknowledgment that you achieved the impossible from your boss, at least you can pat yourself on the back. This Chinatown restaurant does excellent, modern takes on Chinese food that you can order a la carte or from a tasting menu, and either way the boss will be pleased. Besides the excellent things to eat, the interior is well-designed without feeling overdone, and has some nice skyline views out the windows.
Perfect For: The Reasonable And Patient Boss Who You Actually Respect
A reservation at Zuni is doable, provided you’re planning far enough in advance - a few weeks out and you’re golden. Zuni is one of our all-time favorites, because it’s extremely classy, and the relatively short menu is executed to perfection. The chicken takes an hour but is absolutely worth it, and for someone who is planning out their Q1 goals already, it’s totally fine to take some time to get it right. Advise boss to get the fritto appetizer, plan for Christmas bonus.
Perfect For: The Boss Who Isn’t Afraid To Try Things, Including Steamrolling Corporate Card Policies
Maybe your boss needs a foie gras dumpling every now and then or he gets cranky. Benu is an incredible meal that takes up a good part of the evening and certainly costs a lot, but is pretty mind-blowing. The tasting menu is extensive and creative, provided you have a finance department that takes its job pretty lightly.
Perfect For: The Boss Who Wishes He Still Lived In New York
You’ve heard many times how much your boss misses New York. So next time he starts talking about how the West Village is magical, and actually the aroma of summer trash has a certain charm to it, be proactive and make him a reservation at Park Tavern. The North Beach spot has very good food (especially the burger) and enough of a New York feel that he’ll feel like he’s home.
Perfect For: The Extremely Neurotic Boss
Some people get to boss level by being exceedingly good at Powerpoint and having a calendar organization system out of A Beautiful Mind. Your boss definitely likes things the way he likes them. Exactly the way he likes them. Hillstone, on the Embarcadero, is the place for such a person. The spinach and artichoke dip is heated to a precise temperature every time, the salmon is identical in San Francisco and Phoenix, and the drinks are always expensive and good. Yes, it’s basically an upscale Applebee’s, but you know what you’re getting every time.
Perfect For: The Boss Who Likes To Stick Close To Financial District
Akiko’s is one of the more classic sushi options in the city, and the simple, attractive restaurant solely focuses on fish. If your boss actually likes the people she’s eating with, omakase is the move, but there’s also an a la carte menu for when she needs to get out quickly.
Perfect For: The Boss Who Doesn’t Know Anything About Restaurants, But Watches The Food Network
“Have you heard of Tyler Florence? The guy on the Food Network? He has an AMAZING restaurant here.” All of these things are true. The restaurant is Wayfare Tavern and it is a very good place to eat, regardless of who the figurehead chef is. The popovers are the stuff of legends, and the fried chicken is fantastic too.
Perfect For: The Boss You Actually Like Who Lives In The North Bay
Sushi Ran is in an extremely random location, on a side street off the main drag of Sausalito, and you wouldn’t find it unless you were on a hunt for incredible sushi and had a nose like a bloodhound. It has some of the best sushi in the Bay Area, and the small plates and non-sushi options are also amazing. On a nice night, sitting outside is ideal. Your boss will also be very impressed that you know things about the suburbs.
Perfect For: The Boss Who Won’t Stop Talking About Meditation
Your boss has recently become so chill, he's willing to drive (more likely get driven) all the way to the Outer Sunset. While Outerlands is more of a brunch destination, the food is just as good at dinner and the atmosphere is a bit more romantic and upscale than during the daytime frenzy when everyone is too busy taking photos to actually eat their food. The menu is simple but not boring, and will earn you a reputation as a tasteful human.
Perfect for: The Boss Who Wants To Go To The Mission But Is Also Afraid Of The Mission
This is the neighborhood restaurant we wish was in our neighborhood, but instead it’s hidden behind the KQED building and a Muni graveyard/repair depot. The Morris serves exceptional food and wine, is a little under the radar, and is easy to hit on the way home to the ’burbs. The shrimp toast and smoked duck are always good calls, and slightly adventurous but also safe enough for the boss who is easing into city life.
Perfect For: The Boss Who Is A Card Carrying Battery Member
Glass windows and a prime Hayes Valley corner location mean there’s a good chance an underling will trudge by and see the bossman drinking a bottle of 1975 beaujolais and eating foie gras and frog legs. But Monsieur Benjamin isn’t just about being spotted - it’s upscale without being snooty, and generally full of people who know which fork is for salad and maybe even own their own escargot utensil set. Your boss is going to love it.
Perfect For: The Boss Who Secretly Hates Puppies
Some people think ordering $57 antelope off an iPad while sitting in leather recliners in a glass box of an office lobby means they’ve finally made it. If your boss is one of those people, who perhaps openly reads Cigar Aficionado, then get him to Dirty Water. The food is absolutely fine, while the crowd and ordering protocol leans to miserable. If they’re lucky, maybe he’ll even get in a @jack sighting.