Here's a blueprint of what your dinner should look like and some tricks of the trade:
The invite. Don't request a specific night unless it's for a game or concert. Ask the client when they're available within a 2-3 week time frame. It gives them as little room as possible to say no. Because the truth is, they want to say no. If your client doesn't have a preference on where to go, make multiple reservations and ask them to choose. But don't forget to cancel the unused reservation. (When you don't, that's just rude.)
Know your client. A nine-course chef's tasting menu at Per Se is useless if your client would prefer to have grease dripping down their face from a lamb burger at The Breslin. The amount of money spent at a business dinner has very little correlation to the success of it. Gratification trumps all. And remember: There's a huge difference between a happily married guy with three kids who has to take a train home verses a single guy in his 20s who has two roommates on the upper west side. You need to know what you're dealing with — plan accordingly.
Gone fishing. Don't be the one to cancel. Sometimes there's a chess match that occurs around 2 p.m. the day of your dinner. It can be an instant message, an email or a phone call that fishes for an out. It might be something like: I have to run to the doctor after work and then go home and feed the dogs; it might be tough for me to get there by 7 p.m. They're looking for an out. Now you need to make a decision. It might be more beneficial long term to allow your client the easy out. If that's the case, don't get off the phone until you get another date in the book. Of course there are legitimate reasons to cancel, but at all costs you don't want to be the one to do it.
No clown cars. When inviting co-workers to join you, use a 2:1 ratio of sales people to clients – no client wants to go to a dinner with a sales trader, research salesman, the head of trading, a position trader, an electronic trader, a derivatives sales trader, an international guy and the head of equities for one person.
At the bar. This is where you meet your party. Under no circumstances should you talk business. It's like asking a first date what sexual positions they prefer. Stick to the script — this is small talk, getting to know you type stuff. Ask how the kids are doing, talk about how bad the Knicks are, anything but can we do more business. This should be a friendly banter back and forth until the hostess seats you.
What's-her-name. If there's a peer at the bar and you forgot his or her name, introduce the person to the group as a celebrity. As in: "Hi. Nice to meet you. I'm Turney. And this is Taylor Swift." They'll playfully slap you, maybe call you a jerk and then introduce themselves. No one will ever know you didn't remember their name.
Pick your seat. Sit across from the client. This way you can maximize eye contact and keep a steady dialogue.
Back it up. Nobody likes a one-upper so no matter how much better your story is than theirs, avoid one upping.
Ordering. The wait staff isn't one of your assistants, so treat them with respect. Don't say things like, "Take care of us—make it nice," because you aren't even Italian. Avoid the cliché Wall Street over order — if you're wasteful with food, then you'll be wasteful with my money. And stay away from the seafood towers and Pellegrino.
Drinking. A drunken client tells all secrets. Don't drink more than your client.
Business talk. The window between the waiter taking your order and it being served is your best opportunity to sneak in some work talk if absolutely necessary. A great lead in question is: how can we service you better? This conversation should feel secondary to the getting to know you better chatter.
Know your role. If you were brought to dinner as the comic relief then hit your beats. If you're the youngest sell-side person at the dinner, then try and connect with the youngest client. Nobody wins when a bench player tries to take the game-winning shot.
When the check comes. Don't order a second meal and or a desert to take home. Nothing screams cheap like, "The wifey is pissed I'm out, but this should help things out at home." DON"T DO IT. They'll mock you the second the Uber door shuts.
After dinner. Have a plan afterward, even if it's moving to the bar for one more drink. It can be as elaborate and deviant as you'd like, but you should always reference the know-your-client rule. An experienced client will know how to drop hints throughout dinner as what they'd like to do later.
Use your moral compass. The idea is for your client to have fun, but don't cross or snort lines you aren't comfortable with because you'll end up losing in the end. Sorry I didn't want to turn this into an after-school special, but it's true.
The next day. Hangovers love company. Follow up with a phone call and make reference to something you discussed the night before, especially if it was business. Show action from what you learned.
No matter how precise the blueprint is for your business dinner, you have to be nimble. You might have a client who loves to talk about business so talk about business or a situation develops that requires you to call an audible. Like I said before: Entertaining is a lot like dating. So don't try to get to too many bases on the first dinner. Have fun and be genuine.