How to Order Like A Boss

... And not a child.

Warning: I'm drunk and typing madly. This is good advice. [email protected]*k the formatting.

I just came back from a dinner with a senior banker, where he made a bunch of rookie ordering mistakes at a restaurant. This was a dinner with a client and a potential investor (think roadshow). So embarrasing.

Appetizer: order was a mess. He ordered a few things for the table and then "kinda" something for himself. Do one or the other. Not both.

Main: Ordered something "rich". Think "surf & turf", "most expensive thing on the menu" something you'd be embarrased to tell your immigrant parents about. "Zee opulence... don't has it".

Dessert: Was the only one to order dessert once the evening was "clearly over".

Guys. Jesus. Behave like this isn't the first time you've been to dinner.

How an analyst orders for the first time: "Wow. I've never been to a fancy dinner before. This might be my last chance"... vs. someone more seasoned who acts like they've been in the end-zone before.

This is different from how you should order dinner with a girl friend/wife. (read #8):

In chinese there is a saying: if you get invited to dinner... "If someone shoulders the bill... don't shoulder the 'effort'". Meaning: if somone else is paying... don't treat it like a buffet.

Below are a few guidelines for how to act like a human being when at a dinner when THE DINNER IS NOT THE PRIMARY PURPOSE OF THE MEAL AND THE REASON YOU ARE EATING AT A TABLE TOGETHER IS TO GET A DEAL DONE!

Guidlines: who the f are you? Are you a junior guy who should be seen and not heard? In that case, read the f'n room and (just like your clothing choices) don't stand out for all the wrong reasons.

How to Order Like a Boss (who is more concerned about a deal than a meal)

Different Tones: (1) Pitch; (2) Roadshow; (3) Closing

(1) In a Pitch
You are taking a client to dinner with no investors and you haven't been hired yet. If you are working with founders/public equity - you are their agent and you need to spend their money like it's yours (or like you wouldn't mind seeing in the newspaper tomorrow). Order something middle of the road... not the cheapest things on the menu, but not the most expensive. If your client is PE/institutional money, pick something a little richer (top quartile, but not top decile) that says "you get what you pay for" (because you're paying for me).

You pay the bill.

(2) Roadshow

You are representing your client and you are a wing man. Your client has a 18' c0ck and is so f!&king amazing (not YOU... Your client). Even if you are an MD, you (and your firm) are the least important person in the room.

Order big and mildly extravagant. Pick a restaurant where you've been to before on multiple occasions and they know you. Pick a good wine from the menu without having to look.

Give the investor a (small) window to step up and pay the bill to "differentiate" themselves from other investors (and to remind everyone else there that they are "the money"). Otherwise you pay the bill (and charge it back to the client).

(3) Closing Dinner

This is the end-zone. You already won. Think about the next deal. Chances are you already billed the client for this as part of the closing costs. Show them a good time. Make them good references. Make them climax and shout your name from the rooftops.

Always order first: set the tone (Message: "you guys can order whatever you want... you earned it and I got you").

Wine: Order without looking at the menu. It's not about price. It's about control. And taste. And that you've been here before. Or the ultimate power move: let them order.

Dessert: F yeah. Go for it. Share if you want, but order at least one proper desert each. One of everything on the menu if there is enough of you.

And be nice to everyone. Including "Janice in Accounting" who made your life hell during the deal by not being helpful at the most crucial moments because she realized she was a "synergy". Because everyone is a future client.


Rule for drinks... Be 80% of where your primary "counter party" is. If you are pitching, your counter party is a potential client. If you are on a roadshow, the counter party is the investor. If you are closing... Just don't get too drunk.

Drinks at dinner should be like children (adjusted for the year you are living in): generally about two or less:…

The more junior you are, the more you need to read the room: First drink is pre dinner or the aperitif. One drink with the meal and maybe a digestif.

Don't be the idiot who has never tasted success before who is acting like they are looking for a dealer for blow. Calm the F down. Take the W and think about how you can use this for the next one.

F'n idiot who is a drink or two AHEAD of his clients/investors in any situation. Get drunk with your REAL friends. Not with business contacts.

Onward, boys, onward.


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  • Analyst 2 in IB-M&A
Jun 23, 2021 - 9:29am

Reminds me of that time I ordered spicy wings during a closing dinner. Went for a bathroom break without washing my hands first and spent the rest of night squirming in my chair.

Jun 23, 2021 - 7:50pm

I never order anything messy if at a professional meal, no tacos, wings, burgers, etc. If you need to use your hands I'd just avoid it (pizza might be acceptable, but unless you're going to a dedicated upscale pizza place just avoid hand food). 

Jun 23, 2021 - 9:48am

Reminds me of that time when I was a junior banker on the tail end of a deal and my client, having heard that I liked whiskey but not being able to drink anymore himself due to health issues, decided that he wanted to live vicariously through the rest of us at dinner, and whipped out several whole bottles of whiskey. MD and VP were female and able to demur. So I had to pack away pretty much a whole bottle myself (other bottles went to the client's team). Passed out right outside my room for a bit because I could not get the key into the door. Woke up a couple hours later and realized I was on the wrong floor.

So, yes. Try not to get too drunk at dinner. Unless your client and bosses are in cahoots specifically trying to get you too drunk. In which case you take one for the team.

Jun 23, 2021 - 11:07am

What concert costs 45 cents? 50 Cent feat. Nickelback.

Jun 23, 2021 - 11:17am

This is such stupid obvious advice but probably necessary for the spergs that dwell on this board. 

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