This article is part of ADWEEK’s Marketing Vanguard program and was written in collaboration with one of its members.
A few years ago, I invited an intern to join a group of us for dinner with another company we were working closely with.
I was excited to expose her to this side of corporate America in her first-ever business meal, and when dinner ended and it was only our team around, I eagerly asked her to rate the night.
She was blunt: “It was long. Sometimes you all talked about interesting stuff. And other points you talked about things that do not matter. At all.”
She was right. Last year during TV Upfronts week, the typical business dinner I attended was four and a half hours. With a good tailwind, that’s the same amount of time it takes to fly from the West Coast to the East Coast.
At least on that flight, you’re going somewhere!
We need to end the long, drawn-out, overly formal business dinner. Because while I absolutely believe in the value of spending time outside the office with prospective partners, current partners, teammates, agencies, and more—frankly, I’d rather do it over quesadillas.
Here’s how to make it better.
90 minutes—no more
It’s diminishing returns after that. As both the dinner inviter and dinner invitee—share your expectations around timing with one another in advance and again at the start of the meal.
Curate a list of restaurants that set you up for success
This starts with a table where one, unified conversation can be had. Because we’ve all felt the avalanche of despair when small talk with the person next to you runs dry and you glance longingly at the other end of the table that enviably seems to be a total party. There are two restaurants in Los Angeles—Fia in Santa Monica and The Strand House in Manhattan Beach—that my team and I like because they have private rooms with the perfect large square table that lends itself to a singular group conversation. It’s by design that we researched and discovered these spots and continue to frequent them.
I also wasn’t kidding about casual food
The default shouldn’t be Michelin-star dining, elaborate tasting menus, or the much overplayed small plates premise with a never-ending parade of food that is shared.
Let’s be honest—does anyone really enjoy sharing in these settings? We all work hard and on top of our 9-to-5, committed to an after-hours hang by saying yes to a business dinner. The absolute least we can do to reward ourselves is our very own entrée.
And does it have to be dinner?
Of course not! Breakfast, lunch, coffee or early evening drinks. I recently went for a hot chocolate with a partner of ours. 10/10.
And who says it must involve food or alcohol?
Sporting events and the golf course have long been substitutes for the business dinner. What else can we add to this list? If the pandemic taught us about the benefits of a walk-and-talk one-on-one, why not make that the activity. I know what you’re thinking: you can’t take 12 people on a walk. Good. That’s the point. I guarantee more ‘real talk’ will be shared in this setting and with a better end result.
Or consider a musical or play. If you catch up while walking to the theater, during intermission, and on your way out of the theater, that is likely enough time to discuss the business issues at hand. And you get to take in some culture!
If it has to be a long dinner, put a personality in charge
Curb Your Enthusiasm fans will recall the episode centered around Larry being a good “middler,” the person who sits in the middle of a big table and has a vital job: keep conversation flowing.
At one especially long business dinner I attended, the “middler” was great and posed to the table the absolute best sports trivia question I’ve ever heard. (Name the nine sports figures that graced the cover of these four magazines: Life, People, Newsweek, Time)
It got everyone talking and working together. Which genuinely kept spirits up and distracted us from the fact that we were going on minute 97 waiting for our salt-encrusted entire bone-in fish—to share, of course.
I have some go-to out-of-left-field questions I’ll ask during lulls. Like name a classic movie you’re embarrassed to admit you’ve never seen. My answer is The Shawshank Redemption. And at this point in my life, I’m not sure I’ll ever watch it since it elicits such a response from people when I disclose that.
I’m hopeful that shorter, curated points of connection (and quesadillas) can lead to talking about—in the words of my sage intern—more “interesting stuff.”
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