Abolish Onboarding Lunches

Craig Wiroll
4 min readJun 28, 2021
Corporate Onboarding Lunches are Awkward AF

Several of the most awkward moments in my life have come shortly after being hired for a new position. Just immediately after finding out where your desk is located, but prior to having any fricken’ clue what your actual job responsibilities will be, you’ll sometimes get invited out with head-honchos for an icebreaker meal.

(This is usually the only time you’ll ever see or interact with upper-management — so I think it’s either an ego-boosting trick or you’re being used as an excuse for execs to get out of the office for a free meal.)

There’s usually someone invited who’s just senior of you, but was previously in your position in the not-so-distant past.

In my experience, this person is usually incredibly awkward and possibly feels a bit of imposter syndrome — feeling like they should be able to lend you some wisdom, but unable to do so — because despite being at the company for several years, and earning multiple promotions, they still have absolutely no clue what either they, or the company, actually does.

Researching prior to these meetings, the internet advised me that I shouldn’t order the most expensive thing on the menu (too bold and disrespectful) but also that I shouldn’t order anything too small (shows weakness and lack of confidence).

I am primed, prepped, and ready for my big moment.

The big boss orders first. He goes with a classic: a ribeye steak (rare) with a baked potato. Next is VP — she goes with a salmon filet with rice & veggies. Newly promoted awkward guy orders a hamburger and fries — non-offensive and a bit childish. Everything seems to be playing out as expected.

Now it’s my time to shine.

Since we are at the fanciest establishment in town (The Cheesecake Factory) I decide to order the restaurant’s specialty (when in Rome): “I’ll take the, ummm, cheesecake” (seems like the obvious order).

I hear two audible gasps and a laugh. The server just looks pained and confused. I decide to display dominance, fold up my menu and toss it into the pile and fold my hands behind my head like a boss.

After about 4 minutes of awkward silence, the boss starts talking about his golf game and his sailboat but everyone else remains silent and uncomfortable until the food arrives.

I don’t really enjoy eating in front of people. Especially people I don’t know. Especially when I’m eating an entire cheesecake.

But, by the time the food comes I’m ravenously hungry. I’m used to snacking all day at work — but all this smalltalk with these suits has really taken it out of me.

One fun tidbit about me: I’m a four-time speed eating champion. Burritos, doughnuts, and raw garlic (2x). The former fat-kid in me was on full-display once that cheesecake got plopped down in front of me. I started at it with a fork, but soon abandoned all silverware for my natural manforks (hands). I polished off that little cream-cheese-baby in about a minute and a half.

When I finally came up for air, the VP had to excuse herself, and burger boy attempted to scoot as far down the booth as possible. The server eventually asked if anyone wanted any dessert but quickly assumed based on the mood (and my order) that we all had enough.

I felt like a social outcast. I felt humiliated. If my first meal with these people was so awkward, and uncomfortable, how would I make it through the day-to-day grind? I mean…I wouldn’t be manhandling cheesecake every single day in the cubicle…but the desire to do so will definitely come up from time-to-time.

After cleaning myself up at the restaurant, we did the awkward walk-of-shame back to the office. I was the only one not carrying a box of leftovers because my internet research failed to inform me that it’s impolite to consume your entire meal (is that a thing?!).

The VP eventually called me in to discuss the awkward lunch affair.

VP: “So, how’d you enjoy getting to know the President. It seemed like you enjoyed your meal.”

ME: “Ummm, yeah he seems nice. And, yeah, I’d never been to The Cheesecake Factory — but since they have an entire brand devoted to the cheesecake I thought it’d be a good choice. Sorry if it was too expensive.”

VP: “Well, it wasn’t really the price of the cake that was the issue. It’s just not ordinarily ordered as an entree.”

ME: “Well, yeah, I understand that. It’s just, you know, usually I don’t have enough room for both an entree and dessert and didn’t want to miss out on the namesake…so…ya know…”

VP: “Okay, I understand that. It’s just that you could’ve ordered a main course and taken some of it to-go…but…yeah I hear you. Are you sure you want to work at *****?”

ME: “Excuse me?! Yes, of course. I definitely……….no. No I’d actually like to leave right now and never come back.”

VP: “Yeah.”

ME: “Yeah. Okay. Well…bye bye.”

VP: “Goodbye Craig. Good luck.”

¯\_(ツ)_/¯

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