He Said WHAT at Dinner!?

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A final interview dinner with a C-level candidate we had been working on for 5 months. Multiple rounds of conversations, tests, and compensation negotiations, we were finally nearing the end of it all. I was sure of it. I could see the finish line.

Dinner was your typical late night fancy SF restaurant. $500 bottles of wine, and a steak the size of a Snickers bar for $109. It didn’t matter. For a C-level candidate like this, sometimes you need to wine and dine them. It’s not an all the time thing but makes sense at times.

Fast forward when I’m in my Uber headed home, and I’m on the phone with my boss. She says:”He said WHAT at dinner!?”

How did we get here? Five months of work about to be wiped away swiftly because this candidate made a crucial mistake…in fact, the entire dinner was a mistake in hindsight.

Before speculating if the candidate made a scene or yelled at the waiter, it’s even worse. Something so terrible, they probably didn’t even know they were doing it or how bad it actually was. It was, however, painful. Sweat poured down my forehead like an interrogator was interviewing me.

The CEO of our company spoke up and said:”So, how was your trip out?”

Small talk at best. Casual, breaking the ice, just starting to really dive into the evening. This candidate let it fly. I mean really fly. I don’t even think they knew they were doing it, either. Which is an even graver sin.

The candidate went on a 10-minute rant about the flight, hotel, rental car company, the rental car they received, the room they stayed in, the mini bar (yes, the actual mini bar), and the temperature of their steak. They sent it back twice.

When they did finally come up for air, it was to send back the $100 bottle of wine to order a $500 bottle of wine. The was the ultimate face -> palm moment. It got me to thinking, do candidates not know this stuff?

For example, do candidates know what’s etiquette for ordering alcohol with dinner and expensing it as interview travel?

There are a million and one business travel tips you’ll need to keep in mind especially for a potential employer. If you misstep, it could cost you the job.

Tips and Pitfalls to Make Your Interview Business Travel Better

Do research in advance!

Not just for your interview, but for your travel. Research the hotel and be sure you know where it is, what they’ll need for you to check in and where you’ll get food from. If you’re going straight from the airport to the interview, research the airline and flight time. Do they offer food?

Find out what airline you’re flying and the hotel chain. Register for rewards or frequent flier miles. If there’s an option, request a specific airline you normally travel with.

Submit Detailed Expenses

Submit your expenses for travel AFTER they’ve made a hiring decision. Don’t let them make a decision on whether to hire you based on your $30 steak order at Outback Steakhouse.

Save every, little, receipt. For everything. A bottle of water at the airport? Expense it. Tylenol for a headache? Expense it. These are totally reasonable and you should not be on the hook for any of it.

Avoid Upgrades and Announcements

DO NOT upgrade on their dime. Not your flight, room, car, nothing.

DO NOT go on social media with a location track of any kind. If you’re supposed to be home sick and suddenly you’re posting and in New York, that will look very suspicious.

Be travelling to visit your Grandmother

Be that nice. To everyone. Seriously. Who knows when and where the potential employer is watching. Before you think I’m overly paranoid, Google search how many people lose out on a job for being rude to a front desk person or a waiter because they didn’t think they were on stage.


Business travel is great and travelling for an interview is even better. Visiting a place you may not have been before and getting to spend the day talking about yourself and being critically assessed and analyzed….okay, maybe that last part isn’t so fun.

Enjoy your travel responsibly and use common sense when deciding if something seems like a good idea. You can always ask your self, “what would Hired Guru do?”

Categories: Job Interviews