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Advice / Succeeding at Work / Work Relationships

Caught in an Elevator With a CEO? 3 Conversation Starters

It's Thursday morning, you're in the elevator, and the CEO skates between closing doors to join you for a 30-floor ride.

You consider commenting on the unseasonably balmy weather, but inquire about her watch instead. You then exchange a series of jokes and, in perfect unison, toss your heads back in laughter. At the 25th floor, she insists that you join her in the company lounge for a bite to eat—she'd like to get to know you better. You take style points from Sandberg and lean in. Instant promotion.

Real life: Silence. You exit the elevator with pit stains and wonder if she heard you swallow that burp.

Sound familiar? You're in good company—being trapped in a confined space with upper management is sure to send anyone into a tailspin. But, with some simple tactics on hand, you can navigate a terrifying situation with grace. Try on these life vests to avoid drowning like a conversation klutz.

The Trader Joe

Casual and approachable, Trader Joe’s employees are known for their infectious positivity. Whether it’s in the context of goat cheese or lentil breeds, they set a comfortable precedent because they don’t overthink simple human interactions. They wear contagious smiles above relaxed Hawaiian shirts, and they offer genuine inquiries that don’t overstay their word-exchange welcome. They just connect.

And by channeling their easygoing grocer tude, you can do the same.

You: “Hi! How’s your Wednesday going?”

CEO: Good, and yours?

You: “It’s going well, thanks. Just working on [whatever you’re working on] and getting some air. I don’t think we’ve met—I’m [first name, last name]. I work in [this department] with [your boss’ name].”

Throwing out a few details might spark further shop talk—and that’s great. Just go with it. Either way, make sure to flash a winning smile and repeat your counterpart’s name on the way out of the conversation. “[Name], it was nice to meet you.”


The Tactful Admirer

Senior executives are very accomplished people. Accomplished people love to talk about themselves. Therefore, by the power of syllogistic transitive property, senior executives love to talk about themselves. Namely, about their accomplishments.

Put that in your elevator-talk treasure chest.

You: “Hi [Name], I just watched the video from your keynote speech at the annual conference—I really enjoyed it.”

Important person: “Glad you liked it, thanks for watching.”

You: “Absolutely. I really admire your work and had a question about one of the things you touched on during your presentation.”

Take this as your opportunity to show your admiration and your interest in this person’s work. Don’t worry that you sound like you’re brown-nosing. So long as you don’t go overboard, you’ll portray a dialed-in sense of curiosity and community.

The Travel Talker

The following three statements about top executives are all true: They sleep on Egyptian cotton that quintuples the thread count of your jersey-knit blend. Spigots in their autos are more valuable than your entire sedan. And they travel more often than The Biebs on tour.

For the dual purpose of maintaining self-worth and combatting awkward small talk, lets focus on that third point. After all, assuming you’re not a translucent losing your days to meme generators and The Sims, you’ve likely been on a plane at least once. Use that common ground to pose any of the following questions:

“Hi [Name], welcome back! How was your visit to London?”

"Hi [Name], it's great to see you in the office. Where was your last business trip?"

“Hi [Name], I hear you’re heading to Tokyo. Will you get a chance to break away from the office and explore the sushi scene?”

Allow the travel talk to run its natural course, and try not to focus on the differences that separate you and your co-navigator. So what if she fights jet lag in a plush Mandarin Oriental robe while you consider anything other than couch surfing an upgrade? Just be confident and conversational. You’ll prove to this satin-pajama-sleeping, Maserati-driving upper echelon that you deserve a first class seat at the table.

Now, it’s important to note that not even the most non-awkward opening line guarantees conversation. Sure, you can offer your full name with a smile, glorify your talk-mate’s most shining accomplishment, or chat about exchange rates, but even despite your best effort, it may not go anywhere.

That’s entirely okay. So long as you’re not a too-cool-for-school observational humorist, an excessive life-sharer, or a lingering bore, you’re well on your way to a working relationship. Or at least a “Hi there!” and mutual smile next time you cross paths in the hallway.

Photo of elevator button courtesy of Shutterstock.

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