3 Conversation Starters When You’re Caught in the Elevator with the Boss

Getting on an elevator with total strangers is awkward enough. But when you step onto the elevator and your boss is already there, the anxiety level can skyrocket, especially if you don’t know him or her well.

Conversation Starters With Boss

But worry not: here are three helpful conversation starters to keep you moving, with no pressure and no awkward silences.

The Casual, Positive Approach

Perhaps the best middle of the road strategy is to remain casual and approachable, even if you don’t feel like it on the inside. Infectious positivity: this is what you should go with, rather than silence or bland talk about the weather. The key is not to overthink these simple human interactions. Smile, offer genuine inquiries, and above all, don’t overstay your word-exchange welcome. In a nutshell, you want to connect but not creep anybody out.

Try this simple exchange when meeting the CEO of your company (who likely does not know you!) and whom you may have never met:

You: “Hi! How’s your Friday going?”

Boss: Good, and yours?

You: “It’s going great, thanks. I’m just working on {insert project name here} and getting some fresh air. I don’t think we’ve met—My name is [first name, last name]. I work in [name of your department] with {your boss’ name}.”

Then, see where he or she takes it from there. Some may continue with the small talk to learn more about you. Others will nod their heads, give a brief smile, and continue staring at the door. Take your cues from their behavior. If you feel like it would be received well, throw out a few more details to spark further work conversation. Either way, flash that winning smile and repeat their name as they exit the elevator “[Name], it was so nice to meet you.”

The Tactful Admirer Approach

Senior executives are very successful and accomplished people. They also love to talk about themselves and their accomplishments. Keep that in your back pocket the next time you find yourself on a 30-floor ride with the senior exec in your department.

Try this:

You: “Hi [Name], I just saw a clip of your keynote speech at the company conference. I truly enjoyed it and thought what you had to say was insightful.”

Exec: “Glad you liked it. Thank you for taking the time to watch it.”

You: “No problem. I admire your work and had a question about one of the things you spoke about during the presentation.”

Briefly explain what you mean without making it seem like you’re brown-nosing. You can’t go wrong being genuine. This shows you have a well-honed sense of curiosity and community.

The Travel Talker Approach

Many top executives love to travel. They also love to talk about their latest vacations and where they went. Use that common ground and ask any of the following questions:

  • “Hi [Name], welcome back! How was your visit to Greece?”
  • “Hi [Name], it’s good to see you around the office again. Where did you go on your last business trip?”
  • “Hi [Name], I hear you’re heading to Paris next week. Will you get a chance to get out of the office and explore the Eiffel Tower?”

Allow the travel talk to run its course naturally. Be confident and conversational. This shows you know how to talk about things other than workplace stuff.

If your elevator needs service, don’t hesitate to contact us to get it fixed. You don’t want to be caught in an elevator with anyone for longer than you have to!