How To Handle An Awkward Situation With Your CEO

Spending time with your CEO can be eye-opening.

Any amount of time you get with your CEO, is an incredible opportunity.  It’s an opportunity to get noticed through your communication and social skills. Use this time with him/her wisely. And never squander away this opportunity as a gripe session. 

Here is the dilemma:

Q: I’m new to the workplace. About one month into the job, our CEO invited me and my boss out to lunch.  I was pretty nervous, but my boss said our CEO was easy to get along with. Once we stepped into the elevator, I was shocked to hear the profanity and talk about one of our clients.  Just when I thought the awkwardness was over, we head into a restaurant known for the female servers and low cut tops. 

I’m a normal guy, but I expected work-related lunches to have a more professional atmosphere, especially when the CEO is involved.

During lunch I was quiet, possibly giving off an uninterested vibe.  I’m concerned that my lack of participation gave off the wrong message.  Should I have faked it and joined in the conversation?  –Brandon

A:  A awkward situation, indeed. Don’t compromise your principles, for anyone. In this case, you couldn’t excuse yourself, which is what I recommend when a conversation is questionable or unprofessional.  At worst, they could have been testing you. (Not cool, but possible.)  

Here are a few options to consider for future lunches with your CEO, coworker, or client:

  • Accept their invitation on a less regular basis. (A CEO may question it…)
  • Suggest and eat and walk lunch. (Hopefully it’s not a rainy day.)
  • Have a few topics up your sleeve to change the subject.
  • Jokingly point out, “Is that all you guys talk about?”
  • Find a few cases online, “I read that some companies send you to “sensitivity training” if they catch you talking about…”

Business Etiquette, communication, civilityIn my book, “Don’t Burp in the Boardroom – Your guide to handling uncommonly common dilemmas” address a variety of awkward “boss” situations.


Helping Businesses and Individuals Find Success Through Better Communication and Social Skills

having lunch with a CEO, business dining etiquetteRosalinda Oropeza Randall, Social Skills and Civility Presenter, Media Source, and author of “Don’t Burp in the Boardroom.”

Presentations are available to support HR policies, sales teams, up and coming managers, millennials & new-hire orientation process, service technicians, professional development events, conferences, college/university students, interns. For more information, please contact me, 650.871.6200.

©2017 Rosalinda Randall. All Rights Reserved.

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