Leadership Caffeine™—Awkward Moments

Our work lives are punctuated by awkward moments thrust upon us at various points in time.

  • Any first day at a new job.
  • Every last day at an old job.
  • The day you learn your boss was fired. You liked this boss.
  • Meeting your new boss at the firm buying your company.
  • The point in time when someone you worked with, coached, invested in, and protected repays your efforts by storming out of the office and following up with a terse e-mail, announcing his resignation.
  • When you have to communicate to senior management your team is going to miss their numbers.
  • When you communicate to senior management that your team blew their numbers out (on the good side), and their only question is about your poor forecasting.
  • When you are told by your board to run your company like you will own it forever, and then asked to prep and pitch it for sale.
  • When your name shows up on a lawsuit and you are invited to the office of the CEO of this multi-billion dollar company, and asked to explain.
  • When you have one promotion to give and two outstanding candidates.
  • Every day you fire someone.
  • The moment in time when you have to suggest to someone it is time for them to get serious about pursuing something different.

These moments are all framed and filled with emotions, fears, unknowns and discomfort.

Anticipating the New Boss:

A former colleague described his recent awkward moment. His group was shifting to a new boss. Her reputation was one of being excessively tough. He lost sleep for several nights leading up to his first meeting with her.

It turns out her drive to “get things done” was refreshing. The new sense of urgency is motivating for everyone.

When I asked him about his emotions leading up to his first meeting with her, his answer sounded like a blend of anxious and queasy.

When I asked him how long it took in that first encounter for his emotions to shift from anxious and queasy to excited, he answered, “About twenty minutes.”

Twenty minutes. Was it worth all of that unproductive anxiety?

Probably not. Definitely not.

The Bottom-Line for Now:

The next time you encounter an awkward moment, freeze frame. Remember: this is a moment of punctuation. Make the decision to skip the anxiety and embrace the challenge. The awkward moments are rocket fuel for personal and professional growth.

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By |2017-02-12T19:08:06+00:00February 12th, 2017|Career, Leadership, Leadership Caffeine|3 Comments

About the Author:

Art Petty is a coach, speaker and workshop presenter focusing on helping professionals and organizations learn to survive and thrive in an era of change. When he is not speaking, Art serves senior executives, business owners and high potential professionals as a coach and strategy advisor. Additionally, Art’s books are widely used in leadership development programs. To learn more or discuss a challenge, contact Art.


  1. Roz L February 16, 2017 at 12:18 pm - Reply

    Great list of awkward moments. I never had a lawsuit on me but I can only imagine that would be the worst thing to explain to the CEO.

    • Art Petty February 16, 2017 at 12:27 pm - Reply

      Thanks Roz! It wasn’t a high point of my life. Appreciate the read and comment! -Art

  2. […] Art Petty catalogs some of the awkward moments—the ones that trigger our negative emotions—and advises on how to handle them. […]

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