Leadership Coaching – Get moving in your career

How to Talk with an Executive

When the elevator doors opened, I saw two men in the cab.  I stepped on. 

When I went to hit the button for my floor, I noticed that the executive floor was lit up.

That’s when I realized why one of the men looked familiar.  He was the CEO.

In the elevator, I faced a choice

The two men were chatting, so I did have the option of just keeping to myself and listening to the music.

Or.  I could talk to them.

I had nothing to formally report to them.  I had no amazing business insight to share.

I could have looked like an idiot having no clue what to say.  But I quickly decided that was a lower risk than coming across as ignoring the most influential person in the building.

I spoke up

The two of them were talking about hockey.  I was the kind of fan who enjoyed watching a game.  But I wasn’t the kind who knew all the players names and daily monitored the league standings.  And I had not watched the recent game they were reliving.

I think I said something like “I love how hockey really gets the fans tapped into the competitive spirit.  You know?”

I instantly got worried

My self-talk immediately went into overdrive. 

We’re they upset that I dared interrupt their private conversation?  Were they smiling because they appreciated not having to pretend we weren’t sharing the same space?  Were they looking at me quizzically wondering who the heck I was?

Did I need to hit another button to abort this situation?!

Then an amazing thing happened

The worries all disappeared when they quickly responded in agreement.  And asked what department I worked in.  And then the most extraordinary thing happened.

The second man asked if I really liked going to hockey games.  When I authentically said, “Yes!” he reached into his jacket pocket and pulled out two tickets for that night’s game.  He said that he wasn’t able to go and was looking to give them away.  He offered them to me.

I gratefully took them, and got off at my floor, with my mindset forever changed about how to talk with senior executives.


I remembered that story when a mentee shared with me that she had a skip-level meeting coming up, and she wasn’t sure how to make the most of it.  She was looking for advice on what to say.  She wondered if she was expected to give a status report.

I suggested that she have three questions in her back pocket that could spark a meaningful conversation.

1. “What excites you about your job?”

  • If they answer something about “the people” then you can follow-up with “What are you doing with the people that you find exciting?”
  • Be sure to have an answer ready yourself.
  • This question helps you connect and perhaps find something in common or something unique about each other.

2. “What is a current leadership challenge that you are focusing on?”

  • You can offer a suggestion you’re curious about like “Is it keeping people engaged in a hybrid workplace?”
  • This one helps to show that you are curious about more than the work product.

3. “What is ahead for how my team can support the strategic plan?”

  • This question helps to show that you are looking to the future and want to be specific in your contribution to the organization’s success.
  • Be sure to have read the strategic plan recently.

As a bonus – these questions work well with your mentors too!

I can’t promise that you’ll get hockey tickets, but amazing things can happen when you are open to the possibilities.

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Ann Drummie

Ann Drummie is a certified leadership coach, workshop facilitator, and speaker. She helps professionals get moving in their career. She is the author of "Wallet on the Rental Car Roof: A Guide for Young Professionals Growing Their Leadership Skills." She's also an avid traveller and curler.

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