One Great Question

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“What keeps you awake at night?”

As a newly-minted consulting executive, they taught us to ask this ‘go-to’ question when alone with a client executive.

Why is this a great question?

It is ‘other’ focused.  It demonstrates empathy.  It gathers valuable and hopefully action-able information.  And most importantly, the question gauges the level of confidence and trust you have with the client.

I was asked this question once and my answer blew up the intended discussion.

My response?

“I sleep GREAT at night.  Always have.  In fact, when I was in kindergarten, Mom got a call from the teacher….“  and I went on with my childhood story.

The story of my lifetime sleep habits was probably not the discussion the other person wanted.  

Nonetheless, ‘What keeps you awake at night?’ is still a great go-to question to initiate a conversation with an executive.

How do you initiate a great conversation with an awesome question?

Let’s begin with voice.

When you project your voice into the atmosphere, sound waves emanate from you.  When they reach the other person, those sound waves rattle little bones in their ears.

Your voice initiates intimacy.  

As your question rattles bones in their body, those ear bones translate the sound waves.   Their brain fires up to understand the question.  It evaluates you.  It accesses a database of stories, experiences, feelings and facts.  It compiles all that into … a response.  The response goes to their vocal box.  And voila.  A response to your question travels on sound waves and rattles little bones in your body. 

I’m in awe of the complexity of our human-ness.

And when you ask a question, remember you are requesting something from that person.  Their response is a GIFT.   Respect their gift!

Yes, Respect the Intimacy of a Question 

We use questions to initiate conversations at cocktail parties, office gatherings and holiday parties.

And I’m terrible at these contexts and questions.

  •  “How’s the weather in Minnesota?”
  •  “How are you?”
  •  “How’s the family?”

Do you really care about our sub-zero weather in Minnesota?  Do you want to hear about my recent bout with a chest cold?  And seriously, do you REALLY want to know about my latest family drama?

I think not.  

The common response to this question is a horrible four-letter word beginning with F:


Intimacy avoided.  Social courtesy box checked.  Wasted breath and time.  Not my cup of tea.

If you want to engage an authentic discussion by asking a great initiating question, first clear your mind of any expectation of how you want the person to respond.  This provides fertile soil for their answer to land.

I call this True Curiosity.  True Curiosity Carries No Expectations.

When you ask a question from a mindset of True Curiosity, you exchange authentically.  Your relationships deepen.  There’s a greater chance that wisdom is exchanged.  

There are different conversation-initiating questions for different contexts.

  •  PROSPECT:  What one question do you ask a prospect you really want to land?
  •  INTERVIEW:  What is your opening question to interview someone for a job on your team?  
  •  LUMINARY:  You have 30 seconds with a guru, expert, luminary or thought leader.  What one question would you ask?  
  •  ICEBREAKER:  What question do you ask as an icebreaker for your team?
  •  ANYONE:  If you could ask every person in the world one question, what would you ask? 

Challenge:  Create a list of 4-5 ‘go to’ questions for different contexts.  If you have them ready to go, you won’t miss a beat and you’ll get to that deeper intimacy faster.

I have a few ‘go to’ questions at social gatherings.  They aren’t your typical cocktail party questions.  My question usually results in the two of us or a small group locked into an intense conversation in the corner of the room. 

Now that IS my cup of tea!

What’s my ‘go to’ question for social gatherings?

Imagine we’re standing with drinks in our hands.  The room is loud as people all around us are engaged in light social conversation talking about the weather.  We meet.  We smile.  You see me blink kinda long as I seem to transport to a different place.  The noise in the room seems to subside.  I open my eyes and peer into yours.  You see my mouth move and hear the carefully-crafted words in your ears.

What is YOUR SuperPower?


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