Leadership Design Alliance | Chicago Executive Coaching



Check Your Why

Ever have a conversation with a 4-year old?  You give a response to a simple question and then they ask “why”.  Answer that question and they follow up with another “why”. And soon you are down the rabbit hole in the Land of Why.

While we may not want to get lost down the same rabbit hole, the vast majority of us could do a better job of playing the 4-year old Why Game.  We are so busy thinking about what we want or running in the opposite direction because the choice terrifies us, we forget to ask ourselves why.  Whydo we want it?  Whyam I afraid?  

And just as each of us flourishes when we understand our purpose – being what we’re meant to be – the public and private sectors also need to ask the bigger questions.  Why should donors care about our mission? Why are we losing market share? Why are we struggling to grow?  Why are our social change efforts losing ground?  Why is my team unhappy?

In our culture we’re impatient to get to the answers, but less adept at framing the questions. Why?  Because asking why is not especially comfortable.  Why requires deep reflection.  Why requires honest and transparent conversations. And it takes courage to delve into the why.

Following is an example of a conversation a coach may have with a client who has “imposter syndrome” – the “What if I’m not as good as I think?” syndrome. Finding the way to why anchors the letting go of what doesn’t serve us well.

The belief: I feel like an imposter.


  • Is this true? Are you an imposter?

  • When does this feeling surface?  

  • How does it make you feel?  

  • What happens when you feel this way? 

  • Who could you be if you could live without this doubt?

Next Step: Pivot your thinking.  


  • What if you told yourself I believe in me, and I have everything I need to succeed?  

  • How would that make me feel?  

  •  If you own these feelings, what might you do differently?  

  • What might happen if you owned this new-found power?

Client’s Why Question:  So why am I holding on to this belief about myself?

  • What’s the origin of this feeling – “not good enough”?

  • What will it take for you to let it go?

  • How do you remind yourself that you have everything you need to succeed?  

  • What steps do you take to support yourself and live your purpose?

Organizations must also check in on their why periodically.  For nonprofits, the allure of securing a new, significant donor could take them off mission. Businesses losing site of their whymay be inclined to follow the next shiny thing, grow too fast, and forget about how their loyal customers brought success. We can’t be all things to all people. 

We can, however, be loyal to who we are, what we create, and why we create it.  Our strength lies in living our own authentic purpose.  It is here we find our “why”.








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