To Be A Better Leader, Refrain From Asking One Question

To Be A Better Leader, Refrain From Asking One Question

The past few years leadership experts such as Simon Sinek have written books and spoken extensively about the need to ask “WHY?” questions, which give leaders permission to dream, vision, create a better world than what we’ve had before.  Thanks to each of them, I’ve been given permission to be me – the idealist, the dreamer, the visionary, the enthusiast, and the wonderer.  As an INFJ on the Myers Briggs personality profile assessment, I am quite attuned to asking the BHAG (Big, Hairy, Audacious, Goal) type of questions:

  • WHY can’t we do X or Y or Z or XY & Z all at the same time?  
  • WHY can’t we create a system where everyone has access to a great education?  
  • WHY can’t universal healthcare or clean water for all be a goal to shoot for?  
  • WHY do teachers give good grades to students who talk more than they listen–when philosophers like Epicurious clearly stated that we should listen twice as much as we speak?  
  • WHY can’t we do original art, creating from our own unique and varied gifts, instead of being so often told to paint by numbers?  

Those who have been world-changers have been those who haven’t been afraid to ask the big “WHY?” questions.  And I long to be one of them.  However, over the last few years, I’ve also had a love/hate relationship with the question “WHY?”.  And here’s WHY

In our compassionate listening training program, the Someone To Tell It To team has devoted an entire module to the art of asking good questions. WHY? Because quite frankly, so many of us suck at them.  One question, in my opinion, that would benefit all of humanity if it was removed from everyday interactions is none other than the question – you guessed it – WHY?!  


WHY? questions, whether they are in our heads or in our hearts, stir something in us which evokes passion, emotion, fervor, excitement, and wonderment. It also stirs the entrepreneurial part of us to leap for joy. WHY? questions can and do change the world for good. But it’s those WHY questions, when directed towards an individual or group, need to be sanitized from our conversations. And here’s WHY!  

I’ll start with an example. In 2022, I ran a full marathon, the fifth marathon I’ve completed. Thanks to a dear friend, I set a new goal of also running my first ultra-marathon, a “mere” 31 miles. To some, 31 miles seems like a lot. To others, including my running friend, who has run multiple ultra-marathons, including 4/100 mile races, 31 miles is the next step on the running ladder. To others, running 31 miles seems like a mind-blowing endeavor.

A few days after completing the race, I was with a large group of people who knew about my recent accomplishment. Several of those groups quickly affirmed and appreciated what I had achieved; I’m deeply grateful (and humbled) by their acknowledgement.  Several other folks, though, started asking WHY? questions:

  • Why do you do that to your body?  
  • Why do you run through pain? Don’t you worry about what this might do to you when you are older?      
  • For that matter, why do you run at all, at your age?  

Think for a moment about what happens in those types of situations when others ask us WHY questions? We sense judgment. We sense sarcasm. We sense criticism.  We sense a lack of understanding. We are immediately put on the defensive, having to prove to others that we are making wise decisions and have thoughtful goals and objectives.  

Here’s another example. This one happens often in the corporate world (and it’s also happened to me).  As an ideas person, you have a new idea. You present the idea to a supervisor, leader, or co-workers in the organization. You start receiving responses such as:  

  • WHY did you do that? or WHY did you say that?
  • WHY do you think that that would be a good idea?  
  • WHY do you keep coming up with ideas all the time?  

When I am on the receiving end of WHY? questions, let me describe what that feels like:

  • I feel judgment. Judgment closes doors (and lips), fostering disconnection and inhibits progress. I feel unworthy, as if my ideas don’t matter. When there’s a lack of connection in the workplace, people shut down, they don’t work as hard, they don’t find joy or satisfaction, they lose themselves – and the organization eventually loses out. Research from suggests that when employees experience belonging at work they are: “three times more likely to look forward to coming to work and five times more likely to stay at a company for a long time”. 
  • I lose safety. When safety or trust is breached, it’s hard to get it back again. To those on the receiving end of WHY? questions, we sense a lack of trust in us, and trust, we know, is the key to great relationships and great results. Patrick Lencioni in his book, The Five Dysfunctions of a Team, stated that a lack of trust is one of the greatest signs that a team is dysfunctional. But, he says a trusting team believes in each other, advocates for each other, stands up for each other, supports each other, and gives permission to each other to be themselves.  

So, ask two or three other questions that help keep the dialogue going. For example, if someone presents a new idea, respond with:

  • I’d love to hear more about what you are thinking.
  • Can you help me understand your idea a bit more?
  • What might it look like if your idea becomes a reality?  
  • How do you see that idea impacting the future of the organization (or group)? 
  • Thank you for taking the time to think this through and for offering a solution. What do you think might be the next steps to making this a reality? 

There are, of course, other questions we could ask as well, to learn more, to catch the vision, and to dream together about what could be. And we need to ask those questions to elicit a way forward, to learn what might just be possible to create a better organization, or a better culture, or a better world.

But putting others on the defensive and causing them to feel as if their ideas aren’t worthy of a hearing or a discerning conversation, will rarely ever move things forward or enhance them. WHY? questions stifle creativity, ingenuity, and progress. Not every idea will be a great one. But new and possibly wonderful ideas will never be fully shared if we aren’t able to affirm and encourage the ideas in the first place. And when we all can work together to enhance the ideas, moving them closer to perfection, and enabling them to be tried out, who knows what may result – for the good, for the better, for us all. 



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