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Asking the Question

Writer's picture: Cynthia KyriazisCynthia Kyriazis

Category: Leadership


Audience: Leaders, Leadership Teams, Strategic Consultants


Overview: The importance of asking critical 'what if' questions to prevent failures and foster informed decisions.


Read Time: 2 minutes


I was talking to my brother the other day about a goal he was set on achieving. I admire that.


However, he’s been my brother for decades now and I’ve seen a pattern.  


He tends to leave out very specific considerations like what would cause his idea to not go as well as he expected or what would cause it to fail completely. And then, he hopes for the best.


The process of thinking about having something you want to do ‘fail’ is not something many (most?) of us are eager to tackle—or even think about. Yet ironically, the success of what we want to achieve lives in the answers to these types of ‘what if’ questions.


An Example

Women wandering on a purple background surrounded by question marks

A leader I was working with was uber-focused on changing an aspect of one of their programs he believed would help his organization move forward.


There was a discussion among the leadership team members and they all agreed.


I don’t believe the ‘what if’ question was brought up and the decision was made to move forward with his program idea.


When I spoke with him, I began asking some questions:

  • Aside from your leadership team, who else outside of the organization have you spoken to about this?

  • How many individuals in the field have you tapped for their specific knowledge on this?

  • Have you asked employees for their thoughts on both the upside and downside of this type of program change?


Asking employees specific, open-ended questions and listening with an open mind can yield incredibly valuable information that could prevent a disaster.


These discussions bring potential unspoken roadblocks to the forefront.


Leaders can learn something they didn’t know or think about or care about if they engage their employees in this type of process. After all, they are the ones whose eyes, ear and thoughts are in the organization minute by minute, day by day, week by week. 


Metrics and Insights


Our solution revolves around metrics that help drive the outcomes leaders need and want.


Leaders are allowed to ask one open-ended question at the end of each employee Check-In.


Here’s how this has played out for some of our clients:


Example 1: One client asked a question about an idea that was not fully formed. It raised enough concerns to open discussions with multiple segments of the organization, leading to valuable adjustments.


Example 2: Another client asked employees what they liked most about working for the organization. The responses were so positive that she used the comments in her recruiting efforts.


Back to my brother…


I started asking questions about what might happen if the idea fails? 

What types of things could get in the way of success?


After the usual brother-sister squabble, he tried it with a friend. 


And guess what? Sometimes older sisters know a thing or two.


And sometimes leaders do.


And sometimes employees really do.


Cynthia Kyriazis is the Chief Experience Officer at The Culture Think Tank. Her experience includes executive coaching, consulting, and training. Book a 15-minute chat to discuss your people, performance or profit challenges.

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