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Leadership insight: How to create a “learning moment”

Written on Sep 18, 2025

Welcome to a new series of resources from OSCPA and Applegate Talent Strategies LLC. Over the coming months, you’ll have access to this specialized content designed to help you lead, manage and transform your teams.  

 

The workforce you came up in isn’t the workforce you’re leading today. 

What used to work 

When something went sideways, strong leaders stepped in and taught. You knew the answer. You were inclined to use the Socratic Method – the “teachable moment” – as the quickest path forward to guiding others to the answer. That approach made sense when experience equaled authority and you were rewarded for knowing more than the next guy. 

What’s changed 

Today’s workforce, however, is smaller than previous generations. Today’s workers have different values and were raised on collaboration and teamwork. They bring experiences, tools, and perspectives to work and they want to put it to good use. The people you’re leading expect to contribute, not just comply. Leaders who over-teach or steer too hard risk shutting people down. 

What works now 

Make the shift from a teachable moment to a learning moment. That means embracing the mindset that you don’t see the full picture—even when you’re sure you do! It means asking real (not rhetorical) questions—even when you know the right answer! Curiosity and transparency build trust. So does saying, “I have some thoughts, but I want to hear what you think first.” 

Action  

For leaders of leaders. Challenge your managers to notice when they’re asking leading questions of their direct reports. Instead, coach them to say: “Here’s what I was thinking: __________. What’s your take?” 

For leaders of teams. In your next one-on-one, bring up a recent decision, process, or challenge that you disagreed with. Ask, “Can you walk me through how you approached that?” Then pause. Don’t correct. Don’t advise. Just listen to understand, not to steer. 

For yourself. This week, catch yourself when you’re about to lead someone to your preferred answer. Stop. Ask a genuine, open-ended question instead. Notice how the tone of the conversation shifts. 

Learn more 

For a deeper dive into operationalizing learning moments, listen to Episode 454: How to Ask Better Questions, with David Marquet of the Coaching for Leaders podcast. 

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