Moving Leadership Development Into the Flow of Work

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A few years ago, I collaborated with a colleague to develop a one-hour workshop for new hires at the university where I was working. The goal was straightforward: Help people build leadership communication skills, especially for difficult one-on-one conversations with colleagues, direct reports, and students. As any learning and development professional would expect, a significant portion of the session was dedicated to role-playing, followed by peer feedback.

A few years ago, I collaborated with a colleague to develop a one-hour workshop for new hires at the university where I was working. The goal was straightforward: Help people build leadership communication skills, especially for difficult one-on-one conversations with colleagues, direct reports, and students. As any learning and development professional would expect, a significant portion of the session was dedicated to role-playing, followed by peer feedback.

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I was proud of what we built. The scenarios were rich and realistic, drawn from situations that had actually happened on our campus. Participants were engaged and took the activities seriously. We got great feedback. And yet, despite our best efforts, the workshop suffered from some familiar (and at the time, largely immutable) limitations:

I was proud of what we built. The scenarios were rich and realistic, drawn from situations that had actually happened on our campus. Participants were engaged and took the activities seriously. We got great feedback. And yet, despite our best efforts, the workshop suffered from some familiar (and at the time, largely immutable) limitations:

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  As realistic as our scenarios were, they weren’t personalized. We couldn’t possibly know which specific conversations each participant would need to practice going into their new role.

  As realistic as our scenarios were, they weren’t personalized. We couldn’t possibly know which specific conversations each participant would need to practice going into their new role.

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  Even with clear criteria and guidance, peer feedback is inherently variable and subjective. With only two facilitators in the room, we had little choice but to rely on it.

  Even with clear criteria and guidance, peer feedback is inherently variable and subjective. With only two facilitators in the room, we had little choice but to rely on it.

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  And the conversations we were preparing participants for were often weeks, months, or even years away. In the meantime, the well-documented forgetting curve meant that an estimated 70 percent of what participants learned was already forgotten by the next day.

  And the conversations we were preparing participants for were often weeks, months, or even years away. In the meantime, the well-documented forgetting curve meant that an estimated 70 percent of what participants learned was already forgotten by the next day.

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This meant that many learners were still likely to struggle when they eventually faced high-stakes conversations in real life.

This meant that many learners were still likely to struggle when they eventually faced high-stakes conversations in real life.

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But we got some important things right. Real-life, relevant practice works. Active learning works. Immediate feedback matters. I’ve spent the years since then working at Tenor, where we partner with organizations to support managers through real leadership conversations. That perspective has given me a front-row seat to how often leaders continue to struggle, and it’s not because they don’t care or haven’t been trained. It’s because support shows up too early or too late.

But we got some important things right. Real-life, relevant practice works. Active learning works. Immediate feedback matters. I’ve spent the years since then working at Tenor, where we partner with organizations to support managers through real leadership conversations. That perspective has given me a front-row seat to how often leaders continue to struggle, and it’s not because they don’t care or haven’t been trained. It’s because support shows up too early or too late.

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With AI, those limitations have largely disappeared, while the elements that actually drive learning can be dramatically amplified by situating development in the flow of work. That’s transformational, because leadership doesn’t develop in programs. It develops in real-life moments.

With AI, those limitations have largely disappeared, while the elements that actually drive learning can be dramatically amplified by situating development in the flow of work. That’s transformational, because leadership doesn’t develop in programs. It develops in real-life moments.

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If leadership were primarily learned in programs, we’d see far more consistent behavior change than we do today. But most leadership challenges don’t show up neatly packaged in a workshop agenda. They surface in specific moments, often unexpectedly, when pressure is high, and the margin for error is slim.

If leadership were primarily learned in programs, we’d see far more consistent behavior change than we do today. But most leadership challenges don’t show up neatly packaged in a workshop agenda. They surface in specific moments, often unexpectedly, when pressure is high, and the margin for error is slim.

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  A manager preparing to deliver difficult performance feedback to a direct report who’s likely to get emotional.

  A manager preparing to deliver difficult performance feedback to a direct report who’s likely to get emotional.

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  A first-time leader navigating escalating conflict on their team.

  A first-time leader navigating escalating conflict on their team.

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  A leader trying to clear up cross-functional miscommunication before a project goes off the rails.

  A leader trying to clear up cross-functional miscommunication before a project goes off the rails.

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In my work at Tenor, I observe the same patterns emerge across organizations and industries. The highest-stakes leadership moments (performance feedback, conflict, role transitions) are remarkably consistent, even when the contexts differ. However, until now, leaders have largely been left to rely on whatever advice they can recall under pressure to handle them as best they can.

In my work at Tenor, I observe the same patterns emerge across organizations and industries. The highest-stakes leadership moments (performance feedback, conflict, role transitions) are remarkably consistent, even when the contexts differ. However, until now, leaders have largely been left to rely on whatever advice they can recall under pressure to handle them as best they can.

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As we already know, that’s not a very good strategy, especially when most learning from point-in-time training fades long before these moments ever arrive. If leadership development is going to meaningfully change behavior, it must meet leaders in the moments where leadership is actually required. It must be accessible in real time, grounded in real situations, and woven into the flow of work itself.

As we already know, that’s not a very good strategy, especially when most learning from point-in-time training fades long before these moments ever arrive. If leadership development is going to meaningfully change behavior, it must meet leaders in the moments where leadership is actually required. It must be accessible in real time, grounded in real situations, and woven into the flow of work itself.

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And this is where AI becomes the missing bit of infrastructure that allows us to deliver what we’ve long known works (real-life practice, experiential learning, quality feedback) at the exact moment it’s needed.

And this is where AI becomes the missing bit of infrastructure that allows us to deliver what we’ve long known works (real-life practice, experiential learning, quality feedback) at the exact moment it’s needed.

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Instead of relying on memory from a workshop months earlier, leaders can prepare for a real conversation just before it happens. Instead of one-size-fits-most scenarios, they can practice the exact situation they’re facing with context that reflects their role, organization, and constraints. Instead of following a script or receiving variable peer feedback, they can receive consistent, objective guidance that reinforces organizational expectations while still leaving room for them to experiment with their personal style.

Instead of relying on memory from a workshop months earlier, leaders can prepare for a real conversation just before it happens. Instead of one-size-fits-most scenarios, they can practice the exact situation they’re facing with context that reflects their role, organization, and constraints. Instead of following a script or receiving variable peer feedback, they can receive consistent, objective guidance that reinforces organizational expectations while still leaving room for them to experiment with their personal style.

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When leadership development happens this way, it stops happening around work and becomes something that happens through work. It shows up when the stakes are real, and the learning is as meaningful as it will ever be.

When leadership development happens this way, it stops happening around work and becomes something that happens through work. It shows up when the stakes are real, and the learning is as meaningful as it will ever be.

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AI doesn’t change what good leadership development looks like. It simply makes it achievable, at scale, in the moments that matter most.

AI doesn’t change what good leadership development looks like. It simply makes it achievable, at scale, in the moments that matter most.

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For learning and development leaders, the practical question is this: where do your leaders struggle most today? Start by identifying a small set of high-stakes conversations (performance feedback, conflict resolution, or moments of change) where better preparation would make a meaningful difference. Then ask how your development efforts support leaders in those moments, not just around them. That shift in focus may prove more meaningful than any new program or content you design.

For learning and development leaders, the practical question is this: where do your leaders struggle most today? Start by identifying a small set of high-stakes conversations (performance feedback, conflict resolution, or moments of change) where better preparation would make a meaningful difference. Then ask how your development efforts support leaders in those moments, not just around them. That shift in focus may prove more meaningful than any new program or content you design.