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Episode 228: Leadership in Uncertain Times — Don’t Wait for Optimism, Generate It
In this episode, we continue our conversation about the role of Organization Development in unsettled times. Last time we explored what it means to act hopeful when it’s hard to feel hopeful. This time we go a step further: How do you show up when things feel uncertain—and still make a positive difference?
We draw inspiration from Margaret Wheatley’s book Who Do We Choose To Be?, which offers a powerful historical perspective on how societies and systems evolve—and what that might mean for the world we’re navigating today.
If we understand these patterns, leaders and OD practitioners can better assess what is actually happening around them—and more importantly, decide how they want to respond.
In our conversation we explore the practical ways leaders can show up in difficult moments:
• Strengthening connection when people feel fragmented
• Choosing love over fear in how we lead
• Maintaining a willingness to contribute, even when outcomes are uncertain
• And yes—keeping a sense of humor along the way
Because in challenging times, leadership isn’t about waiting for optimism.
It’s about generating it.
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By Bob Stapleton and Joyce Wilson-Sanford
5
1010 ratings
In this episode, we continue our conversation about the role of Organization Development in unsettled times. Last time we explored what it means to act hopeful when it’s hard to feel hopeful. This time we go a step further: How do you show up when things feel uncertain—and still make a positive difference?
We draw inspiration from Margaret Wheatley’s book Who Do We Choose To Be?, which offers a powerful historical perspective on how societies and systems evolve—and what that might mean for the world we’re navigating today.
If we understand these patterns, leaders and OD practitioners can better assess what is actually happening around them—and more importantly, decide how they want to respond.
In our conversation we explore the practical ways leaders can show up in difficult moments:
• Strengthening connection when people feel fragmented
• Choosing love over fear in how we lead
• Maintaining a willingness to contribute, even when outcomes are uncertain
• And yes—keeping a sense of humor along the way
Because in challenging times, leadership isn’t about waiting for optimism.
It’s about generating it.