Scott Barry Kaufman & Chris Shipley: Leading for Tomorrow
Listen Now
SUBSCRIBE ON
Apple Podcastsby The Second City
-
Aug 04, 2026
Kelly welcomes frequent guest Scott Barry Kaufman back to the podcast along with Chris Shipley, a journalist, industry analyst and entrepreneur to discuss the new book that they co-edited, “Leading for Tomorrow: Unlocking Human Potential in the Era of Continuous Change and Endless Possibility.”
This book is made up of a variety of essays. What connects all the different thinkers and their views on leadership?
“The real focus here is human-centered leadership; how to keep that in an age of continuous disruption, because we’re living in this age where it feels like every day a new news headline is coming out telling us that what we thought about the old way in the workplace is wrong and now it’s this new one. It’s getting like every day there’s a new detour that we’re taking in the workplace. So, what can remain? You know, what can be the solid rock? Things like trust in your leadership, creativity, dignity are going to be so important.”
And all the change that has happened requires a change in how we lead.
“For the last 150 years, we’ve had an economy that’s based on wringing out value from resources, right? So how much what can we do with our natural resources? How much productivity can we get out of people? We we call them human resources, right? We’re extracting value from the worker, and I think that we’re coming to a natural end of that kind of very explicit transaction. We’ve wrung everything dry, right? So, if that’s the case, then and we think about where our economics are going. We have to start thinking about how do we create new value together. And to do that, you don’t wring out resources, you nurture them. And that takes a really different style where you are leading with grace, with humanity, with an understanding that together, collectively, we can do so much more than just sort of beat the drum until everybody steps in line and performs.”
There’s a lot of talk about AI – both at Second City and this book. And one thing I know about Second City is that we make a lot of great comedy from our mistakes. And improvisation finds great utility when things are wrong. AI can’t really do that.
“Yeah, I mean I love that framing, right? That ‘wrong’ is really where the value comes from, right? We often talk about failure is a is a point of learning. It’s not, ‘My God, you’re too screwed up and you’re fired.’ It’s, ‘This experiment didn’t work, how do we rethink that?’ And we have a wonderful chapter actually in this book by Amy Edmondson, who talks about how we have to start leading like scientists. And scientists have hypotheses, they do experiments. Sometimes the experiments fail. And it’s not like, ‘Well, we blew it.’ It’s okay, we ask: ‘What did we learn from that?’ And I love the frame of what do we learn from wrong? How do we use wrong to get to some better place? It’s just brilliant and I think is very much at the heart of this.”