My Chat With Winston Churchill

My Chat With Winston Churchill

Much has been made about the incredible power of generative AI and its most widely used application, ChatGPT, to enhance productivity—not just personally but for entire organizations. And it is a wonder—you see some incredibly inventive leaps being made daily to harness its power for nearly every part of a company, from HR to marketing and everything in between.

But this weekend I came to explore another, more unsung use while hiding out from the pollen covering every surface of our town like ash after a forest eruption. It started like this:

ChatGPT, let’s role play and have a conversation. You are Winston Churchill. I’ll set up a leadership challenge I’m facing, and I’d like you to ask me a series of questions, leaning on your experience, especially in the years 1938-40, to help me think it through. Please offer advice throughout based on all historical records of that period and published works by Churchill. I’ll go first, and you can follow with your questions. Please use my responses to guide your follow-up questions.

What followed was one of the more remarkable and entertaining mornings I’ve had in a long time. The “conversation” with “Churchill” was far from perfect—the voice, assuming it was based on the tone of his epic The Second World War, felt a bit like parody at times. But the questions it asked were sound, useful and surprisingly incisive. Call it coaching with Churchill.

Most of all, it was fun. Like really, really fun. I tried other conversations: a long one with Abraham Lincoln about navigating tricky team dynamics, based on ChatGPT’s understanding of Doris Kearns Goodwin’s Team of Rivals and other books. Later, at the suggestion of one of my colleagues, I talked about customer engagement and product strategy with Steve Jobs.

My point: While you’re thinking through your company’s approaches to deploying generative AI—the subject, as most of you know, of our upcoming Masterclass on June 26, join us —do yourself a favor and don’t limit yourself to figuring out productivity gains and work processes. Go farther. Ask it questions, engage with it. Play with it. Learn with it. Explore. Enjoy. Wonder. This is new—and it’s amazing. Learn more about the C-Suite Masterclass on Generative AI >

? Dan Bigman, editor, Chief Executive. [email protected]

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