I wrote earlier this week about the Tim Cook profile I recently enjoyed reading. In addition to the timeless business lessons it offered, I appreciated the revelation that Tim Cook’s number one use case for AI is to summarize long emails. The amount of time that saved, he said, “changed my life.”

But wait, I thought to myself. You’re the CEO of a $3.6 trillion company. Why might you just not ask people to send you shorter emails? Or even if you didn’t want to seem so overt-cum-confrontational, at least tell people that because you receive so many emails, because you’re the, you know, CEO of a $3.6 trillion company, that if they send you a long one, to at least summarize it with a few bullets at the top?

This occurred to me again as I was reading through the strategic plans that our portfolio company boards of directors had submitted for 2025. Consisting of articulated strategies and action items, the intent of these documents is to make sure that everyone is on the same page about what is to be done next year and about how to measure progress against achievement. For the most part, I thought everything was directionally correct, but what struck me across the board was how often more words were used when fewer would do. And not just “do,” per se, but provide greater clarity of intent. It’s one thing to “Build cross-functional capabilities on the marketing team,” for example, and another to “Hire a copywriter.”

Of course, it matters which you are actually trying to do, but if your intent is to “hire a copywriter,” then say that. There is no need to dress up clear intent with complexity.

Yet the fact that Tim Cook’s number one use case for AI is to summarize long emails speaks to how often in writing (and conversation) we all do just that. After all, it’s ingrained in us in school that length (in the form of minimum word or page counts) somehow correlates with quality.

But nothing could be further from the truth. Short, provided it’s thoughtful and considered, trumps long every time. This isn’t a novel observation, of course. We’ve known it for at least 400 years, with Blaise Pascal writing in 1657 that his was a long letter because he did not have time to write a shorter one.

This makes sense. After all, it is far more difficult to distill something than to explore it. Yet here we are, 400 years after Pascal, with people sending Tim Cook long emails and Tim Cook quietly using AI to make them shorter.

– Tim

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