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3 Reasons Why AI Isn’t a Good Planning Partner

3 Reasons Why AI Isn’t a Good Planning Partner

Update: 2025-11-03
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Since writing about the Centaur approach to AI last year, I’ve done even more deep diving into where AI is especially useful, where it’s over-hyped, and where it’s trash. In that piece, I argued for a centaur model — AI augmenting human capability, not replacing our thinking. I warned about the “siren song of outsourcing our thinking” to AI.

Most people get that AI can’t replace them as planners. But what’s less obvious is how badly it fails as a planning partner — even though that’s exactly how most people try to use it.

Important Note: In this article I’m using the term “planning” in the narrowest sense: making commitments, sequencing projects, resolving priorities, etc. In other words, this is the work of the middle, “Designer” productivity persona from our Momentum Quiz. Some of you may be thinking of ideation, visioning, and brainstorming as part of planning, too. They are part of the planning process in the broadest sense, though in this context I’m considering “Visionary” work like those as important preliminaries to the core work of planning. Those visionary tasks (and some of the action-oriented tasks of the “Creator”) are places where AI can be useful.

When I started testing AI as a planning assistant, I approached it with both optimism and a healthy paranoia that it’d make a good bit of my body of work obsolete. I was genuinely hopeful that AI...

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3 Reasons Why AI Isn’t a Good Planning Partner

3 Reasons Why AI Isn’t a Good Planning Partner

Charlie Gilkey