How ChatGPT Is Quietly Rewriting the Way Strategists Think

Описание: AI isn’t just changing how we work. It’s changing how we think. In this episode of How I Strategy, Jenny Nicholson joins How I Strategy to unpack the subtle but powerful ways tools like ChatGPT are reshaping the strategic mind. From the risks of becoming too “AI-fluent” to the loss of weirdness in workflows, this conversation explores how to stay creative, thoughtful, and human in a world increasingly influenced by machines.

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In this Episode of How I Strategy, We talk about:
Why prompts are becoming a crutch for strategists
How to protect your thinking from AI "infection"
The tension between curiosity and correctness
What happens when everyone uses the same tools
How to design workflows that reflect your values (Waldo users, take note)

👤 Featuring:
Jenny Nicholson — Creative Strategist, Founder @ Queen of Swords
Romy Vassileu — Product Lead @Waldo.fyi and host of How I Strategy

Chapter markers:
00:00 Intro
00:32 Who is Jenny Nicholson
02:00 What makes a good strategist: pattern recognition, loving humans, outsider POV
04:02 The big AI misunderstanding (AI isn’t “the point”)
05:59 Creativity vs correctness: models get “smarter” but lose soul
08:35 Pinball/Plinko prompting: using constraints to force interesting paths
10:06 Why iteration matters (and what “months of work” actually looks like)
12:12 More context ≠ better results: memory, profiles, and leakage
15:21 “Data as substrate”: everything becomes analyzable if you know what to look for
19:59 Tools shape us: how AI affects our language & habits
22:18 Agents vs collaboration: choosing a workflow that fits how you think
26:56 What to delegate to AI vs what to keep as your craft
31:00 Live workflow demo: proactive ideation (trends → patterns → ideas → report)
35:45 Model choice for creativity (why Sonnet beat the others here)
36:59 The eye-doctor method: tuning levers to raise taste
37:33 One practical habit for strategists: ask frameworks, not deliverables
40:45 Curiosity over fear: how to start (and keep your agency)

#ai #strategy #chatgpt