Strategizing With It

ChatGPT isn’t just for writing. It’s surprisingly good at helping you think through decisions, simulate reactions, and structure complex ideas. If you use it like a strategist, it’ll start acting like one.

Draft first-pass frameworks

Get a baseline for whitepapers, product plans, GTM slides, or investor one-pagers. ChatGPT is fast at turning messy input into a rough first draft. It won't nail the nuance, but it gets you moving. You can build on it, edit in layers, or use it to organize what you already know.

I dropped a bullet list of priorities into ChatGPT and asked it to shape a product roadmap proposal. It returned a structured doc I could critique and revise instead of starting from scratch.

I had a bunch of notes and market stats. I asked ChatGPT to turn them into a first-draft pitch memo. The version wasn't final, but it was enough to react to.

Simulate stakeholders

Ask how a customer, VC, or engineer might react. This lets you preview different perspectives before making a move. You can test the resonance of your message, uncover hidden objections, or even map the emotional impact of a pitch all by having it "think" from someone else's point of view.

Before building a product prototype, I asked ChatGPT to respond like a skeptical customer. It raised pricing and onboarding questions that helped me make that go-no-go decision with more clarity.

I’ve used it to roleplay a VC reacting to a founder's market slide. It pointed out where claims seemed vague or unsupported.

Diagnose issues

Describe a business or technical bottleneck and ask it to categorize possible causes. This works especially well when you're stuck or overwhelmed. Instead of giving you a single answer, it gives you a lens. You can then apply that lens to focus your problem-solving.

Are you struggling to ship a feature? List the symptoms like scope creep and team tension. ChatGPT can suggest a breakdown of causes such as misaligned incentives, unclear ownership, missing constraints. It can even give you a way to structure the retrospective.

Asked ChatGPT why a marketing campaign might fall flat. I’ve seen it categorize reasons into message, channel, audience, and timing. Often exactly what you need to plan the next iteration.

Create tiered outputs

Request a 1-liner summary, a 3-bullet pitch, and a full-page version. This kind of shape-shifting helps with messaging, presentation layers, and alignment across teams. It also keeps you honest. If the one-liner doesn't work, the full version probably won't either.

I’ve asked it to help me distill a blog post into a LinkedIn post, then a 3-point takeaway, then a summary paragraph. The LinkedIn was the hardest to write, but it clarified what really mattered.

Try variations on headline for users, bullets for support staff, full writeup for internal docs.

Adapt for visual workflows

When creating or editing images, describe the intended result as a full prompt including what you want added or changed rather than giving shorthand instructions like "add logo here." You'll get more accurate and flexible outputs when you treat visuals like structured prompts, not casual commands.

I was iterating a visual brand concept. I asked ChatGPT to generate prompts in three different moods: vibrant, minimalist, and moody. The outputs helped me give clearer design direction.

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