“Positioning” gets thrown around like a magical incantation. What it usually means in practice: someone new visits your landing page, spends 8 seconds, and cannot explain to a friend what you do. Fixing that is a solvable problem, not a Zen quest. Here are five prompts I use before I redesign anything, and after every meaningful shift in the product.
1. Jobs-to-be-done interview simulation
You are simulating a Jobs-to-be-Done interview. You are the interviewer. Product I want to position: [PASTE 3-4 SENTENCES ABOUT PRODUCT] Type of customer: [DESCRIBE — role, industry, size] Simulate a 15-minute JTBD interview with a customer who recently bought this product. Ask, in order: 1. Take me back to the day you first started looking for a solution. What happened that made you start? 2. What did you try first, before anything else? 3. Why did that not work? 4. When did you first hear about us? 5. What almost stopped you from picking us? 6. What is the specific outcome you were hoping for when you signed up? 7. Two weeks later, what have you actually used it for that you did not expect? Play both roles. Make the customer's answers specific and self-contradictory in the way real answers are. At the end, summarise the single job the product got hired to do, in the customer's own words.
Why it works: real JTBD interviews are the gold standard because they surface the “trigger event” that comes weeks before the search, and the actual outcome the customer wanted (rarely the one the product page claims). The LLM simulation is a shadow of the real thing, but 80% of the value at 5% of the cost.
2. Ten hero-line variations, ranked
Write me 10 different hero lines for my landing page. My product is [DESCRIBE]. My audience is [DESCRIBE].
Each variation should come from a distinct angle:
1. What we do (functional)
2. The transformation the customer experiences
3. Contrast with the alternative they are currently using
4. A specific outcome we deliver (with a number if possible)
5. A pain point framed as a question
6. A category we are creating or entering
7. A tribal / identity claim ("Built by ___ for ___")
8. A punchy opinion ("The old way is dead")
9. An implicit promise (starts with a verb, ends with a concrete noun)
10. A pure benefit statement, no jargon
After the 10, rank them best to worst FOR THIS AUDIENCE. Then explain in one sentence per line what would need to be true for the ranking to be wrong.
Why it works: hero lines are hard because the framing choice matters more than the words. Forcing 10 distinct angles makes you notice which framing your product actually deserves. The ranking + counterfactual step is the useful part — it makes you defend the choice against your own doubts.
3. Extract the one job from the whole site
I am going to give you 5 URLs from my site. Fetch them and read them. [URL 1] — landing page [URL 2] — pricing page [URL 3] — a comparison or "vs" page [URL 4] — a blog post I am proud of [URL 5] — the About or Story page Based on ALL five, and ignoring what any single page says in isolation: 1. Write one sentence describing the single job this product is hired to do — in the language a customer would use, not the language I use. 2. List three sentences from the pages above that CONTRADICT that job or muddy it. 3. Suggest one edit per contradicting sentence that would align it with the primary job.
Why it works: sites drift. Every page gets written by a different person on a different day, and after 18 months your site says five different things. Reading five representative pages together and extracting the “actual” positioning is a job an LLM is genuinely well-suited to — it has no attachment to any of the pages.
4. Autopsy a competitor’s pricing page
You are a pricing consultant. Read my competitor's pricing page at [URL]. Tell me: 1. What job the pricing page is doing (what decision it is guiding the visitor towards). 2. Three specific weaknesses — layout, copy, structure, missing information, unclear benefits. 3. For each weakness, whether it would matter more to a small-catalog buyer or a large-catalog buyer. 4. The single change to MY pricing page ([MY URL]) that would exploit their weakness. Be concrete. Name the elements. Do not talk about "visual hierarchy" without pointing at a specific block.
Why it works: pricing pages age badly. A competitor’s four-plan grid or their over-cluttered feature list is often the fastest positioning gap you can exploit. The LLM is a competent copy editor for someone else’s page — it sees things you cannot because you are too close.
5. The “explain it to a smart 12-year-old” test
Take my current landing page (URL: [URL]). Explain in 3 sentences what my product does, as if you were explaining it to a smart 12-year-old who has never used software. Then: 1. Tell me the concept in my landing page that failed the test (something you had to skip or gloss over because it was too abstract). 2. Suggest a concrete metaphor, analogy, or example I could add to the landing page so the 12-year-old test passes. 3. Show me exactly what section of the current page you would replace, and what would go in its place.
Why it works: positioning fails at “abstract nouns you invented” — “AI-powered search intelligence layer” or “programmable observability”. The 12-year-old test forces the language back into concrete verbs and objects. Whatever abstraction the LLM had to skip is the thing your real visitors are also skipping past, just more politely.
A rule I stole from Bob Moesta
You are not competing with the other tools in your category. You are competing with the alternative your customer is currently using, which is usually “a spreadsheet, a person, and no formal process”. If your positioning does not clearly beat that specific comparison, no amount of hero-line rewriting saves you. Every prompt above works better when you keep that comparison in mind.