Best prompts for ChatGPT for brainstorming using reverse brainstorming

You are a product growth strategist. We will use reverse brainstorming to improve trial-to-paid conversion for a SaaS product. 1) List 12 specific ways we could actively cause trial users to NOT convert to paid (focus on UX, pricing, emails, onboarding, value realization). 2) Group the items into 4 themes and rank each item by likelihood and impact on conversion (1–5). 3) For the top 6 causes, invert each into a specific fix, estimate effort (low/med/high), expected impact (low/med/high), and required owner (role). 4) Produce a 90-day roadmap with three prioritized experiments, success metrics (numeric), and an A/B test outline for the top experiment. Output as numbered lists and short tables.

You are a senior marketing strategist. Using reverse brainstorming, list 10 concrete ways a digital campaign could completely fail to reach its goals (consider targeting, creative, CTA, landing pages, tracking). For each failure, derive 1–2 creative campaign concepts or mitigations that directly address the cause. Prioritize concepts by expected ROI and create a 60-day launch plan with audience segments, creative formats, budget allocation, tracking events, and three KPIs to monitor daily/weekly.

You are a customer success lead. Perform reverse brainstorming to list 12 real actions or conditions that would increase churn across three customer segments (new, active, at-risk). For each segment, convert the top 3 causes into concrete retention initiatives (message cadence, product changes, pricing adjustments). For the top 5 initiatives, specify implementation steps, required resources, expected lift in retention (percentage points), and an experiment design to validate impact in 8 weeks.

You are a UX/product designer. Using reverse brainstorming, list 15 specific design, content, and flow elements that would make a new-user onboarding experience fail to deliver first value. Convert these into 15 concrete improvements (microcopy edits, screens, tooltips, progress indicators). Group into quick wins (<=2 days), medium (1–2 weeks), and long (1+ month). Provide example microcopy replacements for the 5 quick wins and an MVP onboarding flow diagram bulleted steps.

You are a security engineer. Use reverse brainstorming to list 12 plausible ways an external attacker or insider could cause a critical data breach in our web app (include dev practices, config, third-party services). For each method, propose one or more countermeasures, estimate mitigation effort and residual risk, and recommend monitoring rules or detection signals. Produce a prioritized 30/90/180-day remediation plan and a short incident response checklist for the top three risks.

You are a finance/operations analyst. Using reverse brainstorming, list 12 specific cost-cutting actions that would most likely degrade customer value or growth (e.g., remove features, reduce support, degrade infra). For each, propose safer alternative savings that preserve value, estimate savings amount (range), implementation complexity, and downside risk. Produce a prioritized 120-day cost-savings plan with owner, savings target, and a rollback trigger for each item.