Real prompts. Tested by practitioners. Copy them, paste them into ChatGPT or Claude, and use them in your next meeting. No fluff, no theory.
[CMO/CEO/Agency Head] evaluating an AI tool for [specific use case]. The vendor claims it will [their main promise]. Help me build a list of 10 specific questions that will reveal whether this tool actually delivers ROI or just creates a new dependency. Focus on questions about data ownership, integration costs, time-to-value, and what happens when we want to leave.
[size] marketing organization in [industry]. Our annual budget is approximately [$X]. Our board is asking for our AI strategy. Help me build a 90-day AI integration roadmap that's specific to marketing and media — not generic IT. Include: which functions to automate first, estimated time savings, required investment, and 3 metrics we'll use to prove ROI to the board. Be honest about what AI can't do yet.
[X] years. I understand [list what you know about AI] but I'm unclear on [list what confuses you]. Without being condescending or oversimplifying, explain the 5 most important things I need to understand about AI's impact on marketing and advertising in the next 12 months. Talk to me like a smart colleague, not a student.
[your industry] sector, specifically by companies like [list 3-4 competitors]. Based on public information, job postings, press releases, and industry reports, identify: (1) which AI tools they appear to be using, (2) which marketing functions they're automating, (3) what roles they're hiring for vs. eliminating, and (4) where they're likely 6-12 months ahead of a company that hasn't started yet.
[$X] in annual media spend across [channels]. Separate AI hype from reality: What AI applications in media buying, planning, and optimization are actually producing measurable results today — not in beta, not "coming soon"? For each, give me: the specific use case, realistic performance improvement range, implementation complexity (1-10), and whether it requires replacing existing tools or integrates with current stacks.
[size] with roles including [list key roles]. Design a non-threatening AI skills assessment I can share with my team. It should: (1) identify who's already using AI tools (and which ones), (2) surface which workflows are most AI-ready, (3) find the internal champions who can lead adoption, and (4) avoid language that makes anyone feel their job is at risk. Give me the actual questions to ask.
[role/team]: [describe 5-7 recurring tasks]. For each task, tell me: (1) Can AI do this now? Partially or fully? (2) Which specific tool handles it best? (3) How many hours per week would we save? (4) What's the learning curve to implement it? I need quick wins I can show results on within 2 weeks, not a 6-month transformation project.
[X%]. Instead of cutting heads, help me build a proposal that uses AI to increase output per person. Current team: [list roles and headcount]. Current output: [what you produce monthly]. Show me a model where the same team produces [X% more] using AI tools, with specific tools matched to specific roles. Include estimated costs for tools vs. savings from increased efficiency.
[specific content piece]. The output should be indistinguishable from our human-written content.
[description] and we currently rank for [key terms]. With AI overviews, generative search (GEO), and zero-click results fundamentally changing how people find information: (1) Which of our current rankings are most at risk? (2) What content formats will survive the shift to AI-generated answers? (3) How should we restructure our content strategy for a world where Google answers the question before anyone clicks? Give me a 90-day action plan.
[title] with [X] years of experience in [industry]. If I were starting a competing agency/company today with full knowledge of current AI capabilities, how would I structure it differently? What roles would I hire first? What tools would form my core stack? What would I automate from day one? What would I absolutely keep human? Help me see my own organization through the eyes of a well-funded, AI-native competitor — then tell me the 3 biggest moves I should make to close the gap.
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