AI Project Devil's Advocate
Before you greenlight an AI project, this tool interviews you for 15 minutes and produces a brutally honest red-team memo: likely failure mode, who will and won't use it, what metric to actually track, and the skeptical questions your board will ask.
Mid-market product and ops leaders being pushed to adopt AI by executives who don't want to hear 'no'
- 15-minute guided interview that adapts questions to your planned AI use case (internal bot, customer-facing, agentic workflow, AI vendor purchase)
- Auto-generated red-team memo with the most common failure patterns for your project type, the metrics leaders usually hide, and the questions a non-technical exec will ask
- Adoption-risk checklist with named warning signs (e.g., 'employees already route around the internal wiki — an LLM won't fix that')
- Quarterly re-read prompt: 'go check on your AI project 90 days later' so you can intervene while there's still time
The Ludicity essay claims a 0% success rate on AI projects observed across the past year, with executives refusing to hear it — leaders who DO want to hear it have no tool to help them push back or design smarter.
MIT (95% fail), Gartner (2% deliver value), RAND (80% fail), S&P Global all confirm massive AI project failure rates — pain is real and exec-discussed, validating pull for a red-team tool.MIT Report Reveals Shocking 95% Failure Rate for Corporate AI Projects ↗AI Project Failure Rate: Why 95% of AI Projects Fail ↗
Direct competitor Pre-Mortem Agent ($9-$49/mo) and several 'Devil's Advocate' prompt libraries (Shannon AI, PolicySolve, PM courses) already serve adjacent users; whitespace is narrower than the idea implies.Pricing — Pre-Mortem Agent ↗Devil's Advocate / Red Team | Skills | Shannon AI ↗
Competitors price $9-$49/mo for founders; mid-market product leaders might pay $200-500/mo but typically outsource red-teaming to consultants — willingness to pay for a self-serve tool at that tier is unproven.Pricing — Pre-Mortem Agent ↗Devil's Advocate and Red Teaming | Adan Corporate ↗
Red-teaming as a discipline is durable, but contrarian-AI sentiment is cyclical — if AI project success rates improve, demand for a 'devil's advocate' tool could wane within 2-3 years.AI project failure rates are on the rise: report | CIO Dive ↗
Core is prompt engineering + interview UX over an off-the-shelf LLM — no proprietary data, no technical moat; shippable in weeks, but defensibility is low.Devil's Advocate / Red Team | Skills | Shannon AI ↗