Market Discovery & Empathy
Day 1 · 09:00 - 13:00
1.1 The Noise Reduction Trap (Data Clustering)
🪤 The Trap
Summarize these 500 customer reviews.
🛑 The HITL Critique
An executive summary hides the bleeding. If users hate the checkout button, the AI will say "Some users experience payment friction." You cannot build a backlog from a summary.
🚀 The Escalation
Act as a forensic data analyst. Ingest this raw feedback. Do not summarize. Cluster the data by "Severity" and "Churn Risk". Extract the exact top 3 bugs causing the highest drop-off rate, quoting the users directly.
1.2 Defeating the Stereotype (Persona Generation)
🪤 The Trap
Act like a typical millennial banking customer and tell me what features you want.
🛑 The HITL Critique
The AI hallucinates a stereotype based on Reddit data. It will ask for "crypto and fast UI." It is not representing YOUR actual angry users.
🚀 The Escalation
Using ONLY the highest-severity cluster from the previous prompt, construct a "Synthetic Persona" representing our most frustrated user. Give them a name, context, and a primary grievance. Do not invent details outside the data provided.
1.3 The Synthetic Interview (Empathy Gap)
🪤 The Trap
Would you like a dark mode feature?
🛑 The HITL Critique
The AI will politely say yes. You are leading the witness. You must force the AI to be hostile and protective of its time to simulate a real B2B interview.
🚀 The Escalation
Stay in character as the frustrated Persona. I am pitching a 'Dark Mode UI' Epic. Respond with extreme skepticism based on your recent transaction trauma. Score my pitch out of 10 for actual value, and tell me what I SHOULD be building instead.
1.4 Competitor Teardown (Blind Spots)
🪤 The Trap
Compare our app to our biggest competitor.
🛑 The HITL Critique
A generic Wikipedia-level comparison. It tells you what everyone already knows. We need actionable product gaps.
🚀 The Escalation
Act as an aggressive disruptor Product Manager. Build a feature-parity matrix comparing us to [Competitor]. Do not list similarities. Identify the "Blue Ocean" gap—the specific feature they are missing that costs them high-net-worth users.
1.5 Churn Prediction (The Silent Killer)
🪤 The Trap
Why do people uninstall apps?
🛑 The HITL Critique
You asked a generic question, you got a generic blog post. We need to correlate our specific data to churn triggers.
🚀 The Escalation
Analyze our support ticket data again. Identify the "Silent Churn" indicators—issues that users mention in passing before abandoning the app entirely, rather than complaining loudly about. Output a risk-mitigation Epic for the backlog.
Value, Revenue & Prioritization
Day 1 · 14:00 - 18:00
2.1 The WSJF Engine (Cold Math Prioritization)
🪤 The Trap
Here are 5 Epics. Prioritize them for me.
🛑 The HITL Critique
The AI guessed based on training bias. It didn't ask for business value or effort. Never let an AI make unconstrained roadmap decisions.
🚀 The Escalation
Act as a Lean Portfolio Manager. I will provide 5 Epics. Force me to score (1-10) for: User/Business Value, Time Criticality, Risk Reduction, and Job Size. Then, calculate the WSJF score for each and output a ranked Markdown table.
2.2 Cost of Delay (Financial Impact)
🪤 The Trap
What happens if we delay Epic 1?
🛑 The HITL Critique
You get a generic "users might be unhappy." You need hard financial projections to defend your backlog to the CFO.
🚀 The Escalation
Using the WSJF table, calculate a hypothetical "Cost of Delay" (CoD) in dollars for delaying the #1 ranked Epic by 4 weeks. Assume our app generates $100k MRR. Draft a 3-bullet executive summary defending why Epic 1 cannot be delayed.
2.3 Stakeholder Negotiation (Pushback)
🪤 The Trap
Write a polite email to the CEO telling him we aren't building his pet project.
🛑 The HITL Critique
A polite email gets you fired. A data-backed counter-proposal gets you promoted.
🚀 The Escalation
Draft a data-backed counter-proposal for the CEO. Use the WSJF matrix and the Cost of Delay calculation to prove that prioritizing his pet project (Epic 4) will cost the company MRR and increase churn among our highest-severity users.
2.4 Regulatory & Risk Mapping
🪤 The Trap
Are there any risks with Epic 1?
🛑 The HITL Critique
The AI will say "There might be software bugs." You need specific industry compliance risk mapping.
🚀 The Escalation
Act as a strict Chief Compliance Officer for [Your Industry]. Review our top-ranked Epic. Identify the hidden regulatory landmines (e.g., GDPR, HIPAA, SOC2 compliance risks) that the dev team will likely overlook. Generate 2 mandatory compliance user stories.
2.5 OKR Alignment Verification
🪤 The Trap
Does this backlog look good?
🛑 The HITL Critique
Sycophancy again. The AI says yes. You need to ensure your backlog actually hits the board's targets.
🚀 The Escalation
Our Q3 Corporate OKR is "Increase User Retention by 15%". Audit our prioritized Epic backlog against this specific OKR. Flag any Epics that are "Vanity Projects" failing to directly drive this metric. Suggest replacements.
Orchestration & Execution
Day 2 · 09:00 - 13:00
3.1 Epic Slicing (The Horizontal Failure)
🪤 The Trap
Break this Epic into user stories for the dev team.
🛑 The HITL Critique
The AI will slice horizontally: "Build DB," "Build API," "Build UI." This creates technical silos and zero usable value until the end of the sprint.
🚀 The Escalation
Slice this Epic VERTICALLY into exactly 6 User Stories. Every story MUST deliver end-to-end user value crossing all architectural layers. Strictly adhere to the INVEST principle. Flag any story that seems too large for a standard 2-week sprint.
3.2 BDD/Gherkin Generation
🪤 The Trap
Write acceptance criteria for Story 1.
🛑 The HITL Critique
It provides a generic bulleted checklist. Developers will misinterpret it, leading to bugs.
🚀 The Escalation
Generate exhaustive Behavior-Driven Development (BDD) criteria for Story 1. Use strict Gherkin format (Given / When / Then). Ensure there are at least 2 Happy Paths and 2 Negative Paths mapped out.
3.3 Edge Case & Negative Path Identification
🪤 The Trap
Did you miss anything in these stories?
🛑 The HITL Critique
The AI will reassure you that it did a great job. It won't find the edge cases until you force it to think like a hacker.
🚀 The Escalation
Act as a chaotic user trying to break the system. Review the acceptance criteria you just wrote. Identify 3 bizarre edge cases (e.g., rapid double-clicking, network drop during save, invalid character inputs) and write new criteria to prevent them.
3.4 Dependency Mapping (Talking to Eng)
🪤 The Trap
Are there any dependencies here?
🛑 The HITL Critique
It will give obvious answers like "You need a database." You need to anticipate blockers before Sprint Planning.
🚀 The Escalation
Act as a Lead Systems Architect. Review the 6 generated stories. Map out the hidden technical dependencies between them. Identify which story poses the highest architectural risk and must be spiked/prototyped first.
3.5 Effort Estimation Sanity Check
🪤 The Trap
How many story points is this?
🛑 The HITL Critique
AI cannot accurately guess story points for your specific team. It hallucinates numbers.
🚀 The Escalation
I do not want story points. I want a Complexity Audit. Compare these 6 stories against each other based strictly on logic complexity and integration risk. Output a relative sizing chart (S, M, L) to help my dev team baseline their estimates during planning.
Quality, Telemetry & Partnership
Day 2 · 14:00 - 18:00
4.1 Adversarial QA (Reflective Prompting)
🪤 The Trap
Review your work to make sure it's perfect.
🛑 The HITL Critique
The AI will literally just reply "It is perfect." You must trigger persona switching.
🚀 The Escalation
Forget your previous persona. Act as the world's most pedantic, aggressive Lead QA Engineer. Interrogate the acceptance criteria. Find 3 massive loopholes a junior developer will exploit to build the wrong thing. Rewrite to close the loopholes.
4.2 Sprint Telemetry Diagnosis
🪤 The Trap
Analyze this sprint data. Why did velocity drop?
🛑 The HITL Critique
The AI states the obvious: "Velocity dropped because fewer points were finished." You need systemic root-cause analysis.
🚀 The Escalation
Act as an Elite Agile Coach. Correlate the Cycle Time data against Code Review Duration and Bug Rates. Diagnose the hidden systemic bottleneck (e.g., Is QA starving because devs batch commits?). Output a root-cause hypothesis.
4.3 The Auto-Retrospective
🪤 The Trap
Give me 3 questions to ask in the retro.
🛑 The HITL Critique
You get generic "What went well / What didn't" questions. This leads to boring, useless retrospectives.
🚀 The Escalation
Based on the bottleneck diagnosed in the previous step, design a targeted 30-minute Retro agenda. Generate 3 provocative, psychologically safe questions designed to help the engineering team realize the batching issue themselves without feeling attacked.
4.4 Release Note Translation
🪤 The Trap
Write release notes for the stories we finished.
🛑 The HITL Critique
The AI writes technical jargon that customers don't care about ("We updated the API endpoints").
🚀 The Escalation
Translate these completed Jira stories into Customer-Facing Release Notes. Do not mention APIs or databases. Focus 100% on the unlocked business value and how this makes the user's life easier today. Match the tone of an Apple product launch.
4.5 The Executive ROI Report
🪤 The Trap
Write a sprint summary for the board.
🛑 The HITL Critique
The board does not care about your sprint velocity or story points. They care about money and risk.
🚀 The Escalation
Draft the Executive ROI Report for the Sprint Review. Map the delivered features directly back to the Q3 OKRs. Calculate the estimated Cost of Delay we successfully mitigated by delivering this on time. Keep it under 200 words.
Data Repository (BYOC)
Bring Your Own Context
Select your industry below. Use this data for Session 1 and Session 2.
Raw Support Tickets (For Session 1)
"App crashes every time I try to deposit a check. Have to drive to branch. 1 star."
"Why did you change the transfer UI? Took me 10 mins to figure out how to pay my rent."
"FaceID login is broken since the iOS 17 update."
"Got hit with an overdraft fee because my pending balance didn't show my Amazon purchase. Unfair."
"Widget takes 12 seconds to load my balance."
The 5 Epics (For Session 2)
Epic 1: Implement AI Support Chatbot (Marketing wants this to sound futuristic).
Epic 2: Fix iOS 17 FaceID Login Crash (High user frustration).
Epic 3: Rewrite Pending Balance Calculation Logic (Legal risk regarding unfair overdraft fees).
Epic 4: Implement Crypto Trading Wallet (CEO's pet project, highly complex).
Epic 5: UI Refresh for Transfer Screen (Revert to 1-click UX based on user confusion).
Patient Portal Tickets (For Session 1)
"I can't find my MRI results anywhere on the dashboard. Is it under Records or Visits?"
"Trying to book an appointment for my son but the system keeps overriding his profile with mine."
"The password reset email never arrives. Blocked out of my account for 3 days."
"Why does this app ask for my Social Security Number every time I log in? Feels insecure."
"Doctor said he messaged me, but I didn't get a push notification."
The 5 Epics (For Session 2)
Epic 1: Single Sign-On (SSO) Integration (High security effort).
Epic 2: Redesign Test Results Dashboard (High patient frustration).
Epic 3: Push Notification Overhaul for Doctor Messages.
Epic 4: AI Symptom Checker (Marketing initiative, high regulatory risk).
Epic 5: Family Profile Management Fix (Complex database dependency).
Enterprise Zendesk Tickets (For Session 1)
"The Salesforce API sync failed again overnight. We lost 400 leads."
"CSV export limits at 10,000 rows. We need 100k rows for our Q3 reporting."
"The new navigation bar hides the Admin settings. Took me an hour to find user permissions."
"I deleted a user and it wiped out all their historical sales data. We need a soft-delete feature."
"Role permissions are broken. Junior reps can see executive dashboards."
The 5 Epics (For Session 2)
Epic 1: Salesforce API Sync Stability Overhaul.
Epic 2: Implement Soft-Delete / Data Recovery Protocol.
Epic 3: Dark Mode Dashboard (Requested by 2 vocal users).
Epic 4: Increase CSV Export Infrastructure to 250k rows.
Epic 5: Role-Based Access Control (RBAC) Security Patch (Critical vulnerability).