The Pre-Mortem Forecaster
Why Your Project Failed (Before It Actually Does)
We're great at celebrating success, but terrible at imagining failure—until it's too late. Today's prompt flips the script by using AI to conduct a "pre-mortem": imagining your project has already failed and working backwards to identify what went wrong. This counterintuitive approach helps you spot blind spots and address risks before they derail your work.
Think of it as time travel for risk management. Instead of waiting for problems to emerge, you're asking AI to be your pessimistic fortune teller—revealing potential pitfalls while you still have time to avoid them.
Task
Use AI to generate a comprehensive list of reasons why your project might fail, then develop proactive strategies to address each risk. The goal is to strengthen your project by confronting its weaknesses head-on.
Sample Problem
Scenario: You're launching a new mobile app that helps people track their daily water intake with gamification elements. The app is set to launch in 3 months.
Pre-Mortem Prompt: "Imagine it's 6 months from now and my water tracking app with gamification features has completely failed. Generate a detailed list of 10 specific reasons why this happened, considering technical, market, user experience, and business factors. For each reason, explain the warning signs we missed."
Solution
ChatGPT 4o
Here’s a detailed post-mortem analysis of why your water tracking app with gamification features may have failed, covering technical, market, user experience, and business aspects.
1. Weak Retention Loop in Gamification Design
Reason: The gamification mechanics lacked compelling incentives to drive daily engagement beyond the novelty phase.
Missed Warning Signs:
Early users dropped off after onboarding despite earning initial rewards.
Metrics like Day 7 and Day 30 retention showed sharp declines.
Gamification features (e.g., streaks, badges) were not being widely used or shared.
2. Overly Complex Onboarding Flow
Reason: The initial setup process was long or confusing, especially with layered gamified elements and hydration goals.
Missed Warning Signs:
High drop-off rates during onboarding (e.g., after 2–3 screens).
Support messages or reviews indicating confusion.
A/B tests showing simpler flows performed better, but weren't prioritized.
3. Lack of Differentiation in a Crowded Market
Reason: The app didn’t offer a distinct value proposition compared to other water trackers or wellness apps.
Missed Warning Signs:
User feedback referencing other apps being “simpler” or “just as good.”
Low conversion rate on paid campaigns or store listing impressions.
App Store reviews highlighting “nothing new” or “uninspired.”
4. Inadequate Integration with Existing Habits
Reason: Users weren’t prompted at moments when they could or would realistically drink water (e.g., post-meal, morning routine).
Missed Warning Signs:
Low engagement with reminders.
Surveys showing users found the app “annoying” or “easy to forget.”
Usage patterns dropping during weekends or holidays, revealing poor habit alignment.
5. Poor Push Notification Strategy
Reason: Either too few notifications led to forgetfulness or too many resulted in uninstalls.
Missed Warning Signs:
Notifications disabled by a majority of users.
Spike in churn after implementing a new push strategy.
Reviews mentioning "spammy" or "annoying reminders."
6. Unclear Monetization Path
Reason: The business model (freemium, ads, subscriptions) wasn’t validated and failed to convert enough users to sustain growth.
Missed Warning Signs:
Free users did not see enough value to upgrade.
Premium features didn’t solve a strong pain point.
Ads disrupted the flow or gamified experience, leading to frustration.
7. Technical Instability or Syncing Bugs
Reason: Sync issues across devices, notification delays, or crash loops eroded trust and usability.
Missed Warning Signs:
App store reviews mentioning bugs, sync problems, or crashes.
Higher-than-average uninstall rate shortly after install.
QA missed edge cases or underestimated device fragmentation.
8. Limited User Feedback Loop
Reason: Users didn’t feel heard, and updates didn’t reflect their needs or suggestions.
Missed Warning Signs:
Feedback channels (email, in-app, surveys) went underutilized.
Feature requests repeated but remained unaddressed.
No community engagement or roadmap transparency.
9. Neglected Offline or Edge Use Cases
Reason: Users on poor connectivity or offline couldn’t use core functionality, causing frustration during workouts, hikes, etc.
Missed Warning Signs:
Complaints in support logs about logging water in remote areas.
No fallback strategy for offline functionality or syncing.
Assumption that hydration tracking only happens indoors/online.
10. Inconsistent Brand or Messaging
Reason: The brand identity, tone, or visual language may have shifted mid-course, causing confusion or alienating users.
Missed Warning Signs:
Marketing and product UI/UX were out of sync (e.g., fun ad campaigns vs. serious app tone).
A decline in conversion after a rebrand or UI overhaul.
Confused App Store reviews referencing expectations mismatch.
If you'd like, I can help turn this into a structured internal post-mortem doc, product decision checklist, or slide deck. Let me know.
Gemini 2.5 Pro
Here is a detailed list of 10 specific reasons why your water tracking app failed, along with the warning signs that were missed.
1. Gamification Felt Like a Chore 😥
The gamification elements, intended to be fun, became tedious. The rewards (e.g., digital badges, points) lacked real-world value and the mini-games were repetitive. Instead of motivating users, the app added another task to their daily to-do list.
Warning Signs We Missed: Early user analytics showed high engagement with gamified features only in the first week, followed by a steep drop-off. Qualitative feedback from user surveys repeatedly used words like "annoying," "childish," or "confusing" to describe the games. Churn analysis revealed a spike in uninstalls right after users unlocked the first set of "advanced" achievements, indicating the novelty had worn off.
2. Saturated Market with No Clear Differentiator 🌊
We launched into an incredibly crowded market without a strong unique value proposition (UVP). Dozens of other apps did the same thing, and many were either more established or offered a simpler, more focused experience. Our gamification wasn't unique enough to stand out.
Warning Signs We Missed: Our initial user acquisition cost (CAC) was alarmingly high, indicating we were struggling to capture attention. App store reviews frequently compared us unfavorably to competitors, stating things like, "It's just like [Competitor App], but with more notifications." Our brand failed to gain any organic traction or word-of-mouth buzz.
3. Aggressive Monetization Alienated Early Users 💸
In a rush for revenue, we introduced an intrusive subscription model and disruptive full-screen ads too early in the app's lifecycle. This broke the trust of our initial user base, who felt baited-and-switched after being promised a free, helpful tool.
Warning Signs We Missed: The day after the monetization update, our app store rating plummeted, and uninstall rates tripled overnight. User support was flooded with complaints about the "paywall" and "ad spam." Our daily active users (DAU) never recovered to pre-update levels.
4. Persistent Technical Bugs and Poor Performance 🐞
The app was unreliable. Users experienced frequent crashes, inaccurate tracking that would reset their daily progress, and significant battery drain. These technical flaws eroded user confidence and made the app unusable for many.
Warning Signs We Missed: Our bug reporting dashboard was consistently filled with critical issues like
NullPointerExceptioncrashes and data sync failures. App store reviews were littered with 1- and 2-star ratings specifically mentioning performance problems. Analytics showed that users with older phone models had a churn rate twice as high as those with newer devices.5. Notification Fatigue Overwhelmed Users 🔕
Our "smart" reminders weren't smart enough. The app sent generic, frequent notifications that users quickly found irritating. Instead of being a gentle nudge, the reminders felt like nagging, leading most users to either disable notifications or delete the app entirely.
Warning Signs We Missed: In the app's settings, analytics showed that over 60% of the active user base had manually turned off all push notifications within their first month. A/B tests on notification frequency showed no positive impact on long-term water logging, only on short-term app opens followed by immediate closes.
6. Failure to Integrate with the Health Ecosystem 🔗
Our app operated in a silo. It didn't sync with major health platforms like Apple Health or Google Fit, nor did it connect with popular fitness wearables like Garmin or Fitbit. Users want a consolidated view of their health, and we forced them to manually enter data in multiple places.
Warning Signs We Missed: "Apple Health integration" was consistently the top-voted item on our feature request board. Competitor apps that prominently advertised this integration were growing faster than we were. User exit surveys explicitly stated the lack of integration was the primary reason for switching to another app.
7. High-Friction Data Entry 💧
Logging water intake was simply too much work. It required opening the app, navigating to the log screen, and multiple taps to input a single glass of water. In a world of widgets and quick actions, our process was archaic and slow.
Warning Signs We Missed: Session recordings and heatmaps showed users repeatedly fumbling with the logging interface or abandoning the process midway. We received numerous requests for home screen widgets, Apple Watch complications, and simpler "one-tap" logging options, but we prioritized developing more gamification features instead.
8. Feature Bloat Diluted the Core Value 🎈
In an attempt to keep users engaged, we kept adding non-essential features like caffeine tracking, mood journals, and step counting. This "feature bloat" made the app confusing, slow, and distracted from its primary purpose: tracking water. Users who just wanted a simple tool were put off by the complexity.
Warning Signs We Missed: Usage analytics clearly showed that less than 5% of our user base ever engaged with the new, non-core features. Despite this, our development roadmap was almost entirely focused on adding more. User feedback mentioned the app was becoming "cluttered" and "unfocused."
9. The Novelty Wore Off Without Building a Habit ⏳
Our gamification provided a short-term extrinsic motivation (points and badges) but failed to help users build a long-term, intrinsic habit of drinking water. Once the initial novelty and challenges were gone, users had no compelling reason to keep using the app because the underlying behavior wasn't ingrained.
Warning Signs We Missed: Our retention cohorts showed a massive drop-off between Day 30 and Day 60. This timeline directly corresponded to when most users would have completed the "starter" quests and achievement tracks. There was no long-term engagement loop; the app was a fun distraction, not a habit-forming tool.
10. Misaligned Marketing and Target Audience 🎯
We marketed the app as a "fun game to help you drink more water," targeting a broad, casual audience. However, our most dedicated users were actually serious health and fitness enthusiasts who found the whimsical design and game elements distracting. We built an app for one group but marketed it to another.
Warning Signs We Missed: Ad campaigns featuring cartoonish graphics had high click-through rates but extremely low long-term retention. In contrast, blog posts that focused on the science of hydration had much better engagement and led to higher-quality users. User interviews with our "power users" revealed they ignored the games and just wanted a robust tracker.
Extra Credit
Take your pre-mortem to the next level:
Probability Rating: Ask AI to rate each failure scenario by likelihood (high/medium/low) and impact (critical/major/minor)
Mitigation Matrix: Create a response plan for each risk: "For each failure reason you identified, suggest 2-3 specific actions we could take now to prevent or minimize this risk"
Success Indicators: Flip the exercise—ask AI what early warning signs would indicate each risk is materializing, so you can course-correct quickly
General Takeaways
Specificity matters: Generic risks ("poor marketing") are less useful than specific scenarios ("influencer partnerships fell through because we didn't account for FTC disclosure requirements")
Timing is everything: Run pre-mortems at multiple project stages—what kills a project at launch differs from what kills it at scale
Embrace the negative: The more comfortable you get with imagining failure, the better you'll become at preventing it
Make it actionable: A pre-mortem without follow-up actions is just organized worrying. Always translate insights into concrete preventive measures
Remember: The goal isn't to become paralyzed by everything that could go wrong—it's to be prepared for what's most likely to go wrong. Use AI as your risk-spotting partner, and you'll build more resilient projects from day one.