Tl;dr (For Executives Who Are Between Meetings)
- AI isn’t a strategy. It’s a tool. Start with a quantifiable pain point, not a demo.
- Failure rates are high because problem fit, data readiness, and change management are low.
- Treat AI as augmentation, not automation. Humans remain the glue for collaboration, feedback, and accountability.
- Scale only after you prove ROI on a narrow use case. Run small, instrumented sprints tied to P&L metrics.
The Hype Mistake I Keep Seeing
Every quarter, I watch organizations plug LLM widgets into everything that moves — ticketing systems, internal wikis, CRM workflows — without asking: “What is the bottleneck? What’s the cost of this pain today? And how will we know if AI actually fixes it?”
The outcome is predictable: more dashboards, more babysitting, and an illusion of progress. Instead of lifting productivity, teams end up in a coordination tax, fighting flaky prompts, drifting models, and brittle automations. You can’t fix a workflow problem with model weights.
The Pattern of Negative ROI (And How It Shows Up)
As a PM, I live and die by two numbers: time-to-impact and cost-to-scale. The majority of failed AI initiatives burn both. Consider:
- Scope before proof: Teams deploy enterprise-wide GPT copilots before validating one measurable win in a single department.
- Data fog: “Let’s just start with the model” turns into six months of data cleanup no one budgeted for.
- Collaboration drag: AI “teammates” can actually slow work when they create uncertainty or unvetted outputs that humans must constantly review.
- Compliance hangovers: Bias, privacy, IP leakage — these aren’t edge cases anymore. They’re mainstream liability.
Five Real-World Scenarios That Should Make You Wary
1. Zillow Offers — Valuation Without Reality Loops
Zillow’s home-buying algorithm missed rapidly shifting market signals and operational constraints.
Result: huge write-offs, mass layoffs, and a fire sale of homes. Lesson: AI predictions without realtime feedback loops amplify risk, not insight.
2. IBM Watson for Oncology — Ambition Without Integration
A multibillion-dollar vision floundered because it couldn’t generalize beyond curated datasets, and clinicians found outputs unsafe or irrelevant. Lesson: If your AI doesn’t fit clinician workflows and messy data realities, it’s an expensive slide deck.
3. Amazon’s AI Recruiter — Bias Goes Brrr
Historical data trained the system to penalize women’s resumes. It never shipped.
Lesson: Garbage in, scaled garbage out. Bias isn’t just an ethics issue — it’s a product quality and trust issue.
4. Dutch Child-Benefit Scandal — Automation Without Oversight
A black-box risk-scoring system flagged thousands of innocent families, disproportionately minorities. Catastrophic social and political fallout.
Lesson: Opaque AI in public services without due process is a recipe for reputational and legal disaster.
5. LLM Coding Assistants — Productivity Isn’t Guaranteed
An RCT with experienced OSS developers showed slower completion times and lower reliability when using AI.
Lesson: For seasoned devs on complex codebases, context-switch and verification costs can outweigh autocomplete gains.
A Product Builder’s Decision Framework: The Problem-First Canvas
Use this one-pager before you greenlight anything “AI-powered.”
Problem Definition
- What is the specific workflow pain?
- How much time/money does it cost today?
- Who owns it and feels it daily?
Success Metric & Measurement Plan
- Define ONE metric tied to P&L (e.g., ticket resolution time, sales cycle length).
- Instrument early. If you can’t measure, you can’t manage.
Data Readiness Check
- Do the data exist, are they clean, and are they accessible?
- What’s the governance, privacy, and compliance posture?
Human-in-the-Loop Design
- Where do humans review, override, or fine-tune?
- How will feedback get captured and improve the system continuously?
- Rollout Plan & Kill Criteria
- Pilot in one team/process.
- Pre-define “stop” thresholds (e.g., no 10% improvement in 6 weeks).
- Scale only after evidence of repeatable value.
The “Wise Use” Playbook (What Actually Works)
1. Anchor on a Bottleneck You Can Price
Example: Walmart reduced shift planning from 90 to ~30 minutes before scaling the tool. They didn’t start with “Let’s AI the entire store.” They started with one measurable pain point.
Checklist:
- Is this a repetitive, high-volume task?
- Is accuracy more important than speed (or vice versa)?
- Do we have a ground truth to compare against?
2. Tight Feedback Loops and Change Management
Zillow lacked fast recalibration when the market shifted. Your AI too needs “reality-check hooks”: user feedback capture, retraining triggers, rollback buttons.
Checklist:
- What’s our feedback channel? (UI button, Slack slash command, etc.)
- Who triages and turns feedback into model/prompt fixes?
- How fast can we ship improvements?
3. Data Foundations First, Models Later
80%+ of failed AI projects cite data quality, availability, or ownership issues. Build ingestion, labeling, governance, and observability pipelines before fancy UX.
Checklist:
- Do we know our data lineage?
- Have we mapped sensitive fields (PII, PHI)?
- Is there a versioned dataset to reproduce results?
4. Augment Decision-Making, Don’t Replace It
Design the AI to propose options with rationale, not final decisions. Outcome: fewer blind spots, more resilience when the AI stumbles.
Checklist:
- Does the AI show its reasoning or evidence?
- Where can a human say “No, and here’s why”?
- Are decisions explainable in audits?
5. ROI-Tied Sprints, Not Endless Pilots
Run 4–6 week sprints against a single KPI. If you hit the target, expand. If not, sunset, learn, and move on.
Checklist:
- Do we have a written hypothesis and expected ROI?
- Is the team empowered to kill the project if it misses?
- Are we tracking both costs (cloud, people time) and benefits?
Practical Tools & Templates
- AI Opportunity Scorecard: Rank prospective use cases on impact, feasibility, data readiness, and compliance risk.
- Prompt/Model Change Log: Track what changed, why, and the effect on metrics. Treat prompts like code.
- AI Incident Register: Document and triage failures (bias, hallucinations, system downtime). Learn and iterate.
The Cultural Shift That Makes AI Work
- Curiosity over compliance: Encourage teams to experiment — but within guardrails.
- Evidence over ego: Ship what works, not what demos well.
- Transparency over magic: If people don’t understand how it works, they won’t trust it.
- Cross-functional ownership: PM + Data + Ops + Legal. AI is a team sport.
Final Thought: The Tool Is Powerful — The Discipline Is Rarer
AI can absolutely transform workflows, margins, and customer experience. But it happens only when you respect the fundamentals of product building : clear problems, measurable impact, tight feedback loops, and human responsibility.
So, before you push another “GenAI Copilot” into production, ask: Is this the sharpest tool for this specific job — or just the shiniest?
Want a One-Pager Template?
Reply with “Problem-First Canvas” and I’ll share a fillable template to qualify AI use cases in under 20 minutes.
If you found this useful, share it with that colleague who keeps saying “Can we just add ChatGPT to it?”


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