A Crash Course in Terrible Prompts, Strategic Clarity, and Executive Survival

Apr 18 / Severin Sorensen
A March 2025 survey by Dataiku revealed that 74% of public company CEOs fear losing their jobs within two years if they fail to deliver meaningful AI-driven gains.

Let that sink in and ask yourself: Why only public company CEOs? In reality, no organization is exempt—and at the speed AI is transforming markets, some companies won’t last two years to figure it out.

The Real AI Crisis Isn’t Technical—It’s Executive

Leveraging Gemini Deep Research 2.5 Pro, Grok3, and ChatGPT4o, I have explored over 50 AI deployments and studied where ambitious AI visions go to die. I've culled through over 80+ websites that explore AI prompt craft, what is statistically significant, and what is just mumbo-jumbo wishful thinking with AI.

When we look at failed AI implementations, a pattern is painfully clear: AI projects don’t fail because the tech isn’t good enough. They fail because leaders don’t know how to think, talk, or lead with AI.

Over 80% of AI projects fail to reach completion. It’s rarely due to model capability. The real root? Leadership misalignment, vague objectives, and poor communication with AI tools

This is why I wrote The AI Whisperer (2nd Ed) Handbook for Leveraging Conversational Artificial Intelligence and ChatGPT for Business—to help leaders prompt clearly and think strategically. But I get it—not everyone has time for 300+ pages. So, I created this:

The 30 Worst Ways to Prompt an AI

A crash course in executive-level AI failure and how to avoid it. These aren’t theoretical. They’re drawn from real-world executive blunders—compiled with help from AI, academic research, and too many tragic project post-mortems.

Part I: Strategic Breakdown (Prompts with No Compass)

Part II: Cultural & Organizational Failures

Part III: Leadership Communication Gaps (How You Speak = How AI Responds)

Executive Takeaway: Prompting Is the New Strategic Communication

These 30 failures are more than funny—they’re diagnostic. If your team is:
  • Vague in their ideas,
  • Misaligned in strategy,
  • Scattered in feedback,
  • Untrained in iteration,

…they’re likely leading AI projects the same way.

What to Do Next

To shift from AI confusion to AI advantage:
  1. Educate your team – Treat prompting as a strategic skillset.
  2. Audit your prompts – Use the 30 fails list to identify gaps.
  3. Practice iteration – Build a culture of refining over expecting perfection.
  4. Tie prompts to outcomes – Never let AI be a toy. It's a business tool.
  5. Lead with clarity – AI mirrors your instructions. Prompt like a leader.

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