CEO AI Briefings

January 2025

AI Project Failures

Why 80% of AI initiatives fail—and how to be in the 20% that don't.

The Session

Most AI projects fail. Not because the technology doesn't work, but because of predictable organizational, strategic, and execution mistakes that mid-market companies keep making.

In this session, we'll examine real failure patterns—not sanitized case studies, but actual situations from companies in our network. What went wrong. What the warning signs were. What could have been done differently.

More importantly: we'll develop a practical framework for evaluating your own AI initiatives before you commit capital. The questions to ask. The red flags to watch for. The organizational conditions that need to be in place.

You'll Leave With

  • A diagnostic framework for evaluating AI project viability
  • The 7 most common failure patterns in mid-market AI adoption
  • Board-ready materials on AI project governance
  • Peer perspectives from CEOs facing similar decisions

Agenda

8:30 AM Breakfast and introductions
9:00 AM The failure landscape: what the data actually shows
9:45 AM Case examination: three failure patterns in detail
10:45 AM Break
11:00 AM Peer discussion: what are you seeing in your organization?
11:45 AM The diagnostic framework: evaluating your initiatives
12:30 PM Working lunch and continued discussion
1:00 PM Session concludes

Cancellation Policy

14+ days: full refund. 7-13 days: 50% refund or credit to future session. Under 7 days: transfer to another CEO from your network, no refund.

Bring Your Team

The Executive AI Briefing on the same topic runs the following week. Send your COO, CFO, or other leaders who need to execute on your AI decisions.

View Executive Session