The Human Capitalist

This AI Decision Guarantees 95% Failure

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Most AI conversations in leadership focus on tools, skills, and headcount — but that's not where AI is breaking companies.

The technology mostly works. What's failing is how organizations are being redesigned around it. Leaders are restructuring before they understand where value has moved — and it's making companies brittle, not leaner.

In this video (Part 1 of 3), I break down the first critical decision error I see leaders making as they rush to "do something" about AI.

🔑 KEY TAKEAWAYS:

  • Why "pilot purgatory" is killing AI ROI across organizations
  • Where value actually moves when AI enters workflows (hint: it's judgment and orchestration)
  • The MIT stat that should alarm every executive: 95% of enterprise AI pilots fail to deliver ROI
  • How Zillow's AI strategy backfired — and the lesson for every leader
  • The rule you cannot violate when restructuring around AI

    • ⏱️ TIMESTAMPS:

    0:00 - The real problem with AI conversations
    0:22 - What "pilot purgatory" looks like
    0:43 - It's not a tooling problem — it's a people decision problem
    0:56 - About this channel
    1:26 - What you're probably seeing in your organization
    1:51 - The first decision error: restructuring too early
    2:21 - Redesigning org charts before understanding value movement
    2:43 - Where value actually moves (McKinsey research)
    3:31 - Why removing the middle makes you brittle
    3:42 - Why 95% of AI pilots fail (MIT study)
    4:19 - The Zillow cautionary tale
    4:55 - The rule leaders keep violating
    5:18 - What's next: Errors #2 and #3

    📚 RESOURCES MENTIONED:

    • MIT Study on AI Pilot Failures: https://fortune.com/2025/08/18/mit-report-95-percent-generative-ai-pilots-at-companies-failing-cfo/
    • McKinsey Research on Human-AI Orchestration: https://www.mckinsey.com/mgi/our-research/agents-robots-and-us-skill-partnerships-in-the-age-of-ai
    • SHRM Article on Zillow Offers:https://www.shrm.org/enterprise-solutions/insights/when-automation-backfires--how-rushed-ai-implementation-can-hurt0

      • 🔗 CONNECT WITH ME:

      • LinkedIn: linkedin.com/in/trentcotton
      • Website: trentcotton.com
      • Book: Sprint Recruiting

        • 👉 This is Part 1 of a 3-part series on AI decision errors. Subscribe so you don't miss Parts 2 and 3.

        #AIStrategy #HRLeadership #WorkforceTransformation #TalentStrategy #FutureOfWork #AIinHR

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        The Human CapitalistBy Trent Cotton & Purple Acorn Network