Analysts Gone Wild: Why October’s Enterprise Software Stories Prove Nothing Has Changed Since 2008

Posted on October 27, 2025

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Join us Thursday, October 30th, at 11:00 AM ET for LinkedIn Live Episode 38


The Pattern I Documented 17 Years Ago Is Repeating With AI Agents

In 2008, I wrote a white paper analyzing SAP public and private-sector implementations. I documented a devastating pattern:

Organizations were inheriting technology from Finance- or IT-driven ERP deployments, then trying to make their procurement practices fit the technology—instead of the other way around.

The result? A 95% failure rate that included:

  • Hershey Food Corp: $112M, 30 months, order fulfillment broken
  • FoxMeyer Drug: Bankruptcy, $500M lawsuit against SAP
  • HP: Lost $400M in revenue from failed SAP rollout
  • Cadbury: £12M hit from SAP supply chain project

But there was one exception: The Commonwealth of Virginia.

They succeeded because they did something radical: They assessed behavioral readiness BEFORE technology deployment.

Everyone else failed because they deployed technology THEN discovered readiness gaps.


Fast Forward to October 2025: The Same Pattern With AI Agents

This month, we’re analyzing 10 major enterprise software announcements on LinkedIn Live with industry analysts Sam Gupta (ElevatIQ), Jan Burian (Trax), Michael Fiouscette (Arion Research), and Robert Kramer (Moor Insights & Strategy).

The announcements include:

  • Daedong USA’s $11.4bn ERP dispute lawsuit
  • Mendix’s “surging demand” for agentic AI
  • OutSystems’ Agent Workbench for “empowering enterprises”
  • ServiceNow’s “AI Experience” platform
  • Salesforce’s context-aware AI in Slack
  • And five more Layer 1 (technical capability) expansions

Here’s what I’m seeing: The EXACT SAME PATTERN repeating with AI agents.

The technology label has changed from ERP modules to AI agents.

The failure mechanism hasn’t changed at all.


What’s Missing? Layer 2: Behavioral Readiness

Every one of these announcements expands technical capability (Layer 1) without addressing behavioral readiness (Layer 2).

  • Mendix responds to “surging demand”—but demand ≠ readiness
  • OutSystems promises to “empower enterprises”—but do enterprises have conversational AI fluency?
  • ServiceNow unveils “the AI Experience”—but are users ready to experience AI as a collaborative partner?

The question no vendor is asking: “Are organizations ready to execute with autonomous agents?”

This is the same question no one asked before deploying ERP systems in the 2000s.

And we know how that ended.


The $11.4 Billion Validation

Daedong USA’s lawsuit isn’t just a legal dispute. It’s the largest single-case validation of behavioral readiness failure I’ve seen in 18 years of tracking procurement technology.

The organization had:

  • ✓ Technical capability (ERP system)
  • ✓ Contractual agreement (now disputed)
  • ✓ Vendor support (disputed execution)

What was missing:

  • ✗ Behavioral readiness assessment before deployment

The cost of skipping Layer 2: $11.4 billion in litigation.


The Devastating Parallel: Then and Now

2008 White Paper Findings:

Failures:

  • Organizations inherited technology from Finance/IT
  • Procurement had to adapt practice to fit the software
  • Resources spent making software “work” instead of serving practice
  • Result: “Organizations are now in the software business”

Success (Commonwealth of Virginia eVA):

  • Process understanding BEFORE technology selection
  • Behavioral readiness assessment BEFORE deployment
  • Stakeholder collaboration THROUGHOUT implementation
  • Result: 1% spend adoption (2001) → 80% adoption (2007)

2025 Announcement Pattern:

Current Trajectory:

  • 9 announcements expanding Layer 1 (technical capability)
  • 0 announcements addressing Layer 2 (behavioral readiness)
  • 1 announcement ($11.4bn lawsuit) proving what happens when you skip Layer 2

What Success Requires:

  • Same as Virginia model
  • But now systematized through The October Diaries methodology
  • And measurable through the Hansen Fit Score

The Quote That Matters

From my 2008 white paper:

“Unfortunately, this has meant that the vast majority of purchasing organizations are now in the software business as they attempt to adapt their practice to an application they would not have chosen to use in the first place. In this scenario, making the software ‘work’ becomes the focal point.”

This is exactly what’s happening with AI agents in 2025.

Except now, organizations are about to be in the “AI training business”—spending resources teaching AI agents about their practice, instead of first assessing if they’re ready to collaborate with AI agents.


Two Futures, One Choice

Daedong’s $11.4bn lawsuit is what happens when you skip behavioral readiness assessment.

Commonwealth of Virginia’s 80% adoption rate is what happens when you don’t.

The October Diaries ensures you end up in the second category, not the first.


Join the Discussion: Thursday, October 30th at 11:00 AM ET

We’ll be analyzing all 10 announcements through this lens with some of the sharpest analysts in enterprise software:

  • Sam Gupta (CEO, ElevatIQ)
  • Jan Burian (Head of Industry Insights, Trax)
  • Michael Fiuscette (CEO, Arion Research)
  • Robert Kramer (VP & Principal Analyst, Moor Insights & Strategy)
  • Jon W. Hansen (Strategic Advisor, Procurement Insights)

What we’ll cover:

  • Why these 10 announcements prove the pattern from 2008 is repeating
  • What behavioral readiness looks like for AI agents
  • How organizations can avoid becoming the next Daedong
  • Why The October Diaries methodology addresses what 17 years of “better technology” hasn’t solved

The Bottom Line

I’m not introducing a new theory on this panel.

I’m presenting 17 years of evidence that the same failure pattern keeps repeating—and a methodology that finally addresses the root cause.

The technology has evolved from ERP modules to AI agents.

The failure pattern has not evolved at all.

Join us to see why—and more importantly, what to do about it.


[LinkedIn Live: Thursday, October 30th, 11:00 AM ET]

Analysts Gone Wild: Analyzing Enterprise Software Stories – October 2025 – Episode 38

[Register/Set Reminder on LinkedIn] – https://www.linkedin.com/events/7388197365100371968/


Jon W. Hansen is Strategic Advisor at Procurement Insights and the creator of The October Diaries behavioral readiness methodology. His 2008 white paper on SAP public and private-sector implementations documented the pattern that continues to drive technology failure—and the exception that proves behavioral readiness is the missing link.

SEE YOU THURSDAY.

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Posted in: Commentary