Context Engineering Without Readiness Is Just a Sophisticated Way to Fail

Posted on November 29, 2025

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Gartner’s pivot to context engineering makes sense — AI systems do need situational awareness, not just prompts. But here’s the question they’re not asking . . .

The recommendation is ‘appoint a context engineering lead.’ The question they don’t ask is whether your leadership, governance, and culture can make that lead effective — or whether they’ll be neutralized by the same structural conflicts that produced the 80% failure rate.

Context engineering without readiness assessment is just a more sophisticated way to fail.

The Gartner Playbook

Think about it:

The pattern: Every time a new technology wave exposes organizational unreadiness, Gartner doesn’t help organizations become ready — they sell a service that works around the unreadiness.


The Business Model

Here’s the real business model behind it:

“Rent out high-priced context engineers to practitioners looking to dodge the question about their readiness.”

That’s exactly it. Here’s how it works:

  1. Acknowledge the problem — “Agentic AI has high failure rates due to poor context.”
  2. Name a technical solution — “Context engineering.”
  3. Create a new billable role — “Appoint a context engineering lead or team.”
  4. Sell the service — Gartner-certified context engineers, context audits, context architecture assessments.
  5. Never ask the uncomfortable question — “Is your organization ready to absorb this?”

The client gets to say: “We hired context engineers. We’re doing context engineering. We followed Gartner’s guidance.”

The client doesn’t have to say: “We examined whether our leadership, governance, and culture could support autonomous AI — and we might not be ready.”


Why It Works (For Gartner)

Because readiness is hard. It requires:

  • Looking in the mirror
  • Admitting capability gaps
  • Possibly delaying a project that the CEO already announced
  • Holding leadership accountable

Context engineering is easy. It requires:

  • Hiring consultants
  • Building pipelines
  • Appointing a team
  • Checking a box

One threatens the power structure. The other preserves it.

Guess which one Gartner sells?


The Question They’ll Never Ask

Gartner will never publish:

“Before you invest in context engineering, measure whether your organization has the governance maturity, leadership alignment, and process capability to sustain it. If you score below 72/100, your context engineering initiative will fail — regardless of who you hire.”

Because that would:

  • Reduce billable hours
  • Delay technology purchases
  • Hold their clients accountable
  • Shrink their market

The 80% failure rate isn’t a problem for Gartner. It’s a renewable revenue source.

REMEMBER: Failure isn’t something that happens to you — it’s a choice. Choose wisely now, or find yourself exactly where you are today, 5 to 10 years from now.


Posted in: Commentary