Gartner just published a striking admission:
“The skills gap is real: 85% of IT leaders report their teams aren’t prepared for future needs.”
Read that again. Eighty-five percent.
This isn’t a minor gap. This is a structural crisis — documented by the same analyst firm whose Magic Quadrants and Heat Maps drive billions in technology purchasing decisions.
And Gartner isn’t alone in knowing this.
The Three-Way Paralysis
In 2019, I wrote about procurement’s digital readiness gap — the uncomfortable truth that CPOs were being asked to lead digital transformations with teams that lacked the skills to execute them. (What Is Your Organization’s Digital Readiness?)
In 2023, I explored the CFO’s Black Box paralysis — the growing fear that AI-driven decisions couldn’t be validated, explained, or trusted. (Assessing the AI Threat)
Now, in 2025, Gartner confirms what we’ve been documenting for years:
All three know they’re not ready. Yet the industry keeps selling.
The Ferrari and the 16-Year-Old
Consider this scenario:
A 16-year-old walks into a dealership the day after getting their license. They have a wad of cash — enough to buy a Ferrari outright.
Should the salesperson sell them the car?
The kid has the legal right to buy. They have the money. They asked for it.
But the salesperson knows — based on experience, based on data, based on common sense — that this buyer has little chance of handling the vehicle safely.
Is completing that sale ethical?
Now apply this to enterprise technology.
Analyst firms, consultancies, and ProcureTech vendors know that 80% of implementations fail. They publish the data themselves. They know most organizations lack the skills, the readiness, the structural capacity to absorb what they’re buying.
And they sell anyway.
The CMO Confession
A Chief Marketing Officer for a major solution provider once told me — off the record — why they routinely take on clients they know will struggle:
“First: If we don’t take them on, a competitor will. And if anyone can make it work, we can.”
“Second: We have quarterly revenue targets to hit.”
This is the Revenue Trap made visible.
The incentive structure rewards selling, not succeeding. The metrics track bookings, not outcomes. The commission check clears whether the implementation works or not.
The Power of Pattern Recognition
Here’s what 35 years of data reveals:
Without Phase 0, 80% of initiatives will fail.
The 20% who succeed aren’t buying better technology. They already had ready teams.
The industry takes credit for the 20%:
- “Our methodology works”
- “Our implementation team delivered”
- “Our platform enabled transformation”
And blames the client for the 80%:
- “They didn’t have executive sponsorship”
- “Change management was weak”
- “The organization wasn’t committed”
But the variable isn’t the technology. It isn’t the vendor. It isn’t the methodology.
The variable is readiness.
The 20% had it before they started — whether they knew it or not. The 80% didn’t.
And nobody checked.
The Ethical Question
If 85% of IT leaders say their teams aren’t prepared…
If CFOs can’t see inside the Black Box…
If CPOs lack the digital readiness to execute transformation strategies…
Then why are we still selling Ferraris to new drivers?
The industry has spent 35 years investing trillions in technology while investing approximately nothing in readiness assessment.
The result? An 80% failure rate that hasn’t improved across four technology waves — ERP, e-Procurement, Cloud/SaaS, and now AI.
What Would Change This?
One simple requirement: Assess before you sell.
Before the Magic Quadrant recommendation. Before the RFP. Before the contract signature.
Ask the question the industry refuses to ask:
Is this organization ready to absorb what we’re about to sell them?
That’s Phase 0. That’s the missing layer.
CIOs, CPOs, and CFOs are all signaling some version of “we don’t fully understand this, and our teams aren’t ready” — whether it’s digital readiness, spreadsheet dependence, or fear of black-box AI in financial decisioning.
Despite that, analyst firms, consultancies, and vendors continue to market advanced platforms and AI as if the only barrier is budget and “change management” — effectively handing the Ferrari keys to a barely-trained driver because the sales quota depends on it.
85% aren’t ready.
The industry knows it.
Phase 0 would prove it — before the crash.
Our industry should be ashamed of itself.
TODAY’S TAKEAWAY
Before you act on anything an analyst firm, consultancy, or ProcureTech vendor tells you, ask one question:
“Is this insight constrained by their business model — or informed by my organization’s actual readiness?”
Because the graphic below admits it plainly:
- CIOs don’t believe their teams have the skills.
- CFOs are suspicious of the AI black box.
- CPOs know their organizations aren’t structurally ready.
Yet the industry continues selling transformation without ever measuring readiness.
That’s not dishonesty.
It’s incentive physics — and once you see it, you can’t unsee it.
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Procurement Insights 
Rajeshkumar Bhatt
December 10, 2025
Fantastic article Jon. Thanks for sharing your thoughts.