From Pilot To Production: Why CIOs Need Better Failure, Not Less Of It
Techstrong.IT, Thursday, April 2nd, 2026
I've been in IT long enough to remember when Windows shipped on floppy disks and enterprise architecture meant racks, not regions. In that time, I've seen the same cycle repeat itself over and over. A new technology shows up. A pilot gets approved. The pilot goes well enough.
Then the tech hits production (and production hits back), and suddenly everyone looks surprised that reality is more complicated than the demo. You might think this is an example of a failure of technology. You'd be wrong.
The uncomfortable truth is that most projects fail not due to a technical shortcoming, but because organizations struggle to learn and adapt quickly enough. Good technology gets implemented in the wrong place or at the wrong time. Or both. Solid architectural choices run up against poor organizational habits. A common saying among I.T. elders is 'projects fail at layers 8, 9, and 10 of the OSI model: Finance, compliance, and politics.