Why do so many enterprise software projects technically succeed but still feel like failures?

I’ve seen many enterprise projects hit every milestone — delivered on time, requirements met, stakeholders satisfied — yet the actual business value is close to zero.

Users avoid the system, teams keep using spreadsheets, and productivity barely changes. On paper it’s a success, but in reality nothing improves.

Is the problem:

  • Measuring success by delivery instead of outcomes?
  • Requirements driven by leadership instead of real users?
  • Too much process and not enough iteration?
  • Software built to satisfy contracts, not solve problems?

Curious to hear honest experiences — especially from people who’ve worked inside large organizations.

Posted Feb 23, 2026, 5:56 AM UTC

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