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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