Why bad software keeps winning
The incumbent’s real moat often isn’t the product. It’s the cost, risk, and annoyance of switching.
Most companies do not keep bad software because they love it. They keep it because replacing it feels harder than learning one more workaround.
01
The product stopped earning the renewal years ago
Legacy software often survives on institutional memory. Someone chose it years ago, the workflows grew around it, and the organization gradually stopped asking whether it was still the best fit.
02
Switching friction becomes the moat
Data migration, retraining, integrations, historical records, and the fear of downtime can matter more than product quality. The incumbent does not have to delight the customer. It only has to make leaving feel expensive.
03
The replacement has to win on the whole transition
A better interface is not enough. The strongest replacement offer owns the migration, preserves the data that matters, recreates the critical workflow, and gives the team a clear cutover path.
04
A useful question
If the software disappeared tomorrow, which five things would the team actually need rebuilt first? That answer is usually much smaller than the feature list on the vendor’s website.
Question to take back to your team
If this software disappeared tomorrow, which five things would your team actually need rebuilt first?
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