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Another pattern I've seen is that the CTO is technical and can do the work, but all their experiences actually coding for the company is from the early days where releasing half-baked bug filled messes was the standard. As the organization grows, maturity around quality, security, reliability, etc. increase but they still have an internalized notion that the company should be able to ship product "like the old days".

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Alternatively, the slight variation where even shipping good clean robust code was easier in the old days because the product was much smaller and didn't have years of accrued product and technical decisions to work around or unpick, all of which were good at the time but don't work a few years later.

The "maturity makes things slower" thing can apply even if the quality of code was always good.

Then there's the 3rd issue, where everything has become a moat and it's just not worth the effort of trying to do a good job anymore.

I've literally seen things that should take an hour be weeks because it ended up involving 10 different teams. And while you may think that's an exaggeration, it's not.

software is often used to assert authority so people CAN'T even attempt to work around these issues. Paradoxically, software can actually make companies less effective.

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