At the highest level, this is a leadership issue. There's a lack of someone at a sufficiently high level (eg: C-suite) that properly understands technology, and

At the highest level, this is a leadership issue. There's a lack of someone at a sufficiently high level (eg: C-suite) that properly understands technology, and that's probably caused by the rest of the leadership team not understanding their limitations. At a lower level, it's allowing individuals to become knowledge silos (or having a bus factor [1] of 1); lack of documentation; not having+testing disaster recovery plans; neglecting systems, code bases, and platforms; letting technical debt accrue endlessly (or worse: not even realize that's what you're doing). How to avoid? Make sure there's a strong, competent technology leader with a vested interest in the company succeeding, and empower them to make the changes they need to. What should that person be doing? Making sure all the stuff I just said doesn't happen. [1] https://en.m.wikipedia.org/wiki/Bus_factor https://en.m.wikipedia.org/wiki/Bus_factor