I bring new software into my organization through two methods:

1. Someone has used it before
2. We are reasonably confident in our ability to use existing staff, possibly with a new expert hire or consultation

It’s pretty rare for a large org to do completely net new software. Training is usually a big deal if that happens. Massive layoffs are also a possibility (see enterprises being dumb about containers). Smaller orgs tend not to have this problem. If they do you can usually tell in an interview and just not go there. Devs are constantly experimenting with net new shit (current libs don’t do the thing; gotta find new libs). Again, smart leaders are open to this.

In general, staffing is a huge part of any of these decisions. You might not see the convo but it is most likely happening.