The meaning of pragmatism as a term has been hijacked to mean subjectively justified hacking and piling up a mountain of cruft.
A "just dump it under the rug while no one is looking" development.

IMHO, part of the value of a migration is to not build parts of the code that don't make sense anymore. Simplify for the current scenario, discard outdated use cases.
I've never tried it myself so I'm genuinely asking, is it possible and how to accomplish that with the help of AI coding tools?

Wild to me that a CEO sets goals about outcomes that have nothing to do with the business (are customers more satisfied? Is the product more reliable? Etc.)

Setting the goal of what % of code should be AI-generated is as useful as setting the goal of how many lines of code devs should write per day

Working in high-quality code improves development speed by as much as 7x. Mob/Ensemble programming can give you a 3x improvement. Getting rid of bottlenecks also yields major improvement. You get the idea.

None of the above impacts outcomes.
4/5

Follow the urge to understand why. Don't settle, fix the code and the system. In small chunks, to the extent that you can, but do something about it.

(Picture is quote from 'The Fearless Organization' by Amy C Edmondson).

Yet sometimes they are so hard to remove, because it means fighting an organizational flaw that allowed them to be created and flourished in the first place: the lack of psychological safety.

Maybe over simplistic, but: set the goal and let the teams rearrange around it. Support them figuring out what works and what doesn't. Start with a big overlap until the "natural" boundaries reflect both in interactions and software?

I'm saving this picture for future reference!