We're at the limits of my amateur knowledge, but I believe this is a fundamental limitation of monadic bind/generators. Instead, you should prefer applicative generators for optimal shrinking. https://github.com/hedgehogqa/haskell-hedgehog/issues/473#is...
In other words, applicative generators do not use "results of generators to dispatch to another generator", but instead shrinking is optimal due to the "parallel" nature of applicatives (I'm using "parallel" in the monadic sense, and not the sense of article's "threading" sense). Since applicatives are "parallel", they can shrink the generators independently. (Whereas monadic generators are in "series" and therefore shrinking one necessarily changes the behavior of the subsequent generator, as you noted.)
Please feel free to link your talk if it's public!