ENT in particular was interesting, when I went back and re-watched it after finally getting to TNG/DS9/VOY (ENT being the first one I saw): They IMO successfully crossed real-world interfaces with TNG-era LCARS [0], creating something that looks vaguely like a tiled window manager, has a minimize function akin to the Windows start-bar (the icons on the right are minimized windows, used on rare occasion in the show for discreet messages), but with a whole bunch of hints of a natural progression into what it would become later in-universe.
It's also interesting how they included design hints of how this would evolve in to TOS era design later (the bulky monitor for example).
It's kind of ironic actually: we as viewers expect that kind of historical consistency, and complain about changes that feel disconnected, but in reality the history of interface design is full of such kind of radical shifts!
[0] https://memory-alpha.fandom.com/wiki/Desktop_monitor?file=22...