...and a partridge in a pear tree...
Set Anova for higher temp / doneness.
Cook first steak which requires being more done / well cooked.
When cooking is finished, pull steak out and chill.
Add ice to water bath to lower temp to that needed for cooking second steak
Cook second steak
About 20 minutes before "done" add first steak back to meat Jacuzzi.
2nd steak will finish, first steak will warm back up without cooking any more.
If steaks are to be very close in doneness (like Medium Rare and Medium) you can just cook both at the same time and sear the more cooked one for a few seconds longer per side.