Ooh... I completely mixed it up with another, similarly named PrC...
I say that you should regain a single maneuver at the beginning of each round, in a FILO stack that they can pull any maneuver out of; so, to give an example, you have 3 readied maneuvers, and you know 5 maneuvers.
At the beginning of the battle, you have maneuvers 3-2-1 readied; you use 2, so next round, you would have 4-3-1.
Then, just let them regain an extra maneuver whenever they feint, or something (you can only use 2 maneuvers in a round (barring Rushes, which not all disciplines have, and a couple Shadow Hand maneuvers), unless you are using Diamond Mind's 8th level stance, or other bonus action shenanigans.)
So, in other words, your PC's readied maneuvers look like this from round to round, if they don't use them:
1. 3,2,1
2. 4,3,2
3. 5,4,3
4. 1,5,4
...
But if they, say, actually used their maneuvers, it might look like this:
1. 3,2,1
2. 4,3,1
3. _,5,1
4. 2,5,1
And so on and so forth.
Think of it as incompletely shuffling cards; hell, in a PnP game, you could just draw off maneuver cards and just put them back in the deck when you use them.