Sorry Basil I now see what you are talking about, and remembering you are talking about a quill stem adapter, compressing the headset by cap bolt is not relevant, and the 1" insert you just mentioned won't be needed at all.
Doesn't the adapter comes with its own top cap and cap bolt as shown
here? It must or else it would be impossible to fix the adapter onto the steerer.
I would have thought the first step is to let the shim and stem sit loosely on the top part of the adapter.
Then the "cap bolt" that comes with the adatper, which is essentially the traditional quill stem bolt, has to be tightened to bind the adapter to the steerer.
Finally the ahead stem binder bolts have to be tightened to fix the stem and shim onto the adapter.