For example, in turning testing there are a standard to make a short duration test that consist in a facing with tool of high speed steel. The idea is to use a number of revolutions per min that brake a point of tool before the tool make only one pass of facing.
If you want you can see Espanish standard UNE 36423.
You can carry out certaing no. of turning and evaluate the tool wear in high magnification microscope. In case of drill tools you can drill n no. of holes and carry out the tool wear .
Some very good pieces of equipment are available to actually measure the tool wear from machining processes. A well known supplier to the tooling industry is Alicona www.alicona.com