If you launch Outlook using "out", only when you will have fully typed "out" will this entry appear at the beginning. After typing "ou", it won't necessarily be above others. Why? Because each entry is attributed points based on how well the typed command matches with their name, and many extra points if the last command typed exactly matches the currently typed command.
The suggestion is to also add extra points when the beginning of the last command is the same as the currently typed command. In my example, after typing "ou", Outlook would probably be first, or at least higher than expected, if it was previously launched with "out".
But simply explaining this to you convinces me it does not make sense. This would create problems when training slimKEYS with new programs. For the moment, I'll stick with extra points on exact matches only.