I have the same issue and haven't yet found a solution.

To me it feels like there is an additional filter required to tie the conditional criteria to a single job assignment.  Users need to meet both criteria in the one job assignment not just meet the criteria individually.

We assign training based on position but reporting needs to be position and organisation specific.  Our managers are having trouble running organisational reports and only seeing people who hold a specific position in their organisation.

I'd be interested to see if anyone else has some ideas.