If you have updated training requirements for a worker type, or if someone should have training requirements based on what you see but they don't, this may fix/update things.
- Click "Training" on the top menu bar
- Click "Worker Type / Training Curriculum"
- Single click on the worker type you'd like to synchronize
- At the top of the screen, click "Synchronize training curriculum", then select "Synchronize selected worker type only"
- Click "Yes" when it asks if you are sure. It usually takes up to a minute.