From my experience with it, as long as you have a consistent schedule, Cortana will learn it. If you start work at a different time every day it would probably be best to input your schedule as a reminder in your calendar. However, I'm not sure if Cortana will automatically bring up the traffic information.
For example, the day I updated to 8.1 I set my home and work address. After 3 or 4 days of tracking my location Cortana picked up on my daily routine and began prompting me with traffic information for my morning commute without me having to input any other information.