Nothing is worse than trying to drag a conversation out of someone...especially if it is someone you are forced to socialize with. If someone asks you a question, answer thoughtfully and use more than "I don't know" or monosyllabic answers. At the very least, ask a question back. Example below...
Me: Hey, how was your day today?
You: (Bad) Okay. (Good) It was great, we did XYZ and ABC. How was yours? (Compromise) Okay, how was yours?
Me: (In response to "Good"/"Compromise") We did 123 and 456. What do you have planned for tomorrow?
You: (Bad) Nothing. (Good) Not much, cleaning. You?