During `checkin`, gets stuck if user doesn't wait for next prompt

Jen got to an unresponsive TIM3BOT by entering an estimate immediately after selecting a task #, not allowing the prompt to appear first (middle of this conversation):

![screen shot 2016-08-24 at 5 14 16 pm](https://cloud.githubusercontent.com/assets/107458/17952362/8c0f902c-6a1e-11e6-8a02-fe44eb0c309b.png)
