In this paper we describe Towel, a task management application that couples a user’s to-do list with a software personal assistant. This to-do list provides a unified environment for managing personal tasks, delegating tasks to the software personal assistant, and collaborating with other users. We use to-do list and instant messaging metaphors to enable the user to initiate, manage, and modify complex agent-executed tasks. Through simple operations on to-do items and direct-manipulation chat, we envision many seamless interactions between the user and various AI technologies that ultimately result in saving the user work, reducing cognitive load, and improving task performance.