Although we may complain about meetings, they are an essential part of an information worker's work life. Consequently, busy people spend a significant amount of time scheduling meetings. We present Calendar.help, a system that provides fast, efficient scheduling through structured workflows. Users interact with the system via email, delegating their scheduling needs to the system as if it were a human personal assistant. Common scheduling scenarios are broken down using well-defined workflows and completed as a series of microtasks that are automated when possible and executed by a human otherwise. Unusual scenarios fall back to a trained human assistant executing an unstructured macrotask. We describe the iterative approach we used to develop Calendar.help, and share the lessons learned from scheduling thousands of meetings during a year of real-world deployments. Our findings provide insight into how complex information tasks can be broken down into repeatable components that can be executed efficiently to improve productivity.