Customer support, and other types of activities in which there is a dialogue between two humans can generate large volumes of conversation records. Automated analysis of these records can provide information about high-level features of, for example, the workings of a customer service department. Analysis of these conversations between a customer and a customer-support agent may also allow identification of customer support activities that can be provided by virtual agents instead of actual human agents. The analysis may evaluate conversations in terms of complexity, duration, and sentiment of the participants. Additionally, the conversations may also be analyzed to identify the existence of selected concepts or keywords. Workflow characteristics, the extent to which the conversation represents a multi-step process intended to accomplish a task, may also be determined for the conversations. Characteristics of individual conversations may be combined to obtain generalized or representative features for a set of a conversation records.