Generating an automated agent enabled to engage in a multi-turn discussion with a user in response to a received request. For example, the automated agent is operative to provide a response on behalf of an agent owner. A knowledge database is generated based on the agent owner's context (e.g., email conversations, calendar data, organizational chart, document database). A request for information is received and analyzed for understanding the request and for gauging a level of frustration of the requesting user. An urgency level of the request is determined based at least in part on the level of frustration of the requesting user. A query of the knowledge database is made for determining a response to the request, wherein the determined response is based at least in part on the urgency level of the request. A response is generated and provided to the requesting user.