In a method of using an observation platform to determine relative expertise of enterprise employees, a computer system of the observation platform monitors communications from and to a plurality of communication devices which have been routed through a radio access point associated with the computer system. Each of the communication devices is associated with a user who is an employee in an enterprise. The computer system extracts information from the communications including identities of the users. The computer system measures performance of a plurality of the users based on aspects of the extracted information which are related to questions on one or more of products and processes of the enterprise, wherein the questions are posed and responded to via the communications devices. The computer system assigns a numerical ranking of the measured performance by each of the measured users, with respect to other measured users, at responding to the questions.