A system to train a customer service agent trainee user, the system comprising: a user interface configured to interact with a customer service agent trainee user and operating to receive a set of annotated media and to receive a set of user responses to a set of training interactions; a data storage device having a non-transitory computer-readable storage medium, the data storage device storing a set of benchmark training data comprising a set of exemplar user training interactions associated with a particular user interaction performance measurement; and a computer processor having an emulator module comprising a dialogue engine and a measurement module, and having a discovery module comprising an evaluation engine, the computer processor having machine-executable instructions operating to: generate a first training interaction between the customer service agent trainee and a simulated customer; receive a first set of user responses to the first training interaction; measure the particular user interaction performance measurement of the user associated with the first training interaction, the particular user interaction performance measurement including at least one of: i) a time duration for the customer service agent trainee user to respond to a query associated with the first training interaction, and ii) a customer service agent trainee user emotional score; assess the particular user interaction performance measurement against the set of exemplar user training interactions and select, based at least on a relative measure of the particular user interaction performance measurement against the set of exemplar user training interactions, a particular exemplar user training interaction associated with the particular user interaction performance measurement; present the particular exemplar user training interaction to the customer service agent trainee on the user interface; identify a user deficiency based on the particular user interaction performance measurement; and select a coaching plan based on the user deficiency. a user interface configured to interact with a customer service agent trainee user and operating to receive a set of annotated media and to receive a set of user responses to a set of training interactions; a data storage device having a non-transitory computer-readable storage medium, the data storage device storing a set of benchmark training data comprising a set of exemplar user training interactions associated with a particular user interaction performance measurement; and a computer processor having an emulator module comprising a dialogue engine and a measurement module, and having a discovery module comprising an evaluation engine, the computer processor having machine-executable instructions operating to: generate a first training interaction between the customer service agent trainee and a simulated customer; receive a first set of user responses to the first training interaction; measure the particular user interaction performance measurement of the user associated with the first training interaction, the particular user interaction performance measurement including at least one of: i) a time duration for the customer service agent trainee user to respond to a query associated with the first training interaction, and ii) a customer service agent trainee user emotional score; assess the particular user interaction performance measurement against the set of exemplar user training interactions and select, based at least on a relative measure of the particular user interaction performance measurement against the set of exemplar user training interactions, a particular exemplar user training interaction associated with the particular user interaction performance measurement; present the particular exemplar user training interaction to the customer service agent trainee on the user interface; identify a user deficiency based on the particular user interaction performance measurement; and select a coaching plan based on the user deficiency. generate a first training interaction between the customer service agent trainee and a simulated customer; receive a first set of user responses to the first training interaction; measure the particular user interaction performance measurement of the user associated with the first training interaction, the particular user interaction performance measurement including at least one of: i) a time duration for the customer service agent trainee user to respond to a query associated with the first training interaction, and ii) a customer service agent trainee user emotional score; assess the particular user interaction performance measurement against the set of exemplar user training interactions and select, based at least on a relative measure of the particular user interaction performance measurement against the set of exemplar user training interactions, a particular exemplar user training interaction associated with the particular user interaction performance measurement; present the particular exemplar user training interaction to the customer service agent trainee on the user interface; identify a user deficiency based on the particular user interaction performance measurement; and select a coaching plan based on the user deficiency.