A system for recommending a communication medium for interacting with a customer of a contact center, the system includes: a processor; and memory, wherein the memory has stored therein instructions that, when executed by the processor, cause the processor to: detect a first interaction via a first medium with the customer; identify a plurality of communication mediums based on constraints for determining one or more candidate communication mediums that are different from the first medium for a second interaction with the customer; for each communication medium of the candidate communication mediums, estimate an expected value to be obtained by utilizing the communication medium for the second interaction; and select a particular communication medium of the candidate communication mediums based on the estimates for establishing the second interaction via the selected communication medium.