Embodiments for implementing an electronic communication coaching service by a processor are disclosed. An appropriateness of a communication may be interpreted prior to a user sending the communication to another party according a plurality of identified contextual factors. The user may be alerted to a possible negative impact of sending the communication to the another party if the interpreted appropriateness is less than a predetermined threshold. A delay in sending the communication may be suggested for a selected period of time to implement one or more suggestive corrective actions to the communication.