The main purpose of this article is to generate a functional model of evaluation that EMSs can be able to empower online communications characterized by imperative decision making task. The evaluation process of EMSs must merge the multicultural strategies of the theory of "Media Richness," and the ethical concerns of the critical approach. "Media Richness Theory" can empower online communications that resolve ambiguity, negotiate varying interpretations, and facilitate understanding. A critical approach can provide online communication designers with the information in detail that elucidate concerns, issues, needs and expectations raised by stakeholders. Therefore, this paper discusses the naturalistic and critical stages of this evaluation process by introducing a critical perspective on "Media Richness Theory" to provide exact directions for EMSs. (Contains 2 tables and 1 figure.)