As an outlet of communication between internet users, digital social media has created opinionated engagement between people that have similar and often contrasting views, just like those in face-to-face communication (Mckenna & Bargh, 2014). The problem is that these digital conversations occur in a synthetic environment, causing users to develop alternative psychological patterns of engagement (Lauren & Hsieh, 2014), that could potentially push them to inadvertently or unknowingly create and participate in negative social interaction with others. The purpose of this study was to determine and assess the needs of a writing heuristic for social media participants to use in engagement with others to increase coherency, civility, and engagement response in content. Research explored existing literature on engagement behavior in digital social media and computer-mediated communication (CMC) and was then used in qualitative sentiment analysis of business-to-consumer social media environments, aiming to recognize the needs in developing a social media writing heuristic. This research found that such heuristic should prompt and advise users to remove ambiguity within engagement practices, encouraging the implementation of salient social markers and nonverbal cues in text. Social media users should also be prompted to create familiarity with others through the posing of messages in an emotional frame that is aligned with their audience’s emotional attitudes, increasing persuasive argumentation and discussion. As well, users should be prompted to thoroughly understand the issues in discussion and follow dynamics to create productive engagement, while avoiding engagement with negative commentary.