A common approach for demonstrating learning in online classrooms is through submittal of research essays of a discussion topic followed by classroom participation. Issues arose at an online campus of a university regarding the originality and quality of critical thinking in the original submittals. Achievement of new course objectives oriented to demonstrating synthesis and analysis were being impacted by questions which typically resulted in paraphrased reports from the course text, websites and articles. This research study posited that conscientiously revising the types of questions, developing writing skills within the course, and utilizing rubrics which rewarded original content (the guidelines) could increase the original content within submittals. A mixed-methods approach was used. The experience of taking a combo Accounting/Operations Management Course for IT Majors was defined as the phenomenological case study. A section with the existing questions provided an "as is" basis for content analysis. Changes to the course were developed by a panel of senior faculty and implemented in a pilot section of the course. The impact of the changes on the pilot section was measured using content analysis. There were varied improvements in the pilot course. While all Discussion Question (DQs) had increased original content, they were not equally improved. Further analysis revealed that ongoing content analysis and writing skills training would continue to improve results.