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Two university professors of education conducted a self-study to analyze their first time teaching in a virtual environment. Research questions included: (1) how do prior expectations influence a professor’s experiences teaching an online course for the first time? (2) how does professional development shape a professor’s experience teaching an online course for the first time, and (3) what pedagogical knowledge and skills transfer from a traditional face-to- face course into an online setting? Using semi-structured interviews across a 15-week period, we document, interpret, and evaluate our experiences using transformation theory. Findings suggest prior expectations can be re-imagined to advance one’s experience teaching online, professional development is critical in successful online teaching, and face-to-face pedagogical strategies are transferable to online environments.