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The importance of self-regulated learning (SRL) in online learning environments has been widely recognized in the literature on children and college students. However, research is limited in understanding working professionals’ SRL in work-place training, especially in asynchronous online learning environments. This study explored the relationship between middle-school mathematics teachers’ employment of SRL strategies (i.e., time management, cognitive strategies, and monitoring) and their learning gains in an asynchronous online professional development (PD) program. Findings indicated teachers’ monitoring of their understanding of program content was positively related to their learning gains in subject content knowledge, even when controlling for their baseline knowledge. However, monitoring was not significantly related to teachers’ learning gains in their knowledge about teaching the subject content.