We pilot tested a carepartner-assisted intervention to improve oral hygiene in persons with cognitive impairment (participants) and help carepartners become leaders who can adapt approaches that foster participants' ability to develop new skills for oral hygiene care. Following the intervention, we conducted interviews with participants and carepartners to understand their challenges in working together to learn new oral hygiene skills. Participants reported challenges such as frustration using the electric toothbrush correctly, lack of desire to change, uncertainty about correctness of technique, and difficulty sustaining two minutes of toothbrushing. Carepartners reported challenges such as learning a new way of toothbrushing, learning new communication techniques, switching from instructing to working together, learning to balance leading with being too bossy, and being mindful of word choices. Findings suggested that despite challenges, participants were able to learn adaptive strategies to support new oral hygiene behaviors with support of the carepartner as the adaptive leader.