Chronically ill elderly patients are concerned about losing the personal connection with clinicians in digital encounters and clinicians are concerned about missing nonverbal cues that are important for the diagnosis, thus jeopardizing quality of care. This study validated the expectations and preferences of chronically ill elderly patients regarding specific communication messages for communication with clinicians in telemedicine. The sample comprised 600 elderly chronically ill patients who use telehealth. We used a conjoint-based experimental design to test numerous messages. The outcome variable is elder patient expectations from communication with clinicians in telemedicine. The independent variables were known categories of patient-clinician communication. Respondents rated each of the 24 vignettes of messages. Mathematical clustering yielded three mindsets, with statistically significant differences among them. Members of mindset 1 were most concerned with non-verbal communication, members of mindset 2 prefer communication that enhances the internal locus of control, and members of mindset 3 have an external locus of control and strongly oppose any dialogue about their expectations from communication. The use of the predictive algorithm that we developed enables clinicians to identify the belonging of each chronically ill elderly patient in the clinic to a sample mindset, and to accordingly personalize the communication in the digital encounters while structuring the encounter with greater specificity, therefore enhancing patient-centered care.