A majority of employees over the age of 40 have hypertension, impacting their health and performance. A two-week self-management support (SMS) intervention was tested, with daily feedback and microlearning cycles to improve health self-management competences. On average, participants (n = 8) reduced their blood pressure from 145/92 mmHg to 126/86 mmHg. User evaluation confirmed the importance of core SMS aspects: information transfer, daily monitoring, enhancing problem solving/decision making, self-treatment using a tailored action plan, coping skills, and skilful coach follow-up. Several lessons are drawn on microlearning, peer coaching, health results, intrinsic motivation, and social learning, which appear useful for other health improvement initiatives.