In this paper we present two different approaches to personality diagnosis, for the provision of innovative personalized services, as used in a case study where diabetic patients were supported in the improvement of physical activity in their daily life. The first approach presented relies on a static clustering of the population, with a specific motivation strategy designed for each cluster. The second approach relies on a dynamic population clustering, making use of recommendation systems and

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... algorithms, like Collaborative Filtering. We discuss pro and cons of each approach and a possible combination of the two, as the most promising solution for this and other personalization services in eHealth.