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During the last decades, significant meta-analytical studies conducted in several sectors, mostly education, argue the existence of a significant correlation between personality variables and learning styles within digital learning platforms. This strong relationship between personality traits and learning styles can explain the board variance in measuring digital workers’ education efficacy, and, consequently, their performance.

The public sector represents an interesting setting where this issue acquires more relevance because of the deep changes occurred especially in terms of the digitalization era.

The Eysenck Personality Inventory (EPI) and Honey and Mumford’s Learning Styles Questionnaire (LSQ), the main instruments validated by the literature, test the two variables and correlations between them, in reference to digital higher education programs. Moreover, Riso-Hudson Enneagram Type Indicator could integrate the information collected through such questionnaires, introducing significant details about nine personality types.

LSQ collects data about how people learn, that is their main learning style: activist (sensation seeking, impulsive, extravert), reflector (introvert, cautious, methodological), theorist (intellectual, rational, objective), and pragmatist (expedient, realistic, practical).

The two personality traits variables tested by EPI, extraversion and neuroticism, and specific learning styles, like reflector and pragmatist, result statistically significant predictors of digital students’ and workers’ education efficacy.

This conceptual study aims to examine how the combination between personality traits and learning styles can affect and be affected by organizational and contextual factors making e-learning platforms more effective and successful. Most organizations, especially public administrations, face great challenges in terms of costs, also related to educational requirements to achieve. For this reason, these organizations introduce numerous alternative educational models characterized by virtual digital interactions. Drawing from the previous contributions in the literature on the topic, this chapter provides a joint reading of the phenomenon with focus on actors involved in the process, public organizations, managers, software houses, and users, considering the combination of personality traits and learning styles of users with the organizational and contextual factors related to the proactive managers and digital workers groups, without missing the link between institutions and people.

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