Skill obsolescence is not a new phenomenon and has become an important issue along with the rapid technological advances. Skill obsolescence creates a pressure that led to the emergence of professional intention to leave. Previous research suggests that both individual internal factors and external factors affect skill obsolescence. The purpose of this study was to determine the relationship between the individual factors, external factors, skill obsolescence, and intention to leave among 200 information technology professionals who are working in manufacturing companies in Surabaya as well as provide suggestions for professionals and companies to overcome the phenomenon of skill obsolescence that occurs. Data is collected through questionnaire surveys, analyzed using semi-structured model, and processed through AMOS program. The results showed that there is a positive relationship between an individual's internal factors, external, skill obsolescence, and intention to leave. The results of this study are consistent with the expectancy theory where behavior is influenced by information technology professionals expected results