Based on the research, the article describes the motivation and expectation of students who entered the first year in the direction of training organization of work with youth. Flexible skills that are important for a future specialist according to students, teachers and employers have been identified. Based on an expert survey of employers in the field of youth policy, the most important ones were identified: possession of professional knowledge, creative thinking, management of one's own development, project management, teamwork and activity planning. Based on a survey of participants of the festival in the field of training "Organization of work with youth", effective technologies for the development of flexible skills were identified, suggestions for further improvement of the event were given.