Nowadays dialogue is recognized as one of the main tools for individual career development and life designing because encouraging reflection and decision-making. The intent of the dialogue has always been aimed at understanding. The main goal of dialogue of students' career guidance in vocational secondary education is to build mutual dialogical interaction among the students, teachers, employers, career professionals, and school leadership. Such understanding provides the basis for a common set of goals and direction on how to help students to explore the labour market, learn to plan their career and make the right decisions in work-based learning. The aim of the study was to assess the findings of theoretical and empirical cognitions and to analyse the goals of dialogue from several points of view in students' career guidance: first of all, the model of the fields of conversations of W. Isaacs is used to reveal how the dialogue is developing; secondly, - the stages of career guidance and, thirdly, work - based learning for understanding the educational context of students' career development and life designing in vocational secondary education. A theoretical and empirical study was conducted. The empirical research was based on the methods of survey and experience reflection. There was used a survey questionnaire. The survey sample included 96 first to fourth-year students from six secondary vocational education schools of different regions of Latvia. During data processing the obtained results are statistically significant. Results show that only one-third of the respondents have established a dialogue with the career guidance stakeholders of secondary vocational education. Goal setting and achievement in dialogue development enables all career guidance professionals to understand, what support is needed for students of vocational education training schools. The hierarchical and successive nature of the goals in the development of the dialogue highlights the need for cooperation and common understanding among the persons involved in the development of students' careers.