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This study aimed to determine the nature and characteristics of professional development that contributes to the success of teachers in helping students in their transition from school to work. Specific research questions were: What knowledge, competencies, and attitudes do teachers who organise and conduct school-to-work activities exhibit? What specific professional development experiences are perceived as helping teachers conduct school-to-work activities? The study spans two years with information collected primarily through long interviews with teachers at 10-12 sites. The paper reports the outcomes from information collected from two sites through interviews with those individuals involved in school-based learning, work-based learning, and activities linking school-based and work-based learning at the two sites. The research found that the perceptions of those interviewed of the knowledge, attitudes, and competencies required by teachers who conduct successful school-to-work programs could be organised into nine themes: understanding students' needs; establishing and maintaining relationships with business and industry; having knowledge of business, industry, and community; ability to communicate; adaptability and openness to change; a positive attitude toward work and toward others; having a professional appearance and conduct; having knowledge of schools and schooling; and applying school learning to the workplace. Professional development needs included: having a broad-based knowledge of the business community; being able to communicate effectively with, and present themselves to, the business community; understanding employers' needs; and understanding the importance of work to students. Professional development activities that could be undertaken to help teachers meet these needs were back-to-industry experiences, surveying the business community, working with advisory committees, and placing and monitoring students in a variety of employment situations.