This study aimed to explore the motivations and aspirations of teachers across generational cohorts (Baby boomer, Generation X, Generation Y, Generation Z) in different professional development (PD) and the perceived challenges and plans of the deans or directors to PD activities that need paramount attention. A total of 91 teachers in the teacher education programs and 7 deans or directors served as the participants of the study using interview as the data-gathering method. Data showed that as to the motivations to pursue professional development activities, majority or 38 (46%) of the respondents are intrinsically motivated (gain more knowledge, personal growth etc.). The PD that all the generational cohorts consider to be their topmost aspiration is to pursue Graduate Studies (Masters or PhD/Ed.D.). Other PDs they aspire the most include engagement in research-related activities, development of IMs and attendance to seminars/workshops. The top five challenges experienced by the respondents in pursuing the different professional development activities according to the deans and directors are the following: lacks financial resources; time constraint; heavy workload/ multi-designation; lacks technological knowledge and; struggle for work-life balance. The challenges confronting teacher’s professional development from the perspectives of college deans and campus directors include: economic status; limited time; multi-designation; and culture. The suggestions and plans provided by college deans and campus directors to strengthen teacher’s professional development include: keep on motivating the faculty members; create and implement the campus strategic plan/ teacher development plan; conduct personalized trainings and seminar-workshops; coaching and; implement and raise the incentives.