Scheduling has been a common problem to all astronomical observatories due to the limited telescope time compared to the time request from the community. However, when the complexity scale of the observatories increases, along with the construction and operational costs, the scheduling optimization becomes a key subject. Experience has shown that small optimization improvements translate into a significant efficiency gain, measured by an increase in the scientific return and diminishing operational costs. When entering an era of big ground based observatories the scheduling problem becomes essential. The scheduling optimization requires a multidisciplinary approach involving the fields of engineering, computer science, data analysis, operations research, and mathematical modeling. It is studied from both a methodological standpoint as well as its applications in different fields and industries. Due to such multidisciplinarity, ADASS is an excellent meeting and exchange point to gather the different communities working on the optimization problem, with a special focus on astronomical scheduling. This ‘Birds of a Feather’ session focused on the scheduling problem definition and solution approaches. The discussion is timely since we are at a point where instruments like ALMA (in the ADASS host country) recently started steady state operations while other big observatories such as SKA or CTA or LSST are currently at designing stage, and are actively developing new optimal scheduling systems. The aim of this meeting was to promote the building of a collaboration network between groups in different projects and disciplines in order to make the most out of the synergies among them. Such network will lead to the creation of joint research opportunities and efforts.