The call for business and IT alignment (BITA) is an everlasting and increasing concern for today’s enterprises. BITA is no longer just a technical or local concern. Instead we need to embrace various dimensions in the concept of BITA, for instance strategic, structural, social and cultural. In addition to this, the development of concepts like digital innovation (DI), internet of things (IoT), cyber physical systems (CPS) has further challenged the success of BITA. As one approach to deal with the multi-dimensional BITA problem and to move the BITA positions forward, enterprise modeling (EM) has been acknowledged as a helpful practice. Particularly, EM provides the opportunity to facilitate the creation of integrated models that capture and represent different focal areas of an enterprise, and allows representing the numerous points of view of the key stakeholders. In order to consider the points of view of different stakeholders and create share understanding between them the participative character of EM sessions can play an important role. This chapter presents various challenges that EM practitioners face during participative EM sessions, and a number of recommendations that can help to overcome these challenges.