Over the past years, a great number of organizations have started utilizing agile principles and practices in their software development [1, 2]. Despite of the promising experience reports, the deployment of agile practices is a challenging task which requires adjustment and dedication from all the stakeholders involved in the development process [3, 4]. In order to fit the agile practices into organization’s software development context, agile specific guidelines and methods to support their selection, deployment and tailoring are needed [5]. However, the existing software process improvement (SPI) approaches have originally been targeted for the context of the traditional software development thus lacking some central aspects such as iterative process adaptation [5] and procedures for suitable organizational learning [6]. Agile Assessment and Post-Iteration Workshops (PIWs) are technologies that can be used in the deployment of agile software development methods.