Digitalization is changing the business environment and companies face challenges to make progress. A first step to support companies is to verify their digital readiness, capabilities, and developing clear plans for improvement. This paper aims to evaluate the digital readiness of seven companies through the application of a self-check tool, followed by a deeper investigation through a case study, to identify reasons, challenges/barriers and enablers towards digitalization. A workshop was conducted to evaluate the use of a self-check tool and collect other analysis. Results include the readiness level and comparison between companies, actions and practices towards increased digitalization.