In the digital age, even more so after Covid19, both public and private organizations have developed an awareness of the need for digital transformation. Indeed, thanks to new digital technologies, it is possible to benefit from services and/or products that were previously unimaginable and that neither people, citizens, users, consumers nor organizations can do without. Moreover, given the upcoming challenges of the PNRR and the 2030 Agenda, which require the pursuit of sustainable digital development and efficiency goals, the topic of transforming organizations is more relevant than ever. However, digital transformation is not a simple process. Although the importance of this process is well known, a Forbes report (2020) demonstrates that about 70% of digital transformation initiatives do not achieve the intended results. One of the main reasons for this is the lack of ability to guide these initiatives through codified protocols or the provision of tools for planning, monitoring and evaluation. Even the literature on digital transformation, while definitive and empirical in terms of describing initiatives, impacts, and benefits, is still under-researched from the perspective of planning, monitoring, control, and evaluation systems. Thus, this research aims to develop a strategic planning model for developing, monitoring, and evaluating digital and sustainable transformation initiatives. The model draws on the soft systems literature. The model is based on the fundamental assumption that digital transformation follows the dynamics of soft systems. In fact, from a performance management perspective, digital transformation initiatives can be compared to the dynamics of R&D initiatives and thus soft systems, namely situations where performance cannot be measured by collecting data and evidence from physical devices or sensors and the focus is therefore on processes (Lazzarotti et al., 2011). With this in mind, the model identifies and describes the compelling dimensions to consider in the planning, monitoring and evaluation phase of digital transformation initiatives (Bremser and Barsky, 2004; García-Valderrama et al., 2008; Gwynne, 2015; Schwartz et al., 2011). In particular, these dimensions result from the combination and adaptation to the digital transformation perspective of the reference models of the balanced scorecard (Kaplan and Norton, 2007) and the logical framework approach (logframe) (Practical conceps, 1978). This combination is necessary to develop a model that is useful both in the strategic planning phase and in the ex-post evaluation. The research makes important theoretical and practical contributions. The study enriches the literature on digital transformation and proposes a model for designing, monitoring, and evaluating digital transformation initiatives. From a practical perspective, the proposed model aims to be a guiding and orienting tool for managers and practitioners that has normative and prescriptive value. Indeed, the model identifies the key dimensions to be considered in the planning phase of a digital transformation initiative, while describing the dimensions to be taken into account when monitoring the development of the initiative and the final evaluation of the impact achieved.