Unlike hard skills, which are quantifiable, delineating the optimal soft skills profile for a project manager (PM) presents a multifaceted challenge due to their multifarious nature. Cultural, social, and political-institutional contexts, along with the dynamic nature of projects, play a critical role in influencing situations that activate and shape the manifestation of soft skills. These factors interact with individual differences and interpersonal interactions, thereby affecting how soft skills are expressed and perceived in various project environments. Furthermore, the diversity among stakeholders, including their differing expectations, communication styles, needs, and behaviors, can significantly impact how soft skills manifest. In response to the growing complexity of grand challenges—global, multifaceted problems that require interdisciplinary collaboration—an off-beat approach based on multidimensional skills integration (MSI), contextual embeddedness (CE), project-specific adaptability (PSA), situational responsiveness (SR), and stakeholders’ diversity (SD) is developed. This framework highlights how multilayer and dynamic feedback loops (MDFL) can generate the activation of various soft skills with distinct nuances and shape. By incorporating all these variables, the “shapeshifter model” offers a dynamic and accurate assessment of soft skills, tailored to the different situations that manifest in each project. Moreover, to address the complex nature of soft skills development and its contextual manifestations, this study introduces a novel maturity model that provides a more precise and context-sensitive understanding of soft skills proficiency, catering to the evolving demands of modern project environments, especially in the context of grand challenges.