Background: The outbreak of COVID-19 pushed organizations towards the adoption of new ways of organizing the workplace, to contrast the diffusion of the virus as well as to ensure the production of goods and services. Many workers and employers were suddenly forced to switch to forms of remote work, quite often without any real preparation to successfully deal with these changes. This exploratory study aimed to investigate the point of view of Italian HR managers on the introduction of these new ways of working in Italian SMEs, to underline both the advantages and risks of remote work and to provide a shared list of best and worst practices related to remote work adoption. A Panel of 19 Italian experts of HR management was recruited in April 2022 to perform a Delphi study. They were asked to take part in an anonymous and asynchronous discussion started with stimulus questions, on their remote working experience during the pandemic. A mixed-methods approach was adopted for data collection and analysis. Results: Five principal themes emerged, related to both the positive and negative implications of the adoption of hybrid and remote work, namely: work-life balance, environmental sustainability, impact of working life on individual wellbeing and health, and technological improvement. The content analysis was realized with the use of the T-Lab software, stressing the risks of inaccurate planning and management of these new ways of work. Conclusions: This is the first application of a Delphi study in the Italian context on the impact of COVID-19 on work-life transformative processes. The results highlight the importance of clear communication, transparency, trust, and technology in successfully implementing remote and hybrid forms of work. By implementing these best practices, organizations can create a work environment that supports remote and hybrid work, fosters collaboration, and maintains productivity. The findings of this study can serve as a useful guide for organizations that are transitioning to remote or hybrid work models.