<p>One-size-fits-all privacy notices and data decisions may no longer suffice for modern privacy management. Personalization, through personalized privacy assistants (PPAs), offers a potential solution. These assistants aim to provide tailored transparency disclosures and assist individuals in making decisions about their data. To actualize a future with PPAs, this paper presents findings from two expert focus groups that explore the challenges of developing these tools. Guided by the three dimensions of agency, accuracy, and accountability, and utilizing backcasting activities, we identified that hybrid PPAs are more desirable and welcomed by experts. However, the approaches to achieving a hybrid PPA that tackles concerns on accuracy, agency, and accountability were not agreed upon. Second, we highlight three main takeaways for successfully implementing PPAs: (1) user agency must be respected, (2) multiple stakeholders should be involved in developing, operating, and improving PPAs, and (3) interoperable standards are fundamental for successful deployment. We conclude that PPAs, and likely any technology concerning privacy protection, cannot be achieved by one stakeholder alone. </p>