Proposal Preparation Tools for Hubble Space Telescope's Second Decade: Challenges and Paradigm Changes Anuradha Koratkar, Nicolas Bernstein, Rob Douglas, Andrew Gerb, Jeremy Jones, Karla Peterson, and Roeland Van der Marel Space Telescope Science Institute (STScI) is expending considerable effort in developing proposal preparation tools that take advantage of the technological advances of the last five years. In this paper we present the key challenges and issues in developing the proposal preparation tools. We also describe the paradigm changes that are being considered to handle these challenges at STScI. From the user's perspective these new tools are moving from scripts to interactive visual tools that can be used at any stage of the proposal preparation, development, and specification process. From the developers' perspective, we see the changes to proposal preparation tools as requiring more research and development time to try new ways of processing data, handling information, and presenting that visually. The new tools are envisioned as an interactive collaboration between user and machine, and thus require developers to think in a different way about the underlying architecture (speed, information). The tools need to be developed in a manner that allows for rapid turn-around of changes. From a software management perspective to preserve a dynamic research and development sub group of developers in an era of declining budgets requires creative management strategies. Widespread use of the Internet, development of Java, CORBA and the increased power of desktop hardware have allowed us to prototype such an environment (Scientists' Expert Assistant). This prototype is now being fully developed into a production line integrated environment for sharing data/objects/code.