In this paper we present a set of four user studies aimed at exploring the visual design space of what we call keyword summaries: lists of words with associated quantitative values used to help people derive an intuition of what information a given document collection (or part of it) may contain. We seek to systematically study how different visual representations may affect people's performance in extracting information out of keyword summaries. To this purpose, we first create a design space of possible visual representations and compare the possible solutions in this design space through a variety of representative tasks and performance metrics. Other researchers have, in the past, studied some aspects of effectiveness with word clouds, however, the existing literature is somewhat scattered and do not seem to address the problem in a sufficiently systematic and holistic manner. The results of our studies showed a strong dependency on the tasks users are performing. In this paper we present details of our methodology, the results, as well as, guidelines on how to design effective keyword summaries based in our discoveries.