In recent years, the proliferation of smart mobile devices has lead to the gradual integration of search functionality within mobile platforms. This has created an incentive to move away from the “ten blue links” metaphor, as mobile users are less likely to click on them, expecting to get the answer directly from the snippets. In turn, this has revived the interest in Question Answering. Then, along came chatbots, conversational systems, and messaging platforms, where the user needs could be better served with the system asking followup questions in order to better understand the user's intent. While typically a user would expect a single response at any utterance, a system could also return multiple options for the user to select from, based on different system understandings of the user's intent. However, this possibility should not be overused, as this practice could confuse and/or annoy the user. How to produce good variable-length lists, given the conflicting objectives of staying short while maximizing the likelihood of having a correct answer included in the list, is an underexplored problem. It is also unclear how to evaluate a system that tries to do that. Here we aim to bridge this gap. In particular, we define some necessary and some optional properties that an evaluation measure fit for this purpose should have. We further show that existing evaluation measures from the IR tradition are not entirely suitable for this setup, and we propose novel evaluation measures that address it satisfactorily.