Diverse data is crucial for training robust models, but crowdsourced text often lacks diversity as workers tend to write simple variations from prompts. We propose a general approach for guiding workers to write more diverse text by iteratively constraining their writing. We show how prior workflows are special cases of our approach, and present a way to apply the approach to dialog tasks such as intent classification and slot-filling. Using our method, we create more challenging versions of test sets from prior dialog datasets and find dramatic performance drops for standard models. Finally, we show that our approach is complementary to recent work on improving data diversity, and training on data collected with our approach leads to more robust models.