Systems that automate the data science cycle have been gaining a lot of attention recently. Similar to smart home assistant systems, however, automating data science for business users only works for well-defined tasks. We do not expect home assistants to have truly deep conversations about changing topics. In fact, the most successful systems restrict the types of possible interactions heavily and cannot deal with vaguely defined topics. Real data science problems are similarly vaguely defined: only an interactive exchange between the business analysts and the data analysts can guide the analysis in a new, useful direction, potentially sparking interesting new insights and further sharpening the analysis.