Despite recent attempts in the field of explainable AI to go beyond black box prediction models, typically already the training data for supervised machine learning is collected in a manner that treats the annotator as a “black box”, the internal workings of which remains unobserved. We present an annotation method where a task is given to a pair of annotators who collaborate on finding the best response. With this we want to shed light on the questions if the collaboration increases the quality of the responses and if this “thinking together” provides useful information in itself, as it at least partially reveals their reasoning steps. Furthermore, we expect that this setting puts the focus on explanation as a linguistic act, vs. explainability as a property of models. In a crowd-sourcing experiment, we investigated three different annotation tasks, each in a collaborative dialogical (two annotators) and monological (one annotator) setting. Our results indicate that our experiment elicits collaboration and that this collaboration increases the response accuracy. We see large differences in the annotators’ behavior depending on the task. Similarly, we also observe that the dialog patterns emerging from the collaboration vary significantly with the task.