All the time.
Documentation is a feature and thus runs the risk of being vestigial. Make sure value drives documentation requirements.
First I would suggest, never add documentation until you know why you need it. Here is why:
Consider the value first. In the case of documentation, it's probably best to start with none and later add it after you have assessed the costs of not having it (training/support). If you will have thousands of users, then you may know what the value could be and in this case it would be prudent to discuss documentation upfront. If you start the conversation with "What would the value of documentation be?", instead of "We need X documentation!", you are more likely to minimize the documentation you create and target it to achieve maximal value. Use the value you hope to achieve as a filter to limit the documentation.
Also, make sure you put yourself in the audience's shoes. Ask them for input and make sure you are thinking about their actual needs versus your perception of their needs. As with any communication, you run the risk of failing to communicate!