If we answer it enough times it's an indicator to fix our documentation. Also, often times the reason someone is asking something leads to learning useful stuff

If we answer it enough times it's an indicator to fix our documentation. Also, often times the reason someone is asking something leads to learning useful stuff about the problem. The downside is repetition, but we invest in doc improvement to avoid that too much. The upside is personalized support which really means building trust with our users and also really trying to understand what they're trying to accomplish. Yea it has overhead but you just build that into your operations. In the long run we probably will start adding things like a Knowledge Base or using other support mechanisms but we've found so far that chat based support is very effective. Anecdotal. YMMV, etc.