Building successful, interactive generative AI applications for troubleshooting or assistive knowledge management system from complex data that is originally meant for human readability is not a trivial task. In an organization documents can range from trouble shooting technical manuals, knowledge articles on specific product descriptions with lot of tables, images, links, and some machine generated outputs like call transcripts. This presentation highlights the key lessons learnt in implementing complex infobots and trouble shooting bots in a multi-tired way to meet use case scenarios for enhancing productivity of technicians and customer facing agents.