Digital and agile companies widely use chatbots in the form of integrations into enterprise messengers such as Slack and Microsoft Teams. However, there is a lack of empirical evidence about their action possibilities (i.e., affordances), for example, to link social interactions with third-party systems and processes. Therefore, we adopt a three-stage process. Grounded in a preliminary study and a qualitative study with 29 interviews from 17 organizations, we inductively derive rich contextual insights of 14 affordances and constraints, which serve as input for a Q-Methodology study that highlights five perceptional differences. We find that actualizing these affordances leads to higher-level affordances of chatbots that augment social information systems with affordances of traditional enterprise systems. Crossing the chasm between these, so far, detached systems contributes a novel perspective on how to balance novel digital with traditional systems, flexibility and malleability with stability and control, exploration with exploitation, and agility with discipline.