Enterprise collaboration software has been essential—and deeply frustrating—for decades. From Lotus Notes to SharePoint to Teams, organizations have struggled to move beyond email, meetings, and file sharing into true, productive collaboration. In this episode, Directions on Microsoft analysts examine why “collaboration” became one of the most disliked categories in enterprise software—and why AI may finally change that.

Rather than replacing people, AI could automate the most painful parts of collaboration—synthesis, context‑gathering, and knowledge reuse—while helping organizations align around shared goals, decisions, and reality. If you care about the future of Microsoft 365, Copilot, or enterprise productivity, this conversation helps explain where collaboration has been—and where it may finally be going next.