Monday.com’s Sidekick assistant evolved from a single general-purpose agent equipped with many tools into a layered system with distinct responsibilities. The redesigned architecture separates orchestration, permission-aware context retrieval, specialized subagents, bounded tools, and sandboxed execution environments. Bounded tools handle discrete operations such as reading boards or updating items, while subagents take on specialized reasoning tasks with focused toolsets of their own. Sandboxes provide isolated workspaces for complex, iterative work involving files and code, keeping intermediate outputs separate from the main reasoning loop.