When a Handoff path matches a large pool of assignees, such as 200 or more, bookers have no way to narrow that pool at the moment of booking based on contextual factors they know but cannot encode into static rules. Building individual paths or booking links for every possible combination of assignees is not feasible. The result is that the booker must either send availability for the entire matched pool or manage the selection outside Chili Piper entirely.

Chili Piper should allow bookers to multi-select a subset of assignees from the matched Handoff path at the time of booking, with the ChiliCal booker then showing round-robin availability across only those selected assignees.

For organizations with large, dynamic assignee pools where nuanced contextual factors influence who should be considered for a given meeting, static rule-based paths cannot cover every combination. Multi-select at booking time is the only scalable solution and has been identified by at least one major enterprise customer as a capability unavailable in any competing scheduling tool.