There are 2 kinds of workflows, task based and event based. Task based will generate only 1 workflow per task and event based generates one workflow per event. If you use event based workflow then you can trigger multiple workflows by triggering multiple events. For e.g. User selects Application 1, 2, and 3 from screen. Write some business logic (may be PX) that assigns 3 provisioning roles or groups (one for each application) to user. This will generate 3 AssignProvisioningRoleEvent or AddToGroupEvent. Write policy-based workflow policies , one for each application. This will trigger 3 workflows, one for each application.