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Using SharePoint 2010 and Visual Studio 2010, and have been tasked with notifying a "manager" when their subordinate creates a Calendar Event. The user adds information using a Calendar Event for a training computer (not a resource, just a calendar designated as "training.") I, as the admin, I have created and added a Microsoft SharePoint Group with "managers" in it, and called it Managers. These are managers or supervisors for these users. There is no check and not every "manager" is going to be listed in Microsoft Active Directory as their "manager," using the Manager Field. I would like it (unless a better way / idea) so that when the user selects the SharePoint Group (people picker) and finds their "Manager" or their "Supervisor" then they have selected "joe somebody" and they fill out other fields and then they submit the Calendar Event. I would like that person ("Manager" or "Supervisor) that was in the (Who is your manager) field to be emailed or have a notification, such as a task, etc. I just want them to have some type of email notification.

What the manager would see (wording is optional): "Sue is taking training." Their subordinate is taking something and the manager is to be notified.

That's basically what I have been requested to do.

I though that I could use a State Machine Workflow to get the user field, once they have been entered or selected in the "who is your manager" field. The "Managers" SharePoint Group all have email information, as we are using Microsoft SharePoint 2010 Enterprise Edition SP1 June 2013 CU, and User Profile Synchronization with Microsoft Active Directory.

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And the question is? I recommend you start with a tutorial on custom state machine workflows, when you get stuck ask here. Your question is just to broad to be answeredLuis

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You're looking at a good bit of custom development here. First, it sounds like you need to build a custom initiation form that will prompt the user to pick who their manager is as the default people picker only shows people / groups, not an interface that lets you pick a group & then a person. From there, you would use a custom workflow that would collect this information and run a process via custom code to implement the business logic you mention here.