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I have a "Choice" column that uses a checkbox to add multiple items to a field in a list.  The choices in the field are in the structure

Malcolm Reynolds - Customer Support Representative

Zoe Washburn - Human Resources

Simon Tam - Project Manager

I would like my workflow to add names to this field when tasks are assigned to them, and remove the names from the field when tasks are completed.  Ideally, the field would also update the name field if a task is delegated from one user to another.

The field must be sortable (so Zoe can filter the list on her name and see items that still need her attention)

We must also be able to check the box to add names manually even if the person doesn't have a task assigned to them.

I suppose I'll want to query workflow status for that particular item, but I'm not sure how to go about doing it so that the field gets updated when a task is added or completed and is still able to be updated manually AND functions during delegation.

I'm assuming you have a parent list where you are running a workflow that is creating tasks that are getting assigned to different people.  And that it's on this parent list that you are wanting to display the names of the people a task is currently assigned to.  Is that correct?

To accomplish what you are asking, I would build the workflow on the task lists itself.  Whenever a new task is created, or the assigned to field changes, you would run your workflow.  Assuming the tasks were create from a workflow, they would have a Related Content field that links back to the parent.  You could use that to query the parent list and find the correct item.  To update your choice field, you'd need to get the name the task is assigned to, and then change it to match the values you have in the choice field.  That will probably be the challenging part unless the choices are static.  Once you have that, then you can update the parent item. 

That being said, it may be easier to just direct people to the task list itself to see items they still have assigned to them?  If the tasks are being created by the workflow, they already have a Related Content field that links back to the parent item.  And the tasks are already assigned to the user, so you can filter your views how you'd like.

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