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Best practice for structuring data

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I have a team who is using a calendar to show tasks. They want to group the tasks using a field the field. Problem is the fields is a text field. Obviously this isn't going to work. I know I need to structure the field with a multi-select dropdown or checkbox group because the projects can be associated with more than one value in this field. I'm also fairly certain that I can create calculated fields for each value and have them populate so that I have them as discreet values - and build the calendar using these. However, I'm wondering what the best practice is when creating a report and grouping these, i.e. is there a way to show the totals of projects by these values other than making separate reports for each calculated field and showing them together on a dashboard? 

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