There will be two parts to this solution: preparing the data in Excel and importing it into Outlook. Because of this, I suggest the user flags all required items rather than doing this one appointment at a time.
In Excel, you will need to arrange your data in a table, with individual appointments on each row. If the column headings (field names) are the same as those used by Outlook, they will not have to be mapped later. You can obtain Outlook's field names, and the default data settings for fields you don't use, by exporting a (small!) calendar from Outlook to Excel format.
You may want to write a simple macro in Excel to select the flagged records and massage the data into the correct output structure in a separate file (Excel 97-2003 .xls format).
Once this is done, your user can open Outlook and import the data in this file (the Import & Export command will first need to be added to their Outlook ribbon if using v 2007 or above). The Import process is a little laborious the first time, but after that, Outlook will remember the settings.
I hope this is enough to get you started. If you would like to have some help with the macro in Excel, please post a sample of the input data.
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