Pull info from Excel to Outlook

I want to setup an excel spreadsheet that will list employees and when exams were completed on them. The exams need to be completed once a year. I want the excel spreadsheet to send out an email to their corresponding supervisors when is within one month or so of an exam needing to be completed so their exam can be scheduled accordingly.

I have searched this forum and read through some of the other posts regarding exporting data from excel to outlook. This seems like what I need to do but I wanted to see if anyone has an advice on what way is better than the other?

Also, if excel is setup to push the data to outlook, does the excel file need to be open? In other words if Jimmy comes within one month of his exam but no one opens the excel file will it send out the email to outlook?

Is it a better option/ or possibility to have Outlook pull/check to see if the condition exists where an employee is within a month of his exam and then let the supervisor know?

Thanks for all your help!

FYI I am posting this to the programming because I assume this is how this is going to end up being accomplished- Let me know if I have posted incorrectly