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Attaching documents to a custom object

I am new to Salesforce and need help.  We have created a custom object called "Candidate Tracker" and I am trying to figure out a way that we can attach a file (a resume, for instance) to the custom object and then email the file to a related contact field (a field called Manager in the custom object) using a workflow rule.  Does anyone have any advice or ideas of how I should go about accomplishing this?  Is this even possible?


I know how to set up the workflow rule, it's the attachment part I am lost on, please help....




I am wondering if attaching the document to the Contact Record and then using a lookup field in the custom object (Candidate Tracker) to retrieve the document to be sent in an email will work?  And if so, how do I attach the document to the Contact Record?  I have seen some discussions regarding APEX triggers, but have no idea where to start if that is the route that needs to be taken.


Thanks to anyone who can offer help of any kind. 



In yours business scinario what is the max size you want to attach.


the attachment would be around 60kb or smaller.