Let me give an example. Let's say you have a Contract record. You just produced the contract and saved it against the Contract record for that client. Now you want to send an email with that Contract document. You click "Send an Email" from the contract record. You can load a document from you computer or from the salesforce documents repository, but not from the originating contract record.
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Custom Development to the Rescue
So the way we've solved this problem for many clients is by writing a Salesforce.com Visualforce page to replace the existing email system. We've approached this from many different angles depending on the exact needs of the client - so the resulting systems have all taken different forms. But here is what I would consider the "ideal" solution.
Salesforce.com Visualforce Email System With Attachment Loader
The main part of the system will be a duplication of the existing email author. While we're duplicating that, we would improve some of the features there to make lookups and associations a little more convenient, but for the most part, our new system would look much like the other one.
The most significant departure from the standard system would be the "Attach File" popup. It is here that our custom functionality would be most evident. In this popup we would start with asking the user from where would they like to load their attachments. The options would be:
> The originating object
> Any other record in the system (provide a lookup where the user can select the object first, then the record, then any attachments found on that record)
> Their own computer
> Documents in Salesforce documents folder
> Documents from Content.
Once functioning like this, the email system would be at its most useful. While we haven't built this system to function in exactly this way yet for any client, we've done several close variations on it.
If you need this functionality, let's discuss your requirements. We can certainly develop a useful system using the power of Visualforce and Apex to get what you need accomplished. Custom development is a lot less expensive these days than in years past and you can have the system you need built to your exact specification for probably less than you think. (Well, some of you have pretty small amounts in your mind, so, besides those people, we may be able to surprise you).
If you would like to chat with me about a development project like this, or any other custom development idea that you have for your Salesforce.com system, please contact me at www.snapptraffic.com