Always add a read request to a specific address

Is there a way to have Outlook always ask for a read receipt if an email is sent to a specific email address?
I know I can do it for all emails going out, but I just want the system to automatically request one if the email is going to a specific address.

You can achieve this by creating an outgoing message rule.

1. Tools-> Rules and Alerts…
2. New Rule…
3. In the section “Start from a blank rule” choose;
   Check messages after sending
4. In the next screen you can select the conditions.
   In our case we select “sent to people or distribution list”
5. In the bottom screen, click “people or distribution list” to select the address(es) from your Address Book.
6. Click Next to go to the Actions screen
7. Here select “notify me when it is read”
8. Click next to advance to the next screen to set any exceptions when needed.
9. Once you’ve done that (or don’t need that), click Next to give the rule a name.
10. Click Finish and then OK to close the open windows.