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Office 365 (Outlook 2016 | Outlook 2013) - Add and request read receipts and delivery notifications
A delivery receipt confirms delivery of your email message to the recipient's mailbox, but not that the recipient has seen it or read it. A read receipt confirms that your message was opened.
In Outlook, the message recipient can decline to send read receipts. There are other scenarios where read receipts are not sent, such as if the recipient's email program doesn’t support read receipts.
On the File tab, choose Options > Mail. Under Tracking, select the Delivery receipt confirming the message was delivered to the recipient's e-mail server or Read receipt confirming the recipient viewed the message check box In the message, on the Options tab, in the Tracking group, select the Request a Delivery Receipt check box or the Request a Read Receipt check box. Open the original message that you sent with a request for a delivery or read receipt. This message is usually located in the Sent Items folder. On the Message tab, in the Show group, choose Tracking.
Track a single message
Tip: As a best practice, consider tracking only single messages of importance instead of all messages. Recipients who occasionally receive a notification that a read receipt is requested on your message are more likely to send a read receipt than if they are prompted every time that they receive a message from you. 
Track receipt responses
Note: Tracking doesn't appear until at least one receipt is received. After you receive the first receipt in your Inbox, it might take several minutes before the Tracking button is available.