Introduction

Not for the first time, an error in the sending of an email has caused the sender problems. This time, BBC journalist Laura Kuenssberg had to cancel an interview with former Prime Minister Boris Johnson, after accidentally including his email address in an email that was intended for an internal BBC team only and, in so doing, sent him a copy of her briefing notes for the interview.

Different email client applications have different features to help avoid common errors when sending emails. We will be looking at Microsoft Outlook. Even within Outlook, the features available depend on the way in which Outlook is set up, with some features being limited to Outlook when it is connected to Microsoft Exchange Server.

Mail Tips

We will start by briefly mentioning Mail Tips, one of the features that does depend on a connection to Exchange Server. The way in which these Mail Tips work depends on how the administrator has configured Exchange Server so it’s important to check how they work on your own system before relying on any of them. If Outlook is connected to Exchange Server, Mail Tips can be found in the Mail section of File, Options.

Outlook Rules

Outlook Rules work with Exchange Server and also with email accounts that are not connected to Exchange Server. Rules are a very useful automation feature within Outlook and, taken to the extreme could, for example, identify emails sent to a particular email address, move them to a specific folder, display a custom notification and reply to the email using an existing email template. This could be used to automatically send an electronic brochure in reply to any incoming emails that are received by a particular email address.

Although some of the most obvious uses of Outlook Rules relate to dealing with emails as they are received, it is also possible to apply rules to emails as they are sent. It is possible to check all outgoing emails for a wide variety of properties including recipient addresses or specific words or phrases in the content. However, perhaps the most useful rule for outgoing emails is a much simpler one. Many email indiscretions become all too obvious about two seconds after you press the send button. In some circumstances, it is possible to ‘recall’ an email that is sent within an organisation, but generally, when sending to an external recipient, once you’ve clicked the Send button, the damage is done. If you are prone to ‘sent email regret’ then using an Outlook rule to delay the sending of all your emails by a couple of minutes could give you the opportunity to grab your email back from the Outbox before it is released into the wild, and your career is irrevocably tarnished.

To set up the sending delay rule, you can use the Rules dropdown in the Move group of the Home Ribbon tab to select Manage Rules & Alerts. The New Rule… button then opens the Rules Wizard which includes template rules but also the chance to ‘Start from a blank rule’ and to ‘Apply rule on messages I send’:

The Rules Wizard includes 4 stages. First you choose how to select the messages to which you want the rule to apply:

We could leave this step blank for our delay rule, to ensure that all outgoing messages are potentially ‘paused’ in the Outbox for a set period of time. The action itself is set in the next stage of the wizard. We can select the ‘defer delivery by a number of minutes’ action, then click on the ‘a number of minutes’ link in the lower, Step 2, window to set our delay period:

Next, we could enter an exception. This might be useful to allow us to override the delay for a particularly urgent message. Here we have chosen to avoid the sending delay if the subject contains the word ‘(urgent)’:

We have enclosed urgent in brackets to reduce the chance of accidentally not delaying a message just because we are replying to an email thread that includes urgent in the original subject line.

We can then give our rule a name and turn the rule on:

If all goes according to plan, any message that we send without (urgent) in the subject line will stay in the Outbox for two minutes, giving us the chance to edit it or delete it if we suddenly realise there is an issue just after pressing the send button.

Conclusion

It’s certainly worth exploring Outlook rules, or their equivalent in different email applications, not only as a means of automating the processing of emails, but also as a way of giving you a second chance after pressing the send button.

Additional resources

You can explore all aspects of Excel, and several articles on other office applications, in the ICAEW archive