Turn off autocomplete 

One of the most common sources of email fails is sending an email to the wrong person. Outlook autocomplete is not your friend here. Suggesting email addresses based on those you’ve previously used looks like a useful tool, but the first suggestion isn’t always the right one! Just a little bit too much haste here can very easily lead to email fail! 

To turn off autocomplete, select File > Options > Mail > Send Messages and uncheck the “use autocomplete list...” option: 


This doesn’t mean you have to type out every email address in full. If you’ve already saved the person into your contact list (or your organisation’s global address book), Outlook will still check and suggest email addresses prior to sending, however the interface for this forces you to slow down and choose a little more carefully (an added bonus of this approach is that it provides something of an incentive to actually keep your contact list or CRM up to date). 


If you want to manually get Outlook to prompt you to select the right email addresses, you can also press alt+k at any time. 

Turn off send email keyboard shortcuts 

Power email users quite often use keyboard shortcuts for things. Two of the more commonshortcuts for lawyers are ctrl+backspace and ctrl+delete (these delete whole words rather than single characters). But those keyboard combos aren’t too far removed from ctrl+enter – the hotkey to send an email. And if you’re trying to delete a few words, odds are that you aren’t ready to send that email!  

To turn off this keyboard shortcut, select File > Options > Mail > Send Messages and uncheck the “ctrl + enter sends the message” option: 


You can still use the alt+s keyboard shortcut to send emails – something much harder to hit by accident. 

Delayed sending 

Mistakes will inevitably happen. And there’s nothing quite like that stomach-dropping feeling of dread when you realise you’ve sent an email to someone, or with something, that you shouldn’t have. 

Outlook allows you to set a rule to delay sending email messages a few minutes. If you have this rule turned on, any emails will sit in your “Outbox” until the allotted time passes. 

For the desktop version of Outlook, there are a few steps to set up a delayed sending rule. Start by selecting Rules > Manage Rules and Alerts > Email Rules > New Rule to create a new rule.  

You will then need to set up the conditions, exceptions and actions for your rule. To delay sending for all emails, select Start from a blank rule > Apply rule on messages I send > Next. On the next screen, click Next again and select Yes when warned that this rule will apply to all messages you send. At Step 1: Select Actions check the “defer delivery by a number of minutes” box. Then at Step 2: Edit the Rule click the underlined blue “a number of” link. Select your desired time (1 minute is fine to start) then Next. Add any exceptions (for example “except if it is a meeting invitation or update” – you can't get in to too much trouble responding to meeting invites in haste) then Next. Give the rule a meaningful name (e.g. “delayed sending”) and ensure that the “Turn on this rule” box is checked. Then click Finish: 


Rules are easy to get wrong. Any time you set up a new rule, you should always check that it is running as intended. To check the delayed sending rule is running correctly, send yourself an email. It should sit in your Outbox (you will see a number next to the Outbox) until the allotted time passes: 


The Outbox is also where the email can be found during the delay before sending. Opening (or deleting) an email from the Outbox will stop the email from being sent. You can edit and resend and email so long as it is still in the Outbox. 

For the web version of Outlook (if you access Outlook in a browser), the steps are much simpler. Click the Settings cog > View all Outlook settings > Mail > Compose and reply. Then find the “Undo send” option and select a time to delay sending: 

Send links, not attachments 

Oh no! You’ve just sent an email to your major competitor containing your highly-personal customer data spreadsheet!  

If you sent that spreadsheet as an email attachment, there is not much you can do (from a technology perspective) to get it back. 

But virtually all major document management systems, including Microsoft OneDrive and SharePoint, allow you to share links to cloud-based documents rather than separate attachments.  

Most of these allow you to set secure log ons and passwords to access those documents. Using this approach, a misdirected covering email to your competitor won’t give that competitor the necessary permissions to access the linked spreadsheet.  

But even if you don’t set a secure log on and password (this is sometimes called “anyone can access this link”), you are still much better off than sending an attached copy. A separate copy of your customer data spreadsheet hasn’t been given to your competitor, rather you’ve pointed them at a copy you control. Any time you realise a link has been misdirected, you can deactivate the link making sure that no-one can access it. Most cloud-based document sharing tools even provide an audit record showing who has accessed a document so you can see whether it has been accessed or not. 

Want to know more? Or do you have an Office hack or cool app for lawyers you would like to share? Email us at [email protected].