Office hacks for lawyers #2 - preventing email fail

Meet Speedy, the email fail snail:

Image credit: OpenClipart-Vectors via Pixabay

Image credit: OpenClipart-Vectors via Pixabay

Speedy gets into trouble with email, because Outlook makes it just too easy to send emails to the wrong people, with the wrong attachments, and without double checking their contents (Speedy may or may not be a thinly-disguised alter ego of the author of this post). Needless to say, this can cause Speedy all manner of problems including privacy breaches, waiver of privilege, and just plain embarrassment.

This blog post outlines some tips and tricks that Speedy can take to help avoid email fails.

Turn off autocomplete

One of Speedy's most common sources of email fails is sending an email to the wrong person. And why? Because Speedy uses autocomplete. Autocomplete suggests email addresses based on those you've previously used. While autocomplete looks like a useful tool - mis-typing email addresses is common - Speedy isn't careful enough. The suggestion at the top of the list isn't always the one he is looking for, but is often the one he picks! Email fail ahoy!

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

Turn off autocomplete

Turn off autocomplete

If Speedy has already saved the person into his contact list (or is in his organisation's global address book), Outlook will still check and suggest email addresses prior to sending, however Speedy is forced to look at the list and choose more carefully:

Picking email addresses with autocomplete off.

Picking email addresses with autocomplete off.

An added bonus of this approach is that it provides something of an incentive to actually keep his 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.

Garbage in the to line

Another way to stop accidentally sending emails before they are ready is to put something clearly not an email address in the to line (Speedy has been known to use "asdf" when he remembers). If you accidentally hit "send", Outlook will prompt you to sort out the garbage email address before actually delivering the message. Not ready to send? Hit cancel and it won't be sent.

The power of garbage

The power of garbage

Attachment checking

Speedy has been known to send emails without the accompanying attachment. While a much more minor email fail than some of the others he's committed, this doesn't reflect well on Speedy's professionalism.

Later versions of Outlook have an option to prompt you if it looks like you've missed the intended attachment. Select File > Options > Mail > Send Messages and check the "warn me when I send a message that may be missing an attachment" option.

Check email attachments

Check email attachments

Turn off send email keyboard shortcuts

Speedy is a bit of a power user and likes to use keyboard shortcuts for things. One thing he uses a lot is ctrl+backspace and ctrl+delete (these delete whole words rather than single characters). Unfortunately, snails aren't particularly dexterous and Speedy has been known to hit ctrl+enter by accident instead. This is the hotkey to send an email - more email fails!

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

Turn off sending hotkey

Turn off sending hotkey

Perhaps inviting trouble, Speedy now uses the alt+s keyboard shortcut to send emails. Fortunately that seems to be much harder to hit by accident.

Delayed sending

Even taking all the precautions outlined above, Speedy can still make mistakes. Or send off a quick, angry/frustrated/tone-deaf/dopey email that he quickly regrets. 

Outlook allows you to set a rule to delay sending email messages a few minutes. If Speedy has this rule turned on, any emails he sends will sit in his Outbox until the allotted time passes. This gives Speedy the opportunity to enjoy that "oh-my-gosh-did-I-just-do-what-I-think-did" feeling followed by that overwhelming sense of "pfew-that-was-a-close-call-thank-goodness-I-have-that-delayed-sending-rule-turned-on" relief.

To set up a delayed sending rule, there are a few steps. 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 then Next. Add any exceptions (for example "except if it is a meeting invitation or update" - Speedy 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.

Delayed sending rule

Delayed sending rule

Rules are easy to get wrong. Any time Speedy sets up a new rule, he always checks 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:

Check your Outbox

Check your Outbox

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.

Other clever rules

Speedy has a number of other clever rules that he uses to help prevent his email fails. These include delayed sending only to contacts outside his organisation (internal emails are delivered immediately) and delayed sending only where the email includes an attachment. Both of these can be achieved with the right rule settings, but the options depend on the version of Outlook you are using. If you get stuck, Google searches will usually provide the answer. But always ensure that you test your rule before relying on it!

You might also like to speak to your IT department about "transport" or "mail flow" rules. These are rules that run on your organisation's central email server and therefore apply to everyone in an organisation; they aren't set up computer-by-computer. These server based rules are also more powerful, and can do things that Outlook cannot unless you want to write some code for your custom rules. For example, a very clever man once observed in Speedy's hearing that you could eliminate the vast majority of the world's data breaches if you just banned spreadsheet attachments. This can't be done (without coding) in Outlook, but can be done with transport or mail flow rules at the server.

Control of attachments

I've posted previously on the benefits of sending links rather than actual attachments in order to maintain control of information. This applies to Speedy too. Yes, he just sent an email to a competitor containing all his highly-personal customer data. Fortunately for Speedy, he followed the linking advice in that previous post. He immediately realised his mistake, disabled the link, and checked the audit record to ensure that no-one had accessed the data. Email fail averted!