Use Outlook Rules to Prevent "Oh No!" After Sending Emails

How many times have you sent an email and then realized a few seconds later that your snarky comment was sent to the entire mailing list, or left an embarrassing typo in an email to somebody you were trying to impress? Or simply that you:

·  wished you had phrased it in another way? or

·  (more commonly) forgot to add the attachment the email refers to? or

·  forgot to add another important point?

·  want to avoid having to use the “recall and resend” facility in Outlook?

I have … and most times I realised it within a few seconds of the email being sent. Using the "Defer" rule in outlook, we can setup a rule that essentially pauses all message delivery for a 1-120 minutes after you click the Send button, to give you a chance to recover. This document explains it all ‘step by step’.

Select Rules and Alerts from the Tools menu, and then click on the New Rule button.

Under "Start from a blank rule", choose Check messages after sending, and then click Next.

Don’t select anything here and just click the Next button again on the "Which conditions do you want to check" screen, and you'll be prompted with this dialog informing you that the rule will apply to all messages. If you want to, you can set this rule up to only work for certain groups (personally, to keep things simple, I don’t).

On the next screen, check the box for "defer delivery by a number of minutes", and then (in the bottom window) click on "a number of" and change the defer minutes to something like 60-120 minutes, although you can change it to whatever you'd like.

I originally tried using a 15 minute delay, but it didn't give me enough time to realize the mistake and then locate the message and fix the problem; I use 120 minutes.

Click the Next button, and then give the rule a name, preferably something memorable so you'll recognize it in the list. I use “2 hour delay” or in the example below “Don’t Send Stupid Emails”.

Now when you send messages, you'll notice that they sit in the Outbox for whatever time period you have stipulated. If you want to stop a message from going out, your best bet is to just delete it from the Outbox, but you could attempt to just fix the mistake and then resend.

Test out the rule: send an email to yourself and see if it sends it straight away back to your inbox or whether you have been successful with the 2 hour delay.


Further Variations

Emails that need sending NOW!

Okay, there are some emails that you may need to send straight away and the problem with the delay system is that it will add (say) a 2 hour delay to all outgoing emails.

You could mark the email you want to send as of “high importance” (just look at the right hand side of the top bar when you create an email in Outlook 2007): this will override the delay system. HOWEVER, when I used this system, I received a gentle reminder from someone that what might be important to me might not be important to others. If people start receiving quite a few emails marked as “important” when they are not (for them anyway), it’s a bit like crying wolf and they’ll then start to ignore your emails.

So, this is the system I use now: just modify the delay rule you created above. I use my initials in brackets as a marker “(RM)” for Outlook to identify emails that need to go out straight away. So, I amend the rule above to tell Outlook that if it sees (RM) in the subject heading, it will override the delay system and send it straight away. I use my initials because it is easy for me to remember and I use brackets so that the rule doesn’t end up excluding emails with subject headings which might contain RM in one of the words eg “OUR TRIP TO THE FARM”

·  Go to Tools – select ‘rules and alerts’

·  Select the delay rule you created (in my case it was called ‘2h delay’) and then click ‘change rule’

·  Now select ‘edit rule settings’

·  On the page “which rules do you want to check” just click next

·  On the page “what do you want to do with the messages” just click next

·  On the page “Are there any exceptions”, under “step1: select condition”, pick ‘with specific words in the subject’. You’ll now see that rule in the bottom part of the window.

·  Click on “specific words” in the bottom box and add your word or phrase: in my case I use my initials in parentheses (RM); then click okay

·  Then click “finish rule set up”

·  You’re done.

Test out the rule: send an email to yourself with your chosen word/phrase in the subject heading. Don’t forget, you can still make effective use of the subject heading, but you just need to add the word/phrase if you want the override rule to apply to it. So, in my case, I might use a subject header like: “What do you think of this idea John? (RM)”

Emotionally Charged Emails – avoid the honey trap

Ever received an email that has really upset you on an emotional level? And then you’ve replied straight back only later to realise your email reply was too emotionally charged and has now upset the other person(s); then the downward spiral of a “tit for tat” conversation sets in? Well, fear not! I have a solution for that too.

The thing about responding to emotionally charged emails straight away is that although they help you to ventilate your feelings (and make you feel better in the immediate term by ‘getting stuff off your chest’) they can be full of things you’ll regret you had said. Time is a good healer: time gives you space for reflection and after a while, when your own internal negativity has settled, you then begin to respond on a more adult level (by adult, I mean more rational and neutral with a bit of ‘give and take’). So, here’s a system that gives you the immediate benefit of ventilating your feelings but at the same time allowing time to be a natural healer and helping you to respond in a more constructive way.

·  After you’ve replied to the initial upsetting email, DO NOT PRESS THE SEND BUTTON.

·  Simply click on the close (X) button on top right hand corner of that message box.

·  It will ask you if you want to save the message. Say yes.

·  It will then save that emotionally charged email in your drafts folder. This will not go out unless you re-open it and click send. This means you can now look at it time and time again (in the days to come) and make tweaks and changes until you’re happier with it.

·  Then, when you’re happy, open it from your drafts folder (double click on it) and press the send button. Now it will send.

The good thing about the email delay system previously outlined is that if you’ve set it up and then create an emotionally charged email and accidentally press the send key, it will have automatically gone into your “Outbox” email folder ( i.e. it won’t be sent for whatever minutes you have stipulated) and that means you can drag it into the drafts folder. So, doing this INADDITION to the above email delay system provides a DOUBLE safety netting procedure.

Oh No, I’ve Sent an Email Using the ‘Send Now’ Rule and I want to Pull It Back

If you’re using an exchange type email account: worry not; for the rest – sorry, no can do. If you don’t know what I mean by an exchange server, then it is highly likely you’re not on one. Most people aren’t on an exchange server. People who use Blackberrys or IMAP are likely to be on one.

With an exchange server, you can recall or replace a message only if its recipient is logged on and using Microsoft Outlook and has not read the message or moved it from their Inbox.

In Mail, in the Navigation Pane (Navigation Pane: The column on the left side of the Outlook window that includes panes such as Shortcuts or Mail and the shortcuts or folders within each pane. Click a folder to show the items in the folder.), click Sent Items.

·  Open the message you want to recall or replace. In the message window, on the Actions menu, click Recall This Message. Note This command does not appear unless you are using an Exchange e-mail account.

Do one of the following:

·  Recall the message

·  Click Delete unread copies of this message.

·  To be notified about the success of the recall or replacement for each recipient, select the Tell me if recall succeeds or fails for each recipient check box.

·  Replace the message

·  Click Delete unread copies and replace with a new message.

To be notified about the success of the recall or replacement for each recipient, select the Tell me if recall succeeds or fails for each recipient check box.

·  Click OK, and then type a new message.

Note To replace a message, you must send a new one. If you do not send the new item (item: An item is the basic element that holds information in Outlook (similar to a file in other programs). Items include e-mail messages, appointments, contacts, tasks, journal entries, notes, posted items, and documents.), the original message is still recalled.

Automatic Delay vs Send to Draft Folder

Some might say that this automatic rule for delaying emails sounds like a waste of time to me; why not just save them to the Drafts folder and then send them when you are ready?

And they’re right! You could save your emails to the drafts folder and then send them out later. The reality however is that this is not the way most people work. We write our emails, click Send and move on to the next email. Even if we changed our method of working, we would then need to remember to go to the Drafts folder periodically to send out all our unsent email(s).

With Automatic Delay, the emails get sent out automatically … unless you change your mind (and you’ve got a 2 hour window to do just that).

Closing Note

Sending emails using the delay system above also makes others think you work hard. For instance, I might send an email at 10pm and nobody will think anything of it. But with the delay system, they get it at 12 midnight and I often get asked “What are you doing sending emails at midnight. Don’t you ever take a break?”. Hey ho....my secret is out!