Simplicity Is Bliss

The way I process my email is as simplified as it can be. It is really designed to help me focus on the message itself to understand what it means to me i.e., action, information or nothing.

However, I work for a huge American company and email is, as in most corporation of similar size, out of control. Consequently I cannot allow everything to enter my inbox, at least not if I want to have a chance to process emails diligently, keep my sanity, and do the other aspects of the job I am hired to do.

As email traffic grew and grew over the past years, the rules protecting my inbox became stronger and stronger. Today, I’d like to share the two strongest rules I have in my arsenal against the corporate email storm. These two rules alone route 65-70% of all emails around my actual inbox, mark them as read and get them out of my primary focus.

Mailing or Distribution Lists

While we have good collaboration platforms in our company, the wast majority of information is still spread by email. Technically you need to opt-in for most mailer lists yourself, but some people are far to kind and do it for you. Before you say ‘unsubscribe’ you are part of at least 40 internal distribution lists. Unfortunately a maximum of 10% of emails distributed via mailer lists are valuable and relevant.

With the exception of some selected distribution lists e.g., my staff distribution or the one of my manager, all emails which don’t have my email address specifically as a recipient get marked read and filed into a separate folder when they arrive. I look at the mailing list folder every other day and press the delete key very, very often.

You may have some mailing or distribution lists that are important to you e.g., virtual management or leadership distribution lists where critical information is shared and you want to make sure you see these emails right away. Simply include them in the rule as I have done in my example.

Carbon Copies (CC)

While the mailing/distribution list rule may not be too new for many of you, my ‘Carbon Copies’ rule may sound fairly radical for some.

I truly believe carbon copies is one of the worst aspects of email and leads to most of the traffic. People just add and add to the CC list: Their manager, their director, three colleagues… so on and so forth. Everyone adds more people and the resulting number of emails grows exponentially.

Very, very rarely there is any valuable information in these emails. Particular as a manager you get CC’ed for many different reasons, most of them not at all requiring you to read the email itself.

Basically this rule is executed after all mailing/distribution lists are already filtered out and looks at emails that have my email address in the ‘CC’ field, not in the ‘To’ field and are not from my primary customer. Particular the emails from my customer is something I definitely like to see in my inbox, even if I am just CC’ed.

If you have more than one customer just add all the domain names from your customers as an exception to the rule. Alternatively you can create (smart) groups in Address Book, which you then exclude from the rule.

The rule takes all the remaining CC-emails, marks them as read and moves them to a dedicated ‘CC’ folder. Shockingly enough I process — well, looked at — this folder even less frequent than my mailing lists folder.

The truth is that I basically stopped reading or even processing my CC emails for quite some time now and nothing ever happened. The world is still turning, my team is doing very well and nothing has fallen between the cracks. It’s actually liberating for me as well as my staff and peers as I stopped worrying about or disrupting activities that were well in hand.

Should the topic be something I am or have been actively involved in I still see the CC emails in my inbox as I tend to have ‘Organise by conversation’ turned on in Mail.app which also pulls related emails from other folders when displaying the contextual thread of a message.

40 emails in your inbox instead of 200

On busy days I can get 200 or more emails. The two rules described in this post filter out about 140 of them. A few others I have employed bring the load of my inbox down to 40-50 emails at max. And these emails are the really important ones, the ones that required focused reading and processing, which happens using my simple Inbox Zero workflow.

Email is not your main job, at least for most of us. But likely it is an important part of your job. Email has become a substantial part of our communication and unfortunately also a primary source of distraction.

You don’t need to like email, I certainly don’t. But you need to deal with it and since you may not like it and it is only a tool to get your real job done, you should deal with it in the most efficient way.

Time-boxing email activities is one element to make sure email does not take centre stage in your daily work. Finding an easy way to file, archive, track and retrieve email is another.

The Magic of MailTags

Many like tagging in Gmail/Sparrow and ‘topics’ in Postbox as a way to organise email. MailTags by Indev - plug-in for Mac OS X native Mail.app - has been around for a very long time and goes way beyond what Gmail and Postbox provide. The Lion-compatible version 3.0 of MailTags has been released recently and allows me to share how I use (a very small part of) it to get my email done.

MailTags allows you to do lots of things with your email. Key features include:

• Assigning tags
• Associate your email with a project (MailTags can access your OmniFocus or Things project list, provided the application is running)
• Assign a tickler date to remind you of the email in the future
• Create a event or task in iCal related to an email
• Add notes
• Assign different colours and up to five different priority levels (now you procrastinators get really excited, right? Five! priority levels!) to your emails

While you can do all of this without taking your hands off the keyboard, the real magic is how deep MailTags integrates with Mail.app. You can leverage all the functionality in searches, Smart Mailboxes and mail rules. And the OmniFocus clipper also works nicely with MailTags-

There is only one downside with MailTags: It is so powerful and feature rich that it invites you to tinker.

Basic email folder setup

My setup is extremely simple and has been recommended often: One single archive folder. Whenever I process new emails in my inbox and decide to keep them they go into my ‘Archive’ folder. No sub-folder structure, no complex filing and no time-consuming browsing to find them back.

Many of the emails I get every day (between 80-150) get automatically processed by rules and go straight to archive, trash or two folders I have for carbon copies and emails to mailing lists I am subscribed to. How these rules reduce my email load by about 50% is something I’ll cover in a future post.

I have been using a single archive folder since years now and have never failed to find back an email using search/Spotlight. In fact I have been faster using search and tags than people with folder structures in 99% of all cases.

Key tags to keep email under control

Tagging is only effective if you use as few tags as necessary. Otherwise you’ll end up in a bigger mess than with any folder hierarchy. I have just a dozen tags defined in MailTags and only six of them are really important to my email management.

• @Action — assigned to emails I need to follow-up, read or respond to as they require more than 2 minutes of my time; Nowadays I often use a flag in Mail.app to mark them; Some emails get automatically flagged for follow-up on arrival
• @Waiting — Waiting for response(s)
• @OmniFocus — for tracking the email follow-up in OmniFocus using this outbox mail rules and this AppleScript
• Expenses — Automatically assigned to expense reports (mine or the ones of my staff) before marked read and filed
• Travel — Automatically assigned to itineraries (mine or the ones of my staff) before marked read and filed
• Staff — Marks emails related to any HR or people management topics

I am not going to discuss the actually processing, whether its manual or automatic by use of Mail.app rules, but I generally process my inbox 3 times a day pretty much following the Inbox Zero methodology.

Navigating your email archive with Smart Mailboxes

When I engage with my email beyond the pure processing I leverage the tags and the tickler date functionality of MailTags heavily through Smart Mailboxes.

The most important Smart Mailboxes live as links in my Mail.app Favourites Bar while I typically have the Mailbox List in the left panel hidden. In a typical scenario I engage with them one by one.

@Action

Looking for emails that have either the ‘@Action’ and/or are flagged, this smart mailbox shows me all the emails I need to read or respond to. Typically they require some more time, quick research or more focus than what I apply during processing.

Most of my email actions are tracked this way. Only emails that require substantial action outside of my email application get clipped to OmniFocus.

Waiting For and Tickler

It always amazes me how much you achieve if you only follow-up consistently. At least you appear on top of things which results in lots of recognition by your staff, peers and bosses.

My ‘Waiting For’ Smart Mailbox, which I look at once a day, gives me exactly that opportunity. It looks for all emails tagged with ‘@Waiting’ and sorts them by tickler date (if applied), allowing me to follow-up on the most urgent, outstanding responses first.

The Tickler Smart Mailbox only looks for emails with Tickler dates, but not tagged ‘Waiting For’. These are typically emails that require some incubation or action in the future. Again, if the resulting action or project is likely to require substantial action outside of my email client, I would clip the email to OmniFocus and tickle it there.

Handy Smart Mailboxes for recently sent or viewed

These two Smart Mailboxes go back to a 43 folders post from 2007 and come in extremely handy during your daily email war.

Recently Sent - Need to quickly forward the email you just sent to another colleague? Add something you forgot to mention to that email that just went out? This Smart Mailbox is the solution as it does not require to scan through your entire, typically huge sent folder. Remember that Smart Mailboxes in Mail.app also define the search scope once selected.

Recently Viewed - If you have a single archive folder and process your inbox with the right level of discipline, you may face the situation where you remember that you have looked at an email yesterday which you need right now.

Corporate mailbox server quota (still exists)

Yes, there are still companies out there that give you a (relative small) email quota on Exchange. Not everyone lives on the endless storage supply that Google provides (for the price of ‘reading’ all your email).

I am required to manage my server space actively to prevent annoying ‘warning’ emails and eventually suspension of my email service. Sounds dramatic, but can be addressed with two simple Smart Mailboxes.

This example also nicely illustrates how you can use one Smart Mailbox as the source for another one.

First I create an ‘Archives’ mailbox which spans multiple folders, most notably the actual archive folder and the sent folder.

My second Smart Mailbox looks at the above Smart Mailbox, but only displays message that have been received or sent more than 30 days ago. Once a month I go into this Smart Mailbox, select all messages and move them into my permanent, local archiving folder.

MailTags and OmniFocus Projects

As mentioned in the overview of the MailTags functionality, it pulls the list of projects from OmniFocus (if running) and allows you to associate emails with a certain OmniFocus project.

There are two reasons why I do not use this functionality at present:

1. MailTags pulls all Projects and Single Action Lists from OmniFocus, regardless of their status, i.e. projects with future start dates appear as well. If you have 60-90 projects like myself, you’d also like to see your folder structure for easier association.
2. My projects typically have a relatively short lifespan and change frequently; Consequently it provides little value to me spending time associating emails to projects that might be done next week

However, I can see where this makes sense for others. If you only have two dozens of projects in OmniFocus or some of your projects have a very long lifespan this feature is definitely worth a consideration.

In summary

MailTags lets you do lots of great things and even offers full AppleScript for those that like to tinker even more. It’s the most powerful solution for Mail.app and you should really consider it, if you are sick of email taking control. Start with a simple setup before exploring and exploiting it. And remember that the tool itself doesn’t really solve the problem you have, it only helps once you have decided to change your approach and habit.

When I recently reflected on flexibility vs. discipline a number of things came to my mind where I am not applying enough discipline, at least not by my own standards. One of them, with little surprise, is email.

There are days where I simply live in my inbox, waiting for the next batch of emails to come and respond to them in the most flexible manner. Email is a prime example of everything that is wrong about being flexible only. You could actually start your day without any plan or goal, open your email and work for 10 hours - easily. However, no satisfaction guaranteed. Email is also highly reactive as most of the time you only respond to external impulses and by doing so you don’t have any time left to engage in proactive work following your goal, vision or desire.

We have all read a million time that we should check email only a few times a day, ideally at predefined times. If we check it, we should process it to zero. Simple, very simple. The only reason we are not sticking to this is lack of discipline. We only keep searching for a better email management method because we are not disciplined enough to build the habit required.

OmniFocus can help you establish the habit, but you’ll have to bring the discipline to the party. One way OmniFocus can help is by adding the right repeating tasks to your routines.

The Email Regime

When I wrote about flexibility vs. discipline I immediately implemented the following tasks, which sit in my ‘Daily’ house keeping list and repeat every weekday:

- Check email and process to zero (6am)
- Check email for emergency (10.30am)
- Check email and process to zero (1.30pm)
    - Check "waiting for" emails
    - Check tickler smart mailbox
    - Check flagged emails
    - Check mailer list folder
- Check email and process to zero (4.30pm)

One of the compromises I have made is that I check emails first thing in the morning. No sure if my job really requires it, but I just feel better. Usually not too many important emails came in after I checked the last time the day before, so processing them to zero isn’t a big deal.

It is the morning where I am most creative and productive. Consequently I try to take on the bigger, more difficult junks of work during these time. To not interrupt the ‘flow’ too much, I only open Mail.app at 10.30am for a quick emergency scan. Primary purpose of this scan is to make sure nothing important (!) requires my immediate (!) attention and that my calls & meetings, which I try to have mostly in the afternoon, haven’t moved.

At 1.30pm it is time for the daily 360° email maintenance. Processing the inbox to zero is priority number one. However, this time I also look at various other folders and by doing this on a daily basis it actually requires very little time and effort:

• I look at all mails I have sent and tagged “Waiting For” (using MailTags 3), following those up which are overdue or still pending.
• The ‘Tickler’ smart mailbox I have setup looks for emails that have a tickler date assigned (again MailTags 3) and shows them sorted by it. If any of these emails is due or overdue, I can take the required action.
• Emails that I need to review, mainly because they are very long, or action are simply ‘Flagged’ in Mail.app - I don’t really add each of them to OmniFocus, but it’ll take me another post to explain why.
• Finally I review my ‘mailer list’ folder, which is where all these emails go on which I am neither in ‘To’ nor in ‘CC’. Some of them are relevant, most of them get deleted straight away.

Finally, at 4.30pm, I check emails the last time for the day by processing the inbox to zero again.

Don’t even touch it

Now the discipline comes in when you can resist touching your email outside of these times. Every time you feel the urge to write an email make a task entry into OmniFocus instead. You can even use the notes field of the action to capture the entire email or just an outline of what you’d like to send.

Process and write your emails in batches at the defined times. In between those times your email client should be only one thing: Closed. I have experimented with taking accounts offline by adding the corresponding icon to my Mail.app toolbar, but it turns out some of my IMAP accounts still get fresh email, hence I decided to simply quit Mail.app outside of my pre-defined email times.

Make your email smarter

Smart mailboxes are great and they become magical if you use tools such as Mail-Act-On or MailTags with them. But the true life savers are mail rules. They can make your email processing so much easier and shorter if applied in the correct way. I will cover my approach to email automation in one of the next posts. Meanwhile implement your email routine in OmniFocus and stick with it!

Indev from Canada have brought enhancements to Apple’s Mail.app for a very long time now and have been amongst the pioneers of email tagging on Mac OS X. Whilst I personally use Postbox instead of Mail.app today, I still dig Indev’s extensions to Mail.app and follow the developments. Most notably MailTags has become an integrated part of many people’s workflows and while Indev has been silent for a long while, they have now released a new version of their flagship product.

While it is ‘only’ a minor version update, the changes are improvements are significant. Most important to all OmniFocus (as well as Things) and Mail.app users: The integration between MailTags and your favourite task manager has been taken to new highs. Since quite a long time OmniFocus had the ability to match the project set for a message by MailTags with a project in OmniFocus when the message was clipped. But you had to manually create or at least import a up-to-date project list for that.

Also the MailTags keywords have been used by people for example to automatically add messages tagged ‘waiting for’ to their OmniFocus ‘waiting for’ context. Assigning certain message to people or agenda is another often practiced use.

What people have been eagerly awaiting is the ability to ‘sync’ the project list between OmniFocus and MailTags. MailTags always had the above mentioned project field, but it was self-maintained inside the MailTags preference pan and despite several attempts even the best AppleScript gurus weren’t able to establish any sort of sync between the OmniFocus and MailTags project lists. All that was left was a clunky text file based import/export option.

These days are gone. You can now simply select to have OmniFocus projects show directly inside (and in addition to MailTags’ own projects) Mail.app’s tagging panel. Only caveat is that you need to have OmniFocus running to get access to it’s project list. You can do the same for CulturedCode’s Things or even for both if you are one of these indecisive productivity nuts that can’t settle with one system.

Once you have enabled the integration, the projects from within OmniFocus are listed in MailTags project drop-down. While this initially doesn’t look like a big deal, it actually can become one depending of what you make of it. Thinking of inbox and outbox rules, Smart Mailboxes and Applescript, I sense a whole new dimension of possibilities here:

• Retrieve all project related emails in one click using a Mail.app Smart Mailbox
• Trigger the access to the Smart Mailbox from within OmniFocus using AppleScript
• Automatically assign emails based on sender, sender group or a string in the subject or even email body to the right project using inbox rules
• Not only track ‘waiting fors’ by context but also by project with no additional effort

I am confident that lots of the smarty pants using the combination of Mail.app, MailTags and OmniFocus will come up with even better use cases and additional bells and whistles. I can only hope that the good folks at Postbox will follow Indev’s example and tighten up the quite natural between email and task management.

For now: Head to Indev’s website and get yourself the latest version of MailTags. Don’t forget to report back and share how you use the new project list integration.

A very long time ago, I published an Applescript I’ve created that uses Mail-Act-On 2 and MailTags by indev.ca to create a task in Omnifocus for messages you send out that you need answer or follow up (“Waiting For’s” in GTD terms). While I haven’t been working on the script ever since, the brave community in the Omnigroup’s Omnifocus forum did.

They refined the script, fixed some issues and when Scott Morrison from indev.ca got involved himself, the script evolved to utilise most of MailTags incredible power, e.g. using the project field of MailTags to add the task to the right project in Omnifocus if there is a matching one or even add a due date to the task based on the Tickler Date (if set) of MailTags.

Awesome community development. Make sure you check out the thread in the Omnifocus forum for more variations and further enhancements.

I believe the latest version has a bit of an issue and isn’t adding the task to Omnifocus, if the Tickler Date isn’t set. It still triggers the Growl notification, but the task never appears in Omnifocus. Hopefully I’ll have time to look into this and provide an update.

I’ve decided to leave the script source in the capable hands of the Omnifocus Forum community. Hence refer to the corresponding thread there to obtain the latest version and any updates.

I’ve published an Applescript that, with some help of MailTags, automatically adds emails by which you delegated tasks to OmniFocus. Since only minimal adjustments in the code were required to made it work for Things as well. I’ve modified the script accordingly.

Script Functionality

1. Based on a specific MailTag in Mail.app you can invoke a outbox rule which will start the script (I use “@Waiting” in MailTags as well and simply applied it to those emails I write which need to be tracked for response)
2. The script adds a task with the title “<recipient> to come back re <subject>”. The text in the middle can be configured in the script and if you have more than one recipient (CC and BCC recipients are ignores) the script will take the first recipient and add “and x more” automatically.
3. The task includes a link back to the original message in the notes section (and the actual mail body, if desired), is automatically assigned with a “@waiting” tag (configurable) and placed into Things’ inbox
4. If you have Growl installed and running, the script will give visual feedback once the task has been created

Installation of the script

1. You will need MailTags from Indev to later built the proper Mail.app outbox rule
2. Download the script and copy it into your standard script directory, e.g. ~/Users/<your username>/Library/Scripts/
3. Modify the script configuration based on your needs and setup
4. Create a outbox rule in Mail.App that invokes the script if specific conditions, i.e. MailTags Keyword of the message is “@Waiting”, are met

Customising the key parameters

Inside the script you can and very likely should change some configuration properties to match your requirements and setup.

• property mailBody : true - You should change this setting to ‘false’ if you do not want the entire body text of the email to be pasted into the Things task’s note section.
• property MidFix : "to come back re" - Change this text to whatever you like to see in the task title between the email recipient’s name and the email’s subject.
• property myWFTag : "@waiting" - This variable needs to exactly match the name of the tag in Things that you’d like to use for “Waiting For” items, i.e. “@waiting”.

Creating the outbox rule in Mail.app

Next you need to create a outbox rule in Mail.app that looks similar to the one below. Again MailTags will be required to perform this action.

With this last step you should be up and running. Enjoy and please let me know how this script works for you.