I have been using all sorts of tricks, methodologies and scripts to manage email follow-up. Since I am getting and writing many emails — it is sort of a corporate disease, in particular if you have a management role — many of them did not work for me. Adding emails you are awaiting response on to your todo list is neither straight-forward nor does it help you keeping your task list clean and focussed.

On a normal day I may be writing as many as a dozen emails for which I am looking to get responses within the next two to five days. Over the course of a week that could result in 50 or more "Waiting For" tasks in OmniFocus which would clutter my task list quite a bit.

With OmniFocus MailDrop it is easy to get these emails into your Inbox — simply BCC your OmniFocus MailDrop address — but that is just where the whole problem starts. Once they are in your inbox you need to rename the task in something meaningful like "Waiting for Suzanne to come back re budget plan" add a context, project and due date.

Keeping track of whether you got a response is even more disintegrated: First MailDrop does not get the nice link back to the email you will get when clipping the email which means you need to search for it and second you need to switch back and forth between OmniFocus and Mail.app to not forget checking off the tasks if a response has been received. Too many times I forgot to check off the task and ended up with a long list of by then irrelevant tasks which in addition became overdue and caused the Forecast in OmniFocus to become deep red.

For many other todo list application the problem is even worse. So why not tracking emails where they reside? Unless an email requires an action outside of my email application I started to use InDev's MailTags andMail-Act-On plugins to track emails in Mail.app. With MailTags 4.0 it became even simpler.

Automated Tracking

In MailTags 4.0 you will find a straightforward setting that enables MailTags to detect messages you are sending and want to track the response. You have to assign a keyword such as "@Waiting" when composing the email and MailTags will automatically list it in the "Awaiting reply" Smart Mailbox it creates in Mail.app. When a response has been received, MailTags automatically removes the "@Waiting" keyword and replaces it with a keyword of your choice, in my case with "@Action".


With the new keyword the response will show up in my "@Action" Smart Mailbox which I process at least twice a day. I can then see if the response is conclusive and take the next action, if any. More often than not I actually need to get back to the person responding asking for more detail, clarification or further activity on their end and the cycle starts from the beginning.

Working with Tickle Dates

MT-Tagging-ComposingMailTags also offers the ability to set a Tickle Date on a message when you compose it. Combined with the "@Waiting" keyword you can do more granular Smart Mailboxes or use the Tickle Date ones that MailTags provides out of the box. You can now specifically look for message that have not yet received a response and are overdue or due today so you can send a gentle or not so gentle reminder.

Managing Tickle Dates

For everything so far you only need MailTags 4 (in open beta at present). If you also get Mail-Act-On you can do a lot more fancy things using only your keyboard. In this workflow I use Mail-Act-On to push out Tickle Dates of any messages that are due or overdue and for which I sent a reminder giving the recipient another day or two to come back.

I go through my due or overdue emails, send reminders and then press any of the following key combos to manipulate the existing Tickle Date:

  • ^1 — adjusts the Tickle Date to be one day from today
  • ^2 — adjusts the Tickle Date to be two days from today
  • ^5 — adjusts the Tickle Date to be five days from today
  • ^M — set the Tickle Date to next Monday
  • ^F — sets the Tickle Date to be next Friday

These keyboard shortcuts are implemented with Mail-Act-On rules which work just like regular Mail.app rules. Both rule sets can access MailTags meta data on message once MailTags is installed.


Mail-Act-On allows for many other cool workflows. If you are filing message into a folder structure, Mail-Act-On is the perfect tool for you. But there are many other things it can trigger which I hope to cover in a future post.

More Email Workflows

For my German-speaking readers and followers I recommend listening to episode #UC008 of the "Der Übercast" — the podcast of which I am a third of. Together with Patrick Welker and Andreas Zeitler we discussed email setups and workflows for nearly 90 minutes and cover, amongst many other things, the approach described in this post.

Tim Stringer has been around the OmniFocus advocates for a while. I had the opportunity to meet him in San Francisco while we were both speaking at the OmniFocus Setup event. Tim does not only know OmniFocus inside out, he also has a passion for coaching and helping people. With his latest project — "Learn OmniFocus" — he is combing both trades to the benefit of many.

"Learn OmniFocus" is a learning platform bringing all knowledge, best practices, tips and tricks for OmniFocus neatly into one place leveraging screencasts, articles and webinars. It is Tim's ambition to cover all OmniFocus versions — iPhone, iPad and Mac — while the initial focus of his content development is on the shiny and new OmniFocus 2 for Mac. That said, you can already find a few iOS tips in the "Learn OmniFocus" catalogue today.

Tim is developing a rich set of resources and is offering a subscription-based membership access to the different courses and resources starting at a 3 months access tier for $29 up to a full year for $59. During the launch month of July you can get off 20% from the annual subscription. Details are on the Learn OmniFocus membership pricing page.

Helpful Articles

If you do not know whether the investment is worth it Learn OmniFocus has a bunch of free resources available that give you a flavour of what to expect. Starting in the Articles section which is comparable to a well structure series of blog posts you can find out how to "Mind map your responsibilities" for a better structure in your OmniFocus setup.

There are a couple more articles and videos you can access without signing up to a membership, but the real gems like creating the basic structure of your OmniFocus database or defining the right set of Contexts require you to be a paying member.

Detailed Screencasts

One of the big things on Learn OmniFocus are the videos, or better: screencasts. Tim has already produced a sizeable number of them and continues adding more. The videos are generally come in bite-sized junks and help you following the individual steps and learn every trick there is in OmniFocus while doing so.


The video section is divided into two main blocks: "Mastering the Basics" and "Beyond the Basics". Basics include a "Getting Started" video, a 101 introduction to projects and context, how to setup syncing and the best ways to get your stuff into OmniFocus' inbox.

When going "Beyond the Basics" Tim covers some incredible advanced topics in a very educational way: Starting from a round trip of OmniFocus' preferences to creating custom Perspectives and engaging in a Weekly Review all bases are covered. Even an introduction on how to work with OmniFocus and AppleScript to manage "complete & awaiting reply" situations is part of the library.

Interactive Webinars

learn-of-coming-soon Starting in September 2014 things will get even better at Learn OmniFocus as
Webinars will launch and make your OmniFocus learning as interactive as possible. As a start Tim plans to use Web Conferencing technology to provide courses on how to start out smart with OmniFocus, how email workflows and OmniFocus go together and how you can automate certain tasks in the application.

Coming Soon

What impressed me most is the clear plan available for future content. There is a lot in the pipeline and many of these subjects will be very valuable even for OmniFocus power users.

Save until end of July

Not very often there is the chance to kill three birds with one stone: If you sign up to "Learn OmniFocus" until July 31st you can save 20% off the annual membership (1st year) using the code JULY2014. By doing so you not only support Tim's great work and future creation of content, but also — with a small percentage — simplicitybliss.com.

David Sparks is a multi-talented and very busy person: Day job lawyer and spare timer podcaster, writer, publisher and presenter. In his latest Field Guide book — releasing on July 21st and available for pre-order now — he is bringing some of these talents together helping others building and delivering better presentations.

In the past David, sometimes together with co-authors, already helped us to make better use of Email, Markdown, Mac OS OX and to live Paperless. This time he takes on the not-so-easy subject of presentations. There are a lot of them and most tend to be bad. That is also why David leaves his typically more tool-focussed path a little and looks into creation, planning and delivering techniques that make your presentation more engaging.

presentations-cover With a large number of screencasts and other interactive elements the book also uses the full set of possibilities offered by iBooks, making it a great learning experience. David also invested in a design overhaul compared to his previous books making 'Presentations' a real pleasure to read and navigate.

I am delivering a lot of presentations and they appear to resonate pretty well, but that did not stop me from pre-ordering David's new book. "You always need to seek getting better." — That is one of my rules for better presentations.


Because OmniGroup knows that many of their customers are keyboard-operated they not only have default keyboard shortcuts for many operations in OmniFocus 2, they also included this impressive keyboard commands cheat sheet straight into the OmniFocus 'Help' menu. It actually comes as a PDF so you can print it and put it under your pillow at night to memorise these key combos better.

As some of the interaction design in OmniFocus 2 has substantially changed there are also some new shortcuts to be learned by long-time users. My favourite at the moment is ⌘! as it helps converting an action into a project when processing your Inbox.

While most of the shortcuts that are already muscle memory for so many largely remain unchanged, there are a few modifications, e.g. hiding/showing all notes, to watch out for.

OmniFocus 1 for Mac has been around since early 2008 and was more than due for an upgrade. After the OmniGroup focussed on the iOS versions of the application for the past years, OmniFocus for Mac received more love and attention over the last two years leading up to a major upgrade. After two large-scale private beta phases exploring two very different UI design concepts and eventually a public beta OmniGroup pressed the button on OmniFocus 2 for Mac last Thursday (find all the details in the OmniGroup blog post).

After many years of theming away OmniFocus' reminiscence of an Aqua interface the application now sports an entirely re-designed UI which is clearly inspired by the last major OmniFocus for iPhone upgrade. While the data model remained largely unchanged, the crew from Seattle managed to reduce complexity and therefore friction in the app while maintaining the power provided by its flexibility and feature set.

As a consequence of OmniGroup's approach you can now chose between a Standard and a Professional version of OmniFocus 2 for Mac. While the Standard version will work perfectly fine for all "casual" users, the Professional version maintains features like Perspectives and the AppleScript interface used by power users. Both versions are available from the Mac App Store (the Pro version comes an In-App Purchase) and Omni's own store and there is a nice upgrade pricing and process for all owner's of OmniFocus whether they bought the software directly from OmniGroup or through MAS.


Whether you just want to get a better overview of OmniFocus for Mac before getting your credit card out for an initial purchase or upgrade, want to learn what is new or to get started with your 14-day trial version and few good people took the time and effort to create some helpful screencast to help you.

Tim Stringer, a long time OmniFocus power user who is in the process to launch his "Learn OmniFocus" website on June 2nd, has produced two screencast as a teaser of what he is working on.

Looking at what has changed from OmniFocus 1 to 2.

For those using OmniFocus 2 for the first time.

Well-known screencaster Don McAllister from ScreenCastsOnline recorded a full OmniFocus 2 tutorial of which the 1st part with 33 minutes (!) is available for free

Also the OmniGroup created three useful screencasts that cover OmniFocus 2 for Mac Perspectives, Forecast and the new icon design. You can find them in OmniGroup's large video repository.


Some of the heavy-weights of my favourite tech writers also wrote their very own reviews of OmniFocus 2 for Mac.

Shawn Blanc has a very extensive review covering his personal use of OmniFocus on the different supported platforms, a visual history of the application from its inception as Kinkless GTD and a solid review of what's new and hot in OmniFocus 2.

This new version of OmniFocus is more feature-rich while also being cleaner, more organized, and more logical. The design brings a structured peacefulness to the wild animal that is my never-ending task list. And that’s quite a feat, because our to-dos are, by nature, neither structured nor peaceful.

In his review Stephen Hackett from 512 Pixels puts more emphasis on providing a short, but complete overview of what comes with OmniFocus 2 for Mac.

If you use OmniFocus, upgrading to the new version should be a no-brainer. It's beautiful, fast and packs the same punch the old version did. It doesn't bring a long list of new features, but it does its job reliably and easily. It's hard to ask for much more from a tool I depend on daily.

Finally Federico Vittici on MacStories admits that OmniFocus 2 is no longer for him, but a great tool for many. Consequently he reviews it through the eyes of a Reminders user

OmniFocus is a professional project management tool that's not meant for people like me who are fine with Reminders. While the new app does make things easier, there's still friction caused by longstanding limitations (lack of sharing, complicated settings for views and perspectives). I don't need to switch from Reminders and Fantastical to OmniFocus, but that's just me.

If you're an OmniFocus 1.0 user, the benefits brought by version 2.0 outweigh the few quirks I found in this new release, and I recommend the upgrade.

Tips & Tricks

Many blogs offer great tips and tricks when it comes to OmniFocus and this little outlet does as well. There is a very active community constantly sharing best practices, scripts and hacks. With the release of v2 there are a few new additions to mention.

First of all OmniGroup goes a lot further than many other software developers and offers free and extremely good user manuals for their applications via the iBook Store. Here is the OmniFocus 2 for Mac user manual fresh of the press.

Matthew Guay has written a great guide to OmniFocus 2 for Mac on Tuts+ worth checking out, in particular if you are getting started fresh with the application.


With "Inside OmniFocus" the OmniGroup has also launched a platform where they share stories and best practices of OmniFocus users along with some helpful tips. At present you can find articles from Sabra Morris, Kourosh Dini, David Sparks, Jan-Yves Ruzicka and yours truly on Inside OmniFocus. The posts vary from good overviews to some really nice geekery.

OmniGroup also curated some useful links and tips covering the usage of Evernote, IFTTT and AppleScripts with OmniFocus.

Scripts & Tools

Speaking of scripts and tools you do not want to miss the free Perspective Icons set from Josh Hughes which perfectly matches the OmniFocus 2 design.


Long-standing OmniFocus scripting guru Curt Clifton has updated two of his most popular scripts to work with OmniFocus 2 for Mac: 'Complete and await reply' as well as 'Populate Template Placeholders'.

Chris Sauve's mother of all OmniFocus templating scripts is also ready to work with v2.

If you have to live through the corporate torture of having to use Microsoft Outlook 2011 my internet buddy Justin Lancy made sure things are not as bad by updating his 'Send Outlook 2011 items to OmniFocus' script right in time.

While many enjoy the white space in the new OmniFocus 2 layout other like a more dense layout with better use of screen estate. Jason Verly shows how the compact layout option is activated using the OmniFocus URL scheme which offers more "hidden" settings documented here.