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 combining 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 month of July you can get 20% off 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 generally come in bite-sized chunks 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.