There has been a gap in how I manage my work for a long time. It's a little thing and is no bother most of the time. But when things get crazy, or if I'm not careful, some important task falls through the cracks of my system. I'm referring to the follow up email.

This is a straight forward concept. I have a task or project that is my responsibility, but depends on others to do some work. I email them, asking for information or for work to be done. Down the road, I will need to check up on that person and currently I depend on my brain to remember this (huge opportunity for failure!) or to catch it when I do a review of all my projects.

This lack of a more automated approach bit me in the butt recently, so I set out to improve my workflow. Here's what I found.

The options

This will not be an exhaustive list; I'm a Mac user, so the options are (almost) endless. Since I use OmniFocus and Mail.app, that's where I focused my research. Here are the various options I've considered:

  • OmniFocus mail drop
  • OmniFocus clippings via the Clip-o-tron 3000
  • Mail.app flags or smart folders
  • Reminders app
  • IFTTT
  • AppleScript

Sadly, although I consider this a fairly straight forward problem to solve, it proved more difficult than I had thought. Each potential solution is lacking at least one aspect of my ideal solution. Here's what I was hoping for:

  1. a reminder of some kind; whether it was a visual indicator in Mail.app, a due task in OmniFocus, or a reminder with a due date in Reminders app did not matter
  2. to initiate the full creation of this reminder at the time I was writing the email; having to switch applications or do more work to the email after sending was not my ideal solution
  3. bonus points would be awarded to a solution that included a link back to the original email

That is my criteria, not the tallest of orders. Here's what I found with each option.

Maildrop

This service from the OmniGroup was intended as an improvement over the clippings functionality in OmniFocus. Managed by the great OmniSync service, it works very well. Simply send any email to your assigned Maildrop email address and a new task is created in your OmniFocus inbox.

Positives

This is a very tidy option. It is easy to use; you can simply BCC your Maildrop address when creating the email. The result is a task that is created straight to your inbox in OmniFocus, so there's not necessarily any remaining work to be done with the task. Last, thanks to the OmniSync service, it’s a task that exists on all your devices.

But it's not a perfect solution.

Negatives

The issue with this option is all on the OmniFocus side. A task sitting in my inbox is not ideal. I would prefer that it be assigned to the correct project, as well as be assigned a context and a due date. The due date is especially important as I always want to follow up on the email within a set time frame. There will be manual work required to massage this task into its final form.

Last, the Maildrop feature only copies the content of the email and adds it as a note to the task, rather than linking back to the original email. Overall, it's a good option, but it only fully meets 1 of my criteria (number 1). I'll give it a half point for number 2 as well, since the task is created at the time of writing the email.

1.5 out of 3

OmniFocus Mail Clipping

This is another solid option. OmniFocus comes with a system wide service that allows you to select content in any application and send it to OmniFocus when you choose the Services sub-menu > OmniFocus: Send to Inbox. You can also create a keyboard shortcut to do the same thing in the OF preferences, as well choose whether the creation of the task opens the OmniFocus Quick Entry panel or is added to the Inbox immediately.

Positives

I like this option because it gives you the ability to add metadata to the task if you set it to open the Quick Entry panel first. I can then assign the project, context and due date if desired.

Negatives

The issue is that you cannot use this service while composing the message. This makes sense as it's not yet a message that is saved to the database and cannot be linked to in the task. And so, like many other options, more work is required after the message is sent.

Another issue here is that there is uncertainty of whether it will be supported down the road. OmniGroup has stated the issue with the OF Mail Rule and Clip-o-tron features:

Each time the OS has been updated recently, we have had to do a significant amount of work to keep basic functionality working, and in some cases have not been able to restore features. While Mail Drop’s functionality is currently basic, we plan on using the time saved to add more features so that it has the best of all of the previous solutions.

There is no guarantee that this option will be around in the future.

2 out of 3

Mail.app

The older I get, the more simple I want my solutions to be. And so I gave the idea of not involving OmniFocus at all a long look. As long as there was an quick easy way to find the necessary emails in Mail.app, that would probably suffice. And so I looked at various options for setting flags or moving emails into folders in Mail.app itself.

At first glance, I would have thought this would be the easiest solution, seeing as there was no involvement of a second application. This was not the case. The issue with only using Mail.app is that there is no way (that I've found) to initiate this process while creating the email. Here's what I found.

Positives

There's a lot of ways to organize a collection of emails in Mail. Folders, flags, and smart folders specifically. And since Mail is available on all devices, one should be able to initiate the addition of a new email to this collection from your iPad or iPhone. Reviewing the collection should also be possible.

Mail, as well as iCloud itself, also come with rules (filters for you Gmail users) that should make this process possible.

Negatives

The biggest I found is that it seems impossible to initiate the process from the compose window. You cannot flag an email while it’s being composed, nor can you specify that it goes to a folder. So the workflow would look like this:

  • create your email
  • navigate to the Sent message folder
  • move email to ideal folder

Not ideal at all.

Back to rules. Unfortunately, there are some issues with rules overall. The rules available in the iCloud service itself are very limited and do not provide enough options to make this possible. And the rules in Mail.app for OS X will only be run on that client, meaning emails created on the iPad or iPhone may not make it into your collection.

So overall, Mail.app itself only meets two of my three criteria; I'm left with a reminder in the form of a flagged email or collection of emails for review, which includes the entire email itself.

2 out of 3

Update The talented Michael Shechter reminds me that Keyboard Maestro could fix all of this. I've yet to fall into the KM wormhole, but it would surely do the job.

Reminders

Another option for Mac users is the Reminders app. I'm perfectly happy to have certain items in Reminders rather than OmniFocus. After all, I have items in my Calendar that need remembering as well, and I create them so that an alarm is used. Same goes for any item I log in Reminders.

Positives

I like Reminders for certain things as it's synced through iCloud and present on all devices. An alarm goes off on each when a Reminder is due.

Negatives

Unfortunately, Reminders is limited out of the box for this particular workflow. Adding a link to the email itself is not possible (that I'm aware of). You're left with a Reminder with a note at best, and the notes in a Reminders task is not all that usable.

It is possible to create the task via LaunchBar, but the end result is once again not exactly what I was hoping for.

1.5 out of 3

Update Here are a couple of good suggestions or tips:

  • the talented crew behind LaunchBar (my favourite OS X swiss army knife) pass on this AppleScript for creating a Reminder with a link to a selected email
  • @abstractpenquin sent over the tip that you can do the same thing as this AppleScript by simply dragging an email onto the Reminders icon

IFTTT

Scratch this option of the list. Email is a great option for the THAT coming out of IFTTT, but is less stellar when using it for the THIS (i.e. the trigger). It makes sense; IFTTT is a service more for web services and has no access to your desktop applications like OmniFocus.

But being such a great service, it was worth a look.

0 out of 3

Update A few folks mentioned other web services that meet this need. Some cost, some don't:

AppleScript

With OS X, the good news is that most anything is possible with AppleScript.

Uh oh, red flag. Once I hit this option, I realized how old I'm getting. I did not have much desire to step into the esoteric world of AppleScript to create my own solution, something I would have relished even 5 years ago.

The bad news is that AppleScript solutions come with a few barriers, opportunities for friction. First, if you don't work with it all the time, it takes a while to gain familiarity and just get something working.

Second, it's an opportunity for endless tinkering. I look back at some of the scripts I've worked on in the past, and I realize that somewhere along the line of machine upgrades, I stopped using those scripts. There are a couple that are still in use, but many have proven to simply be unneeded over time.

And last, this is one more thing to remember when it comes to upgrading to a new machine. The older I get, the less I want to do when I set up a new Mac. Less 3rd party applications, less preferences, less tinkering. What a boring old chap!

0 out of 3

AppleScript would do the job here, of that I am sure. But I had no desire to dive in and solve this issue with it.

In the end, I'm going with the OmniFocus mail clipping for now. The simple fact that it's gives me all the pertinent info without having to navigate to OmniFocus itself is enough for now. If support for it drops, then I'll repeat the exercise.

It was surprising that this is not a simple need that is easily met without some manual work. If you've got a solution I'm not aware of, I'd love to hear about it.