I didn’t intend for this to turn into a series, but as I spend an increasing amount of time bouncing across Outlook’s permutations on the Mac, on Windows and on smartphones, I’m increasingly unable to look at the various little things they got wrong and right across all of them and just want to know why they can’t present all of their right ideas in all of the apps at all times.

Let’s talk about Task Management. In this era of endless iOS apps that can quickly turn a verbally-delivered order to “take a shit on neighbor’s lawn every Tuesday at 7am” into a recurring task that syncs to every calendar without any extra input from me, Outlook’s approach to task management seems over-engineered at best. That said, I’ve been using it for my work tasks for a decade now, so I’m used to it.

What I _can’t_ get used to are the inexplicable differences in how each current version of Outlook handles tasking. It’s understood that everybody handles this kind of thing differently; your GTD advocates are going to have a different workflow than the guys who slam everything into their To-Do list undifferentiated, vs. people with entirely custom and personal workflows that aren’t documented anywhere but in their own heads. That’s fine. The task (ha), then, for the Outlook teams is to come up with something that is flexible enough to adjust to these various schemes.

In this, they have singularly failed through a death of a thousand cuts of indifferent design.

Let’s start with the worst of the bunch: motherfucking Outlook 2011 for OSX.

Fig. 1: Sure. Remind me at fucking midnight by default. That’s when we all check our to-do lists, right? Asshole.

Unlike regular Outlook, OL2011 offers no options for changing the monumentally retarded defaults tasks create to. More annoying? I’m creating this task at like 3pm on 4/10/2013. What in the FUCK good will a reminder THAT HAS ALREADY PASSED do me? Just careless, hostile, and stupid.

Fig. 2: Weekly by default! A default you can’t change? And I’m resetting the date, fucker!

Sigh. Alright, sure, maybe lots of people regularly create new weekly tasks. I don’t. I create daily shit, and monthly shit. But fine; maybe lots of folk create weekly shit. Heaven forbid there be a way to change the default recurrence, though! 

Fig. 3: Monthly resets to the 1st of the month, too.

Just…. ARRRRRRGGGGHHHH. On various, say, Android or iOS apps I’ve used, creating a recurring task is two taps and one sentence, the later either typed or spoken. For example, in Remember the Milk, it’s:

1. Click on the app
2. Click on Add Task
3. Say something like “Take out garbage every Tuesday at 6pm”
4. Click confirm or OK.

Fucking DONEZO. Why the shit does it take literally two dozen clicks to accomplish the same thing in OL2011?

Let’s see how this works in the flagship app, Outlook 2013 on Windows:

Fig. 3: Good thing it’s going to remind me before I even create the task.

Outlook 2013 at least lets one set a default reminder time. I have it set to 9am, as that’s when I typically do a task review for the whole upcoming day. What I don’t understand is why the fucking app doesn’t have some simple logic that says “if a task is being created AFTER 9am on a given day, set the default reminder to 9am the FOLLOWING day”. Because THAT IS THE ONLY BEHAVIOR THAT MAKES ANY FUCKING SENSE.

But no, any task created on a day after 9am requires one to manually reset the reminder to some time that will actually occur in the future rather than in the past, uselessly.

Fig. 4: Okay, not too bad.

For recurrence, OL2013 isn’t too bad. About the only thing I don’t like is, again, the default setting of “Weekly” for recurrence, which I will basically never choose, meaning I have to always manually set daily or monthly in this view. At least, unlike its Alabama stepbrother over in Mac Land, it starts the recurrence on the right date (ie, the day you’re creating the task or the due date you assigned it, instead of the 1st of the fuckin’ month for some reason).

Fig. 5: Monthly recurrence options actually make some kind of sense. Who let that happen?

Fig. 6: A little too simple

Windows Phone 8 doesn’t even offer any recurrence options, so fuck you if that’s a need. That said, it’s a pretty quick and efficient entry screen for simple tasks. I think the expectation is that you’ll do the bulk of your serious task management from a desktop somewhere and sync to your phone so your reminders work, but I really don’t understand why the can’t expose all of the advanced features of an Outlook/Exchange Task somewhere within the phone app. There’s really no technical reason they can’t.

So I’ve recently covered some of the infuriatingly dumber aspects of Outlook 2013 for Windows. I just had cause to install the latest Outlook/Office on my Mac as well. OSX is still rocking the 2011 Mac version of Microsoft’s venerable office suite. And it’s still Office for Windows’ retarded little brother.

I get that Microsoft has absolutely fuckall reasons to make Office for the Mac shine in any particular way. But geez alou, guys, at least let the Windows and OSX teams for Office talk to each other when they’re developing this shit.

For starters, there’s absolutely no calendar or task preview view in the main Outlook window at all:

Because I know you all care SO VERY MUCH about this burning hot-topic issue of our day…

So, check this shit out. This is the view of my schedule today from the full-blown Calendar view in Outlook 2013:

NOTE: Straight-up computer nerdery in the post so if you’re looking for funny poop stories, might want to just skip this one…

Like a lot of folks in the corporate world, I manage my workday via Microsoft Outlook. I live in that goddamned program, and have for well over a decade. Frankly, next to Windows itself, it’s the software I’ve probably used the most in my work life, and I’m sure a lot of other IT-ish folks have had the same experience.

So, when a new version comes out, it’s kind of a big deal. Every little change is scrutinized to hell and gone, because _somebody_ has been using that little buried feature religiously for 12 years now and cannot fucking believe Microsoft would change how it works!

The biggest recent example of this was the ribbon interface introduced in 2007. Blew people’s fucking _minds_, I tell you. Instead of the usual, old-fashioned Microsoft application “File – Edit – View…” menu, each with 1347 treed sub-options, there was now a wider ribbon with the most-used features (discovered after a ridiculous amount of observation testing on Microsoft’s part) prominently displayed upfront rather than buried in those menus. _I_ liked this change just fine, but believe me, even six years and three major releases since it first rolled out, people still bitch about this thing.

I generally like living with the absolute latest, greatest, beta-ist versions of software, so I’ve not been part of the big bitch group about changes to Outlook over the years.

Until now.

They fucked with one goddamned feature that probably seems really minor in the grand scheme of things, but seriously pisses me off every time I have to use it now. Lemme show you: