Why desktop applications still have a place in a cloud-first world

Today, I ended up being the horrible warning instead of the good example: When my work Macbook helpfully informed me there were some upgrades to install and would I like to do that, I went ahead and blithely upgraded my operating system to El Capitan. After all, there's a lot to recommend it, and our own assessment ended:

[T]his is a solid update that shouldn't cause a whole lot of drama or consternation. It's free, compatible, not particularly surprising or jarring.

Unfortunately, there's one big black mark against it: The new operating system does not play nicely with Microsoft's Office products. We're not on Office 2016 here so I'm using Outlook 2011. Or rather, I'm not, thanks to the known issue that is currently being solved by the folks in Redmond.

And in further adventures of horrible-warning-not-good-example: I had not yet made the request to IT to send me an external hard drive so I could do my own Time Machine backups, so I couldn't just roll back the upgrade. (In my feeble defense: I make it a policy that the only digital assets I keep on a work computer are work-related email. I wasn't too bothered about losing that -- until today.)

The net result: I can no longer load my desktop email client, and thus have been working in the Outlook Web App all day. I'm not new to web-based email clients — I have been using Gmail for personal correspondence for a decade — but I rarely venture into Outlook's web-based properties because I'm so happy with the desktop client. Six hours into my new working conditions and I have a whole new appreciation for the challenges we're going to face if we all move into the mobile-first, cloud-first world as foretold.

Here were the most significant differences in my email management experiences:

— It's easier to click and open multiple messages at once in the desktop client. The software experience there "feels" slightly more tactile, if that makes sense. It's easier to drop, drag and resize emails within an email client.

—  It's like 2002 up in this Web app. It's understandable — why go with a pure Web app when there are cloud-based solutions like Office365 that basically do the same thing with remotely managing your email? But it's a little like time travel.

— I'm not going to lie: I like the calendar on the Outlook Web App a lot. I rely on the calendar function in Outlook to block off chunks of time for doing different editorial tasks, or for prodding me to prep for meetings, and the Web interface here is so easy and responsive compared to, say, Google Calendar. It's also streamlined compared to the desktop app, way easier to set up appointments, set up reminders and recurring incidences.

My only complaint is with how reminders work in Outlook Web App. In my desktop Outlook, each reminder is a little yellow pop-up that just hovers until I pay attention to it, and that's a great cue for transitioning from one task to another. In the web app, the reminder pops up in the Outlook window — which is great if you're in that Window at the time, not so great if you're not — and a gentle alarm plays. Be warned, however, that the alarm is difficult to hear if you have any other music or streaming media going at the same time. 

Hearing the weak plink-plink made me wonder: I use Slack to communicate with colleagues, and Slack's desktop notification system is superb — a little window pops up with a noise like the Dyson team just re-engineered the art of popping corn, and while that little window's not as persistent as the Outlook desktop client's, it still provides enough of a jolt to redirect my attention as needed. Why can't the Outlook for Web app follow suit? The point to a reminder should be that it's capable of effectively reminding you. 

— This entire experience has confirmed my belief that storing email on your hard drive is for suckers[*]. As an Inbox Zero type (well, more like Inbox 0.5 or so …), I usually try to read an email message once, then act on it, delete it or toss it in an Archive folder. If something else gets added to the conversation (i.e. someone replies), the pertinent message pops back into my inbox. If not, it waits in my Archive folder and if I need it, I find it via Outlook's generally excellent search tools.

Because of the way our IT department has set up and maintained company e-mail, users have a "permanent" Managed Folder specifically designed for any/all accounting, legal, HR and employment messages you have to keep for reference, but otherwise, don't expect the IT department to back up your local email folders. (I don't blame them: some users have gigabytes upon gigabytes of email they'll never read again.)

As a result, my "archive" is mostly unavailable to me right now: the desktop Outlook app is stuck in the spinning beach ball so I can't look at my folder, and since my archive was a local folder, it's not available in the web app. This isn't what I would call an emergency, but it does remind me to add a few to-dos to my maintenance list: make a quick pass through the archive to make sure there's no critical data I might need later, then find a way to back up this archive externally and have each new entry auto-archive someplace other than my hard drive. Since I'm dealing with a client on a computer (and not a cloud service), I can't just set up an If This Then That recipe, but I'm sure I'll find some small habit or tool that works.

The nice thing about shifting back and forth between clients is that I can use the things I like about one working experience to modify the other.

For example, our company's Outlook Web App comes with a Smart Folder for all your unread mail. I love this, mostly because I like having all the stuff I need to take care of in one place. And with a few clicks, I was able to create a Smart Folder for unread mail on my desktop app before it crashed again. 

We'll see if the folder sticks if/when everything's working on my machine again. If not, it's easy to recreate in an Outlook desktop client:

1. Go to the folder you want to manage. In this case, I clicked on the Inbox.

2. In the upper-right corner of the main Outlook window, click the search box. Then click the "Advanced" icon on the right side of the screen.

3. You'll see a filter pop up right above the inbox, and you can select "Read Status," then "Unread."

4. Click "Save" and name your folder. Boom! It appears in your list of Smart Folders.

Of course, in a really optimal user scenario, my Smart Folders and settings would be perfectly synchronized across both the cloud-based service and my desktop client. When I was tooling around on Office 2016 on the Surface tablet last week, that was one of the features brought up: the user experience you set up is the one that follows you from device to device.

I'll be glad when that day arrives, but I have to say that experiencing the differences in web-based and desktop-based apps has also made me appreciate the opportunity to test-drive ways of working that are outside the usual. Here's hoping that the portable and ubiquitous computing experience still prods me to find new ways to work well.

[*] Or for people who actually do back it up to their Time Machine regularly.