Friday, July 1, 2016

Gmail vs Outlook

I go back quite a ways with email. I first started using email when I was an undergraduate, studying physics. Not a lot of people did email back then (early 1990s) but it was handy to stay connected with my brother who was studying computer science some 1,300 miles away from me.

Back then, I used whatever email client we had installed on the Sun Unix workstations in our computer lab. I think I started with standard Unix mail, then upgraded to pine.

After I graduated, I used email through various local service providers, or through work. I ran Linux at home by then, and I recall using a variety of local email clients, upgrading to whichever had more attractive features. Eventually, I settled on Netscape's Email program, which later became Mozilla and Firefox, then branched off to the standalone email client Thunderbird.

When I adopted GNOME as my default Linux desktop at home, I continued with Thunderbird for a while, then tried a few other GTK-enabled email programs before committing to GNOME's Evolution program. I even used Evolution at work, since I was fortunate to run Linux on my desktop at work.

Fast-forward to 2004, and Google released Gmail. While there had been a few "webmail" systems before that, Gmail was the first that really made "webmail" seem like you were using a desktop email client. Gmail was fast, easy, and great-looking. I switched my at-home email to Gmail around 2005 or 2006.

I worked for a university at the time, and we quickly realized our in-house email system couldn't compete with Gmail. We could only offer 25MB for each user's email storage, but Gmail offered 1GB. In 2005, Gmail expanded email storage to 2GB. That made us sit up and take notice of Gmail. As did others in higher ed. Email had truly become a commodity; we could no longer offer added value to our students, faculty, and staff through email systems we ran ourselves.

So it was in 2007 (I think ) that we launched a pilot initiative to migrate university email to Gmail. I wasn't in the pilot group, but I was first in line when we started moving general university accounts to Gmail. If I'm remembering my timeline correctly, I think I've been using Gmail at work since 2008.

And a few years after that, I seriously adopted my mobile phone (Android) and tablet (iPhone) as platforms for my email. Like probably many of you, I am equally likely to reply to email via my phone or laptop.

I've changed jobs, and we use Outlook at work. I use both the "OWA" web client and the desktop Outlook client. So there's another email client to add to my list.

Doing the math, I've been using email for over twenty-five years. Over that time, I've switched from one email system to another, using whatever had the best features, whatever was most interesting. I mention this by way of highlighting that I'm not a "who moved my cheese"-type of person. I am pretty fluid with technology. I use the technology or application that best suits my needs.

So it is with this perspective that I say this: I don't like Outlook for email. It just feels like a step backwards in how email clients should work in 2016.

Here's one example: tags.

In Gmail, you can tag email conversations. You're reading an email conversation, and you'd like to quickly refer back to it again later. You can tag the conversation with a colored label, also called a "tag," like audit or governance or security, whatever label and color appropriately represents the conversation.

In a way, you can think of tags as a kind of "folder" assignment. And the neat thing about these tags is they stick to the conversation whether or not the email conversation is in the inbox. This presents a very flexible workflow. You can move an email conversation to a folder, which assigns it a tag. If someone replies to the conversation, the whole conversation is resurrected to the inbox with the tag attached. When you're done reading the response, you click the Archive button and the conversation goes back into the folder.

You can assign multiple tags to a single conversation. A discussion about a security item in an audit might have both auditsecurity tags assigned, so you can later find the email conversation in both "audit" and "security" folders.

I really like that feature. I think Thunderbird added some kind of tags support, too, but this would have been after I stopped using Thunderbird.

But in Outlook? Tags don't exist. You can use "Categories" and assign a kind of label to something, but it's nothing like tags. So now it feels like with Outlook, I'm back in the Dark Ages of email. I can move a conversation to a folder—only one folder—but if someone replies to the conversation, the whole conversation reappears back in my inbox. And there's nothing to tell me where I'd put it previously.

At work I have two dozen email folders in Outlook. Most are project folders. And right now, I'm directing a work effort that spans two different projects. We have an active email thread going about the project work, and occasionally someone starts up a new discussion to talk about a different aspect of the work effort.

Even though the conversation relates to two different projects, I have to pick one folder when I archive the conversation. That's weird to me now. That would have been normal "back in the day," but in 2016 that seems primitive. When someone replies to the email discussion, the entire conversation appears back in my inbox, and I have to figure out which of the two projects to save it to. I can't store one email thread in two locations. Where did I store the last conversation? Did I put it in "ProjectA" or "ProjectB"?

This makes searches more difficult. If I need to uncover an earlier conversation about the project (and I do) I have to search across several folders. I can't just go to either of the tags and look there.

There are a few other examples, but if I'm honest with myself, tags are really the thing I miss. Yes, a few other things bug me because they are different from other email systems, but that's the nature of running a different email client.

Maybe tags exist in Outlook, and I don't know how to turn on that feature. Someone please tell me. Or maybe tags are a unique defining feature of Gmail and I shouldn't expect to find them elsewhere. I can just tell you that tags made my workflow so much easier, and I don't have them in Outlook.
images: Wikimedia (Outlook icon: public domain) (Gmail icon: public domain)


  1. Same issue with my company too; after they migrated to OWA. I just redirect all mails to gmails! solved.

  2. Yup, nothing like Gmail/Google-Inbox; best-of-breed indeed.

  3. """Or maybe tags are a unique defining feature of Gmail and I shouldn't expect to find them elsewhere."""

    GMail tags *are* unique to GMail. But the standard IMAP4 protocol has supported a very similar feature since the 1990s. The IMAP4 specification confusingly calls the feature user-defined "keywords", but an IMAP keyword is really just a tag or a label; the IMAP specification's choice of terminology is unfortunate. If you pair IMAP keywords with the IMAP extension for multimailbox search [2], then that's sufficient to recreate the GMail workflow you describe.

    To be honest, though, I'm unaware of any email client that exposes both IMAP features to the user. Thunderbird exposes IMAP keywords (in a limited way, though), but doesn't provide multimailbox search. Ditto with mutt [3] (through an out-of-tree patch set). And FastMail [4] provides a very nice multimailbox search (I prefer it over GMail's), but no IMAP keywords.

    It's really frustrating that all email clients are each missing at least one major feature or have some serious deficiency, despite that we all use email everyday and IMAP has been the standard protocol for for decades.


  4. Thanks for the links, Chadversary! I didn't know about IMAP's keywords feature. That does sound a lot like Gmail's tags. I wonder why more email clients don't take advantage of it?

    A few years ago, I also discovered Sup, a text-mode email client that is very Gmail-like. If I still used email at the console, I would likely switch to Sup.

    But for now, I'd be happy to find a way to get Outlook to behave more like Gmail, especially tags/labels. I miss those.