Now, I think OL2K7 was a significant improvement over 2K3 but that’s not really saying much. I am, however, stunned to see (with the Office 2010 technical preview released this week) that Outlook 2010 has not made the leaps and bounds it truly needs to make in order to remain both relevant and competitive.

What has improved?

Well, the Outlook interface is finally in sync with the rest of the Office platform. Meaning, of course, that the infamous “Ribbon” is now all throughout the application instead of just within new message windows as it was in 2K7. (I read an article on BetaNews.com by one Carmi Levy stating that they wish Microsoft would do away with the Ribbon altogether. I wholeheartedly disagree and think that the Ribbon is a great way – especially for touch displays now and in the future – to quickly find what you’re looking for.) In addition, the overall appearance is very bright and refreshing. There are still some theme options in place but the default is great in my humble opinion.

Conversation view has, at long last, been added to Outlook. It’s still a tiny bit quirky but it acts pretty much the way you’d expect it to. If a message comes in that’s a reply to an existing message, any related messages to that particular subject line are displayed with it.

The startup process, while unfortunately lengthy (see next section), is a bit less annoying. The improvement comes with the new animated launch screen – it stays up until Outlook is fully ready to be used. Previous versions of Outlook were a bit of a tease in that the window would launch but you’d be waiting about 5 seconds for each element of the application to appear: 5 seconds for add-in toolbar A, another 5 seconds for add-in toolbar B, 5 seconds for the To-Do bar to appear, etc. I find I have more patience with the animated splash screen… and patience is a rare commodity these days.

Message clean-up is ever-so-slightly enhanced. You’ll notice in the first screenshot above that Microsoft has finally embraced the concept of “tagging” in Outlook but only barely. In the screenshot above, there’s an area of the first Ribbon section called “Tags.” However, all that area presents is a drop-down allowing you to use the previously-existing “Categories” functionality of Outlook to file a message to categories of your choice. This is exactly what the previously-reviewed Outlook add-in Taglocity does but Taglocity still does it alot better. The aforementioned add-in allows you to jump to a tagging toolbar, begin typing tag/category names (it finds as you type), hit enter and your message is tagged. Hit the escape key and you’re back to your message. The process with the now-slightly-more-visible button is still very much mouse-driven and just doesn’t make sense with frequent Outlook power users.

In addition, there’s a new “Clean-Up” drop-down button in that same section of the Ribbon that allows you to quickly get rid of insignificant, older messages in either the conversation that’s highlighted or all of the conversations currently in your inbox… or even all of your subfolders.

Quick Steps represent a fantastic new feature in Outlook 2010. As you might guess from the name, Quick Steps allow you to create shortcuts for various actions like forwarding to a specific person or department or automatically reply to a selected message and delete the original – all in one action. You can even assign a keyboard shortcut to your quick step. A number of Quick Steps are included by default but it’s insanely-easy to create your own.

Forwarding a message as an attachment now has a designated button in the primary tab of the ribbon. Hit the button and, as you’d expect, a new email comes up with the selected message already as an attachment. This also works with multiple messages… very cool.

What hasn’t improved?

Filing and organizing messages. To my knowledge, there’s still no easy and fast, find-as-you-type way to move a message to a specific folder without a 3rd-party Outlook add-in like SimplyFile. We reviewed TechHit’s SimplyFile (from the makers of QuickJump and TWinbox) way back when and it offers a very Gmail-esque way of moving messages using the keyboard while remaining in your inbox. It’s a beautiful process and while I’d hate for TechHit to lose a revenue stream (still plenty of other great features in SimplyFile), this is functionality that should already be in Outlook… especially when this sucker is released in the year two-thousand and ten. C’mon, Microsoft. Seriously. Gmail also has this with the new “Move To” (keyboard shortcut “V”) and “Label” (keyboard shortcut “L”) features.

It’s most likely due to the fact that it’s a technical preview but Outlook’s performance over that of Outlook 2K7 w/SP2 has TANKED. The migration process was a lengthy 10-20 minute process… and I’m on a dual-core with 4gb of RAM so resources aren’t scarce by any means. Any subsequent, routine launches also take more time than 2007 required.

The reply process still inserts your own email address when clicking reply on an email you sent. Technically, that makes sense since you’re replying to an email that you sent. Intuitively, it makes absolutely no sense at all. In 99.9% of all cases, I’m just going to want to follow-up with someone on an email I already sent them – I’m not following up with myself. Gmail does this correctly. There, you hit reply on an email you sent and the email address of the original intended recipient is automatically inserted in the “to” field.

In addition to bare-minimal support of “tagging,” Outlook has still yet to present us with an option to add notes to an email. Sure, with the 2010 Office suite, OneNote will be included and it’s pretty easy to send a message to OneNote from within Outlook. However, that involves and entirely separate program and is entirely unintuitive… as well as a waste of time. C’mon, Microsoft… you already have a “notes” section inside Outlook… just find a way to marry messaging and notes and give us the option to add a freakin’ note to a message without having to modify the message itself.

What’s regressed?

3rd-party add-ins have taken a significant hit in Outlook 2010 as a result of the ribbon. The one solitary problem with the Ribbon is that it takes the place of loads and loads of various toolbars that previous versions of Microsoft Office required. Instead, each toolbar is replaced with a “tab” on the ribbon. The problem here is that many Outlook add-ins require visibility in order to maintain full functionality and to be as effective as possible. For instance, with the SimplyFile add-in within Outlook 2007, there remained a toolbar at the bottom of the window with a drop-down of folders and a SimplyFile button (among other items.) With a highlighted message, I could hit that button and my message would automatically be filed to the correct location. Now, there’s an extra click in the process as I have to navigate to the add-ins tab on the ribbon to get the button… which really disrupts the natural flow of that process.

Overall

Sure, the list of items under the “What has improved” section of this post is longer (mostly minor items) than the other sections but I’ve been genuinely let down by this version – as it stands now in a Technical Preview. I have absolutely no idea how Outlook will remain relevant over the next few years as Gmail & Google Apps both continue to grow exponentially while we wait for Office 15. Plus, Google has Google Wave coming down the pipeline which, according to pretty much everyone (I seriously have yet to read a non-Microsoft, negative opinion on Google Wave), will be the end-all, be-all of productivity apps. Good luck, Microsoft. You’re gonna need it.

What about you, readers? Have you had a chance to play around with Outlook 2010? What are your thoughts? Let us know in the comments.

If you’re unfamiliar with Taglocity, the software essentially allows you to add "tags" to your E-mails, tasks and calendar items from within Microsoft’s antiquated Outlook product.  To do this, the software takes advantage of Outlook’s "categories" feature and, for each new "tag" you create with Taglocity, a "category" of the same name will be created behind-the-scenes and added to your Outlook personal files folder (.PST) 

I’m guessing the object of enhancing already existing Outlook functionality is to provide you with the option of retaining the methods of organization you’ve established with Taglocity if you no longer wish to use the product anymore.  It makes sense to me…data portability always makes sense to me.

(What never did make sense to me was why Microsoft never made "categories" a more prevalent feature in Outlook to begin with.  It really is a great way to add organization to Outlook.  Regardless, Taglocity helps to enhance and bring focus to this semi-powerful existing feature.)

Whether you’re browsing your inbox or composing a new E-mail/task/appointment, you’re presented with intuitive options via the Taglocity toolbar for adding tags to help you easily find E-mails at a later date:

The average Fans of Tech reader already realizes the benefit of tags over folders but there might be a few of you out there still asking  yourself: "why tags?"  Here’s the answer: after you’re finished reading an E-mail, one would normally file that message in a single folder in a vein attempt to keep your inbox "organized."  The problem is that, after a while, you’ll most likely have multiple folders that pretty much serve a similar purpose.  That leaves you with multiple places to search in order to find the item for which you’re looking.  With tags (or "labels" if you’re a Gmail user), you can assign multiple keywords to the item in question thus improving the likelihood that you’ll find this item whenever you go looking for it.  And, since Taglocity is essentially a plug-in for Outlook, you can do BOTH!  File and tag!

The free product even takes tagging a step further by incorporating two very useful features: Bundles and AutoSuggest.  The latter, as you might guess, makes the tagging process even faster by "suggesting" similar tag matches as you type…start typing a few characters and if the tag suggestion is the tag you want to apply, just hit "enter."  The other feature, Bundles, allows you to assign many tags at once by assigning a bundle tag name.  You might equate this feature to "Distribution Groups" in Outlook where you can send an E-mail to ONE distribution group in Outlook and that message is automatically sent to the many different members you’ve assigned to that DG. 

Taglocity & the Entperise

From what I can tell, Terazen will monetize Taglocity by selling enterprise versions of the product which makes perfect sense to me as it would fit very well into the enterprise atmosphere.  One reason I say that has to do with yet another brilliant feature of the product: "groups."  Here’s what the site has to say about groups:

"Groups are a way of sharing tags and email messages. You can publish common information to our Taglocity groups (with Tags on the message, of course!) which then means other people in the group will be able to search and see. Think of how many CC: email chains you can get rid of!"

I have first-hand experience with the aforementioned E-mail chain problem and I can genuinely see a need for this product in an enterprise setting…especially for non-profits. (*Shudder* So much E-mail.  *Shudder*)

Searching

Now, let’s say you’ve had Taglocity installed for a few months and you want to go find one of the E-mails you’ve tagged.  Use the toolbar (see above) and enter your search query on the far-right.  You’ll be taken to the Taglocity search window (and quickly, I might add.)

You’re presented with your results and a quick way to modify those results using the tag cloud at the bottom and side of the window. I don’t necessarily anticipate using this feature more than the built-in search of Outlook 2007 (as I can typically remember the exact contents of the item I’m looking for) but, for generic searches, this could still prove to be pretty handy.

Of course, all these settings (tags, searching, etc.) can be tweaked using the utility’s configuration window:

Overall, I think the product fills a void (and then some) that Microsoft should have filled a long time ago.  A long time ago.  Install this (in addition to that other useful Outlook tool, xobni) and you’ll actually find yourself becoming…gasp…productive.

Despite my rambling, there are a few areas of Taglocity I didn’t even cover so head on over to their site and check out the product…and then sign up for an account.  This new release is a dramatic improvement over v1.1 and should actually have enough weight behind it to take it into the mainstream.