Back in the day, the people at Microsoft who were responsible for bringing the world Office for the Mac (the Macintosh Business Unit) fancied themselves as outcasts on the company's sprawling Redmond Campus; Outcasts with something to prove. When a new version was on the way, they'd parade into my office talking smack as though they just left the Windows version of Office lying on the canvas after a knock-out blow. They'd proceed to demonstrate how the Mac's underpinnings enabled functionality that the Windows Office guys could only dream of. So, why, after the Mac has come so far, does MS-Entourage suck so bad.Those of you who use Gmail will understand my pain once you realize how you've been spoiled.

It was a few months ago that, for reasons I won't bore you with, I had to finally ditch Gmail (the Google Apps version) for Entourage; Microsoft's equivalent of Outlook, but for the Mac (InformationWeek's parent TechWeb is an Exchange shop). As I've come to learn though, it is no Outlook equivalent and, if anything it's probably the Windows guys who should be talking smack (but not too much of it since Outlook still pales when compared to Gmail which, if you ask me, is now the new standard-bearer).

Whether you use Gmail or not, you should appreciate one of its years-old innovations -- one that for many (including me) takes some getting used to. It's called "the conversation." When Gmail's "conversations" come up in discussion, some email know-it-alls will say "Oh that. That's nothing. Google is just trying to be cool by giving a new name to threads."

Not quite.

Threading, as I remember it, is the ability of an email client or some forum software to accurately sort and sometimes nest entries in a way that makes it easy to chronologically follow a single discussion and any divergent forks it takes. Most email clients can fake threading by doing a primary sort on email subject. If you're lucky, they'll do a secondary sort on date. The latest version of Outlook has a feature that approximates conversations that sorely misses out on the holistic thinking that Google put into Gmail. It's as if Microsoft looked at what Gmail did, stole the idea, but didn't think to steal all of it. Maybe that's because they didn't understand it.

Gmail automagically spots related emails, bundles them together into "conversations," and then sorts those conversations in reverse chronological order based on the time of the most recent activity in each conversation (Outlook's "Conversation View" does this as well). In browsing through a Gmail inbox (essentially, a list of conversations), there could be a conversation that's 10 entries down from the top. But the second something new arrives into your inbox that belongs to that conversation (and Gmail is 99 percent accurate at figuring this out), the entire conversation shoots to the top of the list (Outlook also does this too). Clicking on it reveals, in their entirety, only those messages that you haven't read. The rest of the bundle (including the ones you've sent and the ones you've already read) are there and can be expanded on command, but are collapsed to display just a one-line header.

Outlook doesn't include email you've sent in its conversations. To find them, you must look for the text in the bottom of one of the replies (hopefully, the senders included it), or dig through the Outlook folder that holds sent mail. For those of you wanting a more conversational view to your Outlook inboxes now, you might want to give KM Sciences EasyLinkMail a tryout (there's a free version for personal use).

According to a Microsoft spokesperson whom I interviewed prior to publishing this piece, Outlook 2010 will include sent mail in its conversations. Smart move, but what took them so long? Unfortunately for Microsoft, while Outlook is catching up to the way Gmail does things, Google is revolutionizing the conversation with Google Wave. Google Wave acknowledges that there's usually more to the digital conversation than just email by incorporating everything else that's relevant (instant messages, photos, maps, etc.). If you've ever realized that a wiki would have been the better choice to host an email conversation that ran amuck and then tried using a wiki to actually host the next conversation, Google Wave is to me what wikis should (and will) be.

But back to the conversation and what Gmail and Outlook currently do. For what it's worth, Entourage 2008 does none of this which is one reason my productivity has taken 2 steps backwards now that I must use it.

It wasn't until I stepped backwards to MS-Entourage that I realized how much more productive an email solution can be when it does a good job managing conversations.

Just a few months into my new job now (and into Entourage as well), I'm finding that I have to keep track of dozens of projects and initiatives that I'm either driving, assisting with, or keeping an eye on. Between those projects and the regular flood of inbound email, my inbox is like a tidal wave and my productivity is very much tied to my ability to keep it under control.

To do this in Gmail is relatively simple. First, Gmail doesn't have folders. It has labels. They're essentially keywords and much like the folksonomy and tagging systems behind many of today's social networks (Flickr, YouTube, Delicious, etc.), you can assign multiple labels to a conversation.

For example, let's say I start a conversation to seek travel approval for Interop in NYC November (click here if you want to get into the Expo part of Interop for free). My boss might reply with a question and when he does, I can assign two labels -- "Travel" and "Interop" -- to the conversation (which, at this point, includes my original email and his reply). When I reply to his question, that reply is automatically joined to the conversation which is still sitting in my inbox.

The conversation now includes three messages. Since the ball is now in his court and I think of my inbox as my To Do list, I really don't want the conversation clogging up my inbox. So, I tell Gmail to archive it. When new emails arrive in Gmail, the conversations to which they're assigned have the label "Inbox" automatically applied to them. When you tell Gmail to archive a conversation, you're essentially telling it to remove the "Inbox" label from the conversation (which causes it to disappear from the Inbox). But, in the case of our example, the entire conversation is still accessible by looking under the labels "Travel" and "Interop" (without wasting storage with duplicate copies).

Here's where Gmail's conversational simplicity really kicks in. Let's say my boss replies with his final answer (hopefully, it's "yes"). As I just said, "When new emails arrive in Gmail, the conversations to which they're assigned have the label "Inbox" automatically applied to them." It doesn't matter if you've previously archived the conversation. When a new message belonging to it arrives, Gmail automatically unarchives the entire conversation and puts it at the top of your inbox.

The net effect -- a productivity boon if you ask me -- is that you can move entire conversations out of the way until someone else acts on them and when they do, those conversations spring back into your inbox which for many is essentially your To Do list. Gmail's behavior is identical if, instead of archiving the conversation, you deleted it. You may have thought the conversation was over. But maybe someone else didn't. No problem. If several days or weeks has passed since you last looked at the conversation and someone else responds to it, the entire trail of messages comes right back to the top of your inbox where you can refresh your memory. No digging through folders, deleted, or sent mail.

Finally, when a conversation with one or more labels already applied to it springs back into your inbox and you finish dealing with it, all you need to do is click "archive" button to tuck it away again.

It's sort of like the way your dentist's office works. When you show up for teeth cleaning, they take out your folder containing all of your history, make some notations, and put it back away.

If you're like me (and I think many people are in this respect), your email inbox is one of your main To Do lists (as I said earlier) and with any To Do list, the objective is to knock items off it. For email inboxes, this means deleting or filing emails into folders. But chipping away at a flooded inbox, which we are all compelled to do, is very difficult when all the emails relating to one To Do item or project are chronologically scattered. Sorting an inbox by subject in an attempt to bunch them together (conversation style) is a stop gap which is why I was hoping that Entourage had some other way of keeping me on track.

Entourage will keep a To Do list for me. But it's too simplistic. There's no way to connect a bunch of emails with a single To Do item (if Entourage worked more like Gmail, then maybe I'd be connecting conversations instead of individual emails with To Do items). With Entourage, you can turn an email into a To Do item. Unfortuantely, if you delete the original email from your inbox, it disappears from your To Do list as well. In other words, if you think adding an email to your Entourage To Do list means you can clear it out of your Inbox, think again (sigh).

Entourage has something called a Project Center. But 2 or 3 screens into the wizard for starting a new project, and you start to realize that whipping an entire Entourage Project at a relatively small initiative like fixing a few Web pages (something that still requires a modicum of tracking from beginning to end) is serious overkill.

The solution?

Folders. Friggin' folders! The same kind of email folders that we've been using for 20 years to help keep us organized.

Now, my Entourage folder hierarchy is rapidly morphing into my To Do list. But even that's problematic because Entourage offers me no visual way to flag certain folders as being To Do list items that need to be tracked. Yes, there are a bunch of clichés that apply here: When you have a nail, everything looks like a hammer or perhaps I'm trying to fit a square peg into a round hole.

But my reasons for hating Entourage don't stop here. Can you imagine, for example, a modern email client that can't hyperlink text to a Web destination when composing email? Or how about one that can't forward HTML mail at all? Yeah, that's right. Entourage -- and I'm talking Entourage 2008 -- can't do either. Believe it or not, if I want to forward an HTML newsletter to someone in a way that the forwarded message preserves the formatting of the original (as opposed to forwarding the HTML source code from the original), I need to forward the message with my BlackBerry instead. A Microsoft-spokesperson was quick to point out to me that I could always forward an HTML email to someone else as as an attachment and the formatting would stay intact. But it's not the same (which is why almost nobody ever forwards an email they received as an attachment).

The final insult to my injuries? Although I still have Microsoft looking into the issue, Entourage does something that Outlook doesn't do in BlackBerry environments where a BlackBerry Enterprise Server (BES) is managing synchronization between an Exchange Server and a fleet of BlackBerries. According to Research in Motion (yes, the maker of the BlackBerry is pointing fingers), Entourage wipes out the reference IDs that the BES applies to every message in order to guarantee proper Exchange Server to BlackBerry synchronization. The result? When I delete emails through Entourage on my Mac, those emails are never deleted from the BlackBerry. Outlook on the other hand leaves this reference ID alone. Here at TechWeb, all of our Windows users who have BlackBerries are perfectly in synch. But those of us with Macs and BlackBerries are chopped liver.

I could keep going but I think you get the point. Whereas Microsoft's Mac Office team used to be able to show the Windows Office people how it's done, the reverse appears to be true today. For a product claiming to be born out of 2008, MS-Entourage is a suprisingly lame and highly unWeb-like email client given modern standards (even after the announcing Entourage 2008 Web Services Edition). At this point one can only hope that when Outlook for Mac comes out (Entourage was officially scrubbed by Microsoft in August), that Microsoft will get it right. According to a Microsoft spokesperson, "the date for Outlook for Mac is the US retail holiday season for 2010." Maybe, by then, Google Wave will be able to connect to an Exchange Server or Microsoft will get hip to the conversation.

David Berlind is the chief content officer of TechWeb and editor-in-chief of TechWeb.com. David likes to write about emerging tech, new and social media, mobile tech, and things that go wrong and welcomes comments, both for and against anything he writes. He can be reached at [email protected] and you also can find him on Twitter and other social networks (see the list below). David doesn't own any tech stocks. But, if he did, he'd probably buy some Salesforce.com and Amazon, given his belief in the principles of cloud computing and his hope that the stock market can't get much worse. Also, if you're an out-of-work IT professional or someone involved in the business of compliance, he wants to hear from you.

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