Although I’ve been working with Outlook for Mac for quite some time, there are lots of its features that I don’t use. Because all my mailboxes are hosted on Exchange, for example, I don’t ever use any of the IMAP functionality. In the same vein, because all my calendar and contact data live on an Exchange server, I haven’t had to fiddle with calendar sync for some time. I used to sync my calendar with various Palm devices back in the day using Entourage, Outlook’s predecessor, but it was always a painful and error-fraught process, and I was happy to move to an all-Exchange, all-Exchange ActiveSync environment.
A friend and fellow MVP mailed me with a Mac Outlook calendar sync question, and I didn’t have the faintest idea of what the right answer was. Accordingly, I dragged a third MVP into the fray: Mac/Windows interop expert William Smith. He came up with a workable solution, and as a bonus he wrote a detailed tutorial on how to set up calendar sync.
That got me to thinking about the differences in the Outlook brand between Mac and Windows. The functional differences have been discussed at length elsewhere (like on Steve Goodman’s excellent feature comparison table.) As Steve points out, the Mac version of Outlook feels much like Entourage. Although the user interface has been revamped, and is much more pleasant as a result, many of the same issues that plagued Entourage are still around. For example, I’m running Outlook with 3 Exchange accounts on a MacBook Pro with a 2GHz quad-core i7 and 8GB of RAM. This is a snappy machine… and yet Outlook still frequently takes leisurely breaks to show me the spinning rainbow when I click on messages, and it often gets confused about exactly which messages are, or are not, part of a given conversation.
That’s not to say it’s more or less buggy than Windows Outlook, which of course has its own set of issues. I use both on a daily basis. There are some things that Mac Outlook does better; for example, I love having a single unified inbox for all my accounts, and the integration of Outlook with other apps (like iPhoto) is better than it is, in general, with Windows counterparts. On the other hand, I find it much easier to work with the schedule and calendar views in Windows Outlook; I really like the Outlook Social Connector, and the “Ignore Conversation” and QuickSteps features are both super valuable for plowing through large volumes of mail.
I find Apple’s Mail.app weird and unsatisfying: it doesn’t include all the data I want (like calendar and contact info), and it doesn’t do many of the familiar things that I expect from the Outlook family. That would be OK if Mail provided a better experience than Outlook but in my judgement it doesn’t– I’d rather use Windows Outlook in a VM than the native mail app. In that light, rebranding the Mac client as Outlook has been a success: Outlook users on either platform will find familiar things to like (and perhaps to gripe about) on the other platform. Throw OWA into the mix and overall I’d say that Microsoft has done a good job of building consistency between the platforms.
There are still some major differences between platforms. For example, Outlook 2011 has little to no SharePoint integration; it lacks proper conversation threading (plus the aforementioned QuickSteps and “Ignore Conversation”); it doesn’t integrate properly with Exchange UM, there’s no Personal Archive access, and it doesn’t support VBA (although its AppleScript support is quite extensive, and much improved from Entourage).
Most users, of course, will use whatever version of Outlook happens to run on their preferred platform. That’s natural enough. Overall I’m quite satisfied with Outlook 2010 (well, except that for some reason 64-bit Office Communicator hates it). I’m hoping that the Mac Office team can address some of the performance and behavior issues in Outlook 2011 in the forthcoming Service Pack 2. I’m not as concerned about missing features, as those will come in time, and the Mac team has the benefit of seeing what features in Outlook 2010 are actually worth porting and which ones are not.
Paul's Down-Home Page 
Pingback: Getting used to Outlook 2011 for Mac | Thoughtsofanidlemind's Blog
Outlook for Mac is absolutely crap at handling large mailboxes too.
Apple’s philosophy was not to create one piece of bloatware to handle mail, calendar, and contacts, but to create 3 relatively lightweight applications – mail, address book, iCal – coupled together through open APIs that can be used by other applications easily. Many apps have taken advantage of this data openness.
But in Lion’s version of email, they removed features of Apple Mail like ToDo creation, breaking many people’s workflow of using email as the communication source driving most activity. Along with serious bugs like having to rebuild the indexes every time I want to find an older email, or attachment indicators that may/may not reflect emails with attachments, have forced me to alternatives.
Outlook has serious limitations as well (local folders, for instance), as does Thunderbird, Postbox, MailMate, Mulberry, Sparrow, etc. but at least it does a good job of task management, IF you use the add on Applescript code to overcome limitations in task creation from within the program.
Syncing, if for some reason it does not work the first time, is a very painful process to get working, if even doable.
Kirk, I understood Apple’s approach; I just don’t like it. For my workflow, calendar, contact, and e-mail processing are closely intertwined. People send me meeting invitations, requests for information, or other action items that I have to deal with, and it’s much more convenient to deal with them in a single application. (Not to mention that I find the skeuomorphs in iCal and Address Book to be crazy-making, but that’s a personal problem.)