Entourage: A journey to becoming an Office application

It’s not often that a new Office application is born. That’s especially true on the Mac. This is a story about Entourage, a product that was called Alpaca for the longest time.

I joined Microsoft in January 1999. At the time, the team I joined was publicly working on Outlook Express 4, 5 and secretly building a Personal Information Manager for Mac Office. When we started the project we shared very little to no Office code. Over a 2 year period we morphed into a product that shipped in the Office box. The first thing I got to do when I joined was basically run the Outlook Express 5 project. I was 22 years old. Can you imagine showing up at a Company and being given responsibility like this? It was just unbelievably exciting (coincidentally, my soon to be roommate, Jimmy Grewal, was given similar responsibility on Internet Explorer). Two 22 year old punks who never shipped anything in their lives shipping what became the most popular browser and mail client on the Macintosh. I remember going over to Apple for meetings some times and they would be like, are you kidding? Where are your parents?

Outlook Express was actually a new name for a product that was called Internet Mail & News. No offense to the people who worked on this, but compared to the competition, IMN was a crappy mail product. Microsoft hired a lot of people from Claris and Apple who helped take the IMN code and build OE. Development and features were added at warp speed. However, the group building Outlook Express and IE were folded into the MacBU about 6 months before I joined. At that point OE was viewed as a product that would grow to become the PIM for Mac Office. Since Windows Office had Outlook, we needed something similar on the Mac. At the time there wasn’t a viable product that offered all the functionality of Outlook in a single application. So when I joined we were all really working on Entourage 2001. At the time, we managed to convince upper management (mainly Ben Waldman, our General Manager and Kevin Browne, our Lead Product Planner and soon to be General Manager) that we needed to do another release of OE to stay competitive and compliment IE 5. It really wasn’t until MacBU took on our group that OE was given any attention. Before that, IE was the sexy product and the one that got most of the attention and resources. Office changed all that.

I remember sitting in a room with a bunch of people and trying to convince Ben Waldman that OE 5 was a good idea (this ultimately meant sucking resources away from Office, the big money maker, for a free product). Somehow we were successful, but I remember being scared to death. So the OE 5 project was born and I got to pick the code name [update: corrected mistake per this post from my first manager]. We called it Newman, after the mail delivery man on Seinfeld. He was famous for saying “When you deliver the mail, you control Information”. The code name for Entourage was harder to select. We had some bad ones, but finally, Jud Spencer settled on Alpaca. If you have ever flown Alaska Airlines you’ll note the Alpaca ads that they have in there. “Alpacas, the huggable investment”. If you watch CNN late at night you’ll also see the commercials. Alpaca would remain the code name and the actual product name till months before RTM… finding a name that no one else was using was next to impossible (remember, dotCom days).

Anyway, OE & Entourage were native Mac applications (no ported code, and no Office code), and we didn’t really follow the methodologies that the rest of Office followed. Entourage, OE and IE were developed in North San Jose, while the rest of MacBU was in Redmond (PowerPoint was in Cupertino). None of us had any exposure to the long established processes of the rest of the business unit, and we all got a crash course.

In addition to being a kick ass mail product we also had to build a calendar, contacts, tasks and notes interface, support internet RFCs like iCal, vCard, and create a data store for all this data. We also had to interoperate with numerous different products (wire protocols, authentication, meeting requests, e-mail formatting etc). On top of that we had to have some features that leveraged the fact that we were an Office suite, and of course we had to “Look and Feel” like an Office application.

That final sentence was the source of so much contention, especially for me. Remember, we were a native Macintosh application. Office still had a lot of legacy code, non native Mac UI, and other things. So “Look and Feel” like an Office application sometimes meant look and feel less like a Macintosh application. Let me give you some examples.


In Outlook Express 5 we wanted to have a fresh and pretty look and feel. I went out and hired the Icon Factory to design about 120 icons from scratch. These were 256 color icons, a big deal in that day. The Icon Factory OE 5 page states: “The goal of the project was to give the entire OE icon suite a cleaner, more "mac-like" look and feel.” By comparison Mac Office and Win Office were limited to 16 colors. And they were the most saturated and ugly 16 colors on the planet. We were “told” that we would have to take our beautiful 256 color icons and make them only 16 colors. Ack! That was battle number one. I tried to convince Office to move their toolbars to 256 colors but it was deemed too expensive. Ack! I panicked. In the end we managed to change the 16 colors to a more muted and pleasant 16 colors, redid most of the Mac Office icons in these new 16 colors and updated the Entourage icons to use the same palate but we could keep our 256 colors.


Mac program had their preferences menu in the Edit menu. Office programs have their Preferences menu in the Tools menu. Guess where OE and Entourage had theirs? One of my favorite accomplishments was getting all the rest of Office to do things like a proper Mac application ;-).


Outlook Express and Entourage had docked toolbars while Word, Excel, PowerPoint had global toolbars. Our toolbars were contextual (they changed depending on where you were in the application) where the others were always global and static. We were told to change our toolbar to be more like Office. Well, that was another long battle that we thankfully compromised on by promising to at least make our toolbars look like Office. However, since we didn’t’ share any code with Office we had to write our own implementation. For Office X we ended up throwing this all away when our new Toolbar implementation for Office (to support 32 bit icons) was done.

Spell Checking, Autocorrect etc.

There are many features that are just expected of an Office application. Two of those are spell checking and autocorrect. These were enormously complex things to do. Our application was built on a Macintosh development framework called PowerPlant. Meanwhile Office had its own custom framework and a lot of work was done on both sides to factor our applications such that we could use Office components without the massive overhead of supporting the office framework in its entirety. This was really hard stuff to get right, but when we did it was just so cool to have the red squiggly. We never did grammar checking.

Shared Features

There were lots of ideas for shared features. Some of them never saw the light of day, and others took a very long time to get right. One of these was the Word/Entourage integration. The idea being that you can access the Entourage address book from Word for composing letters, inserting contacts and customizing Word templates based on your personal information (we created the notion of a “Me” contact in Entourage, that allowed us to do some cool things like auto fill personal information in Word templates, or get driving directions to and from people’s work and home addresses via Expedia). This work required a lot of collaboration between to teams that sat many miles away and didn’t always see eye to eye. In the end the feature worked, and worked well, but it was another one of those amazing learning experiences. There were many more of these shared features. They all required extensive work on both ends. We were really building the bridges between Entourage and the rest of Office that would then be used for many years to deliver much more advanced and user centric features that really leverage the entire Office suite (Project Center in Office 2004 is a good example).

Anyway, our team learned a lot in becoming not just an Office app, but in becoming a team and an integral part of the success of the suite. For the next project, Office X, Entourage was the first application to get Carbonized. Because we didn’t share much code with Office, and because we were the youngest code base it only took a few months to get us running on X. It took many more months to make our Look and Feel stunning on OS X and the good news was that the rest of Office really had to purge a lot of the old crust to get to X. Since X was all about a new Look and Feel called Aqua, this was a boon for us, and it meant that all of Office got 32 bit icons. A far cry from the 256 colors in 2001! We also got more and more Office functionality as a result and that was great. Entourage really started to become the hub of Office, and that is so very true in this year’s release.