Tag Archives | Nostalgia

A Guided Tour of Microsoft Bob

When Microsoft Bob officially hit store shelves on March 31st, 1995, it wasn’t synonymous with “tech-product flop of monumental proportions.” Even pundits who weren’t so sure about it tended to buy into the notion that it was a sneak peek at where interfaces were going. And almost nobody would have guessed that Microsoft would kill it a year later.

Given that Bob was estimated to have sold only a measly 58,000 copies during its brief life, many people who mock it to this day never actually used it. Here’s a walkthrough of some of its major features–take a look and judge for yourself. And don’t miss our history of Bob and insider’s look at Bob, Clippy, and friends by a Microsoft veteran.

(Note: I ran Bob on Windows XP to create these screenshots. If you’ve got to see Bob for yourself, finding it, installing it, and troubleshooting it isn’t too hard…)

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The Bob Chronicles

What’s the most efficient way to deride a technology product as a stinker and/or a flop? Easy: Compare it to Microsoft Bob. Bring up the infamous Windows 3.1 front-end for computing newbies–officially released fifteen years ago this week, on March 31st, 1995–and you need say no more. Everything from OS X to Twitter to Google Wave to (inevitably) Windows Vista has gotten the treatment.

Bob’s pervasiveness as an insult long ago transcended its brief period of prominence as a product. By now, it’s unlikely that the vast majority of people who use it as shorthand for “embarrassing tech failure” ever actually used it–any more than the average person who cracks jokes about the Ford Edsel has spent time behind the wheel of one.

But Bob didn’t start out as one of technology’s most reliable laugh lines. It may strain credulity given Bob’s current reputation, but back in 1995, even pundits who had their doubts about the software seemed to accept the idea that it was a sneak preview of where user interfaces were going. And even though Bob died just one year later, Microsoft continued to Bob-ize major applications for years–most notably every version of Office from Office 97 through Office 2003, all of which featured the notorious Office Assistant helper, better known as Clippy.

In its own odd way, Bob is ripe for rediscovery. Hence our fifteenth-anniversary celebration, which includes the story you’re reading; a guided tour of Bob in slideshow form; and memories of Bob and its offspring from Tandy Trower, who worked at Microsoft for 28 years. Whether you’re appalled by Bob, defiantly enchanted by Bob, or never knew Bob at all, read on–and let us know what you think.

(Thanks to Dan Rose, Rogers Cadenhead, and David Worthington for their help with our Bobfest.)

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Bob and Beyond: A Microsoft Insider Remembers

(Tandy Trower spent 28 years at Microsoft, working on everything from Microsoft BASIC to Windows 1.0 to user interfaces to robotics. In this article–part of our commemoration of Microsoft Bob’s fifteenth anniversary–he recalls his initial reaction to Bob and the Bob-like Office Assistant, and his spearheading of Microsoft Agent, a later attempt to build a better “social interface” of the type that Bob represented.)

After I managed the first two releases of Windows, I shifted my focus to helping improve the design and usability of Microsoft’s products, founding the company’s first user interface design services team. For most products, my team’s efforts involved improving window and icon designs, providing usability testing, defining good design practices, and promoting consistency between products. One of my most unique challenges came with the development of the now infamous Microsoft Bob.

Bob was a very different kind of product than Microsoft had ever created before. It was developed out of motivation to improve and simplify Windows and Microsoft’s application user interfaces, and has somewhat unfairly been considered one of the company’s biggest failures.

Bob first came onto my radar after I received an email from Bill Gates asking me to check on a new project he wanted me to review. The message included a document written by Karen Fries, the Bob program manager. In that document, Karen discussed the motivation behind Bob: the increasing complexity of richly featured GUI applications. There were so many choices for the user in terms of commands and options that it was like going to the supermarket and looking down the cereal aisle and trying to make a choice, or visiting a restaurant with a vast menu.
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Hey, There’s a Piece of (Fictional) Apple History in My Hotel Room!

Remember the nifty tech-company reference in Robert Zemeckis’s 1994 blockbuster Forrest Gump? After Forrest (Tom Hanks) and his friend Lt. Dan (Gary Sinese) found the Bubba-Gump Shrimp Company in the 1970s, Lt. Dan invests its profits in a company called…Apple Computer. Forrest makes a mint and showers riches on others. Here, watch it to referesh your memory.

That letter Forrest gets from Apple? I found it in my room when I checked into my hotel in Las Vegas on Monday afternoon for the CTIA Wireless show.

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The Secret Origin of Windows

Few people understand Microsoft better than Tandy Trower, who worked at the company from 1981-2009. Trower was the product manager who ultimately shipped Windows 1.0, an endeavor that some advised him was a path toward a ruined career. Four product managers had already tried and failed to ship Windows before him, and he initially thought that he was being assigned an impossible task. In this follow-up to yesterday’s story on the future of Windows, Trower recounts the inside story of his experience in transforming Windows from vaporware into a product that has left an unmistakable imprint on the world, 25 years after it was first released.

Thanks to GUIdebook for letting us borrow many of the Windows images in this story.

–David Worthington

Microsoft staffers talk MS-DOS 2.0 with the editors of PC World in late 1982 or early 1983. Windows 1.0 wouldn’t ship for almost another two years. From left: Microsoft’s Chris Larson, PC World’s Steve Cook, Bill Gates, Tandy Trower, and founding PC World editor Andrew Fluegelman.
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Where the History of Tech is For Sale

Yesterday I paid a long-overdue visit to one of the Bay Area’s most amazing geek destinations–the Weird Stuff Warehouse, which salvages the hardware and software that Silicon Valley has lost interest in. The place has been in business for a quarter century and throngs of shoppers were roaming the aisles during my expedition. And it was bursting at the seams with shrinkwrapped software for defunct platforms, obsolete gadgets, components and cables of every imaginable type, and much, much more.

View Silicon Valley’s Island of Misfit Tech slideshow.

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Silicon Valley’s Island of Misfit Tech

I’m ashamed to admit this, but I’ve lived in the Bay Area for almost eight years without paying a single visit to one of its most legendary temples, Sunnyvale’s Weird Stuff Warehouse. Today, I happened by it after a visit to its neighbor Yahoo, and stopped in. (I did pay one previous pilgrimage in 1995, as a tourist.)

This amazing, aptly-named store offers surplus and salvaged electronic equipment, but that doesn’t begin to describe it–it’s really a museum of technology where everything’s for sale, usually for only a few bucks. Shopping its aisles today, I felt like I was walking through the entire history of personal computing. And I documented the journey with fuzzy photos from my iPhone.

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Fifteen Consumer Electronics Design Mistakes

You saved and you saved until you could finally buy that shiny new $1000 gadget that promised you everything under the stars. When it came time to plug it in, you found your joy being subsumed by abject horror. Your stomach plunged deep into your gut and you (yes, mortal non-designer you) recognized a fundamental flaw in your flashy gizmo so obvious that it made you want to pick up the device and smash it over the designer’s head.

Even the best designers make mistakes…but this article isn’t about them. We’re about to, ahem, celebrate the worst consumer electronics designers through the lens of their faulty creations. Since I’m far from an all-knowing technology god, I’ve limited our survey to fifteen design problems that have not only bugged me through the years, but that are widespread enough to have bugged many of you too. These problems aren’t limited to current technology, but they all fall into the nebulous realm known as “consumer electronics.” You know: TVs, telephones, VCRs, DVD players, MP3 players, and more.

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I Love the Eighties!

I spent a couple of my formative years as a tech journalist working at InfoWorld–the publication which may have taught more to more tech journalists than any other. Thanks to Google Books, its entire print run is now available to peruse–including the early issues that document many of personal computing’s defining moments.

Even if you never read any of the articles, the early magazine-format covers are wonderfully evocative. I’ve compiled some of my favorites (from way before I worked there) into a gallery.

View The Golden Age of InfoWorld Covers slide show.

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The Golden Age of InfoWorld Covers, 1984-1985

Back in the 1980s, if you wanted to stay particularly up-to-date on the PC business, you read a newsweekly–and there was a high chance that the newsweekly you read was IDG’s InfoWorld. Among the most venerable and successful computing publications–it started in 1978 and thrives online today–InfoWorld was famous back then for its frequent format changes. In 1984 and 1985, it adopted a BusinessWeek-like look and feel. The issues from this era may not have been the best issues of InfoWorld ever, but they’re the most fun ones to revisit. (Thanks to Google Books, revisiting InfoWorld’s entire print run is now easy.)

These mid-80s covers are miniature time capsules. Here are a bunch that capture the period in all its innovative, innocent, silly glory. Click on the covers to read the issues.

(Full disclosure: I’m an InfoWorld alum, having worked there from 1992-1994. It seems like half the people I know in tech journalism are ex-InfoWorlders, such as Calendar Swamp proprietor Scott Mace, author of several of the stories here.)

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