Informed by an IBM software interface design methodology known as “RealThings” introduced in the late 90s, the Microsoft Bob product offered an experience that aimed to mirror the user’s reality. It attempted to overlay real-world physicality onto the digital interface, aligning logical computer actions with their real-life counterparts. You could, for instance, click on an image of a pen and notebook to get to the word processor. It was skeuomorphism on steroids.

When later asked about the reasons for the product’s eventual failure, Clifford Nass, a communications professor at Stanford who’d consulted on Bob’s design, replied: “The problem with radically new things is the first ones are usually atrocious.” He urged the design and programming community to consider the program’s successes as well as its failures.

It’s been nearly two decades since he offered this advice, and with distance comes clarity. Though Microsoft Bob was universally deemed a failure shortly after its launch, insights derived from it have powered improved human-computer interaction and user experience today.

I took a look at three key elements of the Microsoft Bob experience to examine what went wrong, and what lived on.

1. Bob’s Interface Metaphor

What it was

Bob’s interface metaphor was the central feature of the software, creating an environment that was reminiscent of a real-life house. It was a visual metaphor of the (supposedly) average user’s home, presenting computer programs and tasks through depictions of their real-world counterparts. The calendar vector on the wall, for instance, clicked through to a functioning computer calendar. Users could also add and customize rooms and paths.

Why it crashed and burned

In Whiplash: How to Survive Our Faster Future, a book that explores the volatility and stunted adoption of innovation, authors Joi Ito and Jeff Howe explore one of the most infamous moments in cinematic history: the 1896 premiere of the film L’Arrivée d’un Train, directed by the Lumière brothers.

One of the first motion pictures ever created, it told the compelling story of a train arriving at a station, in all of its 50-second-long glory. It was a technological feat. According to film lore, however, rather than marveling at the wonder of the medium, its audience ran screaming from the building, expecting the train to come barreling straight through the crowd. It would seem that the Lumière brothers had never considered the expectations of their users.

Perhaps the confusion (and even hysteria) that users can experience when situational realities do not subscribe to their mental model is exactly what Microsoft was hoping to avoid through their interface metaphor. The assumption was that to a novice computer user, the desktop was a daunting and unfamiliar landscape.

This was a fair assumption to make, derived in large part from insights on previous product designs. But the more important lesson that Microsoft should have learned was what excessive hype and false promises can do to a product.

The product promotion for Bob was insane. A big reveal at the CES convention that year saw a powerful list of attendees in the crowd, including Steven Spielberg and other Hollywood titans. “Bobmania” was unavoidable. As one journalist wrote, “Flights heading into Vegas were supplied with Bob napkins, a plane towing a ‘Welcome Bob’ banner circled above the Las Vegas Convention Center, and senior citizens wearing Bob sandwich boards trudged up and down the Strip.”

Expectations were high for this “social interface” that was the first of its kind. But it ended up falling massively short, in large part due to the manuals and books needed to master it. At Home with Bob, a book released by Microsoft itself, clocked in at 210 pages, undermining their claims about Bob’s ease of use and learnability.

What rose from the ashes

Nevertheless, Bob correctly predicted a shifting relationship between the computer and user via task-oriented software, then termed “social interfacing.”

In much of the interaction between humans and computers leading up to that point, the computer — in its language, commands, and functionality — dictated user behavior. Microsoft Bob was a necessary and insightful stage of the journey from making life easy for the computer to making life easy for the user. While task-oriented software was only the first step in improving user experience in the digital space, this role reversal from a tech giant powered industry-level interest in user-focused design and led to subsequent iterations, getting us to where we are today.

2. Personalization of Experience

A combination of neutrals and bold statement pieces is a MUST.

What it was

Building on the interface metaphor, Bob offered its user the ability to “add swarms of excellent stuff to your home.” (Okay now I’m really confused, is this Bob’s house or mine?) Among the “swarms” of totally radical stuff you could add were decorations to showcase your personal style, personal or shared rooms, and customizable destinations behind each door.

Why it crashed and burned

In providing the user with the ability to customize their space to reflect their preferences, Bob tapped into an incredibly powerful impulse: the quest for individuality and uniqueness. It was one of the first colorful, fun ways to personalize your computer experience, even if your family members were the only ones seeing the results. But therein lies its biggest limitation: the inability to share your digital brand with others. It’s the same logic that leads us to wonder, “if a tree falls in the woods and no one is there, does it make a sound?” When it comes to creating an online persona, the answer is “no.” A huge piece of the puzzle was missing, mostly because the technology was not yet there to support it, and that is the ability to connect online. If no one is there to see and interact with your digital persona, there’s really no reason to create one, because who are you trying to be different from?

Microsoft Bob’s “social interface” wasn’t actually social in the way we think of it today, as in social media. It was actually just a task-oriented program with some annoying “friends” (but more on that later).

What rose from the ashes

Though personal customization only played a small role in the Microsoft Bob experience, the insights that drove the decision to incorporate it have had profound implications over the last 15 or so years.

Bob’s customization features reflected an understanding of the user’s desire to extend one’s individuality and personal brand to the digital space. By offering the opportunity for “decorations that show [their] style,” Bob provided users with a space for digital self-expression.

Given a considerable boost by the increase in digital connectivity in the last decade and a half, specifically in social media, this desire for individualism has become a keystone of the digital experience. We see it everywhere and anywhere that people maintain a digital persona — Facebook, Wordpress, and Instagram, just to name a few.

3. “Friends of Bob”

HEY!!!!!!!! YOU FORGOT A COMMA!!!!!!!!!!

What it was

As an integral part of its “social interface,” Microsoft Bob offered users the ability to customize and utilize a “personal guide.” These guides could be selected from a group of Bob’s 17 closest friends, who apparently are house-sitting for a guy we now put on the same level of omnipresence as Charlie of Charlie’s Angels. I guess that makes these guys Bob’s Angels.

Bob also had two “specialists,” friends who were always around for specific tasks — similar to Bosley and Creepy Thin Man, if we’re making this Charlie’s Angels metaphor a thing. (Ooh, a metaphor inside a metaphor…meta.) The two specialists were Lexi, a bespectacled ledger who helped with accounting, and Hank, a purple elephant who assisted with the educational GeoSafari program.

Each guide had a unique “personality” that ranged from store retailer working on commission-level annoying to a store owner’s cat sleeping. The idea was that there was a “friend” for every Bob user.

Why it crashed and burned

This feature failed for the same reason these memes exist:

They’re just downright annoying and pretty unhelpful.

There can be very little difference between a pop-up ad and a pop-up “friend,” especially when that friend plays a sour note on his horn nose (wha?) anytime you make a mistake in a program. Talk about negative reinforcement.

What rose from the ashes

Bob’s friends have a legacy, however, and that’s the humanization of brands and digital customer experience.

Bob, Rover, and his merry gang of helpers — whose bios offer humanlike attributes and hometowns ranging from Paris to “Wide Open Spaces” — set out to humanize and demystify the digital desktop experience. They created a social atmosphere, giving a personality and approachability to an otherwise unresponsive experience.

This type of interaction has largely migrated to the online e-commerce experience, often manifesting in the form of live chatbots and increasingly live customer service reps on the other side.

There is something truly meaningful and powerful about having another person there if you need them, but only IF you need them.