Summary

Microsoft Office’s assistant Clippy lives as an unkind memory among those of us old enough to remember it, seventeen years after it disappeared for good. But I reckon Clippy was ahead of its time. It doesn’t deserve the bad rep it had back then, and I’ll explain why.

Clippy Was Great for Kids and Beginners

I started school in the late 1990s at the very period when Office-based PCs were really hitting the mainstream, so I was the perfect target user for Clippit, as Clippy was officially known. As an Office beginner, Clippy had great potential as a feature that could guide young users like me to find the features that I needed to find.

I’m not going to pretend it did this perfectly. The Office assistant was widely hated for being a patronizing, passive-aggressive, and rather clownish tool for users that wasn’t actually helpful if you knew what you were doing. However, it was a product of its time—it didn’t have a huge AI model guiding it to perfect answers. This was also the period of the PC ownership boom, with millions of new PCs taking place in homes and offices across the globe.

An example of Clippy, the Microsoft Assistant, in Microsoft Office.

Those beginner PC users needed a helpful hand to walk them through how to use it, which Clippy tried to provide. As a child learning Word or Excel, it did help me to figure out features that I would otherwise have been too scared to try. I imagine a lot of other beginners felt the same, too. When Microsoft removed Clippy, it lost that front-facing guide for new users, and it’s never had anything quite as good since.

Clippy Was AI, Long Before AI

SinceChatGPTfirst gained public release in 2022, every product you can imagine has tried to shoehorn an AI component into it. The future is AI-based, with helpful assistants to guide us through life, figuring out problems. Sound familiar? Clippy was a helpful assistant, too, guiding users through problems and providing helpful tips, long before AI models like ChatGPT’s were ever considered a possibility.

While the user interface could certainly do with an update, I can easily see a Clippy-esque tool in Microsoft Office now, directly helping users with their work. While there isn’t a paperclip to speak to,Copilot Pro is already integrated into Office apps, providing Office users with access to AI, but this tool seems largely focused at productivity-boosting features like text generation.

An example of a letter being written in Word, with the Microsoft Assistant in Clippy form offering assistance.

What Office lacks is a tool that tries to identify what you’re doing and, discreetly, offer assistance. Clippy tried to offer this, but it wasn’t powerful or smart enough to do it effectively. Any future Office assistant would need to be less forceful than Clippy, but also be a step-up from Copilot, avoiding pushing AI generative functions onto users in the same way that Clippy pushed unhelpful tips.

The Science Behind Clippy Made Sense

Clippy didn’t start out as a Microsoft Office assistant, but actually came slightly earlier. It first launched as part ofMicrosoft Bob, a quirky desktop environment alternative forWindows 3.1, offering a simulation of your home that was intended to be more user-friendly. Bob also included an assistant with several characters, one of which included Clippy, that could guide new PC users on how to perform simple tasks.

To navigate around Bob, you’d click different objects in the simulated home—a pencil and paper might simulate opening Word, for instance. Bob had been designed using research from Stanford University, based on a theory that people treat computers like they’re human beings. Creating anthropomorphic assistants like Clippy would embody the humanity that we were already assigning to our PCs.

A Microsoft Bob kid’s room desktop.

Just like Clippy, Bob was created with good intentions, but was ripped apart upon a wider release. Too infantile, too patronizing, just like critics of Clippy in Office would later claim. That’s not to say that there weren’t legitimate concerns—a report in theNew Yorkerexplains how focus groups containing women, for instance, derided the characters for being too male-orientated.

However, if we go back to the science and assume we do treat our computers like they’re human beings, a human-like interface like Bob and Clippy makes sense. Clippy’s bigger problem was a lack of depth—it focused on beginners, and didn’t offer anything useful for more experienced users. That’s why IT journalists, in particular, found it to be so patronizing to use, and ripped it apart accordingly.

An example of a resume being written in Microsoft Word with the Clippy assistant offering help.

Clippy Was Office at Its Best

If you were to open up a Microsoft Office app for the first time, what would your first reaction be? If I started out today, I’m not sure I would be impressed by what was on offer. Office apps feel too business-focused, bloated with endless features, and primarily sold as amonthly Microsoft 365 subscriptionthat hits your wallet.

Clippy harks back to a time when Microsoft Office felt at its best. Simple, fully offline, focused on core features, with little bloat. No upselling required—you owned your copy of Office and that was that. It was also a more upbeat era, with plenty ofhidden Easter eggsand callouts that made it feel more personalized.

Clippy was part of that personalization that, to me, feels missing in Office now. The bigger Office has become, the more it has lost a personal touch. It isn’t as approachable to newbies—where’s the pop-up to help a newbie out, like Clippy used to offer?

Microsoft would do well to take another look at their Office assistant and consider how useful it could be, with an AI super brain behind it, for Office users.

Not just for beginners, too. As I’ve already mentioned, this lack of depth is what doomed Clippy in the first place. All users, from beginners to the most experienced, could find use in an assistant like Clippy if it could be tailored to their needs.

Could Clippy Make a Comeback?

Clippy wasn’t a bad idea. The science behind it made sense, and as a kid, it made Office apps like Word seem more approachable. I didn’t need to look through guides to figure out how to perform a task because Clippy could help me to do it.

The problem is, as I became more experienced, I left Clippy behind. It felt too basic, lacking the depth I needed for it to remain relevant. The passive-aggressive nature of its queries, as well-intentioned as Microsoft may have intended them to be, turned me, and a whole generation, off using it.

In the end, I think that’s a shame. There’s a market for an Office assistant that you can talk to and interact with, which can guide you step-by-step through different actions. The recent AI revolution proves that. If I were a Microsoft engineer, I think I’d be tempted to dig out an old copy of Office, just to see what lessons could be learned today by creating a helpful assistant that humans might just warm up to, even if it isn’t paperclip-shaped.