Lessons from the birth, death, and resurrection of Clippy

📎 Bill Gates called Clippy and other AI assistants “clowns” in early meetings and demos, e.g. “So when I create a chart the clown will pop up and say ‘I’m here to help…’” Can we bring that back? Is “clown” the new “AI”?
Issue #111: blindness as a strength, how to spot a cult, and a trick for remembering
By Harris Sockel

If you’re a close reader of these newsletters, you’ve probably spotted a few stories by one of my favorite writers: Steven Sinofsky. After joining Microsoft as an engineer in the ’80s, he ran the Office team in the ’90s and early ’00s. He supervised the birth of Clippy (the OG human-esque AI) and that red squiggle in your Word docs. Later, he was President of Windows.

On Medium, Sinofsky shares bangers like this 37-minute read on leading efficient meetings, which I’ve referred back to multiple times. One tip: Try a “without” meeting where you meet with your team without the boss of the team. It’ll change the dynamic and make people a little less perform-y.

More wisdom from Sinofsky:

• On crisis leadership: Trust is a resource you develop when things are going well… so you can dip into that reserve when things aren’t.
• On performance reviews: No system is perfect, and any system that claims to rate people in isolation almost always compares them to each other.
• On org charts: No matter which structure you choose (hierarchical, flat, matrixed…) know its weaknesses and how to compensate for them.

Sinofsky is probably best known, though, as the product lead behind Clippy. The iconic sentient paperclip was born when children’s book illustrator Kevan Atteberry was working on Microsoft Bob, an immersive and experimental UI for Windows ’95 featuring 17 virtual assistants that persisted in the bottom-right corner of the screen. (Side note: I used Bob! Even at nine I thought it was beautiful but pointless.) Bob failed, but Clippy sprang from its ashes… basically, the team repurposed Bob’s virtual assistants for their next project, Office.

Clippy’s signature move was popping up right after you’d typed “Dear [whoever]” in Word to say: “It looks like you’re writing a letter.” Yeah, we know.

The team wanted so badly to design an assistant that made using a computer easy and approachable, but as they discovered, the line between being helpful and annoying is very thin. Clippy was killed in 2007 (before being resurrected as an ironic sticker pack for Teams in 2021).

Looking back, Sinofsky realizes they should’ve spent less time dumbing software down and more time empowering people to do complex things with less perceived risk.

Collectively, we all learned a lesson about AI — and about relationships with anyone, human or not — from the rise and fall of Clippy: “There is something truly meaningful and powerful about having another person there if you need them,” writes product designer Elizabeth Nicholas, “but only IF you need them.”

What else we’re reading

• It’s not every day that you read an essay written by someone who was told, at 16: “You will be blind by forty.” In “How Blindness Made Me a Richer Person,” Nancy Solari chronicles living with retinitis pigmentosa — a genetic eye disease affecting 1 in 4,000 people. It slowly erodes the retina, leading to tunnel vision and blindness. I was moved by how Solari was able to reframe blindness as a strength, something that brought her closer to people. She writes: “I learned from that experience to be honest with dates, friends, coworkers, even people I met. I learned to be comfortable asking for help.”
• And now for a sharp left turn: No one who joins a cult ever thinks they’re actually joining one — especially not Doug Bierend, who, in a fascinating Medium tale, describes how he almost took a job writing and editing propaganda for the NXIVM cult, an organization that fronted for sex trafficking and sexual abuse. Two things stuck out to me: Bierend clocked that it was a cult because its recruiters were so defensive about it not being a cult. He also chalks up his vulnerability to being unemployed and desperate: “I am struck by the parallels between the kind of longing that arises when searching for employment, and the sort that accompanies the search for meaning or a sense of inclusion.”

Your daily dose of practical wisdom: about remembering things

If you make getting information more painful or friction-ful in some way, you’ll remember it better. Classic example: A 2021 study found that “the complex experience” of writing by hand helps people retain information with 25% more accuracy than typing.

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Edited and produced by Scott Lamb & Carly Rose Gillis

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