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Rob Girling, Artefact co-founder and joint CEO, with his wife Agnieszka, on the Faroe Islands. (Photo courtesy of Rob Girling)

For those who remember Clippy — Microsoft Office’s animated paperclip assistant — would you have liked him better as a typewriter? What about a stapler?

Back in the mid-1990s, Rob Girling was Office’s only dedicated designer. He was given the job of creating a character to help customers navigate Word and Excel, hopefully cutting down on the volume of calls to support centers being made by people struggling to format their letters and manage their fever charts.

In his initial brainstorm, Girling cycled through all manner of old office equipment, “anything I could think of and slap some eyes on it,” he said.

The team picked a paperclip, whose formal moniker was Clippit. Others animated and tried to build a brain for the tool, which would unexpectedly popup like a less-charming Jiminy Cricket, there to perkily lend advice whether you wanted it or not.

The infamous Clippy from Microsoft Office.

While support calls dropped dramatically, Clippy was a flop. The tool was part of Office from 1997-to-2004 (depending on the product), and ultimately scrapped for essentially bugging the hell out of people.

“It’s hilarious now, I can see the humor of it,” Girling said. “But for years it embarrassed me.”

And as all good fiascos do, this one delivered some formative lessons for Girling, whose resume includes co-founder and joint CEO of Artefact, a Seattle company launched in 2006 that provides tech design and development services. He’s also co-founder of 10,000ft, an Artefact spinoff that builds resource management software and was acquired this month by Smartsheet for an undisclosed sum.

Girling learned the value of being skeptical when promised ambitious tech solutions. The goal for Clippy was groundbreaking at the time: building an AI assistant to monitor for befuddled software users and offer fixes. But the functionality wasn’t there. The tool didn’t deliver on the promise, Girling said. He wished he’d given more scrutiny to the project and hadn’t just gone along with it.

Girling has applied that careful thinking, of questioning the potential and pitfalls of technology, to his work today with Artefact.

“This is a very real discussion in tech design right now,” he said. “In the circles we move in, this is very much where the debate is: How do we design tech that doesn’t have deleterious effects on society and our well being?”

To aid in the conversation, Artefact last year released the Tarot Cards of Tech, a physical deck of cards that encourages designers and developers to slow down and consider the broader, ethical impacts of what they’re proposing and building. Because while it does provide tremendous good, technology can also drive addiction, depression, the spread of misinformation and the undermining of democracy, the erosion of privacy and the abuse of power through facial recognition.

The stakes today eclipse the minor annoyance of a wisdom spouting paperclip.

So Girling and his team talk to their clients about creating responsible, accessible technology. They hold workshops. They talk to investors about incentivizing good behavior in startups. He also wants to see policy and legislation to protect the public from wrongdoing companies.

“It really does mean the tech industry has to do a better job thinking through what kind of future we’re creating,” Girling said.

The Tarot Cards of Tech, from Artefact in Seattle. (Artefact Photo)

We caught up with Girling for this Working Geek, a regular GeekWire feature. Continue reading for his answers to our questionnaire.

Tech project I most regret being involved with? I was one of the designers of Clippy — yes that Clippy at Microsoft. The paperclip was my idea because as a young UX designer I was asked to apply the ideas of social computing to Microsoft Office. I’m not proud, but it’s become an amusing claim to fame! (Editor’s note: This question is not typically part of the Working Geek Q&A, though perhaps it should be. Girling went rogue and added it, and we thank him.)

Current location: Suite 500, 619 Western Ave, Seattle

Computer types: Microsoft Surface Studio 2, Surface Pro 3

Mobile devices: iPhone X

Favorite apps, cloud services and software tools: Adobe Lightroom,,, 500px

Girling owns the fact that his workspace veers into messy. (Artefact Photo)

Describe your workspace. Why does it work for you? At Artefact, I sit — like everyone else in our open plan office — alongside the five other people with whom I share a communal work table. Specifically, I sit opposite Collin Ottinger, our director of finance, and co-CEO Gavin Kelly — which better enables brainstorming and debate! We have a window view to the south, facing Yesler, and the slowly vanishing remains of the Alaskan Way Viaduct. I don’t keep the tidiest of desks, there is a bunch of clutter, but it works for me.

Your best advice for managing everyday work and life? Be kind to yourself. (Go easy on your expectations of self.) It’s a marathon, not a sprint. (Don’t be in too much of a hurry.) Careers are long, but life is short. (Don’t put up with bullshit.)

Your preferred social network? How do you use it for business/work? It’s become LinkedIn because of the ease with which people can reach out to me following speaking events. The platform also helps me find and better understand the needs of customers, partners, and future employees. It’s also a lot of fun to learn how peers and colleagues in the space are making their mark.

(Artefact Photo)

Current number of unanswered emails in your inbox? (1)

Number of appointments/meetings on your calendar this week? 24 — which is atypically light!

How do you run meetings? For our executive leadership team meetings, we’ve adopted the Entrepreneurial Operating System (EOS) Level 10 meeting structure. It works well for connecting, sharing out and problem solving with our company leaders.

Everyday work uniform? Black or grey jeans, boots and a blue-patterned shirt. Maybe a nice hoodie or Patagonia vest — because I embody the tech stereotype but wear it ironically!

How do you make time for family? Most nights, my wife and I walk our dog around the neighborhood for about an hour. Every night, we have family dinners.

Best stress reliever? How do you unplug? Hiking and camping, but my hobbies include landscape photography and digital painting, which uses AI techniques to create digital art.

What are you listening to? Pivot, Kara Swisher, Making Sense, Sam Harris, RSA Podcasts, Should this Exist?, and Team Human/Doug Rushkoff are my go-to podcasts. For music, right now I’ve been listening to Ry Cooder (Paris Texas), Pedro the Lion and the Cocteau Twins.

Daily reads? Favorite sites and newsletters? New York Times, Guardian, Economist, Atlantic Monthly, GeekWire and TechCrunch

Book on your nightstand (or e-reader)? “The Age of Surveillance Capitalism” by Shoshana Zuboff

Girling presenting at the event All Tech is Human in Seattle, May, 18, 2019. (Artefact Photo)

Night owl or early riser? A night owl in the winter, but an early riser in the summer.

Where do you get your best ideas? In the bathtub, during my morning runs or on weekend hikes.

Whose work style would you want to learn more about or emulate? I’m always very impressed by professional writers, designers and/or artists who work from a home or in a home studio. It takes such discipline to commit to a large writing project, design sprint or artistic endeavor, but it’s too easy for me to get distracted and lose focus at home. I have too much fun with my family, or quickly lose myself in a rabbit-hole of digital painting!

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