Old Dogs, New Tricks

If you used Microsoft Word in the early 2000s, you probably remember Clippy, the little paperclip that would pop up with a message like:

“It looks like you’re writing a letter. Need help?”

Most people remember Clippy as annoying. But the idea behind it was actually ahead of its time.

For about twenty years, that idea mostly went nowhere. This week it came back.

Google, Microsoft, and Anthropic all announced major upgrades to the tools millions of people already use every day — Docs, Sheets, Slides, Word, Excel, and PowerPoint.

The common thread across all of them is that these products are starting to behave less like blank canvases and more like collaborators.

Google’s latest Gemini updates embed AI directly inside Workspace. This means it can now generate full drafts using context pulled from Drive, Gmail, Chat, and the web, while also matching the structure or tone of documents your team already writes. Sheets can create entire spreadsheets from a prompt and populate tables with real-time data from Google Search. Slides can generate presentations that match your existing themes and design styles, without you touching a template. 

Google Drive is getting an update too. Instead of just storing files, it can now answer questions across your documents, emails, calendar, and the web, essentially acting as a research layer over everything you’ve written or saved.

Microsoft is pushing the same idea, but at a larger scale.

Microsoft's Copilot is going further. Instead of helping inside a single file, it now runs tasks that span Word, Excel, PowerPoint, and Outlook simultaneously — pulls the numbers, reads the emails, and builds the deck, all in one workflow without a human moving data between tabs.

That might mean pulling financial numbers from Excel, summarizing conversations from email or meetings, and assembling the results into a presentation. The AI isn’t just drafting text; it’s coordinating work across tools.

Anthropic’s updates to Claude for Excel and PowerPoint point toward the same future.

Claude can now maintain conversational context across multiple open files. That means it can analyze a spreadsheet, build a model from the data, and move the results into a slide deck in one continuous workflow.

For years, the biggest innovation in productivity software was collaboration. Tools like Google Docs made it possible for multiple people to edit the same document at once, while Slack and Teams helped coordinate work around those documents.

What’s emerging now is a new kind of collaborator entering the workspace.

These systems can see the context around your work: your documents, conversations, spreadsheets, meetings, and files, and use that context to generate new outputs. Instead of every project starting from a blank page, the workspace increasingly begins with a working draft.

And because this is happening inside tools billions of people already use, the shift doesn’t require learning new platforms. It simply adds a new kind of teammate to the workspaces we already rely on.

Clippy had the right idea. The problem was never the concept — software that understands what you're doing and helps you finish it is genuinely useful — it was that the technology had no shot at delivering on it. The model didn't understand the document, the user, or any of the context around the work.

Today's models do, and they're living inside the most boring, ubiquitous software in the world, not flashy new apps. 

Old dogs, it turns out, can learn new tricks.

Stay curious,

Julia & Russell