Among the Apple productivity apps, I use Keynote every single day in my work. I develop a lot of graphics and many of those get used on webpages or in social media. Having pre-sized Keynote decks for each purpose (Linked In, or WordPress Hero Images) makes it easy not only to pull from previous work, but also ensure that my graphics are the right size (File > Export > Images). Wherein 10 years ago I was in Photoshop constantly, today, it’s Keynote. (Full disclosure, I still use Photoshop and Illustrator, but Keynote is like the tool you’d include in your daily carry!)
I also love using Pages and Numbers. Numbers makes it easy to make really good looking spreadsheets. So when I recently wanted to plan a trip that would involve two others, I turned to create the trip schedule in Numbers. It looked great. Then it was time to share it. This is where things broke down pretty quickly. Full disclosure: I ended up abandoning Numbers all together and going to Google Sheets. But why?
First, I had to save the document into my iCloud account. Fine. Easy enough. Then I used the “Collaborate” button to share this with my friend. The odd way it works is that it sends the invite to collaborate through Messages. I can’t say that this is better or worse than using email like Google does, but I’m used to seeing share announcements in GMail.
Once I shared this via text message (which, frankly, I think sucks now that I think about it, because my friend is on west coast-time and he didn’t need to get a 6AM wakeup because of a spreadsheet), I tried sharing it again and then got an ominous message from within Numbers.
By sharing this document with this user, you’re giving them permission to see the entire contents of the enclosing folder.”
What the heck? That’s my entire iCloud Drive! And no—no!—I don’t want to share my entire iCloud Drive folder with someone just to collaborate upon a spreadsheet.
This message did not appear the first time I shared it, and there was no way to get this message back to confirm what it had said. I quickly went to my iCloud Drive folder, created a new folder within, and moved the Numbers file into that. But did that unshare what was shared before? Would that move break the share? No clue.
So then I decided to cancel everything and move my spreadsheet over to Google Drive. But when I clicked the “Manage Sharing” button from within Numbers, nothing happened! No feedback. Not exactly a smooth experience.
So then I created my Google Sheet, pasted my data, and then shared it seamlessly with my friends’ Google Gmail accounts. Easy. Done. No worry, no over-sharing.
Then back in the Finder, by clicking the Messages icon next to the file, I was finally able to un-share the document with my first friend. Then when I returned to Numbers? It told me it couldn’t display the document and threw up the same warning dialog 5 times, beeping each time. It was like Numbers had really bad gas and had to belch from the experience of trying to share a document.
I chose to write this because I’ve been disappointed with iCloud sharing of documents for many years and figured—even though I don’t share many obviously—that in 2025 with the latest versions of everything, that this stuff should just work. But clearly it’s still a hot mess.
I was once told don’t complain. If you have to lobby a complaint, then offer a solution. Wherein Google’s cloud strategy has been to make everything web-based, both Microsoft and Apple have this dual system where documents can be edited online or through their apps from the point of view of a PC platform like Windows or MacOS.
As much as I dislike the Microsoft ecosystem that I am forced to use at work, it at least does work. But Google’s Drive ecosystem makes sharing documents far more transparent to the user with feedback. When you click, the visual feedback is immediate. I can share without an email, if I want. And I can quickly change the permissions right in the document.
And this is really a shame. Because Apple makes really great software in terms of its productivity suite for many use cases. But it was not designed to be collaborative from its conception, just the same as Word or Excel, like Google’s Docs, Sheets, and Slides are. And this shows.
So if you’ve made it this far, I’d recommend not creating documents in Apple’s “iWork” suite if you need to collaborate. What they could do if they wanted to add this functionality and improve the experience over Microsoft Office is:
- Provide an experience that is idiot-proof with good feedback.
- Dedicate a space in the UI to always know how something is shared and with whom.
- If the back-end cloud system requires sharing an entire folder? Do that for the user without a vague warning. When it flashed that message at me, I am not sure I had any recourse to undo that action. (If I did, I forgot, likely because of the fear it put into me.)
- Any UI buttons should be responsive, even if the feedback may be delayed with app-to-cloud communication (say, a spinning wheel, or at least something).
- Cut back on all the pop-up dialogues that I saw in just trying to share something.
- Make it easy to unshare, and don’t force the user to go to an entirely different app to unshare.