If you’re relying on Apple to get work done, you’re better off going it alone

At last year’s WWDC keynote, Apple spent a surprising amount of time discussing a range of features centered around the idea of ​​collaboration. The company tried to tie together a few disparate ideas, like collaborating on documents in apps like Pages, Keynote, and Numbers with pre-existing communication features in Messages and FaceTime.

The clear message was that Apple was taking a shot at collaborative office environments such as Microsoft Teams and Google Docs. But given those longstanding alternatives with, if not dedicated user bases, then at least entrenched user bases, the question is who exactly are these features for?

That said, as someone who works in a small environment populated entirely by those in Apple’s ecosystem, it seems like I would be the ideal candidate for such positions. But compared to what other companies offer, Apple’s foray feels a bit sloppy and patchy, and my experiences using it have been far from smooth.

File gone

I recently worked with my colleague Jason Snell on looks at Apple’s latest Macs. (You can check out my review of the M2 Pro Mac mini.) Jason shared a draft of his MacBook Pro review with me via Dropbox, a workflow we’ve used many times in the past. Meanwhile, I tried to share my own draft review, written in BBEdit, from iCloud Drive.

This turned out to be a mistake. Not only did the collaboration feature malfunction – I repeatedly pressed the Copy link button in the Finder, which left nothing at all on my clipboard – but it eventually disrupted my own copy of the review, which suddenly stopped syncing reliably between my MacBook Air and the Mac mini test machine. Instead, I had to go through and use BBEdit’s built-in file comparison feature to painstakingly apply changes paragraph by paragraph and make sure I had the most recent text from the copies on both machines. This happened multiple times until I went back and unshared the document with Jason, then suddenly it went back in sync on my Macs.

My impression is that syncing between multiple people and synchronization between one person’s different devices is currently not working well together. And yet this is something that third parties like Dropbox have been able to handle for several years now, and web-based solutions like Google Docs don’t have to worry about it at all. Relying on these features for serious collaboration is certainly a hard sell when they struggle with this basic functionality.

Freeform can cost you

One of the key collaboration features from last year’s keynote wasn’t delivered until late 2022. Freeform is a new app launched with macOS Ventura 13.1 and iOS/iPadOS 16.2. It’s meant to be a shared whiteboard where you can enter text and create diagrams, annotate with Apple Pencil, and even embed files.

But Freeform also has a lot of rough edges that make it not quite ready for everyday use. Until recently, there was a bug that could cause content entered via Apple Pencil to disappear on other platforms. (That would have been patched in last week’s iOS 16.3 and macOS 13.2 updates.) Meanwhile, the Mac version of the app, which I used at one point to create a Freeform board with myself on my iPad and a other user on their iPad crashed every few minutes during use.

One of my biggest frustrations with Freeform is the aforementioned file embedding feature, which I found disappointing. For example, in one board I wanted to try putting an editable table in the document, the same way you can embed a mini spreadsheet in Pages, but Freeform can only add a link to (or a full copy of) a spreadsheet, which shows a thumbnail and cannot be edited in Freeform itself. Similarly, if you’re trying to embed a PDF, you just need to insert a thumbnail and a link to the file, rather than letting users view and mark up PDFs directly on the board.

It feels like Freeform holds promise, but the current iteration is far from stable, and it’s hard to imagine anyone using it for serious collaborative efforts.

The Notes You Don’t Play

This isn’t to say that all of Apple’s attempts at collaboration are bad. There are even a few features that I’m quite happy with. For example, while Jason and I were working on our Mac reviews together, we shared a Numbers spreadsheet with benchmark data so we could both fill in the correct numbers. It worked really well in the end and I didn’t run into any major issues. (Although in my iMessage conversation with him I was constantly asked to see the latest changes to our document, which I found a bit annoying.)

However, in my opinion, the place where collaboration across Apple’s platforms has been really successful is in the Notes app. I know! That surprises me as much as anyone, but in recent years the humble app once defined by its skeuomorphic yellow-outlined paper background and Marker Felt font has become a powerhouse of Apple’s lineup. Recently, it even gained the ability to show live where other users’ cursors are while they’re editing a shared note.

I use Shared Notes with my wife to keep track of many household and childcare related activities, and I also use it with my co-hosts at The Rebound podcast to keep show notes and share title suggestions during our recording sessions. To me, that’s the perfect use of collaboration because it’s a quick and easy gap that doesn’t require us to download a separate app. If I wanted to co-write an entire document, I’d probably use Google Docs, but if I just wanted to share a notepad with a few friends, Notes is where it’s at. It’s something Freeform, and the rest of Apple’s collaboration features, could probably learn from.