If you’re relying on Apple to get the job done, it’s best to do it yourself

By Microsoft 8 Min Read

During last year’s WWDC keynote, Apple spent a surprising amount of time talking about a number of features centered around the idea of ​​collaboration. The company has attempted to bring together a few disparate ideas, like working on documents together in apps like Pages, Keynote, and Numbers with pre-existing communication capabilities in Messages and FaceTime.

The clear message was that Apple was looking into collaborative work environments like Microsoft Teams and Google Docs. But given those long-standing alternatives with, if not devoted user bases, then at least entrenched user bases, there’s a question as to who exactly are these features?

That said, as someone working in a small environment populated entirely by those in the Apple ecosystem, it seems like I’d be the ideal candidate for such features. But in comparison to what other companies offer, Apple’s foray feels a bit squashed and boxed together, and my experiences with using it have been less than smooth.


I was recently collaborating with my colleague Jason Snell on reviews Apple’s latest Macs. (You can take a look my M2 Pro Mac mini review.) Jason shared a draft of his MacBook Pro review with me via Dropbox, a workflow we’ve used many times in the past. In the meantime, I’ve attempted to share my review draft, written in BBEdit, from where it was in iCloud Drive.

This turned out to be a mistake. Not only did the collaboration feature malfunction (I repeatedly hit a Copy Link button in the Finder which put absolutely nothing into my clipboard), but it ended up breaking my copy of the review, which suddenly stopped syncing so between my MacBook Air and Mac mini test machine. Instead, I had to go through and use BBEdit’s built-in file compare feature to painstakingly apply changes paragraph by paragraph and make sure I had the most up-to-date text from copies on both machines. This happened multiple times until I went back and unshared the document with Jason, at which point it suddenly came back in sync across my Macs.

My impression is that the synchronization between multiple people AND syncing across a person’s different devices doesn’t work well together at the moment. Yet this is something third parties like Dropbox have been able to handle for a few years now, and web-based solutions like Google Docs needn’t worry at all. Relying on these features for serious collaboration is definitely a tough sell when they struggle with this basic functionality.

My attempts to collaborate on recent projects involving Apple’s new Macs have not gone as planned.

Dan Moren

Freeform could cost you

A major collaboration feature from last year’s keynote marquee didn’t roll out until late 2022. Free form 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, write notes 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 where content entered via Apple Pencil could disappear on other platforms. (It was presumably fixed in last week’s iOS 16.3 and macOS 13.2 updates.) Meanwhile, the Mac version of the app, which I was at one point using to share a Freeform board with myself on my iPad and another user on the their iPad, which ended up crashing every two minutes during use.

One of my biggest frustrations with Freeform is the aforementioned file embedding feature, which I found disappointing. For example, on a bulletin board I wanted to try and insert an editable table into the document, the same way Pages lets you embed a mini spreadsheet, but Freeform can only add a link to (or a full copy of) a spreadsheet calculation, which shows a thumbnail and is not editable within Freeform itself. Similarly, trying to embed a PDF simply inserts a thumbnail and link to the file, rather than allowing users to view and markup PDFs directly on the whiteboard.

Freeform appears to show promise, but its 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

That’s not to say that all of Apple’s collaborative efforts are bad. In fact, there are a couple of features that I was quite happy with. For example, while Jason and I were working on our Mac reviews together, we shared a Numbers spreadsheet with reference data so we could both enter appropriate numbers. In the end it worked very well and I didn’t encounter any significant problems. (Although I was constantly prompted into my iMessage conversation with him to see the latest changes in our doc, which I found a bit annoying.)

In my view, however, where collaboration across Apple platforms has really taken off is in the Notes app. I know! This surprises me as much as anyone, but in recent years, the humble app that was once defined by its skeuomorphic yellow-lined paper background and Marker Felt font has become a powerhouse in Apple’s lineup. It also recently had the ability to show, live, where other users’ cursors are while they’re editing a shared note.

I use the notes shared with my wife to keep track of many household and childcare related activities, and I also use them with my co-hosts of The bounce podcasts to keep show notes and share headline suggestions during our recording sessions. To me, this is the perfect use of collaboration, because it’s a quick and easy interval that doesn’t require a separate app download. If I want to write an entire document together, I’d probably use Google Docs, but if I just want to share a scratchpad 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.

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