During last year’s WWDC keynote, Apple spent a surprising amount of time talking about a set of features focused on the idea of collaboration. The company has tried to tie together several disparate ideas, such as document collaboration in apps like Pages, Keynote, and Numbers, with already existing communication features in Messages and FaceTime.
The clear message was that Apple is making a move in office collaboration environments like Microsoft Teams and Google Docs. But given these long-standing alternatives with if not dedicated user bases, then at least entrenched user bases, the question is, who exactly are these features for?
However, as someone who works in a small environment populated entirely by the Apple ecosystem, I feel like I would be an ideal candidate for such features. But compared to what other companies offer, Apple’s foray feels a bit sloppy and glued together, and my experience with this product has been far from smooth.
I recently explored the latest Apple Macs with my colleague Jason Snell. (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. In the meantime, I tried to share my review draft, written in BBEdit, from where it lived in iCloud Drive.
This turned out to be a mistake. Not only did the collaboration feature not work properly – I repeatedly clicked the “Copy Link” button in the Finder, which added absolutely nothing to my clipboard – but it ended up causing my own copy of the review to stop syncing reliably between my MacBook Air and Mac mini test machine. Instead, I had to use BBEdit’s built-in file comparison feature to painstakingly apply paragraph-by-paragraph changes and make sure I had the most up-to-date text from copies on both machines. This happened several times until I went back and shared the document with Jason, at which point it suddenly synced again on my Macs.
I was under the impression that syncing between multiple people and synchronization between different devices of the same person is currently not well combined. And yet it’s something that third parties like Dropbox have been able to handle for a few years, and web solutions like Google Docs have nothing to worry about at all. Relying on these features for serious collaboration is certainly tricky when they struggle with that basic functionality.
Freeform can cost you
One of the main collaboration features from last year’s keynote was only released towards the end of 2022. Freeform is a new app launched with macOS Ventura 13.1 and iOS/iPadOS 16.2. It’s designed to be used as a shared whiteboard, where you can type and create charts, write notes with your Apple Pencil, and even paste 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 with the Apple Pencil to disappear on other platforms. (This was presumably fixed in last week’s iOS 16.3 and macOS 13.2 updates.) Meanwhile, the Mac version of the app I used at one point to share a Freeform board with myself on my iPad and another user on their iPad , was crashing every couple of minutes while in use.
One of my biggest frustrations with Freeform is the aforementioned file embedding feature, which didn’t impress me. For example, on one board, I wanted to try putting an editable table in the document, just like Pages allows you to embed a mini-table, but Freeform can only add a link to the spreadsheet (or a full copy of it), which shows the thumbnail and is not editable in Freeform itself. Similarly, when trying to embed a PDF, just add a thumbnail and a link to the file instead of letting users view and mark up PDFs right on the board.
Freeform seems to be showing promise, but its current iteration is far from stable, and it’s hard to imagine anyone using it for serious collaboration.
Notes you don’t play
That’s not to say that all of Apple’s efforts to collaborate are bad. In fact, there are a couple of features that made me really happy. For example, while Jason and I were working together on Mac reviews, we shared a Numbers spreadsheet with test data so we could both type in the appropriate numbers. It ended up working really well and I didn’t run into any major issues. (Although in my iMessage conversation with him, I kept being prompted to see the latest changes to our document, which annoyed me a bit.)
However, in my opinion, the place where collaboration on Apple platforms has really been successful is in the Notes app. I know! It surprises me as much as anyone, but over the past few years, a modest app that once featured a skeuomorphic paper background with yellow lining and Marker Felt font has become a powerful engine for the Apple line. It even recently got the ability to show in real time where other users’ cursors are when they’re editing a shared note.
I use Shared Notes with my wife to keep track of a lot of household chores and childcare activities, and I use it with my co-hosts on The Rebound podcast to take show notes and share title suggestions during our recording sessions. . For me, this is the perfect use of collaboration because it’s a quick and easy break that doesn’t require you to download a separate app. If I want to co-author an entire document, I’ll probably use Google Documents, but if I just want to share a notebook with friends, Notes is the way to go. This is something Freeform and the rest of Apple’s collaboration features could probably learn from.