As far as technology goes, there are few more exciting experiences than unboxing and starting up a new Mac or device, or logging into a brand new version of macOS for the first time. Like other thrills in life, those moments of frisson are accompanied by fear. What if it doesn’t work after all or, most importantly, have its changes gone too far?

Innovation and advance are impossible without change, and implementing change successfully is crucial to many organisations. From its earliest days, it has been central to Apple’s business. Judging how far to change, and how to make that move, is central to attracting new customers and retaining old ones.

With hardware, subtle change may require ingenuity. In 1988, when Apple introduced its first optical drive, a large external SCSI box which could only read CDs, it targeted developers by shipping all its developer tools and support materials on free CD-ROMs. Instead of moaning at how useless this new drive was, every developer was induced to buy one, and to discover its potential.

Removing old hardware is tougher. When Apple started to drop optical drives from Macs in 2012, it already had a smaller and cheaper external drive which could bridge the gap. When the headphone socket was removed from iPhones in 2016, to great outcry from the press, Apple had to provide an adaptor to cushion that change.

In software, Apple often manages change by the process of ‘deprecation’, warning that old features are going away in the future. This should give developers the time to transition to a replacement, and when managed well users won’t even notice what has happened. That only works when developers co-operate, have somewhere else to go, and sufficient time to go there. What Apple sometimes seems to struggle with is keeping the user rather than engineering at the centre of change.

One example of how Apple hasn’t managed change well is with traditional resource forks. Stemming back to the earliest days of the Mac, they had been supported in OS X until 10.8, when Apple decided to deprecate most of its tools for accessing and managing resource forks. The need for those tools hasn’t gone away though, and even in Catalina, Apple’s own Script Editor still seems to rely on them. Save an AppleScript as a .scpt file in Script Editor, and Apple’s own code continues to write a resource fork to the file.

In this case, telling developers to stop using deprecated code poses them an impossible problem, as Apple’s own app demonstrates so well. It’s like telling carpenters to stop using hammers when they’re still committed to nails. What Apple would prefer everyone to do is to use a bundle with the data currently stored in the resource fork transferred into a resource file, but that isn’t a single file solution in the way that a .scpt file is.

Another example of poor change management is the yawning gap which has opened in Catalina’s Accessibility features. Mojave and earlier versions of macOS allow the user to dictate text to be inserted into a document. This comes in two variants: regular Dictation, in which conversion from sound to text is performed remotely on Apple’s servers, and Enhanced Dictation, which is performed on your Mac using additional software. For someone who is unable to use the keyboard, the latter is highly effective, and supports quite sophisticated formatting commands to insert punctuation, select text, correct it and apply styling. Enhanced dictation also includes a small vocabulary of more general commands which provide limited voice control.

I don’t use enhanced dictation, but have periodically tested it out, and have remained impressed with its word recognition, accuracy, and editing power. It is very popular with a broad range of users who find the keyboard challenging, from those who have suffered RSI to many with dyslexia. The shortcoming in Mojave is that voice control is far too limited. If you aren’t able to use conventional input devices, macOS 10.14 doesn’t offer a good alternative using your voice.

Catalina sets out to change this, using a new Voice Control section in Accessibility. This opens up a huge range of commands, which the user can customise to trigger their own actions and scripts by specific phrases. It can replace mouse/trackpad control of menus, divide the whole display area into a numbered grid and plant the pointer in any of those boxes, and more. It has many brilliant design touches, including numbering each item in dropped-down menus.

Where the new Voice Control features fall short is in dictation. You can still – if you don’t turn Voice Control on – opt to enable the old Dictation feature in the Keyboard pane. But Apple has removed the Enhanced Dictation feature which has been so successful and widely used. Your experience of using the new dictation available in Voice Control may be very different to mine, but I was coming close to needing anger management classes in the few hours that I grappled with the new feature. In the end, I had to switch it to using US instead of UK English. As a result I am now recommending Mac users who value Enhanced Dictation shouldn’t upgrade to Catalina until it can at least match a dictation feature as good as Mojave’s.

There are other examples of Apple’s recent changes leaving users wondering why. Perhaps the most overt is in continuing to sell iMacs configured with internal hard disk, knowing that booting Mojave or Catalina from a rotating disk is not, and never will be, a wise choice.

Too excited with its engineering advances, Apple has forgotten the many Mac users for whom features like enhanced dictation have been such a boon. Knowing that much of its business relies on change, we should expect Apple to keep the user at the centre of change processes.