I am still occasionally amazed how, 16 years after the internet became mainstream, big technology companies, household names, cannot seem to get it right.
First in the dock: Microsoft.
I've just moved my client to Office365, from hosted Exchange and Sharepoint. Sharepoint Live, Sharepoint in the Cloud. How easy could it be? You have a widely used browser-based collaboration tool, with all the usual web content management tools and trickery. A web tool, and you're making it web-native. You just need to 'cloud' it. All the usability, without all the server admin hassles. A win-win, surely.
But, no. It's a servER, not a servICE. So to put it on the cloud would involve, well, rewriting big chunks of it. And rather than do that heavy lifting, we'll just mutter on about 'cloud' and shove it up there with some key features stubbed out. Not hidden, mind: stubbed. You can select them, but the computer says no. Despite being a tool that allows people to make collaborative web sites, it is not a web native, but a web immigrant, with a poor grasp of what it is to be truly web-based. It means, for instance, that if something doesn't work, don't show it. Web services are constantly live, so when you fix it later you can just make it available. People don't need to see your under construction bits. They can be there for you, but easily hidden from users. Web native companies know this and use it often (eg. For A/B testing).
Case 2: Office Web Apps. They are the office apps (Word, Excel etc.) but in your web browser. That must mean any web browser, right? I mean they wouldn't be very 'webby' if they didn't work in any web browser. The browser wars stopped in 2004, didn't they? Alas, no. Web apps only really work properly in Microsoft's Internet Explorer - particularly OneNote, which is probably the least complicated app of the suite. So if you own a mac, tough. Same goes for the Microsoft Partnership website, actually: if you try using that (arguably critical to their business) website, you'd better not be using a mac or (ptooey!) one of the other browsers.
You cannot call yourself a web company unless you are browser (and, ideally, platform) independent.
Microsoft has to lose the parochial software dominance mindset if it is to truly transform to a web native. Sure, you used to be dominant, now stop trying to lock people into your platforms and focus on being better than the rest.
Second in the dock: Apple.
I recently downloaded the new iTunes. The old one worked perfectly fine, but evidently was not as good at selling their content, so now it's less about a tool to manage your media, and more a shopfront for urging you to buy content.
What's more, you can't sync your phone with iTunes and iCloud. It's either/or. So all those playlists and albums you had synced. If you switch to iTunes Match you'll have to sync them all over again, over your wifi and Internet connection, which in my case is 2Mb and took about 4 hours. At the end of that I still can't easily tell what synced and what didn't because the little cloud icon next to each song is gone.
So, Apple, you've done it again. For a while there you had us all thinking it was about us, but now it's coming back round to all being about you. Maps: I've blogged about it already. iCloud and iTunes Match: these are designed to lock us into your devices, not beat the competition on an open playing field through simply being better for users. It's now worse for users, and you're relying on their tolerance (or laziness) rather than their preference. That approach has an expiry date.
The web is all about connectivity and freedom of choice. You might be able to captivate, but don't try to capture. It's a short-term win, and if you're about the long term then you have to compete every day, like the rest of us: being better by enabling choice, not by restricting it. The companies who get that are web natives, and successful immigrants.
As any immigrant will tell you (speaking as one), block your assumptions and learn to think like a local; only then will you be able to fully exploit both your old and new lives.