Windows 8: An “Unprecedented Opportunity” or an unprecedented missed opportunity?

I recently started a new job at a consulting firm that is heavily invested in Microsoft products. It has been nearly 13 years since I’ve worked in such an environment. While one would have to pry my MacBook Air from my cold, dead hands, I still have to use Windows on occasion to perform certain functions.

After years of using Apple OS X as my primary operating system, I decided to approach my return the “PC world” with an open mind. Microsoft has had years to address their hostile approach to users, and to steal ideas from Apple for improving the functionality of their software. I figured that I was in for a pleasantly surprising experience.

I was pleasantly surprised, but not for the reasons Microsoft was likely hoping for…

Buy a new PC? Hell no.

Starting my new job, I was asked if I would need a new PC. Sorry, quality is kind of my thing. So a Dell or an HP or ASUS is out right off the bat.

Instead, I opted to set up a virtual machine on an external hard drive using VMWare. There isn’t a need for me to be working full-time in Windows — I just need access to it occasionally.

The process of installing Windows 8.1 Pro onto VMWare was fast and easy. Previous experiences with clean installs of Windows have not been nearly as pleasant as this experience proved to be.

Next, I entered in my personal Microsoft Office 365 account credentials and crossed my fingers. And guess what? It worked! I was able to instantly download the latest and greatest full version of Microsoft Office and it all worked just fine. Maybe Microsoft has changed its approach to end users?

Unfortunately, things went downhill from there.

Authenticate this.

When I was given a username and password for my new account at work, the first thing I did was sign in on my iPhone, iPad and Mac. Simply go to System Preferences (OS X) or Settings (iOS), click on Internet Accounts, and then Exchange. I entered my new email address and then my password. Instantly my email and calendar were connected, allowing me to not just send and receive email, but all the contacts from the company directory were synced, and I could even accept and/or reject meeting requests.

Should be a similar experience on my brand new (virtual) PC, right?

No. Not even close.

I opened up Outlook, added my account details and got errors. I tried every variation of my username I could think of. I tried manually entering in server details. I looked online. I tried everything!

Several hundred dollars of tech support later…

In the end, I had to contact our outsourced IT help desk. They used a remote access program to connect me to the company network. Here’s the thing, though — it took the Microsoft-certified expert multiple attempts on multiple sessions to get me connected. Since I was watching while he took remote control of my computer, I was able to see as he repeatedly failed to get the settings just so.

Once I got connected, everything was much better, but I still have a hard time seeing the vast improvements that the latest version of Windows supposedly offers.


Image courtesy of Wikimedia

What’s the Point?

When Steve Ballmer announced Windows 8, he said that it was a bet-the-company moment. Since then, analysts say that the Windows 8 launch was the biggest commercial failure since the launch of the Coca-Cola Company’s ill-fated “New Coke.”

This was Microsoft’s opportunity to win me over. I mean that quite seriously, too. I was actually halfway considering following my friend Sean Kabo’s lead and switching to a Microsoft Surface 3 tablet as my primary work machine.

Instead, not only did Microsoft underwhelm, but Apple did a better job of connecting to Microsoft’s products better than Microsoft did on its own home turf. Are you kidding me?!

I watched most of the Apple keynote from the recent Worldwide Developer’s Conference announcing the latest versions of both OS X and iOS. There was one slide that really spoke volumes. According to Apple CEO Tim Cook, Windows 8 (and Windows 8.1) has only been adopted by 14% of users. That means that 86% of Windows users are using seriously outdated operating system software. Considering that Windows 8 was launched on August 1, 2012, that is positively frightening, considering that older versions remain much less secure than current versions.

Contrast that number with another fact that Cook shared: 51% of Mac users had the latest version of the operating system, OS X Mavericks, just eight months after launch.

Oh, and one more thing… the latest version of OS X (Yosemite) will cost the same amount as the last version did: $0.


Image courtesy of Wikimedia