To upgrade or not to upgrade?

Last week our support desk received more than a few inquires about the Microsoft Outlook client hanging on MacBooks. What first seemed like an anomaly quickly became a fairly commonplace event for us. As the calls kept trickling in, it was evident the common denominator was El Capitan. One of our technical leaders did some research and determined that it's a widely documented issue with machines running El Capitan and Microsoft Office. More research suggested Microsoft didn't fully test their latest and greatest Office suite with the new OS from Apple.

This leaves us with little options to help a frustrated end user. Our options are simply to wait for a fix from either Microsoft or Apple (Microsoft has not provided an ETA) or rebuild the laptop to the prior state. Neither option is appealing to either the support team or the end user. At the end of the day, we all have our real jobs to do and need our laptops to be functional.

So last week I spent much time answering questions from various end users asking me why I am telling them not to upgrade at this time and to wait it out. One user said "Rob, I don't get it, you are always telling us how important it is to patch our systems, shouldn't we be running the latest and greatest OS from Apple?"

The simple answer is... well there is no simple answer actually. Our laptops are almost as vital as our smart phones, and depending on your role with the company the laptop may be the most important device you have. It is your productivity tool.  The tool you use to produce tangible output. Output that your company can monetize. So my response is to entrust your IT team to ensure your machine is properly patched and up to date with the previous release of the OS and/or applications. 

I'd submit the best thing to do is wait for the initial buzz to wear off and to follow the age old practice of awaiting the first maintenance release. I recognize this is easier said than done. I fully understand we're all curious to see what Apple, Microsoft, etc. are doing with their operating systems and applications. In fact I promise you many of those on my team have already upgraded... Furthermore, I also recognize that if we're in the business of developing software, then it is also important to begin development on these new platforms as quickly as possible as they become mainstream. So what do we do? Do we upgrade or do we wait?

This is where a little bit of reality sets in. Over time I've become a realist and understand the more we tell people not to do something, the more likely they are to do so. For those of you with children or a pet, you understand this well. Given this, I'm going to say we upgrade but with conditions.

The conditions are to partner with IT to develop a strategy for testing new OS environments (IT, this means you have to be completely open to allowing the end user to do things you may not ordinarily permit). The conditions also must embrace an approach that if things go horribly wrong, you're going to have a plan to be up and operational as quickly as possible. In support of these conditions, I recommend the strategy will embrace running a hypervisor on your laptop so you can run virtual machines designed for testing. This will afford you the ability to run the latest and greatest OS while not corrupting your primary machine's image.

Trust me, I recognize you don't want to go to your manager and explain why you missed your deadline on that new software build. At the same time, I don't want to explain to your manager why you lost productivity due to being unable to use your laptop.

My commitment to you as the head of IT is we need your help here. I look forward to working with you!