2. Is Your IT Team On Board?
If you like what you see in Windows 8.1, it's important to ask: Do you have the necessary IT skills and resources for a successful upgrade? It's a particularly critical question for the "S" in SMB, according to Forrester analyst David Johnson. "The smaller the organization, the less likely they are to have the skills and tools necessary to do a full migration of both all of their PCs and all of their applications," Johnson said in an email.
In that scenario, there's a good chance that you rely on outside IT help. Even then, though, don't just assume your provider is ready and able to deploy Windows 8, new touchscreen devices, Windows 8 apps and so on.
"It is a two-step process for SMBs, excluding very small businesses that buy from retail, of moving from operating system to another," Agrawal said. "First, their resellers have to be convinced [of Windows 8's benefits] because they will have to provide support on the new PCs."
3. Will Windows 8.1 Break Stuff You Already Use?
The second step: "SMBs will have to be convinced that Windows 8.1 will not disrupt the functioning of their [existing] accessories, networks, peripherals and applications," Agrawal said. Indeed, compatibility can be a major issue in any OS upgrade -- such headaches are a key reason why some SMBs stick with XP, for example. This gets back to those requisite IT resources: You've got to be able to test, test, and test some more. Otherwise, an upgrade could become an IT disaster.
This could be an easier question to answer if you're heavily invested in cloud applications rather than on-premises infrastructure. Compatibility challenges are often diminished -- or at least outsourced -- for those SMBs.
"Smaller companies -- especially those less than maybe 1,000 people -- can more often move into cloud-based services and other things that make operating system versions less important," Johnson said.
4. What Are Your Alternatives?
There's no rule that says an OS upgrade must be an all-or-nothing proposition. Nor does it always pay off to have the "latest and greatest" version. Do your homework. Test new devices and apps. Take time to make a well-informed decision, especially if you're already on Windows 7. For many SMBs, it doesn't make sense to pay the early adoption tax. Similarly, it doesn't make sense to write off Windows 8 simply because some people don't like it.
As an alternative, consider doing a small deployment for testing, usability and other purposes. Even Microsoft recommends this for companies happy with their Windows 7 environments. Doing so can help answer question three, for starters. "The biggest support issues come into play when the first PC with a new OS is connected to the network," Agrawal said. Beyond compatibility and productivity, this kind of controlled test will better enable you to make the right decision for your business rather than relying on vendor-speak or conventional wisdom. Of course, therein lies the burden of proof for Microsoft and Windows 8.1.
"If the process is not intuitive and smooth, and the experience is not one of delight, the use of Windows 8.1-based PCs will be stalled until it stabilizes and [IT providers] have understood all the potential problem areas associated with working on a new PC," Agrawal said. "If everything fails, the SMBs and the resellers will quickly downgrade to Windows 7 because they know it is a stable OS."