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Navigate the Microsoft roadmap and keep IT pros challenged

Microsoft wants Windows shops to get on board with all of its latest technologies. But that ideal doesn't always mesh with the realities that admins face.

IT managers face multiple challenges. Not only do they need to migrate applications to new server OSes or deploy new web servers, they also must retain a troupe of talented Windows administrators -- despite financial limitations.

Many Windows-based system admins and IT pros typically land in three camps -- those that stick closely to the Microsoft roadmap, those that try to stay afloat with specific upgrades and those who sit back and wait for the hype to cool. And while most shops find themselves in the second camp, their highly qualified IT workers will seek out other -- more exciting -- opportunities.

Shops that hug the Microsoft roadmap

In Microsoft's perfect world, all the engineers in its environments would be PowerShell MVPs, know how to work with the latest server OS and freshly baked tools from Azure, and find ways to ramp customers into the cloud to cut costs and improve agility. This group of early adopters is familiar with Microsoft's latest technologies, and will implement them upon release.

These organizations cannot wait to get out of the data center. Usually, they provide applications and services across a wide range of cloud providers and will crank out new services for any platform a customer uses. There are not many companies that change platforms quite that fast, but there are probably a few who want that new whiz-bang feature for development.

Microsoft -- and many who work with the company's offerings -- would love to move everyone to the cloud, giving users access to the latest technologies. There are potential savings with hardware and compute on demand. The cloud promises more flexibility for companies that need to scale up and scale out quickly.

The move might be more cost-efficient, but many businesses need a proof of concept that showcases that the benefits outweigh the drawbacks.

Companies that partner with Microsoft are usually close to, if not falling over, the edge -- they want to keep engineers knowledgeable on the latest Microsoft technologies. This benefits customers -- someone has to know how to implement features, such as Storage Spaces, and do it in a timely fashion. In addition, administrators can lean on the partner instead of paying for additional support from Microsoft.

But, in reality, a business must consider the benefits of a cloud migration and how it affects the bottom line. The move might be more cost-efficient, but many businesses need a proof of concept that showcases that the benefits outweigh the drawbacks.

Shops that work with what they have

Certain shops have fallen off the Microsoft roadmap; these organizations rarely, if ever, upgrade to a newer version or technology. They use what works until it doesn't work anymore. These shops cannot move an old application to a new platform for a number of reasons, including support requirements.

For other organizations, systems work as they always have in the past, and that's good enough. Some admins fear change, and many end users prefer to remain comfortable with the status quo.

Companies have various reasons to reside in this camp. But, typically, it boils down to money. It can be expensive to get a legacy application to work on a newer server OS or to upgrade the hardware that cranks out the widgets, so they choose to leave things as they are.

Shops that upgrade -- eventually

Many organizations fall somewhere between cutting edge and status quo. These businesses move technology forward as they need to -- or as their budget allows. But they do so at a controlled pace to appease employees, users, shareholders and IT teams.

Technology professionals need to find the middle ground and work to keep organizations on a forward path. They must ensure businesses are far enough ahead of the end-of-support lifecycle to avoid trouble as products fall by the wayside.

Microsoft realizes some customers cannot afford to follow its roadmap and immediately move to the latest technologies due to either financial or business constraints. For IT professionals who need to keep customers and their applications running, this is both a blessing and a curse. Legacy technology, with its predictable quirks and behaviors, enables IT to provide long-term support. But that stick-with-what's-comfortable mentality often prevents the organization from changing gears to take advantage of benefits that new tools and services can bring.

All shops should make IT staff feel important

Businesses that support legacy technologies should make time for IT staff to work on compelling tasks that can expand their skill set and make them feel valued. There are plenty of organizations that require Windows Server 2008 R2, but that might not use advanced features, such as BranchCache and DirectAccess. Give admins a project to put these technologies into production if they can help reduce the number of help desk tickets.

PowerShell is another established technology that administrators can learn to automate tasks on Windows systems. As Microsoft builds on PowerShell's interoperability features, admins can lean on that expertise to manage Linux servers and cloud resources.

Make room for newer Microsoft technologies to keep talented IT personnel engaged. For example, administrators can implement the Server Management Tools suite, a free, Azure-based remote management service, to gain experience with Microsoft's cloud platform.

These measures won't pair administrators with the latest technologies, but they should nudge them into more compelling areas. And that can benefit the organization as a whole.

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