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Should in-house staff or consultants handle Windows Server 2016 upgrades?

Is it better to approach a potential Windows Server 2016 upgrade using in-house staff, or should we seek the help of consultants?

A new version of Windows Server is coming, so organizations should do what they can to get a head start on the...

upgrade process. Actual justifications and planning will vary dramatically and often depend on each organization's size and needs. But organizations must learn the product early and weigh costs and logistics involved in an upgrade in advance of Microsoft's promised Windows Server 2016 release.

But there are two spheres of discussion here. Should your IT staff master Windows 2016? And should your in-house IT staff have the sole task of installing or upgrading the enterprise to Windows 2016?

There is no question that the IT staff should learn and master Windows Server 2016 along with any relevant systems management tools. Operating systems (OSes) form the foundation of any production environment. OSes include bare metal hypervisors such as VMware ESXi or Hyper-V, along with the OSes on legacy physical servers, OSes on all of your VMs and the OSes shared among container instances. Nothing runs without an OS, so it's critical that in-house IT staff is comfortable with installing, configuring, managing and troubleshooting OSes -- this eventually means Windows 2016.

But positioning an IT staff for Windows Server 2016 isn't free or easy. Learning requires initiative, resources, time and money. The initiative starts from the top -- usually from a CIO or an IT executive -- which outlines the mandate to prepare for a Windows Server 2016 upgrade. Management can facilitate most learning goals by providing a budget and the logistical latitude to set up a dedicated test lab for learning. Existing operating system knowledge is largely transferable, and staff can use technology previews now (and the actual release later) to practice working with Windows 2016 deployments, setups and configurations; they can even see how existing workloads integrate with the new OS. Take notes and share ideas. It's unlikely that an experienced IT staff should need formal training for Windows 2016, but classroom-based training may eventually become available if it's needed.

Calling in the experts

Just because the in-house IT staff should master Windows Server 2016 doesn't necessarily mean that they're the best choice to implement the actual OS upgrade plan in 2016 or beyond. In-house IT staff will probably be adequate for small or midsize organizations with a smaller number of servers or workloads to upgrade.

Your IT staff has a lot to do. There are other pressing projects to work on and many daily fires to fight. Huge OS upgrade projects may be too time-consuming or disruptive for the in-house staff, even when done in smaller phases. Your in-house staff may just need to keep the shop open.

If the scope or complexity of a Windows Server 2016 upgrade is too burdensome for your IT staff, it may be necessary to hire new staff or seek help from qualified consultants or contractors.

Staffing up with temporary talent can mitigate some of that strain, but it might be more effective to engage local value-added resellers or consultants to help with large OS upgrade projects. This allows several senior IT staff to manage the upgrade project and oversee the contractors who possess any additional expertise or workarounds that can be shared with the in-house staff. The expense of a knowledgeable contractor's engagement may prove less costly in terms of a faster, less disruptive OS upgrade process.

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This was last published in July 2015

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Would you choose in-house staff or an outside consultant to handle a Windows 2016 upgrade?
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We typically choose in-house staff to perform an upgrade, and will most likely do so for Windows Server 2016. Like the article says, in-house IT staff are going to need to learn and master Windows Server 2016. They will have time to learn, starting before we begin rolling it out in our lower environments. We then generally spend a good amount of time working with it in our lower environments before we make the move to the production environment. If, during that time, we identify the need to being on contract resources we can do so.
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The answer, I think, is that it depends on many factors. As the article points out, in-house staff will need to learn and master any new OS, regardless of whether or not they will be the ones deploying it. But in the end, there is no one best answer, and the decision to use in-house or contract resources needs to be answered based on the in-house expertise and experience levels, available resources, organizational size and structure, and hundred other variables.
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