Moving past the obstacles when implementing a Virtualization solution is certainly the goal, and it is not easy, but it is possible. Automation tools are massively important, but people and process are key too.
For example, to manage licences properly, and to track which VMs are being used and which can be reclaimed, some type of asset and inventory registry is an excellent tool.
However, to really make this valuable, instead of just adding work manually recording VM allocations and movements, it really has to be updated automatically when VMs are provisioned and deprovisioned. This will save resources (admins don't have to manually assign and collect VMs and licenses), save costs (licences can be more easily reused instead of adding new license costs), and help expand virtualization deployment and maturity (admins can move onto virtualizing more complex systems, rather than just babysitting existing VMs).
However, it is also important to address the people & process issues, not just the technology issues. For example, you have to make sure that IT admins and even VM owners don't deliberately find 'workarounds' for the asset registry that might make their job a little easier, and maybe even save their department some money, but which actually end up costing the wider company a lot more in terms of compliance breaches and increased license costs. It is also critical to make sure there is a clear, known, and easily accessed process in place (ideally one which is automatically enforced) to work with VM owners/requestors to identify and deprovision VMs that are no longer in use. This will make sure the technology benefits accrue as expected, but also will simplify some complex and problematic VM management activities.
As to where you start, a lot depends on existing process and technology maturity, organization size, the most pressing problems, and the overall goals. Most orgs will do best to solve one problem at a time with the people they have - perhaps managing VM performance, or controlling licenses, or automating provisioning. But very mature orgs will likely be able to do more up front, like implementing a service catalog and service desk approach to automated provisioning and deprovisioning, or even combining this with resource pools and self-service to start on the journey to cloud computing. Meanwhile, smaller orgs will probably need to bring in experts at least temporarily to help them get over the hump, as they are typically harder-pressed to skill up and resource in-house for such significant IT changes.
Finally, yes, I absolutely believe this will be an in-demand skill for years to come. The evidence is already there, in the higher average pay rates for administrators with virtualization certifications, and I think this will continue. Administrators and managers that can effectively harness tools, processes, and people to overcome virtual stall will end up driving advances in virtualization - not just increasing the number of VMs deployed, but improving their virtualization maturity. This in turn will drive not just the incremental (albeit short-lived) CapEx savings from server consolidation, but also to fundamental and long-term gains in OpEx reduction, business agility, service availability, continuity, and more that comes when virtualization (and cloud) transforms from a tactical IT project to a strategic business enabler.
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