Interview: Evolution of Win Mgmt



Enterprise IT has changed a great deal over the last couple of decades. The job of the administrator has evolved from having god-like control over users’ workstations to managing applications running in the cloud and devices that are not company-owned. Microsoft System Center is now a popular platform for managing both on-premises and cloud-based assets. Those of us who have been around for a while in IT may still remember the platform’s origins in Systems Management Server (SMS) whose initial release in 1994 allowed for the management of systems running Windows NT Server, Windows for Workgroups and MS-DOS. SMS then grew and evolved into a whole suite of tools and will soon be enhanced even more in the upcoming System Center 2016 released described here.

To gain some insight into where Windows management has been, where it is now at present, and what might be coming for us ahead in the next few years, I recently interviewed System Center expert Mike Long. Mike currently works for Windows Management Experts (WME) as a consultant providing client services for Configuration Manager, Service Manager, Operations Manager, Orchestrator, Virtual Machine Manager, OSD, patch management, architecture, migration and troubleshooting. Mike has deep experience engineering and supporting large IT infrastructures and has been responsible for the design and implementation of SCCM hierarchies upgrades/migrations and new installations for a number of different clients. You can find out more about Mike on LinkedIn at

The Interview

MITCH: Mike thanks for taking some time out from your busy job to allow us to interview you here on

Michael: Thanks for having me, it’s nice pull my head out of the computer every now and then and contemplate the industry.

MITCH: Mike you currently work for Windows Management Experts (WME) and the stated mission on their website is to “transform operations through the development of solutions and products that make the job of an administrator easier.” It seems to me there’s a compelling business case for such solutions as the job of the typical IT admin definitely seems to have gotten harder in recent years, would you agree?

Michael: Sure, the tools are developing at a rapid pace, and capabilities seem to expand every month. Keeping your skills up-to-date to keep pace with the technology is a constant and ever increasing challenge. But, it’s fun! In my field, the tools are getting better and better! As a consultant for WME, my clients’ needs to span a wide range of System Center technologies and it’s my responsibility to be able to address a broad spectrum of needs. For example, moving things into the cloud has created immense and ever changing capabilities and learning curves. MS Azure and Mobile Device Management (MDM) are probably the best examples. With Azure, you have immense data center capabilities at your fingertips, but developing expertise is a challenge because it’s a continuously expanding platform. The challenges with MDM are similar to herding cats because user devices are typically unmanaged and come in all shapes and forms. User expectations are that they can access corporate resources from whatever device available.

Since I am not typically engaged in the day-to-day admin work, I am able to stay abreast of developments in the industry and provide the needed solutions.

MITCH: Tell us in your own words how you’ve seen IT operations/management evolve since you began working in this area of IT.

Michael: Well, I’ve been around for a while… IT support has gone from desk side visits to remote management. The early tools for remote management were difficult to use and had limited capabilities. Over the years, they have developed into very robust, sophisticated platforms. Back in the day, IT support staff had to visit each and every PC in the company to deploy updates, applications and OS upgrades. Now, a small team can literally manage hundreds of thousands of computers, delivering patches and OS upgrades, protecting against vulnerabilities and reporting on assets, among other functions. Today, this technology has expanded beyond corporate boundaries and includes user devices of all kinds.

MITCH: What do you think are the biggest concerns enterprise IT admins have today?

Michael: Security has certainly been making big headlines in the news. Protecting corporate assets has become top priority. Providing additional ways for customers and employees to access resources makes securing computer systems more challenging. The trend to support bring-your-own-device (BYOD) has made securing corporate systems more complicated. The expectation that anything and everything is available online makes engineering secure IT systems a delicate task. Creating quality views into vulnerabilities, activities and configuration management is important to organizations with this type of exposure.

MITCH: How about admins working for smaller companies? How do the challenges they face compare and contrast with those working in the enterprise sphere?

Michael: Heroes! These folks are usually working way above their pay grades with little appreciation for their efforts and a huge lack of positive reinforcement. They are expected to cover many disciplines that in a larger organization would be represented by teams of people focused solely on a specific technology or product. For example, I had a recent client that had one person responsible for managing SCCM, SCSM, Exchange, Active Directory and application packaging. While he is a very talented programmer and technician, his workload spans an overwhelming variety of areas in which he is required to support. I was brought in to quickly set up and configure the features in SCCM that weren’t being utilized. The goal was to reduce his workload so that he could pick up where I left off and use things like MS Deployment Tool-kit (MDT), automatic deployment rules (ADR) and compliance reporting. In comparison, an admin in a larger organization has the luxury to specialize and hone expertise in a specific IT area, and has teammates with whom to collaborate and share knowledge.

MITCH: Microsoft System Center Configuration Manager (SCCM) seems to be your key area of expertise. Have you been hearing anything yet from customers about whether the upcoming SCCM 2016 release will impact their operations? Are customers looking to embrace it or will they take the usual wait-and-see approach to new releases of Microsoft products?

Michael: Things have changed a little bit with SCCM and how it’s named. In the past we’ve had releases based on the year, release and service pack (e.g. SCCM 2007, 2012, 2012 R2 SP1, etc.) and now it’s just become SCCM. Using a servicing model similar to Windows 10, SCCM’s designation for the current release changes every few months. Currently, we’re at SCCM 1602, 16 being the year, and 02 being the month the update was released.

Much of our new business inquiries are related to supporting Windows 10. It appears fairly obvious that most companies have skipped over 8 and 8.1 and are moving directly from Windows 7 to Windows 10. A typical answer that we provide is that the current release of SCCM makes it easier to support Windows 10 deployments and management.

Organizations planning to, or in the process of deploying Windows 10, and supporting mobile devices, really should be on the current release because of new features that support these areas. The upgrade process is fairly painless so I’m very optimistic that the new release will be adopted faster than in the past because of the new functionality to support Windows 10 and MDM. It’s an easy upgrade.

MITCH: Is there anything in SCCM 2016 that you think may provide tangible benefit to the average enterprise customer who uses SCCM?

Michael: In the past, upgrades to SCCM were major planning efforts and required a lot of preparation and testing. With the new servicing model, updates are delivered on a regular basis and address existing bugs and/or add new features. It’s not open heart surgery anymore. For example, the first release of the new SCCM servicing model was SCCM 1511 and had an issue where supporting Windows 10 servicing plans triggered 600+ MB of updates to represent every version of Windows 10 that has been released. When 1602 came out that issue was resolved by allowing you to filter on only those versions you need to support. The whole process has become a lot more automated even to the point where if you have an SCCM console installed on your computer, after the upgrade, the next time you open it, it automatically updates to the installed version. From what I’ve seen, Microsoft has made good use of the telemetry data that is uploaded for testing and refinement of the new version.

I like to advocate with my customers setting up a separate SCCM hierarchy for testing and development and keeping that environment in place permanently. Development, sandboxing, new image deployment, package development, can all be done in this test environment. Once the engineering and testing is complete, the updates can be moved into the production hierarchy using a migration connecter. As the servicing updates come down from Microsoft, validation of the new version can be done in the test environment and production can follow shortly thereafter. So, basically, in this scenario, you would be running two identical systems with the same bits so the vetting process can take place in a meaningful way. Isolated test environments or labs are bad because they become out of synch and not relevant very quickly.

MITCH: Is there anything you would have liked to see coming in SCCM 2016 that Microsoft hasn’t promised or delivered yet?

Michael: I believe that SCCM maintenance windows can be a very powerful tool for controlling update deployments and preventing unplanned outages, particularly in datacenter server environments. I would really like to see a maintenance window scheduling option that is tied to patch Tuesday (2nd Tuesday of the month). For example, patch Tuesday +1 day, +2 days, +5 days, etc. Currently, you can choose which day of the week, and you can choose which week in the month but, there are sometimes instances when the second Wednesday occurs before the second Tuesday of the month, like when the month begins on a Wednesday. Typically, organizations want to make sure their lowest risk servers get updates first and with the current scheduling options, you can’t consistently do that on a monthly basis.

MITCH: Where do you think this whole area of systems management is headed over the next five years? Tell us what you see in your crystal ball as far as IT operations and management are concerned…

Michael: I see three important things, which have already begun to take shape over the last few years. They are virtualization, virtualization, and virtualization. Performance issues typically associated with virtualization have all but been eliminated. Recovery and availability options are plentiful, and cost reductions are a big motivator. Microsoft Azure is a prime example of leveraging this technology, but it doesn’t have to live in the cloud. You can implement the same technology on premises for companies that desire to, or are required to, keep data onsite.

MITCH: What suggestions or advice would you give to someone who’s just starting out in IT administration? What would you recommend they spend their time and energy on learning and gaining experience with to help them advance their career?

Michael: Pursue the technologies that you are good at and enjoy. Different technologies require different skill sets and personalities so matching it up with your own skills and preferences is important. Once you are comfortable in a technology field, an important area of development is a customer focus and understanding the business that you support. To make good decisions about technology, you have to understand the organization it supports. Great technology that doesn’t fit the business needs is counter-productive. I see time and time again product selection decisions being made on “best of breed” without consideration of how that product integrates with the existing IT infrastructure and business needs. If you buy a great product and then spend multiple times more to integrate it, when a lesser product would meet the business needs with minimal integration, then it should be considered a bad purchasing decision. I’ve seen this played out over and over throughout my career.

MITCH: Let’s end by having you tell us a bit about yourself, like what you do in a typical day, how you first got into IT, whatever…

Michael: I started my career as an MBA out of college, and the organization I was working for supported my career development. At the time, IT was a growing need and an area of interest for me. My employer paid for a great deal of training and I’ve been enjoying it ever since. As a consultant, I’m constantly faced with new challenges and new tasks, which fits my personality well. I enjoy learning new things and dealing with new challenges. I also like playing the fire fighter role. When things aren’t working, my interest is piqued and my adrenaline starts pumping.

MITCH: Mike thanks again for giving us some of your valuable time. Best of luck in all your future endeavors.

Michael: Thank you, it was my pleasure. 

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