Major Windows updates used to happen every five years or so, and could take a couple of years to roll out across a large enterprise. Today, Microsoft issues major updates annually, and only supports older versions of Windows for 30 months. Organizations have no choice but to deploy Windows 10 updates every year.  

Managing Windows 10 updates has always been a challenge for any large enterprise, and it’s even more complicated now. The sheer number of endpoints, devices and environments has grown exponentially. And, let’s be honest, deploying a Windows update to 5,000 employees across multiple office buildings was difficult enough, but now you may be deploying that update to 5,000 employees in their homes – each with a different equipment and bandwidth.  

Most enterprises can’t take the risk of deploying a Windows update without extensive testing of critical applications, careful planning of deployment waves and careful execution. To take this careful approach at scale for every annual update, enterprises need to automate as much of the process as possible.  

There are many tools on the market designed to facilitate updates, but which Windows 10 deployment tools do project managers most need to understand?  

The available tools 

You’ll find quite a few Windows 10 deployment tools – many of them from Microsoft. The work these tools do falls into four broad categories, with many tools in more than one category: 

• Systems management tools, which include configuration managers, endpoint managers and inventory platforms. These will scan your company’s devices, create an inventory of hardware and installed applications, and deploy updates or new software. You may also use these tools to request periodic deployment success/fail reports. Systems management tools include BigFix, Microsoft’s Service Center Configuration Manager, Altiris, Ivanti, Kace, Configuration Manager and Microsoft’s InTune.  

• Access management platforms, which include identity management tools and cloud access security brokers. Used to manage and control user access to online systems, these can help you understand which online applications and resources users need. They include Okta, MCAS and Azure AD.  

• Configuration management databases, which are the “systems of record” for inventory information. These include ServiceNow, Ivanti, BMC Helix, Cherwell and Flexera.  

• IT service management systems, which manage delivery of IT services (usually via tickets) and may also be used to create service tickets to schedule deployments. These include ServiceNow, Ivanti, BMC and Cherwell.  

• Microsoft Desktop Analytics, which helps you plan testing and pilot deployments based on installed desktop applications and drivers. However, it requires Microsoft Configuration Manager to function and will not interface with other systems management tools.  

• Spreadsheets, which are often needed to bring together data from all these other tools, as well as to track and schedule deployments.  

What these tools don’t do 

Successful execution of a Windows 10 deployment requires:

• Accurate, up-to-date data on users, hardware and software 

• The ability to do use that data to plan your deployment 

• Automated workflows and a reduction in administration tasks 

These Windows 10 deployment tools are designed more for engineers than for project managers. They automate portions of the technical aspects of Windows deployments, but leave project management to be done with spreadsheets and a lot of manual data entry, correlation, planning and reporting.  

For instance, while systems management tools scan your network and report back what is connected, they aren’t usually able to figure out where connected devices are geographically located, who uses them or which business unit they belong to. This information often has to be manually cross-referenced with data from a configuration management database – which may rely heavily on manual data entry. Then, the cross-referenced information is usually added to a spreadsheet.  

Plus, network scans are only a snapshot in time. As employees join the company, leave or move to different departments, these spreadsheets have to be constantly manually updated. Add to this keeping track of hardware lifecycles and lease expirations – which none of these tools integrates into your deployment data or planning – and you have a labor-intensive process. 

These tools also don’t handle communication or really any interaction with users, which is a critical part of any project. Communicating with users, dealing with questions and support issues, and keeping managers updated on deployment progress can take a significant amount of a project manager’s time. So can scheduling done manually through spreadsheets or IT service management systems tickets.  

Reporting is also a largely manual process with these tools. Systems management tools can generate periodic deployment success/fail reports, but to report on deployment progress based on factors these tools don’t track – such as business unit or physical location – records need to be cross-referenced, usually in a spreadsheet. Any reports typically have to be manually “translated” for managers and executives to consume. You have no real-time visibility into your project’s status. 

All this manual data entry, updating and coordination doesn’t only make Windows 10 updates costly and time-consuming. It also makes them risky due to inaccurate and missing information or accidental human error.  

The ReadyWorks approach to Windows 10 deployment tools 

Without a high level of reliable automation, your entire IT budget for every year could end up being spent just to maintain Windows. ReadyWorks breaks the paradigm of needing to budget for thousands of hours of work – whether by in-house staff or external consultants – to deploy Windows updates. It correlates data and activities from a variety of Windows 10 deployment tools to allow you to automate both the technical and project management parts of the process.  

Through data correlation, systems interoperability and automation, ReadyWorks can cut the time your teams spends on manual data entry and reporting by more than half. You can complete a deployment in several weeks, rather than in several months. Plus, less manual data entry and fewer errors mean deployment costs are reduced by at least 40%.  

ReadyWorks allows you to take a more granular, conservative approach to Windows 10 deployments without spending a fortune in time and money. It: 

• Uses data from multiple sources to help you assess your users, equipment and applications. 

• Facilitates extensive, controlled testing of critical applications before roll-out. 

• Facilitates deployment waves that allow you to continue testing critical applications. 

• Within your planned waves, automates users’ self-scheduling of their deployments.  

• Works with systems management tools to automatically deploy updates at the times users schedule.  

• Offers a constantly updated, easy-to-understand dashboard showing deployment status. 

• Creates a detailed audit trail showing that all systems were updated properly. 

ReadyWorks tells systems management tools when to inventory a computer and when to deliver software or updates to each user or device. It works with access management platforms to see which online applications users are accessing and reports this to you. And it brings together data from those two types of tools with information in your company’s configuration management database to give you an accurate picture of which applications users regularly access. ReadyWorks helps you get an accurate, up-to-date picture of which applications are most critical – including grouping usage by department, physical location or other factors.  

Going a step further, ReadyWorks integrates lease information with all your other information about users, applications, departments, devices and locations to automate decision-making about which devices not to update as they approach the end of their lifecycles. 

Armed with accurate and current data gathered from a variety of Windows 10 deployment tools, ReadyWorks helps you plan, execute, constantly monitor and report on your deployment. This includes coordinating the application testing process, automating communications with users and their managers about Windows 10 deployment plans, creating deployment waves that match your company’s needs, facilitating users or managers scheduling deployments, reporting on progress and more.  

You can ditch the spreadsheets, manual data entry and hours of creating reports by hand for an automated, single source of current data and a command and control platform that allows you to drive your migration.  

Learn more about how ReadyWorks can make Windows 10 deployments easier, faster and more successful.