You've no doubt heard the buzz that the end of support for Windows 7 now has an imminent date: January 14th, 2020.
So if you're still on Windows 7, you have between now and then to upgrade to Windows 10. Seems like plenty of time, right? We've talked before about why it's such a painful process for people. But let's revisit some of those reasons now so that you can understand the actual process and learn how to make it (practically) pain-free.

*If you're still not convinced, listen to MVP Greg Shields along with 1E's Steve Campbell as they discuss the reality of Windows 10 Servicing in an on-demand recording of their Fireside Chat courtesy of Redmond, this Wednesday.

The Five Phases of the Windows Servicing Process

Because Windows 10 will keep IT teams in a constant state of the rollout, you’ll cycle through these phases over and over – and sometimes be at two stages at once for different feature updates.

  • Hardware & Software Inventory & Analysis: who’s using what, where and how – discovering which apps are Windows 10 ready and which aren’t.
  • Assess & Prioritize: Plan any remediation work that’s required before you upgrade.
  • Ready: Confirming hardware, infrastructure, asset, application and business readiness before you proceed.
  • Schedule: For end-user communications, self-service upgrades and manual upgrades.
  • Deploy: Push/pull the actual upgrade.

Then it’s on to next Service update – back to Inventory & Analysis.
It’s important to establish a long-term deployment strategy. Options are:

  • Stay on the Long-term Servicing Channel: Only consider if you don’t care about OS feature updates for the next few years. This is not a common choice.
  • Deploy every release to all assets: This is best suited to smaller organizations – keeps you in a constant 6-month upgrade cycle.
  • Skip a release for all assets: Best suited to larger enterprises – but keep in mind that feature updates expire, so if you skip one, you may have to accelerate the next before your earlier version goes end-of-life – for this reason, many large organizations choose to deploy every release.
  • Phased releases for asset groups: Best suited for the very largest enterprises – with 30K seats or more.

Five things you can do to alleviate the headaches of Windows 10 Servicing

As you can see, IT teams will have to greatly accelerate their deployment velocity in a Windows 10 environment. This is not only a cultural change, but also may require new skills for your IT staff. With that in mind, here are five things you can do prepare:

  • Change the way you think about managing Windows and apps – in today’s security-aware world, you must be proactive about staying current.
  • Define your Windows Servicing and deployment strategies as outlined above and get business buy-in.
  • Budget and create a function in BAU with responsibility for managing the Windows Servicing process. Create a roles and responsibilities matrix to show who needs to do what and when to remain in the cycle.
  • Define your end-to-end timelines and workflow for Windows/desktop as a service.
  • Put tooling in place to support your repeatable process:
    • Continual Assessment
    • End-To-End Process Support
    • Application Testing & Remediation Workflow
    • Self-Service Deployment

To learn more about Windows 10 and Windows 10 management, don't miss this exciting tech talk this Wednesday!