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You may not be poised to migrate your users to Windows 10 just yet, but you can benefit from conducting a pilot program now to uncover the pitfalls and determine your best-case deployment.
Migrating an organization to a new operating system takes time and costs money. Historically, that's why many businesses have settled on an every-other-release upgrade plan.
Beginning with Windows 10, that option is no longer on the table. In the Windows-as-a-service world, you get to do one last "big bang" upgrade. When that's complete, feature upgrades will arrive at your users' desktops along with security updates and bug fixes.
This continuous-delivery software model is uncharted territory for most IT pros. I've already gone on record as suggesting that businesses wait for a year to deploy Windows 10. But that doesn't mean you should just ignore it until after New Year's Day.
Nothing is more effective than real-world experience at making the case for change (and smoking out potential compatibility and deployment issues). That's why I recommend that organizations begin small, focused pilot projects to test Windows 10 within their organizations.
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If your IT infrastructure is built on Windows, you need to be thinking right now about when and how to move desktop PCs and mobile devices to Windows 10, either as part of the hardware refresh cycle or as upgrades to existing devices.
Here's what to focus on during a pilot project.
Mix up the update tempos
For most IT pros, the instinctive reaction will be to focus on the most conservative option of all—the Long Term Servicing Branch, or LTSB. That's the option that is closest to the current model, letting you set your own pace for those pesky feature upgrades.
Microsoft added the LTSB for mission-critical devices, and you shouldn't have any of those in your pilot program. So instead consider letting most of your pilot users run on the Current Branch, getting feature updates as they're delivered.
In fact, why not consider enrolling some of your advanced pilot users in the Windows Insider program? They can help you get an early look at new features as they arrive in preview releases.
Try the latest hardware
Some important features in Windows 10 require specialized hardware. The rootkit-blocking Secure Boot feature, for example, requires UEFI firmware. If you're testing on an older PC with a conventional BIOS, you won't be able to use Secure Boot.
Only a handful of devices today include the biometric hardware to support the Windows Hello feature. The Surface Pro 4, for example, is equipped with the infrared camera required to enable signing in via facial recognition. It's almost magical to watch this feature at work, and it's a tremendous relief not to have to type a complex password over and over. If you can find hardware that supports Windows Hello, I recommend seeding a few units to some of your pilot members so you can get their feedback on it.
The setup options are in Settings, under Accounts, as shown in Figure A.
Add a cloud-based directory
Azure Active Directory is a remarkably easy way to add authentication services to manage devices. If your organization uses Office 365, setting up matching Azure AD accounts is a great way to let people sign in automatically.
You'll find the option to join Azure AD in the Accounts section of Settings, as shown in Figure B.
The basic feature set of Azure AD is free. Turning on paid Azure AD features (Basic and Premium options are available) offers single sign-on for Azure and Office 365, as well as for popular cloud-based applications like Box, DocuSign, Dropbox, Google Apps, Salesforce, and ServiceNow, among others.
Test deployment tools, too
Most big organizations are used to deploying Windows by building standard images and then wiping new PCs and loading those images.
You can still do that, but there are newer alternatives that make the process less disruptive. In theory, you can build deployment packages that allow you to modify the OEM Windows installation instead of throwing it away completely.
Microsoft is delivering its deployment tools using the same "as-a-service" development model as Windows itself, so you can expect to see new deployment features regularly as well.
The unique challenge of a Windows 10 pilot project is that the thing you're testing is changing at regular intervals, as are the apps and cloud services that run on Windows. One of the most important things to take away from your pilot program is how to help people adapt to that faster pace of change.