The crucial key to deploying Windows as a service

Jan 30, 2017   |  

If you’re thinking about moving your company to Windows 10, chances are you have questions and lots of them.

How disruptive is this going to be? How long will my employees be unable to work? Will my applications keep working, especially the handcrafted, legacy ones? And why all the fuss about Windows as a service?

“These are some of the same things that I talk to customers about all the time,” says Robert Van Winkle, a principal program manager who leads the team in Microsoft IT that deploys Windows 10 to the company’s 114,000 employees.

There are answers to your questions, but first walk with Van Winkle as he explains the transformation Microsoft IT had to go through before it could start deploying Windows as a service.

The team had to reboot the way it thought about deployment in the first place.

“We had to change our mentality around Windows adoption,” says Van Winkle. “We had to move away from a waterfall, major project deployment approach, and shift to an agile model.”

That meant preparing to deploy continuous updates, small ones all the time and bigger ones every six months or so.

For Microsoft IT, it was a big job (and a big change from deploying our flagship operating system every three years).

Microsoft IT manages more than 250,000 global machines (which includes employees, vendors, and test machines). The only way to continuously deploy at that scale is to do small proof of concepts and pilot deployments, learn from those, and then deploy broadly, Van Winkle says.

In other words, be agile.

“Now we’re doing small proof of concepts and pilots all the time,” he says. “This allows us to validate user and IT pro experiences as we bring updates to the operating system online.”

For example, consider Windows Hello, a major security feature in Windows 10. It allows you to log in using your fingerprint or face, a first step in getting away from using passwords. Van Winkle’s team and the Information Security team in Microsoft IT deployed it to a small group, iterated and made sure it worked, and then rolled it out to a cadence of larger and larger groups of employees. Learn more about how Van Winkle and other IT professionals deployed Windows at Microsoft by checking out this Microsoft IT Showcase case study.

Equally important, says Van Winkle, is to get your early adopters excited about what you’re doing. At Microsoft, our early adopter community is called Microsoft Elite. Through gamification, Elite members have access to several early builds of the operating system. They are also among the first to find bugs and provide feedback for many of the applications and programs that we eventually deliver to all of our employees.

“You need a core group of early adopters who are willing to do this,” he says. “They will end up letting you know what’s working and what’s not working through moderated forums and Yammer. They will also will be your biggest voices to articulate the benefits of the new technology with other users as you go broad.’”

Van Winkle knows that many people considering deployment spend a lot of time worrying about what will happen to their applications, especially their custom ones.

To that end, Microsoft IT adopted a new process for making sure applications work the way you expect on Windows. Taking the same agile approach as before, the key is to test just 10 percent of your critical applications. Once you make sure that small handful works properly, you can count on the rest of your applications working almost 100 percent of the time, Van Winkle says.

“Testing just a small sample size has worked, and worked very well. It ends up being a surprisingly accurate predicator of how well all your apps will work,” he says. “Windows 10 is very consistent that way. We’ve seen a significant cost reduction in app testing.”

Learn more about our app compatibility process by checking out this case study.

To gauge how well your apps perform after deployment (give me the data please!), IT also started using Upgrade Analytics, (you can Learn more about Upgrade Analytics here.) “We started using Upgrade Analytics to replace manual testing and do application validation through the POC, pilot and broad deployment,” Van Winkle says.

Microsoft IT will keep listening to customers and asking Microsoft employees questions about how to improve Windows deployment, and then agilely iterate.

Go here to learn more about the way Microsoft deploys Windows 10, including best practices on change management and links to post-deployment training.

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