This was the first time UIT delivered a major OS upgrade remotely. New technology helped, but it was our dedicated team members who made it a true success. From design to deployment, the project team kept the focus on the community and ensured they communicated early and often, solicited and actioned on feedback, and offered personalized scheduling and support when needed. The best upgrades go unnoticed, but it's important that we take a moment to reflect on the lessons we learned (especially the positive ones) and celebrate the accomplishments that brought us to where we are today.

Phase 1: Design

The design phase involved multiple groups coming together to share what has and hasn’t worked in past deployments and to apply those lessons to create a new strategy centred on delivering the best possible experience to our community.

The project’s success was due to its teams, but more importantly, to the incredible individuals who make up those teams. The following people were instrumental to Phase 1’s success.

CTS were among the earliest adopters of the new OS, taking the initiative to test and familiarize themselves with what would quickly become the new normal. As that early work progressed, CTS partnered with OEWB to help shape the design approach. OEWB promptly assessed the impact of Windows 11 on the 91��ɫ community, confirming the upgrade as a critical technological change. They also collaborated with Employee Relations to keep YUSA staff updated throughout the project. Infosec was responsible for creating our Windows 11 security baseline and ensuring it aligned with the Center for Internet Security (CIS) benchmarks. WTS identified the compatibility and readiness of core Infrastructure services and business-critical software applications. They also designed standard OS images and automated the migration and upgrade workflow from Windows 10 to 11. Together, their teamwork set a strong launch pad for the next phase’s successful rollout.  

Phase 2: Deploy

If a traditional OS upgrade wasn’t already hard enough, the Windows 11 deployment was complicated by Microsoft’s tight support deadlines and exacerbated by the new challenge of remote deployment. CTS not only met these short deadlines but ensured the pace of work didn’t leave the community’s needs behind. The secret to CTS's success was their conscious effort to deliver human-first customer support; throughout both phases of the project, CTS acted as the community’s voice. This included an early-and-often approach to communications as well as a form-based feedback mechanism used to gather community information and input. You may even have received one of their forms asking you to join the early adopters or to provide feedback on the apps you use.

CTS did an incredible job scheduling and executing the rollout stages. They created customized adoption schedules based on end-user role responsibilities and organizational needs, while avoiding peak periods for key resources. The team also scheduled key blackout dates during which critical systems wouldn’t be touched. They started small with an initial deployment of 40 people, and steadily expanded outward. This phased approach allowed the team to scale support, control early issues, validate the rollout process, and apply valuable lessons before moving to the broader community.

Kudos

The upgrade would not have been possible without Rick, Jeremy, and Prabhjot from CTS. They oversaw communication, scheduling, troubleshooting, and the implementation of changes. While known for their incredible operational work, the CTS members stepped into the project lead and team roles and shone. That meant the rest of the CTS team had to step up and cover for their team members, and so our first Kudos goes out to the too-oft-unsung operational staff doing the good work of keeping the lights on and the macro-machine that is 91��ɫ running. Thank you to Jeffrey Ciprian, Paul Clack, Jeff DeRosa, Akhil Justin, Alireza Kharazmi, Akash Mahmood, Ninara Sada and Liana Simons for taking on the extra work to make this success possible.

“With proper planning, deploying smoothly to the whole community (over 4000 machines) is not that daunting of a task. Having grace with people who have technical debt was crucial, and was done by identifying technical limitations early on, and working with affected groups to maintain continuity of service without having unforeseen expenses. I am most proud of not needing to purchase any Windows 10 extensions.”  

Prabhjot, Microcomputer Analyst, was also integral in the Windows 11 deployment. She was thrown into the deep end of this project only a few short months after joining UIT. Charged with managing deployment schedules and maintaining communication with managers and directors, Prabhjot more than equalled her task. She showed an aptitude for adapting her communication style to fit 91��ɫ’s different team and individual needs. In any moment, she might be going toe-to-toe with our most technically minded IT workers, then switching it up to explain it to the people who couldn’t tell you what an operating system even means. Prabhjot effectively instructed thousands of remote users with high-quality, step-by-step guidance. Prabhjot demonstrated the courage and verve she has since become famous for, rising to meet a daunting challenge early in her time at 91��ɫ. A team player to her core, when we sat down to talk to her about her accomplishments and what she was most proud of, she took the opportunity to praise her colleagues:

“I am proud of the entire project. Jeremy was a great team member who constantly provided me with technical support, while Rick was there every step of the way to encourage me. I am thankful to him for giving me a chance to work on such a big project and always pushing me.”  

The crew's success depends on a steady hand at the wheel. We need to acknowledge and celebrate the man who steered the ship. CTS Manager and project lead, Rick Sambhi, led his team masterfully, keeping his finger on the pulse of the entire project. Rick led daily standups to keep his team ahead of problems that crop up on projects of this scale and ensured everything stayed on schedule. His constant support of the team and belief in them played a huge role in the project’s overall success. Rick had the following to say to his team:

"This project’s success was driven by strong collaboration, careful planning, and effective execution. With support across UIT and valuable feedback from early adopters, we were able to confidently deploy Windows 11 to the UIT support community."

The implementation was a huge success. The feedback that CTS received was very positive. We wanted to take a second to share some feedback we got back from the community. One member wrote, “Just wanted to send a note to say that I’m impressed with how smoothly this upgrade went. Ran like clockwork per the instructions that were provided. In comparison, my wife’s workplace upgraded their laptops to Windows 11 last month, and it did not go well, at least for her.  After something like 5 attempts, they gave up and just replaced her laptop.”  

Kudos to the team behind it all!

The post Human Touch in a Virtual World: The Windows 11 Upgrade appeared first on Office of the Chief Information Officer.