With Windows 10 support ending in October 2025, Kiwi organisations are under pressure to ensure a smooth, secure, and future-focused transition.

We sat down with Rob Baird, Modern Workplace Architect at Cyclone, to talk through what CIOs, CTOs and IT Managers should be thinking about, before, during and after their Windows 11 migration.

For CIOs: Budget, Risk and Lifecycle Strategy

For CIOs, Rob says, the focus is squarely on risk, costs, and lifecycle planning.

“No CIO wants to face unexpected budget blowouts because half their fleet turns out to be incompatible. The priority should be ensuring your devices are being life cycled correctly,” he explains.

He notes that risk and compliance also come into play, especially where legacy or line-of-business software is involved.

“There’s always going to be that one critical app that quietly depends on Windows 10. It might be tied to your ERP, or something equally major. CIOs need to know what can and can’t run on Windows 11, and whether it’ll still be supported post-upgrade.”

For CTOs: Modernisation and Architecture

Where CIOs are thinking cost and continuity, Rob says CTOs are more likely to zoom out and look at long-term architecture and modernisation.

“Windows 11 migration is about more than just upgrading an operating system. It’s a chance to modernise and ask whether your current tools and processes are still the right fit.”

CTOs will likely be reviewing their device management tools, exploring cloud-first platforms like Intune, and validating whether their current model supports hybrid work and security at scale.

“You’re looking at enterprise architecture, how you’re managing endpoints, whether it’s the most modern way for your org, and what the impact will be on firewalls, networks and your security posture.”

He also flags the importance of identifying hardware compatibility, critical app support, and building in visibility for reporting and device budgeting.

For IT Managers: Frontline Support and Practical Rollout

At IT Manager level, the focus in larger companies often turns tactical. That includes internal support processes, device provisioning, and preparing frontline teams to handle the human side of migration.

“If someone new is joining your organisation, don’t give them a Windows 10 device. Get them straight onto your Windows 11 pilot” advises Rob.

User support matters too. Rob emphasises that even small differences in interface can create friction.

“We’ve seen people ring up because the start menu isn’t where they expect it. A cheat sheet or internal guide can save your support staff a lot of time and reduce those repetitive tickets.”

Final Advice: Prepare Early, Lean on Experts

“I think every upgrade is a chance to improve,’ says Rob. ‘Security, user experience, support tools, the lot. But the key is starting early. Assess your environment, know your risks, and don’t wait until October 2025!”

Cyclone works with organisations across New Zealand to manage device lifecycles, modernise infrastructure, and ensure a stress-free upgrade to Windows 11.