IT isn't the problem - it's your leadership

With the Windows 10 EOS deadline looming, I’ve been seeing a lot of chat online about how to make your migration to Windows 11 successful. My opinion? The difference between success and failure executing an operating system (OS) upgrade comes down to one thing - leadership.  

If my long-lost hair is a bit of a giveaway. I’ve been through more OS upgrades than I can count – from Windows 95 and NT to what was likely New Zealand’s first 1000+ seat Windows 8 rollout (pre the 8.1 update).  
 
And while the world wide web is filled with useful information on how to make an OS upgrade a success, I still see the same patterns happening today.  
 
Projects stall. Rollouts get delayed. Teams burn out. And more often than not, it’s not because the technology failed. 

It’s because leadership didn’t show up and champion the change. 

So, I wanted to share my take on what makes the difference. Because whether it’s an OS upgrade, a cloud migration, or a new enterprise platform, the outcome often hinges on how the change is led. 

It's Not Just IT’s Job 

IT upgrades are business transformations. They touch every department, every user, every process. 

And they fail when they’re treated as IT’s problem – because they overlook the broader organisational impact.  

When leadership treats these projects as “IT’s job,” they stall. When the C-suite steps in to lead, they gain momentum, clarity, and buy-in. 

The Cost of Getting It Wrong 

Failed or delayed upgrades don’t just cost money. They erode trust, burn out teams, and create long-term complexity. Every workaround, exception, and custom fix adds weight to the system and makes future change harder. 

I’ve seen organisations spend months building custom interfaces just to replicate old behaviours. Not because the new system couldn’t work but because no one was guiding the business to adapt.  

So, what separates a seamless upgrade from a support desk nightmare? 

What Successful Upgrades Have in Common 

Whether you're moving 50 or 5,000 users, successful enterprise rollouts always include: 

• Executive Sponsorship That Leads and Supports Change. Real, visible and engaged leadership. When execs show up, speak up, and stay involved, teams follow. OS upgrades are not easy, they require ongoing support and change management to ensure they’re a success. Stay involved throughout the process from initial announcements and deployment, to education and feedback.

• Stakeholder Engagement Across Departments. Bring every department along on the journey early. From key stakeholders to everyday end-users. If they help shape the rollout, they’ll help deliver it.

• Clear Objectives and Scope. Know your “why.” Is it security, productivity, supportability? Define success before you start and make it measurable. 

• Thorough Assessments and Planning. Audit hardware, software, workflows and don’t forget shadow IT. You can’t fix what you don’t see. 

• Pilot Testing with Real Users. Not just the tech-savvy. Test with everyday users. Gather feedback. Adapt. Make the experience better before scaling. 

• Strong Communication and Change Management. Tell people what’s coming, when, and why. Then tell them again. Clear, consistent messaging builds trust and reduces resistance. 

• Phased Rollout with Iteration. Roll out in stages. Pause. Refine. Improve. Each phase is a chance to learn and get better. 
• Celebrate Progress and Success. Track milestones. Share wins. Recognise the effort. It builds momentum and keeps morale high. 

A Leadership Framework for I.T. Change 

If you're preparing for a major upgrade, ask yourself: 

• Are we clear on the business case and outcomes? 

• Have we involved the right stakeholders early? 

• Have leadership been visible and clearly engaged throughout the process? 

• Are we testing with real users and adapting based on feedback? 
• Do we have a plan to communicate, iterate, and celebrate? 

If the answer to any of these is “not yet,” it’s time to step in. 

Final Thought 

If you plan well, engage your people, and stay focused on the “why”, you won’t just get through it, you’ll come out stronger – and maybe keep your hair in the process.