The Cost of Cloud Naivety: Why Experience Must Lead the Way

By: Tim Lyons
Editor @ OSINTsights | Builder of Infrastructure | Breaker of Silos | Tamer of AI Agent Armies

Here’s something that comes up far too often in government and large enterprise IT:
The cloud journey gets hijacked by good intentions and bad assumptions.

A close friend of mine recently went through a major cloud transformation effort inside a large public-sector organization. The goal was to modernize everything—applications, infrastructure, operations. But what unfolded was a masterclass in how not to run a cloud initiative.

In the end, only a handful of applications were lifted and shifted—not modernized—despite the original vision. The project stalled under the weight of internal politics and inexperience, and ironically, those same delays were later used as justification for a power grab. Certain individuals—who had designs on “owning the cloud” from the beginning—pointed to the slow progress as proof that the original team couldn’t deliver.

But here’s the twist: the people now demanding ownership were the same that caused most of the delays. The hypocrisy wasn’t lost on the team. It became clear this wasn’t about modernization or mission impact—it was about empire building.

And that’s the trap many government and enterprise orgs fall into. Cloud becomes less about transformation and more about control.

There’s also a persistent—and dangerous—belief in these environments:

“We’ll train everyone first, then move.”
“Everyone deserves a seat at the table.”
“We’ll figure it out together as we go.”

The intention is noble. The execution? Often disastrous.

Cloud isn’t a committee exercise. It’s a shift in architecture, culture, and pace. And when timelines are tight and goals are ambitious, learning on the job just isn’t enough.

Cloud-native transformations need to be led by people who’ve done it before—folks who understand the nuance, have scars from past projects, and can move with confidence. That doesn’t mean existing teams get left behind. Quite the opposite.

The winning formula looks like this:

• Bring in seasoned cloud architects & Engineers to lead the effort with real authority.
• Empower them to make architectural decisions without constantly relitigating legacy approaches.
• Build a parallel path for existing staff to upskill—so they’re ready to own and operate once the foundation is in place.

When the opposite happens—when transformation is led by those still thinking in racks and subnets—you don’t just slow things down. You actively undermine the very progress you’re trying to make.

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Familiarity doesn’t equal readiness.
Inclusion doesn’t replace expertise.

Train your teams—yes. Grow your internal talent—absolutely. But don’t confuse participation with qualification. If you want real progress, you need real experience at the helm.

Otherwise, you’re not building the future—you’re just repeating the past in a shinier interface.

If you’re in government or enterprise and have been through a similar journey—I’d love to hear your story. These are tough conversations, but they’re long overdue.