Cloud Adoption Is a Mess – And That’s Okay

I’ve had a lot of conversations recently with CIOs, architects, and cloud leads at organisations that weren’t born in the cloud, and by that I mean not startups, not fintechs — but long-established enterprises with decades of IT infrastructure, layered technology, contracts, and teams stretched thin enough to keep the lights on.

And here’s the truth no one really says out loud:

Cloud adoption is a mess.

When will we stop thinking Its just a technical and cost saving exercise. But it’s certainly not as simple as “lift and shift.” It’s a web of strategy, fear, legacy, politics, vendors and promises — both real, under and overstated. I wanted to pull together some recurring themes I hear when these conversations get honest and sometimes brutal.

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❌ “Cloud Is Just Too Complex”

Many businesses are paralysed by the sheer complexity of their estate — a tangle of applications, suppliers, interdependencies, and institutional memory locked away in tribal knowledge. When everything is interlinked, change feels risky.

Its not just their own complexity. The cloud is full of solutions from the Hyperscalers and ISV’s can leave organizations feeling totally confused, particually the orginizations that don’t have access or budget to engage with large IT outsources or the Tech Analysts.

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💸 “It’s Cheaper On-Prem”

This one comes up a lot — and sometimes, it’s not wrong. If you’ve sunk millions into hardware, you’re naturally reluctant to walk away. But what’s often missing in that cost conversation is context: workload profiles, underutilisation, egress costs, and the hidden cost of inflexibility. Don’t forget the magic word ‘Strategy”

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⏳ “We Don’t Have Time”

This one hits hardest. The teams keeping legacy systems running are flat-out. Cloud feels like a luxury project — something you do when you’re not fire-fighting. Ironically, the very thing that could improve operational breathing room feels unapproachable because of… well, the lack of breathing room.

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🛑 “What If We Find Something We Don’t Want To See?”

Cloud assessments can uncover technical debt, bad decisions, or forgotten services. There’s a fear of triggering complexity we’re not ready to deal with. But delaying discovery doesn’t make the mess disappear — it just pushes the cost and risk further down the road.

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🧍‍♂️ Job Protection: “If We Move to Cloud, I’m Out of a Job”

A real and valid fear. Teams who’ve built careers supporting infrastructure on-prem worry cloud means automation, outsourcing, and obsolescence. What’s missing from many cloud programs is a people strategy — a way to bring existing talent along, not just replace it. This drives a lot of the other statements and decsions that ultimatley lead to delayed or failed cloud adoption strategies

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🔁 On-Prem vs Cloud vs Hybrid

It’s not either/or — it’s both/and. Some workloads make perfect sense to keep on-prem: predictable, latency-sensitive, tightly coupled to hardware. Others benefit from elasticity, scale, and speed to market. Hybrid is the new normal — but only if it aligns with business objectives, not because it’s a compromise born out of fear.

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🎯 Strategy Before Migration

I’ve said it before. Every successful conversation I’ve had about cloud comes back to this:

Know what you’re trying to achieve?

What is the problem your trying to address?

What are your expections?

Cloud isn’t the strategy — it’s a tool to help you execute the business strategy. Without that clarity, cloud becomes an expensive sandbox rather than an enabler.

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💡 FinOps Isn’t Just for Finance

People joke about the shock of the first cloud bill — but behind the laughter is real pain. Cloud spend, if unmanaged, will spiral. The right approach involves not just tracking spend, but building a service that continuously monitors and optimises usage without compromising service levels.

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🧱 Infrastructure-Centric Migrations Miss the Point

Yes, you can lift and shift. But if you don’t also modernise, or at least plan to, you’re just moving technical debt to someone else’s data centre. That’s not transformation — that’s deferral.

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🧩 Culture and Contracts

One of the biggest blockers in enterprise cloud is not technical at all — it’s contractual. Especially in organisations where IT is outsourced to multiple vendors, with rigid SLAs, overlapping scopes, and commercial models that don’t incentivise change. Culture matters. Contracts matter more than we often admit.

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🤔 So… Is Cloud Worth It?

Absolutely — but only if you go in with eyes wide open. Cloud isn’t a shortcut. It’s a shift in how you think about IT, about accountability, and about alignment with the business.

There’s no silver bullet, no one-size-fits-all roadmap. But there is a right way for you. And that’s what I’m interested in helping organisations figure out.

We’ll be exploring each of these topics (and more) in future posts, and I hope they spark some thoughts of your own. If any of this resonates — if you’re facing similar challenges and want to talk — feel free to get in touch. I’m part of a specialist Cloud Advisory team that’s been helping businesses navigate these Cloud Continuum Complexities for over 15 years.