Why Your Cloud Strategy Keeps Failing (And How I Fixed It)

Let’s be honest: most cloud “strategies” I come across aren’t really strategies — they’re glorified lift-and-shifts. On paper, migrating to the cloud promises flexibility, scalability, and cost savings. But in reality? Many organizations just copy their on-prem setup into AWS, Azure, or GCP — and call it done. As someone who’s spent years helping companies build scalable, secure, and cloud-native infrastructure across multi-cloud environments, I’ve seen this mistake over and over. But one project in particular made this painfully clear. The Lift-and-Shift That Didn’t Shift Anything I had just joined a mid-sized financial services company as a Cloud Transformation Lead. Leadership proudly told me they were “70% in the cloud.” That should’ve been a good sign, right? But what I found was this: 1.All their web, app, and database servers were provisioned on EC2 instances — configured almost exactly like their legacy setup. 2.They managed access using manually configured Security Groups and Network ACLs — trying to mimic their old firewall rules. 3.Scaling decisions were triggered manually: CloudWatch alarms were set to ping when CPU utilization went above 80% or dropped below 30%, at which point someone had to manually launch or terminate instances. 4.All developers operated under IAM user credentials in a single shared AWS account - no role-based access, no federation, no real audit trail. To them, this was “cloud.” To me, this was a rented data center — with all the old problems, now in a shinier interface. It wasn’t a cloud strategy. It was a technical translation with none of the cloud-native benefits. How We Fixed It: From LIFT and SHIFT to CLOUD NATIVE I knew we had to shift our thinking — this wasn’t about fixing servers, it was about fixing mindset, processes, and architecture. Here’s how we turned it around:

May 12, 2025 - 23:11

Why Your Cloud Strategy Keeps Failing (And How I Fixed It)

Let’s be honest: most cloud “strategies” I come across aren’t really strategies — they’re glorified lift-and-shifts.

On paper, migrating to the cloud promises flexibility, scalability, and cost savings. But in reality? Many organizations just copy their on-prem setup into AWS, Azure, or GCP — and call it done.

As someone who’s spent years helping companies build scalable, secure, and cloud-native infrastructure across multi-cloud environments, I’ve seen this mistake over and over. But one project in particular made this painfully clear.

The Lift-and-Shift That Didn’t Shift Anything
I had just joined a mid-sized financial services company as a Cloud Transformation Lead. Leadership proudly told me they were “70% in the cloud.” That should’ve been a good sign, right?

But what I found was this:
1.All their web, app, and database servers were provisioned on EC2 instances — configured almost exactly like their legacy setup.

2.They managed access using manually configured Security Groups and Network ACLs — trying to mimic their old firewall rules.

3.Scaling decisions were triggered manually: CloudWatch alarms were set to ping when CPU utilization went above 80% or dropped below 30%, at which point someone had to manually launch or terminate instances.

4.All developers operated under IAM user credentials in a single shared AWS account - no role-based access, no federation, no real audit trail.

To them, this was “cloud.” To me, this was a rented data center — with all the old problems, now in a shinier interface. It wasn’t a cloud strategy. It was a technical translation with none of the cloud-native benefits.

How We Fixed It: From LIFT and SHIFT to CLOUD NATIVE
I knew we had to shift our thinking — this wasn’t about fixing servers, it was about fixing mindset, processes, and architecture. Here’s how we turned it around: