We recently came across a fascinating discussion on Reddit where IT managers shared their hard-won lessons from major cloud migrations. The thread, titled “IT Managers who’ve been through a major cloud migration – what would you do differently the second time around?”, sparked brutally honest insights that every organization considering a cloud journey needs to hear.
As infrastructure experts who’ve guided countless organizations through these transformations, we found ourselves nodding along to many of these points. Let’s dive into what experienced IT managers wish they’d known before their cloud migrations—and how you can avoid learning these lessons the hard way.
1. The Hidden Timeline: Why Data Cleansing Takes Longer Than You Think
One of the most upvoted responses came from a user who learned a critical lesson about data preparation:
“All those years of band-aid custom solutions? Using fields for unintended purposes to handle a situation? Fields allowed to be blank or reflect values that aren’t current for various historical reasons? They all bite you when trying to migrate this data into a new rigid data structure.”
The recommendation? Add 2-3 months to your schedule specifically for data cleansing. As they put it, “If you beat that, everyone will be happy. If you don’t include it, everyone will be doing damage control.”
This resonates deeply with what we see in the field. Organizations often underestimate the technical debt they’ve accumulated over years of quick fixes and workarounds. Those creative solutions that kept things running? They become migration nightmares when you’re trying to fit square pegs into the round holes of standardized cloud infrastructure.
2. Process Over Technology: The Real Key to Cloud Success
Another IT manager emphasized a point that might feel counterintuitive: “Change your business processes to work with the new standardized system, rather than try to manipulate the new system to fit your current business.”
They explained that this is “the whole point and benefit of moving to industry best practice and expedited feature/update release cycles. The moment you stick to legacy thinking is the moment you nullify the largest benefit to the migration.”
We’ve seen this play out countless times. Organizations invest millions in cloud technology only to recreate their on-premises limitations in the cloud. The real transformation happens when you’re willing to evolve your processes alongside your infrastructure.
3. Partner Selection: Why the Lowest Bidder Often Costs the Most
Perhaps the most financially impactful advice came regarding implementation partners: “Do not choose the implementation partner based primarily on their (lowest) price.”
The warning is sobering: “This can easily double the cost of implementation and put internal resources who are unfamiliar with the product into an impossible and frustrating situation.”
One manager shared their experience: “Choose the best proof for implementation success and thank yourself later.”
4. The Network Reality Check
A particularly detailed response highlighted the importance of understanding your network dependencies: “I would do being a bit more expensive than expected. Additionally, performance was a bit worse than my jaded expectations.”
They learned to ask critical questions like: “How stable has the biggest player at work been compared to my on-premises? Do our ISPs have dedicated routes to cloud data centers cheaper than they can do to on-premises?”
5. The Human Factor: Communication Is Everything
Several managers emphasized the organizational and political challenges that often overshadow technical ones. Key takeaways included:
- Start with pilot deployments: Test thoroughly with representative workloads before committing
- Document everything: From baseline performance metrics to cost projections
- Over-communicate with stakeholders: Nobody should be surprised at any point in the migration
- Plan for resistance: Technical teams comfortable with on-premises infrastructure may need extra support and training
The Bottom Line: Migration Success Requires More Than Technology
What struck us most about this Reddit discussion was how little of it focused on the actual technology. The challenges these IT managers faced weren’t primarily about choosing between AWS, Azure, or private cloud solutions. They were about preparation, process alignment, partner selection, and managing organizational change.
The consensus was clear: successful cloud migration isn’t just a technical project—it’s a business transformation that requires careful planning, realistic timelines, and the right partners who understand both where you are and where you need to go.
Your Cloud Migration Journey
Every organization’s path to the cloud is unique, shaped by your specific workloads, compliance requirements, and business objectives. Whether you’re considering public cloud, private cloud, or a hybrid approach, the lessons from these IT managers underscore a critical truth: having an experienced partner who’s navigated these waters before can mean the difference between a successful transformation and an expensive learning experience.
At Data Canopy, we’ve guided organizations through every type of cloud migration, from VMware environments seeking alternatives post-Broadcom acquisition to regulated industries requiring compliant hybrid solutions. We understand that the technology is just one piece of the puzzle.
Ready to explore a cloud strategy that learns from others’ experiences rather than repeating them? Contact our team to discuss how we can help you navigate your cloud journey with confidence, avoiding the pitfalls that others have already mapped.
Have your own cloud migration lessons to share? We’d love to hear them. Connect with us on LinkedIn to join the conversation.
