What is the biggest challenge in migrating existing infrastructure to a Cloud Platform?

3.2k views6 Upvotes8 Comments

IT Cyber Security and Compliance in Healthcare and Biotech, 1,001 - 5,000 employees
responsability of data and its management
IT Head Infra in Real Estate, 1,001 - 5,000 employees
data confidentiality is a major challenge.
Senior Data Scientist in Miscellaneous, 1,001 - 5,000 employees
Corresponding administration know-how for managing the Cloud platform securely and performant.
Engineer in Education, 1,001 - 5,000 employees
Some applications are not designed to be cloud-friendly, which can make it difficult to migrate them to the cloud. In some cases, it may be necessary to re-architect the application to take advantage of cloud-specific features and capabilities.
IT Manager in Software, 201 - 500 employees
The only concern of our existing customers is cost.  
Data Science & AI Expert in Miscellaneous, Self-employed
Policies and compliance. Then, the readiness of legacy systems including data. 
Lead Cloud Transformation Architect, 10,001+ employees
Based on my experience:
1) Lack of a valid cloud strategy. Without answering the WHY Cloud with a clearly defined business outcomes, the cloud adoption is unlikely to yield any business value. 
2)  Determining the right migration strategy for workloads (using 7R framework). Lack of proper assessment will likely lead to overspend, performance issue, security compromise, non-compliance, etc.
3) Cost Management. Many think the cloud is cheaper .. it is not! Cheaper should not be your top reason for migrating to cloud. Migrating without measures in place to monitor and enforce cloud spend controls will likely lead to a heart attack moment when you get your first bill. 

There are other gotchas but  the above are the common ones I see often.

Head of IT in Software, 5,001 - 10,000 employees
You need to have a defined roadmap first, this is assuming you know what you want with your apps, data etc. once you have that, you need to map your resources (people + time + money) to the roadmap, by then you will have red, yellow and green flags, with those in place, it should be easier (not easy though) to do the migration

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