How can you tell if your org isn’t ready to go cloud native?

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Director in Manufacturing, 1,001 - 5,000 employees
One indication is how willing are they to change processes and use standards across the enterprise

In my experience if the business wants the software to change to match their decades old processes you will be facing a lot of challenges and expensive customization costs that are hard to estimate
Executive VP & COO in Retail, 1,001 - 5,000 employees
If the org is siloed by: server team, network team, and security team, this is an obstacle that must be overcome as these concepts converge in the cloud. 
Fractional CTO/CIO/CPO in Travel and Hospitality, 51 - 200 employees
Going from an On-premise to a cloud native solution is a huge lift from the entire organization. The organization isn’t ready if the leadership doesn’t invest in retraining the staff and create space for the organization to experiment and fail early.
Chief Technology Officer in Software, 11 - 50 employees
Do you mean cloud native, or just going to cloud? Assuming an org is already in the cloud, going cloud native means rebuilding apps to take advantage of cloud, such as taking advantage of serverless. This requires a value assessment, as well as training and engineering expertise, either internal or external.
No org is 'ready' to go to cloud. It needs to be business led, and built on more than just cost efficiencies. Cost of change, staff efficiency and time to value should be measurable in some way
CTO in Healthcare and Biotech, 11 - 50 employees
When there is no buy-in from the C-level to fully understand the benefits of being in the cloud.

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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