As a CIO, how do you gauge the readiness of various teams in your organization to adapt to changes introduced by IT?

Beyond empirical skill readiness, I also use "sentiment".  How has the conversation about what your are rolling out changed through the course of the project?  Is if more advanced questions about how the tool works, are people talking to each other and self promoting the tool or change, or is adoption low from the POC or first deployments, are there alot of technical challenges people are finding - It requires that you are out listening and asking questions in the later stages of the project so you can get this sense. 

There are some excellent platforms that can objectively assess as well as train the teams readiness. Coursera, Pluralsight, Udemy (to an extend) are examples. And yes, continuous communication and an open feedback loop would be ideal. Establishing trust with the team is essential. Also ensuring there is a roadmap and vision is essential.

I assess readiness by evaluating team skills, openness to change, past adaptability, and communication. Frequent feedback loops and training sessions are key to aligning everyone with IT changes.

I have a BA spend time with them to understand their readiness and help shape the change management journey. 

Each project has a defined change management stream. This stream includes power users in the business (coached as experts in the functional elements of IT) and key process operators in advance of go live. Capacity and capability are assessed in advance are part of the go/no-go decision. this is mandatory. Post implementation reviews also take place several weeks after to review capability.