Software Training - Training Analysis Questions

Hello folks. I've recently begun round two of creating training materials for an enterprise software currently in development. The training design is going in a cycle aligned to the Agile development cycle (we have six 2-week sprints). The way we've designed the design cycle is to build materials for what has previously released, that is, what's been developed in the last release. In order to make sure my design is solid, I conduct a needs analysis (duh).  But there was a huge discrepancy between my quantitative and qualitative data this time around, which seems to indicate something's janky with the questions. So my question is this: for those who do software simulations or software training, how do you formulate the questions to get the most accurate data about executing particular processes?

The most obvious example is "How competent do you feel executing x, y, and z?" But is there more than that? Examples would be super handy.  Thanks, all!

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