I usually ask what big challenges will they be tackling in the next 4-5 months. Then try to use that as an entry point into discussing technical details at a sl

I usually ask what big challenges will they be tackling in the next 4-5 months. Then try to use that as an entry point into discussing technical details at a slightly deeper level. In many cases it works well. In some cases it does not since people say that the roadmap is sensitive.