Ask HN: Questions with 1-1 with skip manager or above?

Rather than thinking of this as a way to get information, a skip level is also an opportunity to be recognised by someone senior. The fact that you have a good grasp of the roadmap gives you a chance to demonstrate strategic thinking and alignment with that strategy. I would tend to ask open ended questions that demonstrate your understanding, show you've thought about the issues, and give the manager a stage to explain and guide.

Have a concrete action that you are proactively working on for your career this year that lines up with something useful. E.g. Completing online course in UX because you've recognised this as important for project blah blah blah.

Making your direct manager look good never hurts either.