describe Midsize Company? you need to understand where they are at in the Growth Journey, What phase? is it a startup? series A, B, C, etc.. if its a CPO, typically they would be further along more mature organization... find out his or her market, and start asking yourself youd like to know about the market, then scope it into a insight question, meaning you understand the market but wanted to get his take on such and such growth... what state are that at in the Product Lifecycle, will drive alot of what he will want to know. I was a VP/Sr.Director for 6 Yrs Experience, I always wanted to find Character first, People willing to do what ever to get the job done, then from there I wanted to know your technical skills followed by actual Product experience, ability to develop relationships, story tell and what kind of executive experience like presenting to C-level quarterly ... Good luck!