During an interview with the head of the team, can I ask about his career choices

Hi guys,

I've got a chat scheduled with the head of the team I'd be working in if I were to get hired (quantitative team). I'm OK with the place and what they do and I've got a fair bit to contribute to them because they are going into a field in which I've got a lot of experience.

I want to run over his linkedin profile with him and ask him about his career choices which I've got a lot of questions about. For example, he has a lot of positions where he's worked for a year and a bit. More recently, he's got a couple of positions that he's held for a few months. He's also ventured outside of finance but not in a meaningful way. There are probably reasonable explanations but I'd like to ask these questions the same way they run down my CV in minute detail and asked me about everything. My worries about him are his judgement abilities, his commitments and his personality - did he make poor decisions joining companies, was he not committed, did he not get along with colleagues after 1 year or so. I certainly don't want to go into a team headed by a poor decision maker with a bad temperament - I guess his lack of commitment then becomes a positive thing!

However, if I were to do this, the interview will turn into me interviewing him. He might also get a feeling I don't trust his leadership from the get-go and won't play ball. Do I ask him these questions and if I do, do I do it after/if I get an offer or as early as possible?