Uncommon questions to ask MD

I work in a very flat team. Everyone's super transparent and it's pretty easy to go up to and talk to senior team members. As a first-year analyst, I've sort of gathered and re-heard the same tidbits on "managing and understanding expectations", "how to succeed as a first-year analyst" and "what leads to long-term success in this industry". I also feel that VP's and up are semi-tired of answering these questions because senior analysts and associates already do a thorough job of it. 

My question is, if I'm having conversations and 1-1's with VP's and up, what sort of questions are worth their time? I'm talking Nardwuar-level shit. I feel that these people hold buckets of wisdom having been working in the space for so long and must have real illuminating stories. My question is also quite diverse. Questions regarding perspectives on life and relationships are more than welcome. I just really want to have a mutually fruitful discussion next time I ask someone to pick their brains.

3 Comments
 

I mean I'm not looking to bring this stuff up on a casual day, or at a post-work event. I was asking more for 1-1 15-minute meetings. If I've put down time on the calendar to have a meaningful discussion, might as well be prepared with questions rather than talking about how Brady and the Bucs are gonna do this year. Plenty of time to mull over that over drinks.

 

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