Depends on what your objective is. If you want to stay on the good side and build a stronger career there, I'd take the explorer and get him to do most of the talking.

Get the company or team objectives out and ask him about which ones he is most focused on and how you can help. This might all sound like kissing up but if you are trying to grow your paycheck or a career trying to build a relationship with management is always a good move.

Never dress above or drive vehicles above what your management does in front of them. People are funny about these things and it can be a real CLM (career limiting move) if the guy is a tool.

View this as an opportunity. Good luck.