informal settings (i.e. not scheduled meeting)
For your own good, consider all the interactions with your manager as formal, even if you meet him when buying potatoes at the market. Additionally, consider all interactions on the premises of the company as formal - regardless of who is present and why.
there is room for upward movement in the company and how the owners are trying to bring our branch more inline with the company value
That is pure propaganda. Speeches done by bosses to show their employees how bosses they are. Trying to really understand what they say is not a good idea. "Forcing" them to actually explain what hey mean, and do it in a way that is understandable - well, you better swallow a live grenade (figuratively speaking).
I had a similar situation. Our direct manager informed us about some organizational changes. Among other, we were informed that was promoted to "DP" (or whatever meaningless letters). Trying to be proactive and involved (the way you want to be), I asked what is "DP". You cannot imagine the hate I received from my direct manager as a result - the hate being expressed especially by the mimic of the face. The only answer I received was: "But you do not know until now what "DP" is?" Of course, nobody knew, the title was just invented for that person. Colleagues (kissers up) of course followed, expressing their horror that I do not know what "DP" was.
So, out of 30+ people, nobody knew what was going on, but somehow I was the only "idiot" for not knowing.
But he just went on a tangent and talked so long everyone had to get back to their other responsibilities without any time for questions.
This only comes to confirm that whatever he said was a propaganda which he had to deliver, and that questions are not welcome or needed.
Bottom line: when your manager just serves propaganda, do not ask questions, just pretend to be positively surprised.