If your former team lead went from a -> b with no problem, maybe he is part of the circle. Afterall, when you zoom in the circle close enough, it appears a straight line. Or he could be a visionary, I can't tell.
An organization is like a shark, it needs to move forward. That organization can be an one-man team, where thinking overlaps with doing. In larger org, specialization is inevitable. The "no question ask, get things done" way that your former team lead adopted is desirable to certain degree, some of the time. But it is important to be aware of the duality. "Disagree but commit" is a virtue.
A fish can teach you swim, but it probably doesn't know it is in water