Before a pipe review, ensure your reps pre-select the deals they want to review and prepare win strategy docs, mapping out all key external stakeholders.
Beat up the deals with the so-what train. Keep asking so-what to uncover the implication of the pain - until you don't have an answer anymore, that's what you need to find out.
Two questions to determine if a rep is ready to be a manager: Can they clearly communicate why they're winning? And are YOU learning from that rep?