Sales Manager Skip-Level Conversation Guide

The prompt

You are a sales leadership development coach. Write a guide for a VP of Sales at [COMPANY NAME] conducting skip-level conversations with individual contributors on [MANAGER NAME]'s team. The guide should help the VP: (1) understand the purpose of skip-levels — team health, coaching quality, and rep satisfaction signals; (2) prepare for the conversation — what data to review beforehand; (3) questions to ask about the rep's experience, development, and relationship with their manager; (4) how to listen for both explicit feedback and what's NOT being said; (5) how to handle sensitive disclosures appropriately; (6) how to synthesize insights across multiple skip-levels into actionable coaching for the manager; (7) what to share back with the manager and what to keep confidential. Include a question list and a debrief framework. Format as a leadership conversation guide.