Your best reps are often "unconsciously competent" and can't explain their own success. Before an SKO, leaders must help these individuals deconstruct their process and build a prescriptive presentation, translating their individual "art" into a replicable science for the entire sales team.

SKOs often fail with high-level corporate presentations. A better approach is to put top-performing reps on stage to share specific, tactical "how-to's" for key sales activities like cold calling, email outreach, and champion building, fostering peer-to-peer learning.

To make deep qualification a team-wide habit, sales managers must do more than just talk about it. They need to 'lead from the front' by joining customer calls and personally asking the critical questions. This demonstrates the correct technique and signals that it's a non-negotiable part of the sales culture.

To make role-playing an effective training tool, sales leaders must demonstrate vulnerability by going first in front of everyone. This signals that the goal is collective improvement, not performance evaluation, and encourages reps to engage openly without fear of judgment.

Even a top-tier sales professional has a career pitch win rate of just 50-60%. Success isn't about an unbeatable record, but a relentless focus on analyzing failures. Remembering and learning from every lost deal is more critical for long-term improvement than celebrating wins.

A sales background teaches more than customer centricity. It instills resilience and the fearlessness to approach anyone in an organization to get things done, a vital skill for navigating the cross-functional demands of product management.

In the pre-product-market fit stage (the first ~20 deals), the sales leader's primary role is not just closing revenue, but acting as a product manager. They must be in every meeting to gather objections, find pockets of value, and translate raw market feedback into actionable insights for the engineering team.

First-time leaders often feel pressure to have all the answers. Instead, they should embrace a "beginner's mind," openly admitting what they don't know. This creates a safe environment for the team to share mistakes and learn collaboratively, which is crucial for building a playbook from scratch.

Unlike corporate roles where activity can be mistaken for success, sales provides direct, visceral feedback. This "winning" mentality, born from the pain of losing a customer, keeps product leaders grounded in the ultimate goal: winning the customer, not just executing processes.