Promoting top individual contributors into management often backfires. Their competitive nature, which drove individual success, makes it hard to share tips, empathize with struggling team members, or handle interpersonal issues, turning a perceived win-win into a lose-lose situation.

Instead of pushing advice, the most effective initial strategy with an unwilling team is to simply observe. This 'pull-based' approach builds trust and rapport, making the team more receptive when they eventually ask for your input, rather than feeling like you're forcing changes on them.

A sales leader's job isn't to ask their team how to sell more; it's to find the answers themselves by joining sales calls. Leaders must directly hear customer objections and see reps' mistakes to understand what's really happening. The burden of finding the solution is on the leader.

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.

When you lack personal authority to challenge a senior stakeholder, leverage external expertise. Instead of presenting your questions as your own opinion, frame them using research or insights from established experts. This "borrowed credibility" makes your challenge more persuasive and encourages senior leaders to engage with the idea rather than dismiss your lack of experience.

Sales professionals frequently encounter their most significant conflicts within their own organizations. Achieving internal buy-in and navigating cross-departmental friction can be more demanding than persuading an external client, underscoring the necessity of strong internal persuasion and relationship-building skills.

To avoid influencing their team's feedback, leaders should adopt the practice of being the last person to share their opinion. This creates a psychologically safe environment where ideas are judged on merit, not on alignment with the leader's preconceived notions, often making the best decision obvious.

Private equity and investment banking teams know a company inside out, creating blind spots. An external coach with the same limited information as a potential investor can identify confusing messages or unintended negative impressions, preventing costly misinterpretations.

Managers often enforce sales tactics rigidly without understanding the underlying principles. To be a true coach, a leader must grasp the 'why' behind every tactic (e.g., 'no demos on the first call'). This enables them to teach reps not just the rule, but also the context for when it's smart to deviate.