Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.

Over a long career, great leaders accumulate a "snowball of talent"—A-players who follow them from one venture to the next. This becomes a powerful litmus test when hiring executives: if they have no network of past colleagues eager to join them, it's a major red flag about their leadership ability or the quality of their past teams.

Unlike a line manager who can train direct reports in a specific function, a CEO hires experts for roles they themselves cannot perform (e.g., CFO). A CEO's time spent trying to 'develop' an underperforming executive is a misallocation of their unique responsibilities, which are setting direction and making top-level decisions.

At the VP or C-level, a leader's primary role shifts from managing their function to driving overall business success. Their focus becomes more external—customers, market, revenue—and their success is measured by their end-to-end impact on the company, not just their team's performance.

Many leaders, particularly in technical fields, mistakenly believe their role is to provide all the answers. This approach disempowers teams and creates a bottleneck. Shifting from advising to coaching unlocks a team's problem-solving potential and allows leaders to scale their impact.

Successor CEOs cannot replicate the founder's all-encompassing "working memory" of the company and its products. Recognizing this is key. The role must shift from knowing everything to building a cohesive team and focusing on the few strategic decisions only the CEO can make.

The founder hired an experienced CEO and then rotated through leadership roles in different departments (brand, product, tech). This created a self-designed, high-stakes apprenticeship, allowing him to learn every facet of the business from experts before confidently retaking the CEO role.

The young founder hired an experienced executive who became a mentor and effectively his boss. He learned more from observing this leader's actions—how he interacted with people and approached problems—than from direct instruction. This demonstrates the power of learning through osmosis from seasoned operators.