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.
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Drawing on Charlie Munger's wisdom, investment management problems often stem from misaligned incentives. Instead of trying to change people's actions directly, leaders should redesign the incentive structure. Rational individuals will naturally align their behavior with well-constructed incentives that drive desired client outcomes.
The most common failure mode for a founder-CEO isn't a lack of competence, but a crisis of confidence. This leads to hesitation on critical decisions, especially firing an underperforming executive. The excuses for delaying are merely symptoms of this confidence gap.
Firing decisions should be a function of both incompetence and business constraint. Not all underperformers are equal priorities. Some are like a "trash can on fire in the driveway"—a problem, but not the company's main bottleneck. Focus firing efforts on roles that are the direct constraint to growth.
Unlike a functional manager who can develop junior talent, a CEO lacks the domain expertise to coach their entire executive team (e.g., CFO, VP of HR). A CEO's time is better spent hiring world-class leaders who provide 'managerial leverage' by bringing new ideas and driving their function forward, rather than trying to fix people in roles they've never done.
A manager's highest duty is to an employee's fulfillment, not just their performance. When a top performer is not personally aligned with their role, a leader should actively help them find a better fit—even if it means using their own social capital to place them at another organization.
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.
When confronting a talented but abrasive CTO, don't just critique bad behavior. Frame the conversation around their effectiveness. Horowitz suggests saying, "You're a fantastic Director of Engineering, but not an effective CTO," because a true CTO must marshal resources across the entire company, not just manage their own team well.
When making tough personnel decisions, leaders should frame the choice not as a personal or purely business matter, but as a responsibility to the rest of the organization. Tolerating poor performance at the top jeopardizes the careers and stability of every other employee, making swift action an act of collective protection.
