When diagnosing a failing department, stop looking for tactical issues. The problem is always the leader, full stop. A great leader can turn a mediocre team into a great one, but a mediocre leader will inevitably turn a great team mediocre. Don't waste time; solve the leadership problem first.

Leaders struggling with firing decisions should reframe the act as a protective measure for the entire organization. By failing to remove an underperformer or poor cultural fit, a leader is letting one person jeopardize the careers and work environment of everyone else on the team.

As an organization scales, some leaders become skilled at managing up while being poor managers to their teams. Executives must conduct regular skip-level meetings with frontline employees to get direct, unfiltered feedback and catch these bad behaviors that would otherwise be hidden.

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.

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.

Aspiring leaders often assume that at the executive level, everyone "gets it" and operates with high maturity. The reality is that C-suites are composed of imperfect people with biases and baggage. Expect the same—or more intense—dysfunctions, not a utopian state of rational business.

When a startup fails due to team issues, the root cause isn't the underperforming employee. It's the CEO's inability to make the hard, swift decision to fire them. The entire team knows who isn't a fit, and the leader's inaction demotivates and ultimately drives away top performers.

High-performing CEOs don't hesitate on talent decisions. One mentor's advice was to act immediately the first time you consider firing someone, as indecision only prolongs the inevitable and harms value creation. This counteracts the common tendency for CEOs to be overly loyal or fear disruption.

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.