When an executive leaves, the CEO should step in to run their department directly. This provides invaluable operational context for hiring a replacement and empowers the CEO to make necessary but difficult changes (org structure, personnel) that a new hire would hesitate to implement.

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.

When a CEO finds themself repeatedly telling a functional head how to manage their team, the problem isn't the team's execution—it's the leader. The correct action is to replace the leader, not to become a micromanager. Constant intervention indicates a fundamental misalignment or capability gap.

A common mistake for new leaders is prioritizing and defending their functional team. The correct approach is to view the executive leadership team as their "first team." This requires prioritizing the overall business, understanding cross-functional needs, and acting as a business leader first.

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.

Companies typically promote CEOs from within. An external hire implies a crisis or a failure of succession planning. Therefore, an incoming external CEO has a mandate for significant change. Playing it safe with incremental adjustments squanders the opportunity and fails to address underlying issues.

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.

While founders focus on product or market pivots, the most regrettable decisions are often delayed personnel changes. Waiting and hoping an underperforming team member will improve is a mistake; the moment a founder knows a change is needed, they should act.

A common leadership failure is being too slow to get the right senior team in place. New CEOs should prioritize this, aiming to have their ideal team established by their one-year anniversary. Time passes quickly, and delaying these crucial personnel decisions is a major regret for many leaders.