A board member's role is to provide outside perspective to help a CEO think through a problem, not to make the decision. CEOs who ask 'what should we do?' risk abdicating responsibility to someone who lacks the deep operational context to make the right call. This can be destructive to a CEO's development.

A key source of executive team dysfunction is the "empire builder"—a leader who is skilled at managing up but is ineffective in their role and hard on their team. A strong CEO identifies and removes these individuals quickly to maintain a high-performance culture.

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.

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.

CEOs are often exceptional at building relationships, which can co-opt a board of directors. Directors become friends, lose objectivity, and avoid tough conversations about performance or succession, ultimately failing in their governance duties because they "just want them to win."

To counteract his own forceful personality and enable candid discussion, Jamie Dimon mandates that his board holds a session without him at every single meeting. The lead director then provides him with direct coaching and feedback, creating a powerful accountability mechanism.

The ongoing, high-level turnover and internal conflict at OpenAI is a major red flag for board members, regardless of external success. This level of C-suite "load balancing" consumes CEO time and signals deep-seated organizational dysfunction that can derail even the most promising companies.

The most valuable board directors go beyond fiduciary oversight and serve as a confidential peer and sounding board for the CEO. This relationship is crucial in a role that often lacks internal peers for strategic counsel.

In contrast to leaders who surround themselves with unqualified loyalists, effective CEOs are judged by their ability to mentor and promote talented executives who could one day take their job. A lack of viable internal successors is a major red flag for a company's long-term health and a board's key evaluation metric.