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.
Related Insights
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.
All founders make high-impact mistakes. The critical failure point is when those mistakes erode their confidence, leading to hesitation. This indecisiveness creates a power vacuum, causing senior employees to get nervous and jockey for position, which spirals the organization into a dysfunctional, political state.
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.
When a big-picture leader communicates with a detail-oriented team, friction is inevitable. Recognizing this as a clash of communication styles—not a personal failing or lack of competence—is the first step. Adaptation, rather than frustration, becomes the solution.
Executives often avoid acknowledging a team's technical skill gaps, believing it damages morale. In reality, this sets the team up for failure by forcing them to say 'yes' to impossible tasks. Openly identifying gaps allows for a realistic plan to train, hire, or partner.
Leaders are often insulated from the daily operational friction their teams face. This creates an illusion that tasks are simple, leading to impatience and unrealistic demands. This dynamic drives away competent employees who understand the true complexity, creating a vicious cycle.
Aspiring leaders often believe a promotion will finally empower them to fix everything. In reality, each level up—from Director to CPO—introduces a more complex set of problems, constraints, and stakeholder dynamics, not fewer. The feeling of being "unchained" is a myth.
Leaders with high status often experience "advantage blindness," causing them to misjudge their own approachability and overestimate how comfortable their teams feel speaking up. They project their own ease of communication onto others, creating a dangerous "optimism bubble" where critical feedback is missed.
Leaders who complain their team isn't as good as them are misplacing blame. They are the ones who hired and trained those individuals. The team's failure is ultimately the leader's failure in either talent selection, skill development, or both, demanding radical ownership.
