Dysfunctional leadership creates a self-sustaining cycle where employees vying for promotion mimic the toxic behaviors of their boss. They do this to endear themselves to the decision-maker, believing that demonstrating a better leadership style would disqualify them from the role.

Promoting top individual contributors into management often backfires. Their competitive nature, which drove individual success, makes it hard to share tips, empathize with struggling team members, or handle interpersonal issues, turning a perceived win-win into a lose-lose situation.

Organizations mistakenly conflate visibility with value. The skills for self-promotion—taking credit and controlling narratives—are fundamentally different from those of actual leadership, which involve empowering others. This confusion leads to promoting the best self-promoters, not the best leaders.

Leaders in investment organizations are often promoted for their exceptional technical skills—analysis, presentations—not for their management abilities. This creates a leadership deficit that requires deliberate focus and coaching to overcome.

Don't conflate confidence with self-assurance, which is the *accurate* assessment of one's skills. Many top performers downplay their expertise out of a false sense of humility. This incongruence can be misinterpreted by others as manipulation, confusion, or a risky inability to self-assess.

A leader focused solely on personal wins creates a toxic environment that ultimately leads to their own apathy and burnout. They become disconnected from the very machine they built, creating a job they personally loathe despite their apparent success.

While not all insecure people are narcissists, all narcissists are deeply insecure. The critical distinction is the desire for personal growth. An insecure person seeks ways to improve and connect. A narcissist believes they have already achieved perfection and cannot be improved upon, seeking only support and praise.

To assess an internal candidate's readiness for promotion, give them the responsibilities of the higher-level role first. If they can succeed with minimal coaching, they're ready. This approach treats promotion as an acknowledgment of proven performance rather than a speculative bet on future potential.

The romanticized idea of not caring what others think is fundamentally anti-social and prevents personal growth. Empathy and the ability to internalize feedback are core human skills; a genuine inability to do so is a clinical trait, not a sign of strength or leadership.