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.

Due to demographic shifts and a post-pandemic re-evaluation of work, employees now hold more power. This requires a fundamental leadership mindset shift: from managing people and processes to enabling their success. High turnover and disengagement are no longer employee problems but leadership failures. A leader's success now depends entirely on the success of their team, meaning 'you work for them'.

The transition to managing managers requires a fundamental identity shift from individual contributor to enabler. A leader's value is no longer in their personal output. They must ask, "Is it more important that I do the work, or that the work gets done?" This question forces a necessary focus on delegation, empowerment, and system-building.

Individual contributors are rewarded for having answers and sharing their expertise. To succeed as a leader, one must fundamentally change their approach. The job becomes about empowering others by asking insightful questions and actively listening, a diametrically opposed skillset that is difficult to adopt.

Moving from a technical expert to a leader is jarring because the skills that made you successful are no longer the priority. This shift from valuing your own output to enabling others' expertise often creates a profound, temporary sense of incompetence that few adults enjoy or are prepared for.

Effective leadership prioritizes people development ('who you impact') over task completion ('what you do'). This philosophy frames a leader's primary role as a mentor and coach who empowers their team to grow. This focus on human impact is more fulfilling and ultimately drives superior business outcomes through a confident, motivated team.

Transitioning from a top-performing rep requires a mindset shift from doing to enabling. A new leader's role is not to teach their specific 'Michael Jordan' method, but to align company and personal goals, then focus on removing obstacles for each team member's unique path to success.

The transition from a hands-on contributor to a leader is one of the hardest professional shifts. It requires consciously moving away from execution by learning to trust and delegate. This is achieved by hiring talented people and then empowering them to operate, even if it means simply getting out of their way.

A founder's role is constantly changing—from individual contributor to manager to culture builder. Success requires being self-aware enough to recognize you're always in a new, unfamiliar role you're not yet good at. Sticking to the old job you mastered is a primary cause of failure to scale.