The primary reason people fail to delegate is the correct belief that they can do a task faster and better themselves the first time. The key is to accept this initial time cost as a necessary investment in long-term leverage and compounding efficiency, rather than a reason to avoid delegating.

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 long-term leadership isn't static; it's an 'accordion' that flexes between deep involvement and granting autonomy. This adaptive approach is key for different company seasons, knowing when to lean into details and when to empower the team to make 'foot fault' mistakes and learn.

It is almost always faster and better to do a task yourself once. However, this is a trap. The "cardinal sin" is failing to invest the extra upfront effort to delegate and train someone, which unlocks compounded time savings and prevents you from ever having to do that task again.

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.

People naturally start their jobs motivated and wanting to succeed. A leader's primary role isn't to be a motivational speaker but to remove the environmental and managerial barriers that crush this intrinsic drive. The job is to hire motivated people and get out of their way.