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.

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.

Once a task is successfully delegated and handled by a team member, never take it back. Doing so sends a powerful, destructive message: "I don't believe you are competent enough to handle this long-term," undermining their confidence and your leadership.

Founders often hoard tasks they dislike, feeling they shouldn't burden others. Shopify's CEO realized this leads to misery and that every task he dreaded was an exciting growth opportunity for someone else. This reframes delegation from burden-shifting to opportunity-creation.

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.

Effective delegation isn't just handing off a task. It's about codifying your personal preferences and decision-making process into a repeatable algorithm. This allows an assistant to replicate your desired outcomes autonomously over time, moving beyond simple task completion to genuine leverage.

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.

Successful delegation is not an abrupt handoff but a gradual process. Bring in a senior person and collaborate with them, then slowly cede specific responsibilities (e.g., customer interviews). This allows you to transition your own role from day-to-day operator to an internal advisor, ensuring continuity.

Top performers' primary need is opportunities for growth, not necessarily promotion. Delegating significant responsibilities forces them to develop new skills and fosters a sense of ownership, which is more valuable than simply clearing your own plate.