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.
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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.
Shift your problem-solving mindset from personal execution to delegation and leverage. By seeking out mentors, coaches, or employees who have already solved your problem, you can achieve your goals more efficiently and avoid common pitfalls.
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.
Many entrepreneurs love their core business but lose motivation as their role expands to include responsibilities they dislike (e.g., finance, operations). The solution is to reinvest early profits into hiring employees to handle these tasks, freeing the founder to focus on their strengths and passions.
Danny Meyer performs a quarterly audit of his daily tasks, identifying 20% of activities that others could do better. He frames delegating these as an act of generosity that enables team members to grow and frees him to focus on his unique value-adds.
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.
The primary goal of delegating low-value tasks isn't just to work on more sales or marketing. It's to reinvest that time into becoming a leader who can attract A-players, high-level partners, and bigger opportunities. Scaling requires you to become a person capable of attracting that next level of success.
Many founders feel guilty about outsourcing home tasks. The reframe is to view it like any business expense. If hiring help to manage laundry and meals frees up mental energy for strategic work, it becomes a high-ROI investment in the business's success and the founder's well-being.
Founders often feel guilty delegating tasks they could do themselves. A powerful mental shift is to see delegation not as offloading work, but as providing a desirable, well-paying job to someone in the developing world who is eager for the opportunity.