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.
Senior executives are, by definition, excellent at interviewing, making the process unreliable for signal. Instead of relying on a polished performance, ask to see the 360-degree performance reviews from their previous company. This provides a more honest, ground-truth assessment of their strengths and weaknesses.
High achievers often apply immense rigor to their companies while neglecting their personal lives. To avoid this imbalance, treat your life like a business by implementing formal processes like quarterly reviews for relationships and personal goals, ensuring they receive the purposeful investment they need to thrive.
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.
It's a misconception that ambitious people hire assistants. The reality is often reversed: gaining leverage by delegating small tasks frees up mental space, which in turn unlocks a higher level of ambition. As you offload the daily annoyances, you naturally start thinking bigger about what's possible.
Just like in venture capital, personal and professional goals often follow a power law. Each month or quarter, one single accomplishment is typically worth more than all others combined. The key is to identify that 'one thing' and go all-in on it, rather than diluting focus across a long list of lesser goals.
Don't wait for a large budget to learn delegation. Start with inexpensive tools like ChatGPT to practice offloading tasks and articulating needs. This 'ladder of leverage' allows you to build the core skill of delegating, making you far more effective when you eventually hire human assistants and chiefs of staff.
Don't confuse the roles of an Executive Assistant (EA) and a Chief of Staff (CoS). A CoS is typically a future founder with high 'slope' hired for a 1-2 year tour of duty to solve complex problems. An EA is a career caretaker hired for a decade-long relationship where trust and intimacy compound over time.
The most efficient delegation method is using your voice, which is 2-3 times faster than typing. By sending voice notes to an assistant between meetings to capture takeaways and action items, you can process work in real-time and prevent tasks from accumulating into a daunting end-of-day list.