Work expands to fill time, and organizations expand to fill available work. People instinctively want to hire direct reports to increase their status, creating a supply of labor that then invents low-value tasks to justify its existence, leading to bloat and inefficiency.

CEO Dylan Field combats organizational slowness by interrogating project timelines. He seeks to understand the underlying assumptions and separate actual work from "well-intentionally added" padding. This forces teams to reason from first principles and justify the true time required, preventing unnecessary delays.

To fix a failing process like cash collections, the CEO should hold a daily 8 a.m. meeting with the team. By repeatedly asking a direct question like, "Where's my money?", you force the rapid resolution of small, overlooked blockers and create an unscalable but effective communication channel.

As companies scale, the supply of obvious, valuable work dwindles. To stay busy, employees engage in "hyper-realistic work-like activities"—tasks that mimic real work (e.g., meetings to review decks for other meetings) but generate no value. It's a leader's job to create a sufficient supply of *known valuable work*.

To avoid stifling teams with bureaucracy, leaders should provide slightly less structure than seems necessary. This approach, described as "give ground grudgingly," forces teams to think actively and prevents the feeling of "walking in the muck" that comes from excessive process. It's a sign of a healthy system when people feel they need a bit more structure, not less.

According to the 'dark side' of Metcalfe's Law, each new team member exponentially increases the number of communication channels. This hidden cost of complexity often outweighs the added capacity, leading to more miscommunication and lost information. Improving operational efficiency is often a better first step than hiring.

Instead of over-analyzing and philosophizing about process improvements, simply force the team to increase its cadence and ship faster. This discomfort forces quicker, more natural problem-solving, causing many underlying inefficiencies to self-correct without needing a formal change initiative.

As companies grow from 30 to 200 people, they naturally become slower. A CEO's critical role is to rebuild the company's operating model, deliberately balancing bottom-up culture with top-down strategic planning to regain speed and ensure everyone is aligned.

Most entrepreneurs are trapped doing things they believe they *should* do, leading to burnout with minimal results. The Pareto Principle suggests 80% of your results come from 20% of your efforts. By auditing your activities to find that 20%, you can eliminate busywork and focus only on what truly moves the needle.