Amplitude's CEO describes the painful transition from founder (running to the hardest problem) to large-company executive. The latter role requires embracing hierarchy, saying "no" to most things, and managing through leverage rather than direct contribution—a skill set many founders resist and fail to learn.

While founder-led accountability is crucial, it's often misinterpreted. Leaders adopt a caricature of decisiveness, like mimicking Steve Jobs' harshness, which leads to micromanagement and alienates talented individual contributors who are key to scaling.

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.

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.

What's often negatively labeled as micromanagement is a crucial skill for early founders. When there is no team to delegate to, you must do everything and be obsessed with the details. This isn't a scaling strategy, but a necessary mode of operation for starting from nothing.

A founder's role is constantly changing—from individual contributor to manager to culture builder. Success requires being self-aware enough to recognize you're always in a new, unfamiliar role you're not yet good at. Sticking to the old job you mastered is a primary cause of failure to scale.

Many leaders, particularly in technical fields, mistakenly believe their role is to provide all the answers. This approach disempowers teams and creates a bottleneck. Shifting from advising to coaching unlocks a team's problem-solving potential and allows leaders to scale their impact.

Many leaders "abdicate" tasks by handing them off and mentally disengaging, leading to frustration when results fail. True delegation is an active process requiring structured training, clear expectations (what, how, when), and scheduled follow-ups, which can often take months to properly implement.

After eight years of grinding, the founder recognized he had taken the company as far as his skillset allowed. Instead of clinging to control, he proactively sought an external CEO with the business acumen he lacked, viewing the hire as a "life preserver" to rocket-ship the company's growth.