When leading a function outside your expertise (e.g., a comms leader managing BDRs), success depends on hiring a great functional leader. Your role becomes asking them to explain concepts simply until you understand, trusting their expertise, and advocating for their needs, rather than trying to become the expert yourself.

When an executive leaves, the CEO should step in to run their department directly. This provides invaluable operational context for hiring a replacement and empowers the CEO to make necessary but difficult changes (org structure, personnel) that a new hire would hesitate to implement.

Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.

Marketing leaders often fail when hiring for functions they don't deeply understand. Success comes when you've done the job yourself first, like Capsule's marketing lead who ran events before hiring a specialist. This first-hand experience allows you to know precisely what "good" looks like and evaluate candidates effectively.

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.

Unlike a functional manager who can develop junior talent, a CEO lacks the domain expertise to coach their entire executive team (e.g., CFO, VP of HR). A CEO's time is better spent hiring world-class leaders who provide 'managerial leverage' by bringing new ideas and driving their function forward, rather than trying to fix people in roles they've never done.

The founder hired an experienced CEO and then rotated through leadership roles in different departments (brand, product, tech). This created a self-designed, high-stakes apprenticeship, allowing him to learn every facet of the business from experts before confidently retaking the CEO role.

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.

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.