To become a more effective leader with a holistic business view, deliberately seek experience across various interconnected functions like operations, marketing, and sales. This strategy prevents the narrow perspective that often limits specialized leaders, even if it requires taking lateral or junior roles to learn.

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.

A simple yet powerful way to assess your career trajectory is to evaluate your direct superior's role. If you have no desire to eventually hold that position, it's a strong signal that you are on an unsuitable path and need to change direction.

For high-level leadership roles, skip hypothetical case studies. Instead, present candidates with your company's actual, current problems. The worst-case scenario is free, high-quality consulting. The best case is finding someone who can not only devise a solution but also implement it, making the interview process far more valuable.

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.

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.

Early-stage companies need experienced executives not just for their skills, but for their 'borrowed credibility.' A well-respected leader like former CEO Bob Muglia lent Snowflake instant legitimacy, which inspired belief in the team, reassured customers, and empowered the young founders.

When a key leader left Cloudflare for a CEO job, Michelle Zatlin reframed the frustration. She views it as a positive signal that other public companies recruit from their team for top jobs. This perspective validates the company's talent caliber and helps manage the pain of recruiting again.

Eschewing a direct corporate ladder for a varied, non-linear "jungle gym" path exposes aspiring leaders to diverse challenges. This broad experience fosters adaptability and a more holistic business understanding, ultimately creating more well-rounded and effective senior executives.