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After failing to hire the right leader for Expedia's largest business unit twice, Dara Khosrowshahi realized he didn't understand the job's requirements. He took on the role himself for several years. This hands-on experience gave him the deep operational understanding needed to finally identify and hire the right person.
ElevenLabs' CEO avoids ineffective delegation by first immersing himself in a new function (like sales or legal). This allows him to understand the fundamentals, which is crucial for assessing and hiring the right expert leader for that role.
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.
Before hiring for a critical function like growth marketing, Gamma's CEO spent 6-12 months doing the job himself. This immersion taught him what "great" looks like, preventing a bad hire and ensuring he could properly lead the function he was delegating.
At Larroudé, the executive culture is "hands-on." Leaders are not just strategists who delegate; they must be able to execute tasks themselves. Furthermore, a critical hiring criterion for leadership is the ability to recruit, with the expectation that they can build out their own high-performing teams.
Harvey CEO Winston Weinberg asserts that if you've never done a role, you will hire the wrong person 100% of the time. For first-time founders, spending even three months in a function provides the necessary context to understand the job's demands and successfully hire a leader for that position.
To truly understand a business, leaders should spend time in a non-scientific, operational role like IT. This 'back of house' experience provides an invaluable perspective on how an organization functions, what other teams value, and the real-world impact of change, creating a more empathetic and effective leader.
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.
Ather's founder learned that hiring senior leaders for non-core functions too early fails due to value system clashes. Founders must first build the function themselves, establish principles, hire into that mold, and only then step back. This ensures cultural alignment.