The most effective operators, dubbed 'dolphins,' can fluidly move between altitudes: operating strategically at 10,000 feet with founders, managing at 5,000 feet, and executing tactically in the weeds at 1,000 feet. This ability to oscillate is a key trait to hire for, especially in advisory or early-stage leadership roles.
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.
Simply hiring superstar "Galacticos" is an ineffective team-building strategy. A successful AI team requires a deliberate mix of three archetypes: visionaries who set direction, rigorous executors who ship product, and social "glue" who maintain team cohesion and morale.
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.
The most promising hires are often high-agency individuals constrained by their current environment—'caged animals' who need to be unleashed. Look for candidates who could achieve significantly more if not for their team or organization's limitations. This is a powerful signal of untapped potential and resourcefulness.
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.
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.
The most valuable professionals are neither pure visionaries nor pure executioners; they are "step builders." This means they can understand a high-level strategic vision and then map out the granular, sequential steps required to achieve it. This skill is critical for turning ambitious goals into reality.
The young founder hired an experienced executive who became a mentor and effectively his boss. He learned more from observing this leader's actions—how he interacted with people and approached problems—than from direct instruction. This demonstrates the power of learning through osmosis from seasoned operators.
In rapidly evolving fields like AI, pre-existing experience can be a liability. The highest performers often possess high agency, energy, and learning speed, allowing them to adapt without needing to unlearn outdated habits.
Most VCs fail at talent support by simply matching logos on a resume to a portfolio company. A better model is to first embed operators (e.g., fractional sales leaders) into the startup. This provides the deep, nuanced context required to find candidates who fit the specific business and culture, leading to better hiring outcomes.