The difference between a true partner and an employee is whether you seek their counsel on complex problems. If you consistently go to them for advice when you're unsure, they're a partner. If you only give them direction, they are not a "thought partner," which is a red flag for a C-level executive role.
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A mentor isn't someone who provides step-by-step instructions. The most powerful learning comes from finding someone you admire and closely observing their every move, how they speak, and how they behave in the face of obstacles, rather than seeking direct guidance.
Orlando Bravo argues valuable mentorship isn't found in occasional calls. It's cultivated through daily work with colleagues who have direct context on your challenges. Proximity allows for the deep, nuanced guidance that scheduled, low-context conversations cannot provide.
Senior leaders now value candidates who ask excellent questions and are eager to solve problems over those who act like they know everything. This represents a significant shift from valuing 'knowers' to valuing 'learners' in the workplace.
Over a long career, great leaders accumulate a "snowball of talent"—A-players who follow them from one venture to the next. This becomes a powerful litmus test when hiring executives: if they have no network of past colleagues eager to join them, it's a major red flag about their leadership ability or the quality of their past teams.
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.
Unlike a line manager who can train direct reports in a specific function, a CEO hires experts for roles they themselves cannot perform (e.g., CFO). A CEO's time spent trying to 'develop' an underperforming executive is a misallocation of their unique responsibilities, which are setting direction and making top-level decisions.
To clarify difficult talent decisions, ask yourself: "Would I enthusiastically rehire this person for this same role today?" This binary question, used at Stripe, bypasses emotional ambiguity and provides a clear signal. A "no" doesn't mean immediate termination, but it mandates that some corrective action must be taken.
Don't confuse the roles of an Executive Assistant (EA) and a Chief of Staff (CoS). A CoS is typically a future founder with high 'slope' hired for a 1-2 year tour of duty to solve complex problems. An EA is a career caretaker hired for a decade-long relationship where trust and intimacy compound over time.
To find the true influencer, ask how a low-level problem affects high-level business goals (e.g., company growth). The person who can connect these dots, regardless of their title, holds the real power in the decision-making process. They are the one paid to connect daily actions to strategic objectives.
The biggest unlock for a successful long-term partnership is to stop keeping score. Instead of tracking contributions and demanding reciprocity, one should define their own standard for being a good partner and live up to it. This approach avoids the bias of overvaluing one's own contributions, preventing transactional resentment.
