Public company boards often hire CEOs using fuzzy adjectives like 'leader.' A better method is to first define 3-5 key strategic goals, creating a 'scorecard of success,' and then find a candidate whose track record specifically matches those objectives.

During due diligence, it's crucial to look beyond returns. Top allocators analyze a manager's decision-making process, not just the outcome. They penalize managers who were “right for the wrong reasons” (luck) and give credit to those who were “wrong for the right reasons” (good process, bad luck).

CEOs provide a curated view of their company's culture. To get an accurate picture, talk to people who have left the organization on good terms for an unfiltered perspective. Also, ask behavioral questions like 'What would you tell a friend to do to be successful here?' to uncover the real cultural DNA.

Investor Mark Rampolla argues that a brand's potential is capped by its leader's personal development. His firm seeks self-aware founders committed to "inner work," believing this psychological resilience is a key predictor of building a billion-dollar company.

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.

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.

Venture capital should focus on what a founder does exceptionally well, rather than penalizing them for past failures or weaknesses. Ben Horowitz uses the Adam Neumann example to illustrate their principle: judge people by their spectacular talents (like building the WeWork brand) and help them manage their flaws, which is a more effective strategy than seeking perfectly flawless individuals.

Senior executives are, by definition, excellent at interviewing, making the process unreliable for signal. Instead of relying on a polished performance, ask to see the 360-degree performance reviews from their previous company. This provides a more honest, ground-truth assessment of their strengths and weaknesses.