When evaluating talent, the biggest red flag is "hand-waving." If you ask a direct question about their area of responsibility and they can't give a crisp, clear explanation, they likely lack true understanding. Top performers know their craft and can explain the "why" behind their actions.
When hiring, top firms like McKinsey value a candidate's ability to articulate a deliberate, logical problem-solving process as much as their past successes. Having a structured method shows you can reliably tackle novel challenges, whereas simply pointing to past wins might suggest luck or context-specific success.
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.
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.
Don't conflate confidence with self-assurance, which is the *accurate* assessment of one's skills. Many top performers downplay their expertise out of a false sense of humility. This incongruence can be misinterpreted by others as manipulation, confusion, or a risky inability to self-assess.
To gauge an expert's (human or AI) true depth, go beyond recall-based questions. Pose a complex problem with multiple constraints, like a skeptical audience, high anxiety, and a tight deadline. A genuine expert will synthesize concepts and address all layers of the problem, whereas a novice will give generic advice.
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.
Ineffective interviews try to catch candidates failing. A better approach models a collaborative rally: see how they handle challenging questions and if they can return the ball effectively. The goal is to simulate real-world problem-solving, not just grill them under pressure.
When confronting a talented but abrasive CTO, don't just critique bad behavior. Frame the conversation around their effectiveness. Horowitz suggests saying, "You're a fantastic Director of Engineering, but not an effective CTO," because a true CTO must marshal resources across the entire company, not just manage their own team well.
True A-players are 'undeniable' drivers whose impact is immediately obvious. If you find yourself constantly wondering or second-guessing if someone is the right fit, they are a B-player. Trust that indecision as a signal to cut them fast, as B-players create drag on the entire team.
For cutting-edge AI problems, innate curiosity and learning speed ("velocity") are more important than existing domain knowledge. Echoing Karpathy, a candidate with a track record of diving deep into complex topics, regardless of field, will outperform a skilled but less-driven specialist.