For leadership roles, the interview itself is a critical test. If the candidate isn't teaching you something new about their function, it's a red flag. A true leader should bring expertise that elevates your understanding. If you have to teach them, they will consume your time rather than create leverage.
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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.
The length of an interview can be a powerful diagnostic tool. A good, engaged candidate conversation should naturally last about an hour. If it ends in 15 minutes, the candidate is likely disengaged. If it stretches to two hours, they may lack the self-awareness to be concise. Use time as a simple filter for cultural fit.
Citing Oprah Winfrey, Rubenstein argues the key to great interviewing is not having the best questions but being a great listener. True listening allows the interviewer to pivot and follow up on unexpected answers, turning a rigid Q&A into a genuine conversation that uncovers far deeper insights than a prepared script ever could.
If an interview feels easy because you are exclusively discussing your deep functional expertise, you are likely failing. Boards hire "T-shaped" directors who can connect specialized knowledge to broad strategic issues. You must resist going too deep and instead demonstrate wide-ranging strategic thinking.
In a complex field like ad tech, curiosity is as critical as experience. Interviewers should assess this by seeing if candidates drive the conversation with insightful questions. A lack of curiosity is a major red flag, suggesting they won't thrive in a dynamic environment.
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.
Ditch standard FANG interview questions. Instead, ask candidates to describe a messy but valuable project they shipped. The best candidates will tell an authentic, automatic story with personal anecdotes. Their fluency and detail reveal true experience, whereas hesitation or generic answers expose a lack of depth.
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.
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.