Harvey CEO Winston Weinberg's top interview question for leaders is to map their future organization at three, six, and twelve months. A candidate's ability to detail specific roles and profiles reveals their strategic thinking and capacity to build leverage, a key indicator of their potential to scale.

Executives often interview by recounting past achievements, a "rear-view mirror" approach. To win a board seat, candidates must adopt a forward-looking governance mindset. This involves asking thought-provoking strategic questions about the future, demonstrating they can operate as a peer from day one.

To find its first engineers, Boom invited several top candidates to a multi-day workshop to critique the entire business and technical plan. This "audition" not only generated valuable feedback but also revealed which candidates were the most collaborative and insightful thinkers.

Instead of guessing a nominating committee's priorities, ask them directly. A powerful question is, "What was it about my background that made you want to interview me?" Their answer provides a cheat sheet to their key criteria, allowing you to tailor your responses to what they truly value.

Instead of asking hypothetical questions, present senior candidates with a real, complex problem your business is currently facing. The worst case is free consulting; the best case is finding someone who can implement the solution they devise.

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.

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.

Instead of a traditional interview, Parker Conrad sends candidates his investor materials beforehand. The first meeting is dedicated to their questions. He finds that the quality, depth, and skepticism of their questions is the best predictor of success, as it simulates the actual working relationship.