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.
To improve hiring decisions, founders should proactively meet top performers in roles they anticipate needing in 2-3 quarters. This isn't for immediate hiring but to build a mental model of excellence for that specific function and stage, which sharpens intuition when you do start recruiting.
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.
Treat hiring as a compounding flywheel. A new employee should not only be a great contributor but also make the company more attractive to future A-players, whether through their network, reputation, or interview presence. This focus on recruiting potential ensures talent density increases over time.
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.
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.
At Larroudé, the executive culture is "hands-on." Leaders are not just strategists who delegate; they must be able to execute tasks themselves. Furthermore, a critical hiring criterion for leadership is the ability to recruit, with the expectation that they can build out their own high-performing teams.
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.
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.
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.