To assess critical thinking, send C-level candidates your board deck under NDA before the interview. Use the conversation to gauge their feedback. A candidate who only offers praise is a red flag; the best candidates will challenge your thinking and provide constructive criticism.

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.

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.

First-time CEOs often change their entire strategy after talking to a few investors. This is a red flag signaling a lack of conviction. Investors want to see a CEO who listens and evolves but ultimately sticks to their core, well-researched beliefs, especially when faced with disarming questions.

Employees should test their managers by asking how they make decisions. A manager who cannot articulate their decision-making framework is a significant warning sign, suggesting a lack of clarity and potential organizational chaos. This serves as a powerful "reverse interview" technique for assessing leadership.

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.

CEOs don't just appear on challenging podcasts for external publicity. A key, often overlooked, motivation is to demonstrate strength and competence to their own internal teams. Successfully navigating a tough interview proves to employees that their leader can handle pressure, something that can't be authentically conveyed in a controlled corporate setting.

Instead of broad questions, Musk drills down into a single problem, often one he knows well, to gauge a candidate's depth of knowledge and detect if they are exaggerating their contributions. This 'video game' approach tests how many layers of a problem a candidate can get through.

To gauge a leader's coachability and the company's health, ask them to describe a time they were wrong about the market and how the organization pivoted. A leader who can't admit to missteps or share learnings is a major red flag, signaling a lack of self-awareness that will hinder growth.