Since CEO candidates are already qualified, interviews should skip past achievements. Instead, boards should probe how candidates would navigate implausible but possible "black swan" scenarios, like sudden deglobalization or a tripling in capital costs, to truly test their strategic thinking and adaptability.

The true value of management interviews emerges over time. Speaking with the same executives repeatedly, quarter after quarter, allows an investor to establish a baseline for their credibility and assess whether their past statements and promises have materialized.

When a CEO is evasive, it may not be skilled media training but a genuine inability to articulate business fundamentals. A challenging interview can serve as a potent diagnostic tool for leadership competence, revealing whether a leader truly understands their own company's operations and strategy.

Experience taught Herb Wagner that great leaders consistently surprise on the upside. He now weights leadership quality far more heavily, assessing CEOs not by interviews or charisma, but by their verifiable track record and through trusted backchannel references who have worked with them directly.

When hiring for the C-suite, the importance of domain expertise varies by role. For Chief Product Officers, a deep passion and knowledge of the problem space is critical for setting vision. For engineering leaders (CTOs/VPs), specific domain experience is less important than relevant tech stack knowledge and transformation skills.

While AI can automate interview prep, it actually increases the value of being a great interviewer. Eliciting unique qualitative data through skilled questioning provides a proprietary information advantage that AI can then analyze, amplifying potential alpha.

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.

Technical executives often fail in interviews with PE firms because they can't articulate the business value of their work. Candidates must prepare to speak like they're in a board meeting, clearly connecting their initiatives to measurable outcomes like cost savings, revenue lift, or efficiency gains.

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.