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  1. Yet Another Value Podcast
  2. Management interviews: the most underdeveloped skill in investing | Ross O'Toole
Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast · Aug 2, 2026

Author Ross O'Toole shares tactics for improving management interviews, a critical but underdeveloped skill for investors seeking an edge.

Use 'What' Instead of 'Why' Questions to Disarm Defensive Executives

When questioning management on poor performance, framing questions with 'What were the reasons...' instead of 'Why did you...' avoids making them feel attacked. This reduces defensiveness and elicits more thoughtful, expansive responses rather than terse answers.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Longitudinal Interviews Establish a Crucial Credibility Baseline

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.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Strategic Silence Compels Interviewees to Reveal Deeper Insights

Inspired by filmmaker Cameron Crowe's technique, being silent after a response can be a powerful tool. It creates a space that the interviewee feels compelled to fill, often leading them to elaborate and share more candid, unscripted thoughts.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Interview Value Is Higher in Tech Than in Commodity-Driven Sectors

Management interviews are not equally valuable across all industries. In sectors like tech, understanding a CEO's vision is critical for alpha. In commodity businesses like coal, where external factors dominate, financial analysis is more important than management's qualitative input.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Dedicated Note-Takers Are Essential for Effective Interviewing

It's cognitively impossible to actively listen, formulate follow-up questions, and take detailed notes simultaneously. The ideal interview setup involves a lead interviewer focused on the conversation and a second person whose sole responsibility is taking meticulous notes.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

AI Amplifies Alpha from Skilled Interviewers by Analyzing Unique Data

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.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Counterbalance Positive Customer Stories by Demanding Negative Examples

Management teams use compelling positive examples to build conviction. To avoid being swayed by a single, unrepresentative story, an investor must immediately ask for a negative counter-example, such as why a customer was lost. This provides a more balanced perspective.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Ask Management to Grade Its Own Performance to Expose Dishonesty

To test for self-awareness and honesty, ask executives to grade their own execution on an A-F scale. If a team that repeatedly blames external factors (like weather) gives itself a high grade like a 'B+', it's a significant red flag about their integrity and accountability.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Sequence Questions to Build Rapport Before Probing for Weaknesses

An effective interview follows a structured arc. Begin with 'softball' questions about strategy or culture to get management excited and comfortable. Save the most contentious or difficult questions for later in the meeting, after you have established trust and rapport.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago

Reframe Open-Ended Questions by Anchoring to a Specific Number

Instead of asking a vague question like 'What can margins be?', anchor the conversation by positing a specific, aggressive number: 'I think you can do 25% margins. Tell me why I'm wrong.' This forces a more detailed, data-driven response rather than a generic, non-committal answer.

Management interviews: the most underdeveloped skill in investing | Ross O'Toole thumbnail

Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Yet Another Value Podcast·2 months ago