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

YAVP #410

Management interviews might be the most underdeveloped skill in fundamental investing. Ross O’Toole has been investing for 25 years and read over 500 investment books, and he couldn’t find a single one on how to actually conduct an investor-management interview.... so he wrote Breaking the Script, a field guide to getting management teams off their rehearsed talking points. We get into why “what” questions beat “why” questions, whether you should grade a plastic surgery CEO and a coal company CEO on the same curve, the case for recording your management meetings, and why asking for examples is one of the biggest double edged swords in investing.

I push back with my standing worry: management teams are really, really good salesmen, and I always walk out of these meetings wondering if I’m the patsy at the poker table. Ross’s answers (build a longitudinal baseline over repeat interviews, ask for the negative example every time you get a positive one, and save the hard questions for the crescendo) are why this book went straight to the top of my “hand it to an intern” list.

---

This podcast is sponsored by fiscal.ai

Fiscal AI is a modern data terminal built for investors who want an institutional-grade platform without the complexity. I use Fiscal AI to research my holdings, find new investment ideas, and deepen my analysis. It’s fast, intuitive, and has genuinely helped my research process. Check it out at fiscal.ai/yav —for two weeks free, plus 15% off any of their paid plans.

---

Please follow the podcast on Spotify, iTunes, or YouTube! And please be sure to rate / review the podcast if you enjoy it, or share it with someone else who would enjoy it (more listeners is a critical part of the flywheel that keeps this Substack and podcast going!).

Transcript for paid subs begins below (The initial transcript is AI-generated and is replaced with a professionally edited version when available)

Disclaimer: Nothing on this podcast or on this blog is investing or financial advice; please see our full disclaimer here. The transcript below is from a third party transcription service; it’s entirely possible there are some errors in the transcript.