Management Interviews: The Most Underdeveloped Skill in Investing

He recommends recording every management meeting. Memory is unreliable, O'Toole said. A meeting that felt impressive in the room can look thin on replay. 'You catch things you missed the first time,' he said.

The request for examples is a double-edged sword. A positive example can confirm a thesis. A negative example, one that reveals a failure, is often more valuable. O'Toole said investors should ask for the negative example every time they get a positive one.

The host of the Yet Another Value Blog podcast said he worries that management teams are too good at selling their story. O'Toole's answer: build a longitudinal baseline. Interview the same executives repeatedly over years. Patterns emerge. The ones who consistently dodge the hard questions eventually reveal themselves.

O'Toole said the hard questions should be saved for the crescendo of the meeting. Lead with rapport, then hit the toughest topic when the executive is least likely to retreat into a script.

O'Toole's book has already earned a rare endorsement from the host. 'This went straight to the top of my hand it to an intern list,' he said.