Ben Perreau

Ask an exec team how the last person who brought the board bad news early got treated. The answer sets how early the next one arrives.

Review season. At a lot of companies, a VP is about to argue for a rating on someone they've met twice, against a peer who argues louder. Ask everyone to bring one piece of that person's work from the last month, and see how many ratings change.

Twelve priorities on the board slide means each team picks its own three. They rarely pick the three the CEO would.

Plenty of exec teams spend all of Monday's meeting on last week's numbers and never get to next month.

Most companies track how long it takes to hire an executive. Almost none track how long it takes the new one to make their first decision that sticks. The second is the one the team underneath them is waiting on.

What's the most useful thing a new executive did in their first month at your company? Something specific you'd tell the next one to copy.

A project that's been green on the status report for eleven months straight deserves a question. Real work turns amber now and then.

A cheap strategy check: ask five team leads what they'd drop if the top priority slipped a quarter. Five different answers means five different strategies are running. Agree the order now, while it's cheap to.

CEOs: what's a decision you handed to someone on your team that came back better than you'd have made it?

The Angels fired Kurt Suzuki last week after 100 losses in his only season as manager. Baseball at least publishes the scoreboard. A new VP brought in to turn a team around gets about a year too, and is rarely told which number decides it.

Every company has a project that's been dead since spring and still has a weekly meeting. Halloween seems a fair day to ask who's allowed to end it.

Founders: at what headcount did you notice people agreeing with you more than they used to?

Promote your best salesperson to run sales and you're betting the skills transfer. You usually find out from the forecast two quarters later.

A founder hires a CRO and hands over sales. Six months later the three biggest customers still text the founder when something goes wrong, and the founder still answers. The CRO owns the number and none of the relationships that decide it.

If Goldman is right that AI layoffs wait for a recession, plenty of companies are building the list now without calling it one. Every role a team quietly stops backfilling is a line on it.

What's the best handover note you've had from the person who held your job before you? What was in it?

Whoever sets the CEO's agenda decides which problems get discussed this quarter. At a lot of companies that's a chief of staff, and few people outside the exec team know their name.

The month before a reorg is announced, nobody below the exec team makes a decision they'd have to defend to a new boss.

Ask an exec team which weekly meeting they'd cancel if AI took perfect notes and tracked every action. Most say the status update. Six months after the tools arrive, most of those status updates are still on the calendar.

AI can now give a CFO three versions of next year's forecast before lunch, each one clean and plausible. The job that's left is knowing which assumption in which version is wrong, and that's mostly years of watching the business miss.