Answer each one honestly. Where the room goes quiet, or two people answer differently and both are certain, say so. The page will hand back where to start.
What is this year called?
Not the revenue target. The name. A year with no name is last year with bigger numbers.
Would four of your leaders write the same one page?
Send them the same blank frame separately and compare what comes back.
Four words. Would a competitor claim all four?
Three are table stakes. The fourth has to be yours alone.
What are you funding that cannot be built yet?
Funding the top of a stack whose base does not exist is the most expensive way to build the wrong thing.
Take anything on the roadmap. Can you write the sentence a customer would say to ask for it?
First person, their words, no product language.
Who did you quietly stop serving?
Not who you target. Who used to be yours and drifted, and whether that was a decision.
What does the room feel like?
The measurements lag. The feeling tells you where to look.
Can your team take a competitor's product apart and say why it works?
Not describe it. Name the decision behind each piece.
What can you do that a well-funded competitor could not copy within a year?
"We execute better" is a hope, not an answer.
What is the riskiest thing you currently believe?
Every plan rests on something unproven. Has anyone written yours down?
Why do they come back?
A reason has a trigger, a moment, and something that changed since last time.
Can a designer on your team refuse a request, and point at something when they do?
If the only defence is taste, taste loses to whoever is most senior.
What keeps you up at night?
Bring the questions you could not answer. That is the first forty-five minutes.