fourteen questions to open the ai conversation most organisations are avoiding. print them. take them into a room. see what happens.
each card is a question worth sitting with for ten minutes. some are mirror questions for individuals. some are room questions for teams. some are the honest questions nobody puts on the agenda. they are not in order, and they don't need to be.
print on a4 or a3. cut along edges. laminate if you want them to last. they don't need to be precious — the conversation does.
mirror 01
When did you last ask someone in your team what they actually think about AI — and really listen to the answer?
Not in a briefing. Not on a survey. A real conversation where their answer surprised you.
mirror 02
What decision about AI are you avoiding — because you're not sure you want to hear the honest answer?
The avoidance itself is data. What is it telling you?
mirror 03
If AI made half your team's current role redundant within three years, what is your responsibility to them?
Not legally. As a person. What do you actually owe them?
room 04
What would you do differently at work if you could use any AI tool, without anyone knowing?
Not hypothetically. What would actually change tomorrow morning?
room 05
What's the most tedious part of your job that AI could take? And how would that make you feel?
Both parts of the question matter equally. Don't skip the second one.
room 06
What's one thing you wish the people making AI decisions in this organisation actually understood?
Assume goodwill on all sides. What's the gap between what they know and what you know?
room 07
If you were designing this organisation's approach to AI from scratch, what's the first thing you'd do differently?
You don't need to know the answer. What's your instinct?
honest 08
Has anyone in this room used an AI tool for work that wasn't officially approved? What happened?
This is a safe space. The question is about understanding what your organisation is actually doing versus what it thinks it's doing.
honest 09
What are you afraid AI will reveal about your work that you'd rather stayed hidden?
Not a trick question. About the parts of work we rely on that we're not sure survive scrutiny.
honest 10
The official line says AI won't replace you — someone using AI will. Do you believe that?
There's also a version where AI replaces both of you. That's a conversation worth having too.
next 11
What would good AI governance look like in this organisation, if it were designed by the people in this room?
Write it on a whiteboard. It doesn't have to be perfect. It has to be yours.
next 12
If we get this wrong, what does that look like in two years? And who in this room would feel it first?
The person who feels it first usually already knows. Give them space to say so.
next 13
What's one concrete thing this organisation could do in the next 90 days to get this right?
Not a strategy. Not a committee. One thing. What is it?
next 14
What question isn't on any of these cards that this room actually needs to answer?
The best question is usually the one nobody put on a card. Name it.
when you've sat with the cards, the diagnostic is the next step. nine questions, ten minutes, anonymous if you want.