Questions to Ask a CEO of Your Company
For employees who get time with their own chief executive at a town hall, a skip-level or a company event. Twenty questions on what they would protect if budgets were cut, the numbers they watch, decisions people still do not understand, how headcount and pay get decided, and what they wish they were hearing from your level.
The questions
Open any question for the note
Of everything we're doing this quarter, what would you protect if we had to drop half of it?
Why ask it
Priorities only become real when something has to go, and this is the phrasing that gets a ranked answer rather than a list. Whatever they name is where your own work is safest.
What's the first number you look at on a Monday morning?
Why ask it
Small, concrete, and quietly the most useful thing you can learn in a town hall. If nobody in the room recognises the number, that is a communication gap worth raising with your own manager afterwards.
What did we stop doing this year, and why?
Why ask it
Companies announce launches and bury cancellations, so the reasoning behind stopping rarely gets shared. The answer tells you whether projects here end deliberately or just quietly lose their people.
What decision from the last six months do people here still not understand?
Why ask it
Gives them an opening to re-explain something without anyone having to accuse them of a bad decision. If they cannot name one, it usually means the internal grumbling is not reaching them.
Was there something you couldn't tell us at the time that you can talk about now?
Why ask it
Acknowledges that some silences were necessary, which makes it easier to answer honestly. A chief executive who takes this up builds more trust than one who insists nothing was ever held back.
Which team do you worry about most at the moment?
Why ask it
Riskier to answer than it looks, so expect a careful reply about a function rather than a person. Even a hedged answer tells you where attention and headcount are about to go.
What actually reaches you about the work my team does?
Why ask it
Most people are surprised by how little, or by which single metric stands in for a quarter of work. Once you know what they see, you know what to make sure is accurate.
How are decisions about headcount made, and where are we adding next?
Why ask it
The process matters as much as the answer, because it tells you whether your manager's request for another person ever had a chance. Watch for whether hiring follows revenue, a plan, or whoever asks loudest.
How much financial room do we have, in whatever detail you can share?
Why ask it
Phrased so a listed company or a nervous founder can still answer something. The reluctance or ease of the reply is itself a signal, and vague reassurance from a private company is worth taking seriously as a warning.
How is pay decided here, and when does it get reviewed?
Why ask it
Ask about the mechanism, not your own salary, and you will get an answer in a public setting. Bands, review timing and who signs off are the things that let you have a useful conversation with your manager later.
What would make you change the policy on office and remote working?
Why ask it
Asking what would change it gets you the criteria rather than the current line. If there are no criteria, the policy will move with the mood of whoever is loudest, and you can plan accordingly.
If we miss this year's targets, what happens first?
Why ask it
A calm way of asking about cuts without using the word. Whether the first lever is hiring, marketing spend, contractors or headcount tells you what kind of company you are working for.
What does the company actually reward, as against what we say we reward?
Why ask it
Everybody in the room already knows the answer, so asking it out loud is the point. A chief executive willing to name the gap tends to be one who will close some of it.
Which internal process do you know is broken that we're living with?
Why ask it
Shared frustration, safely expressed, and it invites a genuine answer about approvals, tooling or a legacy system. If they name something, ask who owns fixing it, because the answer may be nobody.
What are you personally spending your own time on this quarter?
Why ask it
Where the chief executive's own hours go says more about the real strategy than the strategy slide. It also tells you which decisions can be moved quickly and which are queued behind them.
What have you changed your mind about recently?
Why ask it
Rarely asked internally and usually answered generously. Someone who cannot produce an example is either not listening to anyone or not willing to say so in front of the company.
Where do you expect us to look different in a year: product, customers, size?
Why ask it
Concrete and near enough to be checkable, which makes it harder to answer with ambition alone. Compare the answer with what you hear next quarter, and you will know how much weight to give the one after that.
What do you wish you were hearing from people at my level, and what do you get instead?
Why ask it
Turns the question into an instruction you can act on this week. Most answers come down to wanting problems earlier, with a recommendation, and without the softening.
If I think something is going badly and my own chain isn't moving on it, how should I get it to you?
Why ask it
You want a named route: a skip-level, an email, a specific forum. Asking in public also makes the route harder to close later, and the reply tells you whether escalation here is normal or career-limiting.
What should someone in my position be building towards to still be useful here in three years?
Why ask it
Better than asking about promotion, because it invites a view of where the work itself is heading. Vagueness usually means nobody has thought about your function's future, which is worth knowing now.
Asking without it costing you
Practical guidance for the conversation itself
The setting changes the question
A town hall with an open microphone
One question, one sentence, and something the whole room benefits from. Questions about strategy, priorities and processes work here; anything that sounds like a complaint about a named person or team does not.
An anonymous question tool
This is the right channel for the harder ones about runway, missed targets or the gap between stated and actual rewards. Upvote rather than duplicate, since a question with fifty votes is far more likely to get a real answer.
A skip-level meeting
Bring two questions and one piece of information they will not have. Skip-levels are more useful when you arrive with something from the ground than when you arrive only with concerns.
A chance encounter
Keep it to one short question and let them leave. This is a good moment for what are you spending your own time on, and a bad moment for anything requiring a considered answer.
Go through your manager first
If your question is really about your team's problem, raise it with your manager before the town hall. Not for permission, but because being surprised in public is the fastest way to lose an ally, and because they may already know why the decision was made. Tell them what you plan to ask and you often get a better version of the question.
Phrasing that gets an answer
- Ask about the criteria rather than the decision. What would make you change this can be answered when why did you do this cannot.
- Ask about a mechanism rather than an intention. How would that reach you gets specifics; do you care about this does not.
- Give them a way to answer partially. In whatever detail you can share lets a listed company say something instead of nothing.
- Leave names out. The same question about a process rather than a person gets a straight answer and costs you nothing.
- Avoid the multi-part question. Two questions in one gets you an answer to the easier half.
What to do with the answer
- 1Write down the wording, particularly any figure or date. Answers drift in the retelling, and yours will be quoted back to you.
- 2Tell your own team what you learned, plainly and without editorial. This is the most valuable part of having asked.
- 3Act on the one instruction you were given, whether that is bringing problems earlier or fixing what they see about your work.
- 4Check the answer against reality next quarter. Two questions asked six months apart tell you more than any single conversation.