Questions to Ask Company CEO
Questions for an employee who has the chief executive's attention: an all-hands Q&A, a skip-level, a coffee that got scheduled after a chance conversation. Written to get past the prepared talking points to what is actually funded, what is being dropped, and how decisions get made above your manager.
The questions
Open any question for the note
What are you personally spending most of your time on this quarter?
Why ask it
Stated priorities and calendar priorities often differ, and the calendar is the honest one. If the answer is fundraising, an acquisition, or one large customer, that tells you where attention and budget will go regardless of what the strategy deck says.
Of everything in the plan this year, which single thing has to go right?
Why ask it
A chief executive who can name one thing has a strategy. One who lists six priorities has a wish list, and you should expect resourcing fights all year, because six equal priorities means the tradeoffs get pushed down to your level to resolve.
What has changed in your thinking since you last talked to us about strategy?
Why ask it
This is a polite way of asking whether the plan is still the plan. Leaders who update in public are easier to work for than ones who quietly abandon last quarter's goals, and hearing what moved them shows you which evidence they actually weigh.
Which parts of the plan are already funded, and which still depend on how the year goes?
Why ask it
Announced initiatives and funded initiatives are not the same list. Knowing which side your project sits on tells you whether to plan for hiring or to plan for doing it with the people you have, and it is information your manager may not have either.
How will we know in six months whether this is working?
Why ask it
Look for a number and a date. If the answer stays qualitative, the goal cannot fail, which means it also cannot be managed, and mid-year you will be told progress is strong with nothing to check that against.
What are we deliberately not doing this year?
Why ask it
Strategy is mostly subtraction, and this question tests whether any subtraction has happened. A concrete answer, a market skipped, a product frozen, a customer segment declined, is a good sign. Hearing that everything still matters means nothing has been decided.
Where does our revenue actually come from, and how concentrated is it?
Why ask it
Employees routinely misjudge which part of the business pays for their team. The concentration figure matters most: if a handful of accounts carry the company, your job security is tied to renewals you never hear about.
Which competitor do you worry about, and why that one?
Why ask it
The reasoning is more useful than the name. Worrying about a cheaper entrant, a bundled incumbent, or an in-house build each implies a different response, and it tells you how they think about why customers actually leave.
What are you hearing from customers that we do not hear inside the building?
Why ask it
Chief executives sit in conversations most staff never see, so this is genuinely privileged information rather than a test of their character. Vague enthusiasm about customer love suggests they are not in those rooms as often as they claim.
When something is going badly, how do you want it to reach you?
Why ask it
You are asking whether bad news is welcome and by what route. A specific mechanism, a standing forum, a direct message, a weekly report with a red section, is usable. An open-door answer with no mechanism usually means problems travel by rumor instead.
What is a decision you have changed your mind about, and what changed it?
Why ask it
This separates leaders who revise from leaders who defend. The interesting part is the input that moved them: a customer call, a metric, one person's pushback. That is the kind of evidence worth bringing when you want something reconsidered.
Where do you think we are slower than we should be?
Why ask it
The answer names the friction the chief executive is aware of, which tells you which process fixes have air cover and which do not. If the diagnosis is simply that people need more urgency, expect pressure rather than any change to how work gets approved.
What is the case for someone in my role staying here three more years?
Why ask it
Asked directly, this gets either a specific picture of how the work grows or an appeal to the mission. The second answer is the informative one, because it usually means no one above you has thought about the trajectory of your job.
How do promotion and pay decisions get made above the manager level?
Why ask it
Most companies have a calibration process that staff never see described. Learning who is in the room, what evidence is used, and when the cycle happens is directly actionable, and evasiveness here tells you the process is more political than documented.
How much of next year's hiring plan is growth versus backfill?
Why ask it
A plan that is mostly backfill means attrition is doing the work of a hiring freeze, which nobody announces. The ratio also tells you whether the ambitious roadmap you were shown has the people behind it.
What would have to happen for us to need to cut costs, and what would go first?
Why ask it
Asking calmly and in advance usually gets a straighter answer than asking during a bad quarter. Whether or not you like the answer, knowing the trigger conditions and the order lets you judge your own exposure without relying on speculation.
Whose work here do you think is underrated internally?
Why ask it
The answer shows how far their attention reaches into the organization. Naming a specific team, especially one that is not customer-facing, is a sign they read past the highlight reel their direct reports send up.
What feedback about leadership have you heard recently that was hard to hear, and what did you do with it?
Why ask it
The second half is the real question. Anyone can recite a survey result; what matters is whether a specific thing changed afterward. No example, or a change that turns out to be another communication initiative, tells you the feedback went nowhere.
If you left tomorrow, what unfinished thing would bother you most?
Why ask it
This gets at genuine commitment rather than the official narrative, and the answer is often a structural problem rather than a product. It is also a fair way to hear whether they are staying, without asking that outright.
What is something people here wait for permission to do that they should just do?
Why ask it
Useful in two directions: it may hand you real latitude, and the answer reveals whether they understand why people hesitate. Leaders who blame timidity while running a culture of reversed decisions are describing a problem they created.
What do you wish people asked you in sessions like this?
Why ask it
A good closer when time is short, because it lets them raise the thing they came prepared to discuss and nobody surfaced. It also shows you what they consider the important conversation, which may not be what the agenda said.
Using the time well
Practical guidance for the conversation itself
How to ask
Bring one question, not five
In a room of two hundred people or a fifteen-minute skip-level, you get one real question and maybe a follow-up. Choose the one whose answer would actually change what you do next week, and let the rest go.
Say who you are and what you work on
One sentence of context makes the answer specific to your situation instead of generic. It also means the chief executive can place you later, which is most of the value of having spoken at all.
Ask the follow-up that pins it down
Most first answers are directional. The useful moves are asking for a number, a date, or an example: by when, compared to what, has that happened yet. Do it once, politely, then stop.
Take the sensitive questions to a private setting
Layoff exposure, a stalled promotion process, or a specific leader's behavior will get a careful public answer no matter how well you phrase it. Save those for a one-on-one, or send them in writing where a considered reply is possible.
Reading the answer
- A specific number with a date attached is a commitment you can revisit later. A direction with no measure is a sentiment.
- Watch what they name first when asked about priorities. First is what is real; the rest of the list is coverage.
- If a chief executive can describe the tradeoff they rejected, the decision was actually made. If everything is still possible, it was not.
- Redirecting your question to another executive is normal and often correct. Note whether the handoff actually happens afterward.
- Pay attention to which questions get a scripted answer. In a company that is genuinely open, the script comes out only for legal and financial-disclosure topics.
What goes wrong
Using the moment to escalate your own complaint
Raising a problem your manager has not heard yet puts everyone in a bad position, and the answer will be that they will look into it. Escalate through your manager first, then ask the chief executive about the pattern rather than your instance of it.
Asking a question to be seen asking a question
Long preambles and questions that are really statements are obvious from the front of the room. Being remembered for that is worse than not asking.
Asking what is already in the deck
If the answer appeared on slide four, you have spent your one question. Read the material beforehand and ask about what it left out, which is usually the tradeoffs and the funding.
Only asking about vision
Vision questions are comfortable and produce answers you cannot check. Funding, sequencing, headcount, and what is being dropped are the topics where you learn something that affects your work.
Never following up
If the answer was a commitment, note the date. If it was a referral, send the email that week. A question that gets a good answer and no follow-up leaves the same amount of trace as no question at all.
By setting
All-hands Q&A
- 1Pick a question a hundred colleagues also want answered, since the public forum is worth using on shared information.
- 2State your team, then ask in one sentence.
- 3If the answer is directional, ask once for a measure or a date, then hand the floor back.
Skip-level or one-on-one
- 1Open with something they can answer easily, such as what is taking most of their time this quarter.
- 2Move to the one question that affects your work directly: funding, sequencing, what is being dropped.
- 3Close by asking what they would want someone in your role to be paying attention to, and write down the answer before you forget it.