Questions to Ask CEO of Your Company
Questions for the rare occasions when you get time with your own chief executive: a skip-level, a coffee, a small group session. They cover how the business really runs, what leadership is betting on, and what progression looks like here.
The questions
Open any question for the note
What does a good week look like for you?
Why ask it
A gentle opener that gets a concrete answer. Where a chief executive spends time, customers, hiring, fundraising, product, tells you what the company is actually organized around.
What are you spending most of your time on right now?
Why ask it
Different from asking about priorities, because time is finite and cannot be faked. If the answer looks nothing like the stated strategy, the strategy is not what is being executed.
What do you wish more people here understood about the business?
Why ask it
Invites the explanation they keep having to repeat. It usually concerns money: margins, cash, or how long a sale genuinely takes from first contact.
How is the company doing, in the terms you use internally?
Why ask it
Asks past the version prepared for outsiders. Even a partial answer shows which numbers leadership treats as the truth rather than the presentation.
What are we betting on this year?
Why ask it
Most companies can only really place one or two bets at a time. A list of five means the choice has not been made yet, and teams will feel that as constant redirection.
What's most likely to knock us off course?
Why ask it
A named risk is worth more than reassurance. Whether the answer is a customer, a hire, a competitor or a date on which cash runs short tells you what to watch.
How do you want decisions made when you're not in the room?
Why ask it
Practical, and rarely asked. The answer, written proposals, a named owner, a threshold for escalation, is directly usable by anyone who leads a piece of work.
What have you changed your mind about in the last year?
Why ask it
Specific and hard to fake. A leader who can describe a reversal and what caused it is describing an organization where evidence can still move a decision.
Where do you think we're weakest as a company?
Why ask it
Most chief executives have a candid answer and are seldom asked somewhere they can give it. Compare what you hear with your own experience of that area.
What work here is undervalued?
Why ask it
Shows whether leadership sees the unglamorous parts: support, documentation, maintenance, internal tools. If only revenue-facing work gets named, that is what will be rewarded.
How do you decide what to stop?
Why ask it
Stopping is harder than starting and reveals more about discipline. Ask for a recent example of something cancelled and what happened to the people who were working on it.
What does progression look like for people who don't want to manage?
Why ask it
Tests whether there is a real individual contributor track or only a title. The answer decides whether staying hands-on here is viable for years or only for now.
How much of our roadmap comes from customers versus our own view?
Why ask it
Both extremes cause trouble: purely customer-led work produces an incoherent product, purely internal vision misses the market. Where a leader places the company is worth knowing.
What do you look for when you promote someone into a senior role?
Why ask it
Concrete and directly useful. Listen for behaviors and results rather than traits, and check whether recent promotions actually match the description given.
How are you thinking about where we work?
Why ask it
Ask what would have to change for the current policy to change. That is the part employees are usually left guessing about, and it is answerable without committing to anything.
What's the most useful feedback you've had from someone junior?
Why ask it
Tests whether feedback travels upward and survives the journey. A detailed answer means the channel works, and a vague one means it is decorative.
What keeps you here?
Why ask it
Ask this late. The answer separates someone building a company from someone managing an asset, and it is the closest you will get to their private assessment of the place.
Is there something you'd do differently if you were starting the company today?
Why ask it
Invites a real critique of the current setup without asking anyone to defend it. Common answers concern hiring order, pricing, and how long a bad decision was left standing.
What should someone in my role be getting better at?
Why ask it
More specific and easier to answer than a request for general advice. Even a short answer gives you something to act on, and it signals that you intend to.
What's one thing you'd like me to take back to my team?
Why ask it
Ends the conversation with something usable and respects that the time was limited. Whatever message gets chosen also shows what leadership thinks is not landing.
Making Use of Time With Your Chief Executive
Practical guidance for the conversation itself
Getting the time in the first place
Use the channel that already exists
Many companies run skip-levels, office hours or rotating lunches that are quietly under-subscribed. Signing up is usually easier than requesting a meeting cold.
Say what it is about when you ask
A request with a subject attached is far more likely to be accepted than a general request to connect. It also lets them arrive with something useful to say.
Tell your manager first
Not permission, but courtesy. A manager who hears about the meeting afterward will reasonably wonder what was discussed, and that costs you more than the conversation gains.
Running a short conversation well
- 1Pick three questions and accept that you will only get through two.
- 2Open with something easy and concrete rather than your most important question.
- 3Ask, then stop talking. The pause is where the real answer usually arrives.
- 4Follow one thread properly instead of covering more ground.
- 5Close by asking what would be useful to take back to your team.
What not to bring
- A complaint about your manager, which puts everyone in an impossible position.
- A request for a raise or a promotion, which belongs in your own reporting line.
- A pitch for your project, unless you were invited to bring one.
- Questions answered in last week's company update.
- A list of grievances collected from other people who did not agree to it.
Afterward
- Send two or three lines of thanks with what you took from it, not a summary of the meeting.
- Act on any specific advice within a few weeks, since that is what makes a second conversation likely.
- Share anything generally useful with your team, leaving out anything said in confidence.
- Keep a note of the claims you heard and check them against what happens next quarter.