Questions to Ask a CEO of a Company
For employees, job candidates and students who get time with a chief executive. Twenty questions on what the company is trying to finish this year, what carries the revenue, what constrains growth, which decisions are still open, how bad news travels upwards, and what gets someone promoted.
The questions
Open any question for the note
What is the company trying to finish this year that an outsider wouldn't guess?
Why ask it
Sidesteps the rehearsed vision answer and gets you the internal priority list. If the reply matches the press release word for word, you are talking to the public version of the person.
What did you get wrong last year?
Why ask it
Every chief executive has a stock answer about ambition and none about error, so this is where the script runs out. Naming a specific decision, rather than a market condition, tells you the company reviews itself honestly.
Where does the money actually come from: which product or customer carries the rest?
Why ask it
Companies usually have one profitable line quietly subsidising several interesting ones. Knowing which it is explains most of the decisions that look strange from the inside.
What is stopping you growing faster: people, cash, demand or regulation?
Why ask it
Forces a single constraint instead of a list of opportunities. It is also the most useful answer for you personally, because work that relieves the constraint gets noticed and work that does not gets absorbed.
Who is your most dangerous competitor, and why that one?
Why ask it
The named competitor is often not the obvious one, and the reasoning shows whether they think in terms of products or of customer habits. An answer that dismisses everyone is worth remembering for later.
What do customers complain about that you haven't fixed?
Why ask it
Any chief executive who reads support tickets can answer this immediately. Hesitation suggests customer feedback reaches them only after it has been through several layers of summarising.
What are you spending on now that won't pay back for two or three years?
Why ask it
This is where the actual strategy sits, since it is the spending nobody has to do. If nothing comes to mind, the company is being run quarter to quarter whatever the strategy deck says.
Which decision are you least sure about at the moment?
Why ask it
You are asking for live uncertainty rather than settled history, which is harder to answer and more revealing. Some will decline, and how they decline still tells you how much candour circulates here.
What would have to be true in three years for you to call this a success?
Why ask it
Ask for the conditions rather than the target, because conditions are checkable later. Vagueness here from a founder usually means the exit plan and the stated plan are different documents.
What is the company bad at that you have stopped trying to fix?
Why ask it
Mature answers exist: slow hiring, weak documentation, a legacy system nobody will touch. An insistence that nothing fits this description is the least believable answer available.
Which part of the strategy is hardest to explain internally?
Why ask it
Whatever they name is the part your own team is probably confused about too. It also shows whether they think of communication as their job or as somebody else's.
How do you find out when something is going wrong two or three levels down?
Why ask it
Listen for a mechanism rather than a sentiment: skip-level meetings, a support queue they read, one honest person they trust. An open-door policy on its own is not a mechanism.
What behaviour gets someone promoted here, and what quietly gets them stuck?
Why ask it
The second half is the part nobody publishes. If the answer to it is that nothing gets people stuck, you have learned that promotion decisions are not being examined.
What do you wish people brought to you, and what do they actually bring?
Why ask it
Gives you a practical instruction for your own next conversation with them. Most answers come down to wanting problems earlier and with a recommendation attached.
How do you decide when to stop something that isn't working?
Why ask it
Stopping is the hardest management act and the one most companies do badly. A named example of something they killed is worth more than any description of the process.
What did the board or your investors push you on most recently?
Why ask it
Reframes the chief executive as someone who is also accountable, and the pressure they are under explains targets that otherwise look arbitrary. Expect a general answer, since some of it will be confidential.
What does your week actually look like, and what would you drop if you could?
Why ask it
Concrete and easy to answer, and it shows where their attention really goes as against where the org chart implies it should. The thing they would drop is often the thing they should delegate to someone like you.
What kind of risk do you think about that rarely comes up at an all-hands?
Why ask it
Phrased to make room for a serious answer without asking them to disclose anything they cannot. Key-person dependency, a single supplier, or one customer being most of the revenue all live here.
If I were starting here tomorrow, what would you want me to spend my first month on?
Why ask it
Turns the conversation into something you can act on, and candidates who ask it get a much clearer picture of the role than the advert gave. Note whether the answer is about learning or about output.
Who taught you the most about running a company, and what did you take from them?
Why ask it
A closing question that people usually enjoy, and the borrowed habits they describe are the ones they will expect from you. If the only teacher named is themselves, that is also an answer.
Making the most of limited time
Practical guidance for the conversation itself
Match the question to the setting
Thirty seconds at an all-hands
Ask one question, in one sentence, on a subject that helps the whole room. This is the wrong venue for anything about your own career, and the right venue for asking what the priority is or what customers are complaining about.
A scheduled skip-level or one to one
Two or three questions is the realistic number. Open with something concrete, keep the harder question for the middle, and leave the last few minutes for whatever they raise themselves.
An interview as a candidate
Use your questions to test the story you have been told. What constrains growth, what carries the revenue and what the first month should look like will tell you more than asking about culture.
A student or research conversation
Send one question in advance so they can prepare something useful, and keep the rest about decisions rather than opinions. Ask for the story of a specific choice and you will get material nobody else has.
Before you go in
- 1Read what the company has already published: the last set of results, any shareholder letter, the careers page, recent interviews. Asking something answered there wastes your one turn.
- 2Write your question down and cut it to a single sentence. Long preambles get answered from whatever the executive heard first.
- 3Decide what you want to walk out with: a fact, a judgement, or a working relationship. They call for different questions.
- 4Have a second question ready in case yours gets answered by someone else before your turn arrives.
What they cannot tell you
- Anything price-sensitive at a listed company, including revenue trends and deals in progress, is off limits before it is published.
- Individual pay, performance and dismissals will not be discussed, and asking makes the rest of the conversation more guarded.
- Live acquisition or redundancy plans will be denied or deflected. Ask about the criteria they would use instead.
- A refusal to answer is still data. Note whether they say they cannot answer, or answer a different question and move on.
After the conversation
Write down the exact phrasing of anything you intend to rely on, since the difference between we are hiring and we would hire for the right person matters later. If you were promised a follow-up, put it in an email the same day, short, with the specific thing you were offered. If you are an employee, the strongest follow-up is to do something about the constraint they named and tell them in one line when it is done.