Questions to Ask C Level Executives
Time with a chief executive, finance chief or technology chief usually comes in small amounts: a skip-level meeting, a final interview, one question at an all-hands, ten minutes after an offsite. These twenty questions are built for that slot, aimed at what they know and nobody below them will tell you.
The questions
Open any question for the note
What has to be true in two years for you to say this period went well?
Why ask it
Executives answer this readily and the answer is concrete, usually a market position, a margin or a product. It also tells you which parts of the company are on the path to that outcome, which is useful if you are choosing where to work.
Which number do you look at first when the board pack comes together?
Why ask it
The metric an executive personally owns emotionally is not always the one on the strategy slide. Whatever they name is what will actually be defended when budgets are cut.
What are we deliberately not doing this year?
Why ask it
Strategy is mostly a list of refusals, and executives who can name them are running a real plan rather than a wish list. If the answer is that nothing is off the table, expect the organisation below to be thinly spread.
What is the biggest assumption in the plan, the one that would be embarrassing if it turned out wrong?
Why ask it
Invites genuine thinking rather than a summary, and senior people are often glad to be asked. The assumption named is also the risk you should watch, since your own work probably depends on it.
Where does growth need to come from: new customers, existing ones, or price?
Why ask it
These three imply completely different priorities for sales, product and support, and confusion between them is a common source of internal conflict. The answer tells you which teams are about to be under pressure.
If the year comes in short, what gets cut first?
Why ask it
A blunt question that gets a surprisingly honest answer, because most executives have already thought it through. It is also the most practical thing you can know about your own project's security.
What do you wish people two or three levels down understood about how decisions get made here?
Why ask it
Executives usually have a frustration ready: that decisions look arbitrary because the constraints are invisible, or that a request they made was heard as a mandate. It is the most immediately useful answer for anyone mid-level.
What kind of information tends to reach you too late?
Why ask it
Reveals both the reporting gaps and, indirectly, an opening for you. If they say customer churn reasons or delivery risk, someone who can surface that early has just found a way to be useful.
What do customers complain about that we have not fixed?
Why ask it
Chief executives hear complaints directly, in a form filtered out by the time it reaches an internal dashboard. The gap between what they hear and what the company is working on is often the most interesting thing in the conversation.
What did the company get wrong in the last year, and what changed because of it?
Why ask it
The second half is the test. A candid failure with a specific change attached suggests a functioning organisation; a failure with only a lesson learned attached suggests nothing was actually altered.
Whose work here is currently underrated?
Why ask it
Points you at teams doing real load-bearing work without visibility, which is where an ambitious person should often go. It also tells you what this executive personally values.
What behaviour gets someone promoted here that is not written in the competency framework?
Why ask it
Every company has an unofficial promotion criterion, whether that is volunteering for a mess, being trusted with clients, or writing clearly. Executives know it and will usually say it plainly when asked in this form.
What would you want to hear from someone in my role that you are not hearing?
Why ask it
Turns a networking conversation into an actual mandate. If they name something specific, you now have both permission and a reason to write to them again.
How much of your week is spent outside the company, with the board, investors, customers or regulators?
Why ask it
Explains a great deal about why decisions take the time they do and who is really shaping them. It also corrects the common assumption that an executive is available to think about your area at any depth.
What has changed in your own thinking since you took this job?
Why ask it
Asks for reflection rather than a philosophy, which is the difference between a real answer and a rehearsed one. Executives who cannot name anything have usually stopped updating on evidence.
What will look different about this industry in three years, and what are we doing about it now?
Why ask it
The second clause prevents a generic trends answer. Whether they can connect their view of the market to a current investment tells you if the strategy exists below the slide.
What sort of disagreement do you want brought to you directly, and what should stay with my manager?
Why ask it
Genuinely useful and rarely stated, since escalation norms are usually learned by getting them wrong. It also protects you from the mistake of going around your manager on something routine.
What makes you conclude a few months in that a hire was the wrong one?
Why ask it
Particularly worth asking in a final-round interview, where you get the real performance expectation rather than the job description. The answer is often about pace, judgment or asking for help too late.
Who do you go to when you need an honest read on something?
Why ask it
Identifies the informal power in the organisation, which is rarely the same as the reporting chart. Those are the people worth knowing, and the executive has just told you who they trust.
If I could take one thing off your plate this quarter, what would actually help?
Why ask it
Ends the conversation with an offer instead of a request, which is unusual enough to be remembered. Keep it to something you can genuinely deliver, since the follow-through is the whole point.
Using a Short Slot With a Senior Executive
Practical guidance for the conversation itself
Preparing for the Meeting
Match the question to the seat
A finance chief will engage with margin, cash and capital allocation; a technology chief with build versus buy and technical debt; a chief executive with the portfolio and the board. Asking someone about a topic they do not own produces a polite non-answer.
Read what they have already said publicly
An earnings call, an internal memo, a conference talk. Opening with a follow-up to their own words shows preparation and skips the answer they have given three times this quarter.
Pick three questions and expect to ask two
These conversations run short and get interrupted. Decide in advance which single question you would most regret not asking, and ask it early rather than saving it.
Tell your manager first if it is a skip-level
Not permission, just information. Executives frequently mention conversations to the person in between, and being the reason your manager was surprised costs more than the meeting gains you.
In the Room
- Lead with the question, not the context. Thirty seconds of setup is enough, and senior people will ask if they need more.
- Do not use the slot to raise a grievance or route around your manager. It is the fastest way to become a problem rather than a person.
- Take a note when they say something specific. It signals you intend to act on it, which is rarer than they would like.
- If they ask you something, answer briefly and honestly, including when the answer is that you do not know.
- End on time yourself rather than waiting to be ended. It is the single easiest way to be invited back.
Common Mistakes
Asking about topics with a required answer
Questions about strategy in the abstract, culture, or their leadership style produce the version they say publicly, because that is what those questions are for. Ask about a decision, a constraint or a trade-off instead.
Trying to impress instead of learning
A long question that demonstrates your own analysis uses the time you had for their answer. Senior people notice who was listening far more than who sounded clever.
Fishing for confidential information
Unannounced results, a live acquisition, a named person's future. Asking puts them in an awkward position and ends the candid part of the conversation for good.
No follow-through
If they suggest something and nothing happens, the next conversation will be shorter. The value of this kind of access comes almost entirely from what you do in the two weeks afterwards.
Afterwards
- 1Write the answers down the same day, especially any number or name they mentioned.
- 2Send a short note referencing one specific point, with what you plan to do about it.
- 3Do the thing you offered, then report back briefly once it is done rather than while you are doing it.
- 4Share what is shareable with your own team, since being a useful conduit is most of the value of the access.
- 5Keep the questions that produced real answers and drop the ones that produced the company line.