Questions to Ask an Executive
Questions for the rare half hour with a senior executive: a skip-level meeting, an internal fireside chat, a panel, or a coffee you asked for. They aim at how decisions actually get made rather than the version in the strategy deck. The last group holds questions for interns to ask executives at a summer Q&A or a leadership lunch, where nobody expects you to know the business yet.
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The questions
Each question, and why to ask it
The Business
What has your attention this quarter that was not on your list a year ago?
Why ask it
Opens on something concrete and current, and it exposes the gap between the published strategy and what is actually consuming leadership time. The new items are usually the honest ones.
What is true about this business that is not obvious from the outside?
Why ask it
Invites them to correct a public narrative they are probably tired of. The correction often points at a cost structure, a customer concentration, or a dependency the marketing never mentions.
Where does the money actually come from, and is that where you expect it to come from in three years?
Why ask it
Most people cannot answer this about their own employer. The gap between the two halves of the answer is the strategy, stated more plainly than any deck will state it.
What are we deliberately choosing not to do?
Why ask it
Strategy is mostly refusal, and executives who cannot name a rejected option are describing a wish list. The rejected options also tell you which internal arguments have already been settled.
What is the constraint on growth right now: people, cash, product, or demand?
Why ask it
Forces one answer instead of four. Whichever they name is where budget and attention will go next, which is useful if you are deciding what to work on.
What would make you say this year went badly?
Why ask it
Inverting the usual goals question gets past rehearsed targets to the specific failure they are actively steering away from. Vague answers here suggest the targets are not really operative.
Which number do you look at first on a Monday?
Why ask it
The metric they check by reflex outranks whatever the company officially reports. It also tells you what evidence would change their mind in a meeting.
What risk do you think about that we do not discuss publicly?
Why ask it
Phrased so they can decline gracefully, and what they choose to share signals how much candor is normal at their level. Refusing to name any risk is itself an answer.
What has changed in your thinking about the business over the past year?
Why ask it
Executives who cannot name a single revision are either coasting or performing certainty. The useful version names a belief they held, what contradicted it, and what they do differently now. Ask what convinced them, because that shows you what evidence carries weight with them.
How much of next year's plan is settled, and how much is still open?
Why ask it
This tells you whether there is any point pushing an idea upward this quarter. It also flushes out a common gap: the plan is treated as fixed at the top and as negotiable in the middle, and nobody has said which.
Which customer conversation has stuck with you most recently?
Why ask it
Whether they have one at hand tells you if they still talk to customers directly or only see them summarized. A specific story with a name and a complaint is a good sign. A generic answer about 'customer feedback themes' means they are two layers removed from the customer.
What is the bet we are making that you are least sure about?
Why ask it
Asking for the weakest bet rather than the biggest one gets past the pitch. The answer tells you which roadmap items could vanish, which is directly useful if you are deciding what to attach your own work to.
Where do you think we are slower than we should be?
Why ask it
Executives usually have a specific answer to this and rarely get asked for it. Notice whether they name a process, a team, or themselves. The last is rare and worth trusting.
Decisions
How do you decide what to say no to?
Why ask it
Reveals their filter: financial thresholds, gut feel, deference to whoever asked most recently, or an explicit set of priorities. The answer predicts how a proposal from you would be received.
How do you find out when something is going wrong three levels below you?
Why ask it
Tests whether they have real channels or rely on a filtered reporting line. Executives who name specific practices, such as reading support tickets or skip-levels, tend to be harder to surprise.
What kind of information stops reaching you, and how do you compensate?
Why ask it
Asks them to describe their own blind spot, which most senior people have thought about and rarely get asked. Watch for anyone who claims nothing gets filtered.
What do you wish people brought to you sooner?
Why ask it
Practical and immediately usable: it tells you the threshold at which escalation is welcome rather than resented, which is normally learned by getting it wrong.
What is a project you killed, and what tipped it?
Why ask it
The tipping point matters more than the project. Killed on a metric threshold means the company runs on evidence; killed because a senior person lost interest means it runs on sponsorship. Someone who has never killed anything is either new or not deciding much.
If you could reverse one decision from the last few years, which one?
Why ask it
The interesting part is whether they name a decision or a piece of timing. Naming a decision means they hold themselves accountable for judgment; naming timing means they attribute outcomes to circumstance, which predicts how they will treat your misses too.
When a decision reaches you, what usually makes it hard?
Why ask it
The honest answers are narrow: missing data, two good teams wanting the same headcount, or a promise made to someone outside the company. This names the real bottleneck, which is often not analysis but an unresolved political tradeoff.
How do you decide when the data is split and the deadline is now?
Why ask it
Useful answers describe a tiebreaker: take the reversible option, follow the customer, hand it to whoever owns the outcome. Answers about gathering more input and getting alignment describe a process rather than a decision, which usually means choices get made by delay.
When a proposal comes to you from two levels down, what makes you say yes?
Why ask it
This answer is directly usable. Most people pitch upward with detail and enthusiasm when an executive needs the decision, the cost, the reversibility, and who else is affected. Ask what a good one-page version looks like to them and your proposals will start moving.
What do you wish people further down understood about how decisions get made here?
Why ask it
This invites them to correct a misconception rather than defend a policy, so it tends to get a real answer. Expect to learn about a constraint nobody announced, like a contractual commitment or a cost ceiling that explains decisions that looked arbitrary.
When you and another executive disagree, how does that usually get settled?
Why ask it
Answers cluster into three types: escalate to the CEO, whoever owns the number decides, or it stalls until circumstances resolve it. The third is the most common and the least often admitted, and it explains projects that quietly never start.
What do you do when you have to carry out a decision you argued against?
Why ask it
This is one of the defining tasks of senior work, and the answer tells you whether disagreement is survivable here. Watch whether they distinguish between disagreeing privately and undermining publicly, or treat the whole question as loyalty.
What do you hear from the board that does not make it down to us?
Why ask it
Usually pressure on a specific number, or impatience with a timeline. They will not repeat anything confidential, but the shape of what they can say tells you which constraint is really driving the next two quarters.
Whose judgment do you lean on when you are unsure, and why theirs?
Why ask it
The answer maps the real influence network, which rarely matches the org chart. It also tells you what they respect in other people's thinking, which is the closest thing you will get to a description of their own standards.
How do you tell the difference between a team that is struggling and a team that is failing?
Why ask it
You are asking for the signals they watch, and they are usually behavioral rather than numeric: how a team talks about its own deadlines, whether problems arrive with proposed fixes, how fast bad news travels. Those signals apply to your own team immediately.
Career
What does a normal week look like for you now compared with five years ago?
Why ask it
Easy for them to answer and unusually informative, because the shift from doing work to reviewing work is the part of senior roles nobody describes accurately from the outside.
What made you take this job, and has it turned out to be the job you expected?
Why ask it
An easy opener that is rarely asked, and the gap between expectation and reality is where the honest part of the conversation starts. You often learn what they were promised on the way in, which tells you how the company sells itself at that level.
What did you actually get promoted for?
Why ask it
Asked plainly, this usually produces a far less tidy story than the official one: a project nobody wanted, a boss who moved, a market that turned. It corrects the idea that advancement follows a documented path, and it shows what gets noticed in this company.
What did you have to stop doing to work at this level?
Why ask it
People think about promotion as adding responsibility rather than giving something up, usually the hands-on work they were best at. The specific thing they surrendered, and whether they miss it, is the clearest preview of what the trade would cost you.
What made you promote the last person you promoted?
Why ask it
A specific case beats any list of stated values. If the reasons are visibility and tenure rather than judgment or results, that is the real promotion standard.
What advice did you get early on that turned out to be wrong?
Why ask it
Gets a reflective answer without asking them to criticize anyone present, and it often surfaces the conventional career wisdom they now think is useless.
What part of this job did nobody warn you about?
Why ask it
Usually produces something about isolation, the loss of direct work, or the weight of decisions about people. It is the most human question on the list and it rarely gets a rehearsed answer.
Who taught you the most about running something, and what did they do differently?
Why ask it
Specific behavior they copied is more instructive than a list of admired traits, and the story shows what they are still trying to imitate.
What is the hardest decision you have made about a person, and what did you learn?
Why ask it
Places the question late, when there is enough trust for a real answer. Leaders who describe only the outcome and none of the difficulty are telling you how they handle these decisions now.
What is the hardest piece of feedback you have gotten in this job?
Why ask it
A real answer is specific and slightly unflattering, and it signals that feedback travels upward here. A polished answer about 'learning to delegate' means it does not, or at least not to them.
What does this job cost you outside of work, and how do you think about that?
Why ask it
Ask late and without judgment. Answers range from a considered set of limits to a quiet admission that there are none, and either is worth knowing before you decide you want their trajectory. Some people will not answer, which also tells you something.
If you left in a year, what would you want to have finished first?
Why ask it
This gets at what they consider their real work, as distinct from what their title implies. Whatever they name is where your help will be most visible, and the effort most likely to survive the next round of reprioritizing.
From where I sit, what could I be doing that would actually be useful to you?
Why ask it
Turns a networking conversation into a working one, and the answer is often narrower and more actionable than anything in your objectives document.
What should I be learning now that will still matter in five years, and how would you actually learn it?
Why ask it
The second clause is what makes it worth asking. Naming a skill is cheap. Naming the assignment, the person, or the kind of problem that builds it is not, and that is the part you can act on next month.
What should someone who wants your job be doing now that they probably are not?
Why ask it
Phrasing it as a gap rather than a path gets past the standard advice about hard work. Expect something specific about reading financials, owning a P and L, or managing sideways rather than down.
What are you still trying to get better at?
Why ask it
A closing question that invites candor without pressure. A specific, current answer suggests someone still learning; a polished non-answer tells you the conversation was performance throughout.
For Interns
What do you remember about your own first internship or first job that still shapes how you work?
Why ask it
It starts from the one thing you have in common with them, which a strategy question from an intern cannot do. The detail they reach for, a boss, a mistake, a habit, is usually what they would tell you to watch for this summer.
What did you study, and how much of it do you use now?
Why ask it
Short and friendly, so it suits the first minutes of an intern lunch. Follow up by asking what they had to learn after school, because that list is closer to a real job description than the degree is.
What do you look for when you meet someone at the very start of their career?
Why ask it
With no track record to go on, they are reading something else: curiosity, follow-through, how a question is put. Whatever they name, they are probably noticing it in you while they answer.
What do new graduates tend to misread about how work is judged here?
Why ask it
School marks what you hand in. A workplace also weighs what you noticed, who you told and when, and each company draws that line in its own place. Hearing their version now is cheaper than finding it in a first review.
What is a project an intern worked on here that ended up mattering more than anyone expected?
Why ask it
Asking for a story gets more than a compliment about the program would. If they can name one, you learn what kind of intern work travels upward. If they cannot, you learn how far the program sits from their desk.
When a team asks to bring an intern back full time, what are they usually telling you about that person?
Why ask it
Return decisions are mostly made by the team, so this asks what reaches the top about them. How and when offers are made differs by company and by year, so take the answer as how it works here and ask your manager about timing.
Which entry-level roles here do you expect to look different in a few years?
Why ask it
You are choosing a first job that has to turn into a second one. Listen for whether they describe new tools or a change in what gets handed to junior people, since the second affects how you would learn the work.
If you were starting out today, would you choose this industry again?
Why ask it
Blunt, and easier to forgive from an intern than from a director. A yes with reasons is worth having, and a pause followed by a different field is worth writing down.
Which team should I spend an hour with before I leave, and why that one?
Why ask it
It asks for something small they can grant on the spot. Their pick tends to be where the company's next problem sits, and being able to say who suggested it makes the introduction easy to request.
What would you want every intern to understand about this company by the last week?
Why ask it
Built for a group Q&A, because the whole room can use the answer. It also hands you a yardstick for your own summer: if you cannot explain what they named by the end, you know what to ask your team about.
What is a question you wish an intern would ask you?
Why ask it
Keep it for when an intern Q&A has gone quiet. It hands them a subject they care about, and it shows what they think new people overlook.
Making Use of Time With an Executive
Practical guidance for the conversation itself
Before the Meeting
Read What They Have Already Said
Check the latest earnings call, all-hands recording, or public interview. Asking something they answered in detail last month wastes the slot and signals you did not prepare. Their own words also give you a specific thing to follow up on.
Pick Three Questions, Not Twenty
Half an hour holds about three real questions with follow-ups. Choose which one you would ask if the meeting were cut to five minutes, and lead with it.
Know What Sits Inside Their Remit
A chief financial officer and a chief operating officer will give very different quality answers about the same problem. Aim your questions where they hold actual authority, and you get decisions rather than opinions.
Decide What You Want to Leave With
An introduction, a decision, permission, or simply a better mental model of the business. Being clear stops the conversation ending pleasantly with nothing to act on.
If You Are an Intern at a Group Q&A
You will probably get one question in front of the whole intern class. Choose one that everyone in the room can use, keep it to a sentence, and hold the personal one for the minute afterward when people line up to say hello.
During the Conversation
- Ask one question at a time. Stacked questions get answered at the easiest one.
- When you get an abstract answer, ask for the most recent example.
- Do not fill silence. Senior people often pause before the useful part.
- Take notes on paper if you can, and write down the exact numbers they mention.
- Skip questions whose answer you could look up in the annual report.
- If they say something surprising, stay there instead of moving to your next item.
Common Pitfalls
Using the Slot to Present Yourself
Long preambles about your own work eat the time and rarely land. If you want them to know something about you, put it in one sentence and get back to the question.
Asking Only Strategy Questions
Executives answer strategy questions all day and have polished versions ready. Questions about how they work, what they missed, and what they refused produce fresher material.
Raising a Grievance Out of Nowhere
A skip-level is a poor venue for a complaint your own manager has not heard yet. It usually travels back down the chain and costs you more than it gains.
Not Following Up
If they offered an introduction or a document, send a short message within two days referencing the specific thing. Offers made in the room expire quickly.