Questions to Ask Executive
Questions for the thirty minutes you get alone with a senior executive: how they spend their time, how they decide, what reaches them and what does not, and what they would tell you about building a career from where you sit. Written for a skip-level or an introduction that came through someone you both know.
The questions
Open any question for the note
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 does a normal week actually look like for you?
Why ask it
Titles hide the work. Hearing that most of the week goes to hiring, or to two accounts, or to internal meetings, tells you what the job really is and whether you would want it. It also tells you what they have no time for, which is useful the next time you need something from them.
What part of this job did nobody warn you about?
Why ask it
Senior roles carry costs that never appear in the job posting: the isolation, the delay before information reaches you, defending decisions you privately doubt. Whatever they name is usually the thing they are still working out, which makes it the most candid answer of the conversation.
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.
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.
What is the last thing you changed your mind about?
Why ask it
Recency is the test. Anyone can describe a shift in thinking from ten years ago. A recent, specific reversal, plus what caused it, shows whether new information reaches them and whether it can move them once it does.
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.
What is the most useful thing someone in my role could bring you?
Why ask it
It turns the meeting into an exchange rather than an extraction, and executives answer it concretely: an early warning about an account, what the field is hearing, the truth about a deadline. It is also the fastest route to being someone they contact directly.
What kind of information reaches you later than you would like?
Why ask it
Every layer of an organization filters bad news, and executives know they sit on the wrong end of that. The blind spot they name is often something visible from where you sit, which turns telling them into a contribution rather than a complaint.
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.
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.
How do you handle it when you have lost confidence in someone you hired?
Why ask it
The answer reveals how long people are left in roles they are failing at, which shapes the experience of everyone around them. Someone who acts quickly and says so directly runs a different organization than someone who waits for the annual cycle.
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 do you look for in the people you keep pulling onto important work?
Why ask it
Everyone has a short list of people they trust with the difficult thing, and the criteria are rarely about raw skill. They tend to be about who brings bad news early and who does not need managing. Hearing that out loud beats any competency framework.
Which piece of common career advice do you now think is wrong?
Why ask it
It invites disagreement with received wisdom, where anything original tends to live. You also learn what they think worked by luck rather than by design in their own path, and that distinction is missing from most advice.
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 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.
If you were sitting where I am, what would you be asking that I have not?
Why ask it
A good closing question: it hands them the last word and often produces the thing they were waiting to be asked. It also surfaces internal context you had no way of knowing to ask about.
Making the most of executive time
Practical guidance for the conversation itself
Before and during
Send the purpose in advance, in two lines
Say why you asked for the time and what you hope to leave with. Executives arrive at back-to-back meetings with no context, and two lines in the invitation means they are thinking about your topic instead of spending the first five minutes working out who you are.
Bring three questions, not fifteen
Thirty minutes holds about three real questions with follow-ups. Choose them beforehand and ask the most important one first, because these meetings routinely get cut to twenty minutes and the last item is the one that never happens.
Give something in return
One accurate observation from your level, a pattern in customer complaints, why a deadline slipped, what your team believes about a new policy, is worth more to them than anything else you can offer, and it is what turns a single meeting into an open door.
End on time yourself
At the five minute mark, say you want to give them the last few minutes back. Being the person who reliably returns time is remembered, and it makes a second meeting much easier to get.
Afterward
- Send a short thank-you the same day naming the one thing you took away. It confirms you listened and gives them a chance to correct you if you misheard.
- If they suggested you talk to someone, do it within two weeks and report back. Nothing else demonstrates that time spent on you produced a return.
- If they offered something, to read your draft, to make an introduction, take it up specifically and once. Vague follow-ups die and repeated ones become a cost.
- Write down what they said about how decisions get made while it is fresh. That part is the most useful and the first thing you will forget.
- Do not broadcast the meeting. Candor at that level depends on discretion, and an executive who hears their own words quoted around the office will be careful with you next time.
Common pitfalls
Using the meeting to ask for a promotion
An executive two or three levels up will not overrule your manager, and asking puts them in an awkward position while straining the relationship with the person who does decide. Ask instead what the level above you looks like when someone is doing it well.
Asking for their leadership philosophy
Abstract questions produce abstract answers, and you will hear the same four sentences from the last all-hands. Anchor every question to a real decision, a real week, or a real person, and the conversation becomes worth having.
Bringing a complaint about your manager
It reads as an escalation whatever your intent, and it will get back to your manager. If there is a genuine problem, take it through the channel built for it and keep this conversation about the work.
Talking for most of the time
Nerves turn into narration of your own projects. Prepare a thirty second version of what you work on, deliver it, then ask your questions. If you are speaking for more than a third of the meeting, you are not getting what you came for.