Good Questions to Ask Upper Management
Good questions to ask upper management are short, specific and hard to answer with a slogan. These 53 are for the rare time you get with top management: a skip-level, a town hall, a site visit, or a small session with your management team. They run in the order the conversation tends to go: what the people at the top are working on, the state of the business, how decisions get made above you, how your team looks from up there, careers, and how to close so that there is a second meeting. Nobody gets through more than a handful, so pick the two that fit the room you will be in.
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The questions
Each question, and why to ask it
Priorities
What are you personally spending most of your time on this quarter?
Why ask it
Calendars reveal priorities more honestly than strategy decks. If the answer is a project nobody below has heard of, you have learned where attention and budget are heading.
What is the one thing the management team has to get right this year?
Why ask it
Asking for one forces a ranking that a list of five priorities avoids. If two members of the management team would give different answers, the ranking has not been settled, and your own team's priorities will keep moving until it is.
Which of our current bets are you least sure about?
Why ask it
A named doubt marks the part of the plan most likely to be revised, and it is better heard now than in the memo that revises it. Complete confidence in every bet is an answer too, and a less reassuring one.
What did the management team decide not to do this year, and was it a close call?
Why ask it
A plan is easier to read from what was left out of it. A close call tells you the dropped item still has supporters at the top and could come back at the next budget round.
What has changed in the plan since it was announced?
Why ask it
Plans drift between the kick-off and the middle of the year, and the changes are seldom announced with the same energy. Hearing them directly saves your team from working to a version that upper management has already moved on from.
Which of this year's goals is furthest from being met?
Why ask it
Upper management usually knows which target is in trouble well before it is said aloud. The goal they name is where pressure, extra reviews and borrowed people will show up next.
If I had to explain this year's plan to a new hire in two sentences, what should I say?
Why ask it
You get the plan in the words they would use themselves, minus the slides. If they cannot do it in two sentences, that explains why it has been hard to follow from where you sit.
What are we doing today that you expect us to stop doing in two years?
Why ask it
A product line, a manual process, a market: whatever they name already has an end date in their mind, announced or not. If your own work is on the list, you have heard it early enough to move toward whatever replaces it.
The business
Where does our revenue actually come from now, and is that mix shifting?
Why ask it
Dependence on one product or a handful of customers shapes a good many decisions above you without ever being mentioned. In a charity or a public body, put the same question about funding. A leader who can give the split from memory is close to the numbers.
What do you hear from customers that does not reach us?
Why ask it
Senior managers take the escalation calls, the renewal meetings and the complaints addressed to whoever is in charge. One remark from those rooms can settle an argument your team has been having for months about what customers want.
Which competitor concerns you most, and why that one?
Why ask it
The why matters more than the name, because it exposes what they think our advantage rests on. If no competitor worries them, ask which one is winning the deals we lose.
If the next two quarters come in below plan, what happens?
Why ask it
Half the room is wondering and few will say it, so asking it calmly does everyone a favor. Pay attention to the first lever they reach for, whether a hiring pause, a price change or a spending cut, since the first one named is usually the one already talked through.
Which cost are you watching most closely right now?
Why ask it
The line they name is the one most likely to be squeezed, whether that is travel, contractors, software or headcount. If your work depends on it, you now know to make the case for it before the review and not after.
What decides whether a team gets to add people this year?
Why ask it
Headcount is often the scarcest thing upper management hands out, and the rule for it is seldom written down. Ask whether it follows revenue, a named priority or whoever asked first, because each one calls for a different case from your manager.
Which part of the business gets less of your attention than it should?
Why ask it
It is a rare chance for a senior person to admit a blind spot without being accused of one. If the neglected area is yours, the follow-up is what would help them see more of it.
What outside the company could hurt us most in the next year?
Why ask it
A new regulation, a supplier, a currency, one customer's budget: the answer depends heavily on your industry and country. It tells you which bad news would be nobody's fault, and which targets might be rewritten because of it.
How do you expect AI tools to change the work people do here?
Why ask it
Ask for the management team's actual position: which tools are approved, what is being piloted, and whether the aim is more output from the same people or the same output from fewer. Employers differ widely on this and many are still deciding, so ask when the current line is due to be looked at again.
What do the owners or the board ask you about most often?
Why ask it
Top management has bosses too, and their questions set the agenda several levels down. Who that is depends on the company: a board, a parent group, a founder, investors or a government department.
Is there a reorganization coming that you are able to talk about?
Why ask it
Ending on 'that you are able to talk about' gives them an honest way to decline. A flat no, a careful 'nothing I can share yet' and a long pause are three different answers, so note which one you got.
Decisions
When a good idea gets turned down here, what is usually the reason?
Why ask it
The reply tends to be one of a few things: no money this year, bad timing, a clash with a stated priority, or no senior person willing to own it. Whichever they pick is the gap to close before you bring a proposal of your own.
What do people at my level tend to misunderstand about how decisions get made here?
Why ask it
Correcting a misconception is something senior people enjoy, so this one seldom gets a guarded reply. The correction is often about timing: the budget was fixed months before the request arrived, or the person everyone lobbies is not the one who signs.
When two people on the management team disagree, who makes the call?
Why ask it
In some companies the most senior person decides, and in others the argument runs until somebody gives up. Knowing which kind you work in tells you whether a stalled project needs a better case or simply someone to rule on it.
Which decisions come up to you now that you would rather were made lower down?
Why ask it
Senior teams tend to say they want to delegate more, so ask for a specific example. If they give one, check whether your manager knows the authority is on offer, because that message can stop a level above you.
How long should something that needs your sign-off take, and where does it usually stall?
Why ask it
With the real timetable you can plan a request around it instead of chasing it. The sticking point may not be the senior person at all: a form, a finance check or a committee that only sits once a month.
When the strategy changes, how do you want the reasons to reach people at my level?
Why ask it
A decision that arrives without its reasons gets second-guessed all the way down. If they describe a route, such as a memo, a briefing for managers or an open Q&A, you can say plainly where it broke down the last time.
Who outside the management team do you talk to before a big decision?
Why ask it
Their list shows whose view carries weight: a finance partner, a long-serving engineer, a key customer, an adviser. It also shows whether anyone close to the daily work is heard before the choice is made.
What decision from the past year would you make differently now?
Why ask it
Most leaders have one they have already turned over in private, so the question is less rude than it sounds. Notice whether they describe what they changed afterwards or only what went wrong: that is the difference between a lesson and an anecdote.
How do you find out something is going badly before it becomes a crisis?
Why ask it
The mechanism matters: a metric, a weekly review, or someone willing to tell them. If the honest answer is that they find out late, follow up with what would have helped them hear sooner, since the people who knew first were probably at your level.
What do you suspect the people around you are reluctant to tell you?
Why ask it
Seniority filters what people say, and a thoughtful senior manager knows it. Whatever they guess at is a subject you can raise with less risk than most, since they have just said they want to hear it.
Your team
How is my part of the business measured at your level?
Why ask it
The metric your team watches and the number reported upward are often different, and that gap is behind a lot of puzzling requests. Once you know the figure they look at, you can describe your own work in it.
What do you actually see of our work: a dashboard, a monthly report, or what our director tells you?
Why ask it
Each of those shows a different slice, and none of them shows the work itself. The channel they name is where a problem has to appear before anyone at the top can act on it.
What does our team do that you would be most reluctant to lose?
Why ask it
The answer is your team's value in upper management's own words, and it is not always the thing the team is proudest of. Borrow their wording the next time you have to justify a budget or a hire.
What do you think my team should be doing less of?
Why ask it
Teams collect work that once mattered and was never cancelled. Permission from this level to drop something carries further than permission from your own manager, so ask whether you may quote them.
What do other departments tell you about working with my team?
Why ask it
Complaints about a team tend to travel upward through other managers and never come back down. One specific gripe, such as slow turnaround or unclear ownership, is something you can fix quietly before it colors a budget discussion.
When did you last sit with people who do our kind of work, and what did you notice?
Why ask it
A recent, concrete memory means their picture of the work is current. If it has been years, offer a visit, a shadowing hour or a demo, which is an easy thing for a busy person to say yes to.
What should we bring straight to you, and what should always go through our manager first?
Why ask it
The easiest mistake after a skip-level is going around your manager without meaning to. Many leaders want safety and conduct concerns directly and nearly everything else through the line, but the boundary differs by employer, and some have a formal reporting channel for the first kind.
How do you want to be told when a date we have given you is going to slip?
Why ask it
Preferences differ: some want it early and in writing, some in person, most with options attached. Learning theirs in a calm week beats learning it on the day the date goes.
What would you like to see from us in the next six months that you are not seeing now?
Why ask it
It turns a general impression of your team into a request you can act on. Write the answer down word for word and take it to your manager, so the two of you are not guessing at what the level above wants.
If you were in my job, what would you want to understand about the company that I probably do not?
Why ask it
Putting them in your seat gets past the reflex to reassure. The reply is often a single piece of context, such as a contract up for renewal or a deadline set from above, that reorders your next month.
What is the best way for someone at my level to get an idea in front of you?
Why ask it
There is usually a real route, whether a particular forum, a one-page document or a certain director who filters what goes up. Being told it saves a year of guessing, and using it afterwards shows you listened.
Careers
How are promotions into senior roles actually decided here?
Why ask it
The written criteria are one thing and the conversation in the room is another, and a senior manager has sat in that room. A committee comparing candidates against each other needs a different case from one sponsor's say-so, so ask which it is here.
What do you notice about the people who get asked to take on more?
Why ask it
Who gets handed the next hard problem is settled informally, long before any promotion round. The useful parts of the reply are habits you could copy, such as closing things out or writing clearly, more than traits like confidence.
How does the management team decide where raises and bonuses go?
Why ask it
Pay processes differ a great deal by employer and country, and parts may be confidential or fixed by an agreement, so ask how it works here. Even a rough account of the pot, the timing and who has a say helps you raise it with your own manager at the right moment.
Which skills do you expect the company to be short of in three years?
Why ask it
It is a forecast and not a promise, but it comes from the people who approve the training budget and the job openings. A skill they mention twice is a reasonable place to put your own development time.
How do people at my level get onto the projects the management team cares about?
Why ask it
Visible work tends to be handed out by invitation, and the invitation has a source. Ask who puts those teams together, because that is the person who needs to know you are interested.
What did you have to learn the hard way when you first started leading?
Why ask it
'When you first started' pins them to one period, so you get a story with a year and a mistake in it instead of a leadership philosophy. People tend to drop the stage voice while they tell it.
Which move in your own career looked like a mistake when you made it?
Why ask it
A sideways step, a smaller employer or an unfashionable posting can look like a setback on the day. Hearing how one turned out for them makes it easier to judge an odd-looking offer of your own.
What would you say to someone who wants to be on the management team one day?
Why ask it
Asked plainly, it tells them you are ambitious without asking for anything. Good answers are specific to the company: which function to spend time in, which experience everyone now at the top happens to share.
Closing
Is there anything you have told me today that I should keep to myself?
Why ask it
Senior managers sometimes say more in a small room than they meant to. Checking protects both of you, and it marks you as someone who can be told things.
What can I do in the next month that would be useful to you?
Why ask it
A month is short enough that they will name something small and real. Doing it gives you a good reason to get in touch again.
Who else on the management team should I talk to, and about what?
Why ask it
An introduction from one senior manager to another opens a door that a cold request may not. The 'about what' gives you the first line of the message you will send.
Would it be all right to come back to you once I have acted on this?
Why ask it
It sets up a second conversation with a reason attached, which is easier to agree to than a standing meeting. Keep the promise, even if the update is two lines.
What should I have asked you and did not?
Why ask it
It hands them the last word, and some use it for the thing they came in wanting to say. Leave a pause after asking: the first reply is often 'nothing', and the real one comes a moment later.
Talking to Senior Leaders
Practical guidance for the conversation itself
Before the meeting
Read what they have already said publicly
Recent all-hands notes, an internal memo, the annual report or earnings call if the company publishes one. Asking a question that was answered on stage last month is the fastest way to look uninformed, and the material usually suggests a sharper follow-up.
Pick two questions, not ten
Skip-levels run short and get interrupted. Two questions you actually care about, asked properly, get better answers than a list worked through at speed.
Decide whether you want information or visibility
Those call for different questions. If you want the leader to remember you, ask something about the business they will have to think about, not something about your own career progression.
Which group suits which room
A skip-level with one senior manager
Start with a single Priorities question and give the remaining minutes to Your team. Nobody else can ask how your group is measured or what it should drop, and a private room is the only place those get a straight answer.
A town hall or all-hands
One question, said in a breath, that helps everyone listening. Priorities and The business suit a crowd. Careers and anything about your own team sound like special pleading from the floor.
A session with the whole management team
Use Decisions, plus the Priorities question about what was left out of the plan. Who makes the call when two of them disagree only means something when the people involved are sitting side by side. Watch who answers and who looks at whom.
An elevator, a corridor or a site visit
You have about a minute. Ask what they are spending most of their time on, listen, and finish with a question from Closing. The aim is a reason to speak again, not a full answer.
In the room
- Ask one question at a time, since stacked questions get answered selectively.
- Follow up on the part they skipped rather than moving to your next question.
- Do not use the time to complain about your manager unless you are prepared for it to be repeated.
- Take a note of any number they quote, because it will be useful later and often gets misremembered.
- If they ask you something, answer briefly and factually rather than presenting.
- Send a short thank-you with one line about what you took away, which makes the next meeting easier to get.
What to avoid
Questions designed to display your knowledge
Long preambles about market dynamics read as performance and rarely produce a useful answer. A short, concrete question makes you look more senior, not less.
Asking for a decision they cannot make on the spot
Pushing for approval in a five-minute conversation usually produces a soft yes that evaporates. Ask instead who needs to agree and what the process is.
Treating a town hall like a private meeting
Anything you ask in front of two hundred people is also a message to your own manager and team. Save the genuinely difficult question for a setting where the answer can be honest.