Questions to Ask a Senior Leader
Questions to ask a senior leader when you get a short stretch of their time: a skip-level, a coffee, a mentoring session or the microphone at a town hall. The 54 questions are grouped by what you want from the meeting: where the company is heading, how decisions really get made, what they want from teams like yours, how they built a career, how they lead, and how to close so there is a second conversation.
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The questions
Each question, and why to ask it
Priorities
What is taking up most of your attention this quarter?
Why ask it
They can answer it without preparing, which makes it a safe first question. Compare what you hear with the last company update: where the two differ, you have learned what is urgent as opposed to what was announced.
What is the biggest challenge facing the company right now?
Why ask it
The staple, and worth asking because the candid version rarely makes it into a company update. Follow with what is being done about it and who owns it. If nobody owns it yet, it may still be a worry and not a project.
What are you most excited about in the year ahead?
Why ask it
An easy one to answer, which makes it a good choice in a room full of people. Notice whether the excitement is about a product, a market or a person they hired, because that is usually where time and money go first.
Where do you see the company in three to five years?
Why ask it
Expect the rehearsed version first. The useful part comes from the follow-up: what has to go right in the next twelve months for that to stay possible. If nothing near-term is attached to the picture, treat it as an ambition and not a plan.
What are we saying no to this year?
Why ask it
Any leader can list priorities. Naming what was rejected shows there was a real trade-off, and it gives you something concrete to check your own team's work against. Vagueness here usually means everything is still officially a priority.
How would you know if the strategy was not working?
Why ask it
Look for a specific indicator and a date. Leaders who can name the signal they are watching have a plan that can be falsified, and leaders who describe only success conditions are likely to keep going long past the point of doubt.
Which part of the plan depends on something outside our control?
Why ask it
A regulator, a supplier, a single large customer, a hiring market. Knowing the external dependency tells you which internal goals are likely to move, and it stops you reading a change of course as indecision.
What is the first number you look at each week?
Why ask it
Whatever they name is what gets attention in their reviews, whether or not it leads the strategy deck. If your team does not move that number, ask which one they would look at to judge your area.
Which competitor do you take most seriously, and what are they doing right?
Why ask it
Praise for a rival is hard to give from a stage, so this works better in a small room. The thing they admire is often the thing your own company is about to try, and it tells you which comparisons carry weight when you make a case of your own.
What is a customer telling you lately that surprised you?
Why ask it
Senior leaders often sit in the conversations with the largest accounts, and little of it travels down. A fresh, specific story means they are still close to customers. If the latest example is a year old, the picture they are steering by may be too.
How do you expect AI and other new technology to change the work my team does?
Why ask it
Ask about your team's work and not about the technology in general, or you will get the conference answer. Listen for whether they talk about tools people will be given, roles that will change, or both, and ask what they would start learning now in your seat.
What keeps you up at night about the business?
Why ask it
The familiar wording, so expect a ready answer about the market or a competitor. Save it until the conversation has warmed up, then ask which risk the company does not talk about enough. That second answer tends to be structural: dependence on one customer, ageing systems, a skill nobody is replacing.
Decisions
Which recent decision do you think was misunderstood internally?
Why ask it
Invites them to explain reasoning that never made it into the announcement, which is usually where the actual constraint lives. It also tells you where they know communication failed, and whether they intend to fix it.
How do you make a big decision when you only have half the information?
Why ask it
Most decisions at their level are made this way, so they should have a method: a deadline, a person whose judgement they borrow, a cheap test first. Ask for the last time it went wrong as well. A quick, specific example suggests they go back and check their own calls.
When the leadership team disagrees, how does it get settled?
Why ask it
You are asking who really decides. Some teams argue until one person calls it, some wait for agreement, and some leave the room with two different versions. The third kind is why two departments can each believe they were given the go-ahead.
How does budget actually get decided, and when should a team be asking?
Why ask it
The calendar is the part people miss, and it differs from one company to the next. A request that arrives after the money is allocated can be turned down for timing and still feel like a verdict on the idea. Ask who needs to have seen a proposal before that date.
What did the last reorganisation fix, and what did it leave unsolved?
Why ask it
Only worth asking if there has been one in recent memory. A candid answer admits that a new structure trades one set of problems for another. If you hear only improvements, ask what the teams that were moved would say.
How do you decide to reverse a decision you have already announced?
Why ask it
Reveals how they weigh consistency against being right. A leader with a threshold and an example has changed course before, and that makes it safer for people below them to raise evidence that something is not working.
What takes far longer here than it should?
Why ask it
Leaders usually have a candidate: approvals, hiring, decisions returning to the same committee. Ask what they have tried already, because the answer tells you whether the bottleneck is a process nobody owns or one they cannot get past.
Which decisions do you want pushed down to teams, and which do you want to see first?
Why ask it
Ownership is easy to promise and easy to take back. A leader who can name the line, by size of spend or by which customers are affected, saves you from guessing. A reply that it depends is the cue to ask for one recent example on each side.
Your team
How does my team's work look from where you sit?
Why ask it
Brace for a short answer. They may know one project, one number or one person, and that is the reputation your team has upstairs whether or not it is fair. Anything they leave out that you think matters is your next update to them.
What kind of news reaches you late, or not at all?
Why ask it
Senior people are usually aware they are the last to hear certain things, and they will often name the category: quality problems, attrition risk, a customer quietly leaving. Ask whether they want that news the moment you see it or once you have a proposal to go with it.
When two priorities pull my team in different directions, which one should win?
Why ask it
Bring a real pair, such as hitting a launch date against fixing what customers keep reporting. A reply of 'both' means the choice is being left to your team, so ask who to go to the next time it happens. Put it as a request for a rule, or it will sound like a complaint about workload.
What is the best way to bring you an idea?
Why ask it
You are after format and route: a one-page note, ten minutes in a meeting, through your manager or straight to them. Plenty of ideas stall because they arrived in the wrong form at the wrong time, not because anyone weighed them and said no. Then use exactly the method they describe.
How do you want to hear disagreement from someone at my level?
Why ask it
Some want it in the meeting, some in writing beforehand, and a few do not really want it at all. An example of somebody who pushed back and was thanked for it means the invitation is real. No example means go carefully, and go through your manager.
What do you wish people at my level understood about the business?
Why ask it
Usually it comes back as money or time: how thin a margin is, how long a contract takes to close, what one delayed launch costs. Take it as a gap in what has been explained, not as criticism, and ask where you could go to learn more about it.
Where could my team be more useful to you than it is today?
Why ask it
It asks what they are not getting without turning it into a complaint. A named gap is close to a commission, so repeat it back and agree who should see the first result. If they say everything is fine, they may not know your team's work well enough to say.
What do you want people to stop doing?
Why ask it
Asked less often than what to start, and more actionable. A report nobody reads, a meeting that outlived its purpose, a habit of copying them on everything. Expect at least one thing you personally do.
If you were in my seat, what would you be pushing for?
Why ask it
The 'what would you do in my position' question, pointed at action. Say in a sentence what you can see from your seat that they cannot, or the advice will be about their job and not yours. If they name something specific, ask whether you may say the idea came from them.
Career
How did you get from your first job to this one?
Why ask it
Everyone can tell this story, so it suits a first meeting or a fireside chat. Listen for the moves that were not promotions: a sideways step, a spell in another function, a role that did not work out. Ask which of them they would repeat.
Which single move made the biggest difference to your career?
Why ask it
When time is short, this beats asking for the whole path. Ask what the move looked like beforehand, because the ones that matter often resemble a risk or a step down at the time, and that is the part you can use.
What do you wish you had learned earlier in your career?
Why ask it
Do not be surprised if the answer has nothing to do with technical skill. Asking for things, managing upward and leaving a role sooner all come up. Follow with how they eventually learned it, which tells you whether it can be taught or only lived through.
Which career advice held up for you, and which turned out to be wrong?
Why ask it
Advice ages, and what worked when they were starting out may not fit your field now. A leader who can name advice they followed and regretted is also giving you permission to weigh theirs the same way.
What went wrong early on that you still think about?
Why ask it
Asking for their biggest failure invites a polished story with a happy ending, and this wording gets something smaller and truer. Leave a pause after the answer. If they do not say what they changed afterwards, it is not yours to press for in a short meeting.
Who backed you early in your career, and how did that start?
Why ask it
The mentor question, aimed at how the relationship started and not at the praise. It may have been work that person saw up close, a project they shared, or a plain request for advice. Whichever it was is a route you can try with someone senior to you.
What skills should someone at my level be building for the next few years?
Why ask it
Say what your level and function are, or the advice will be generic. Good answers name something the company is short of, such as people who can read a balance sheet or run a difficult customer call. Ask where in the company you could practise it.
What tells you someone is ready for a bigger role?
Why ask it
They sit in the meetings where this is decided, so ask what gets said there. Common answers are that the person already does part of the next job, or that other teams ask for them by name. Ask which of those is harder to show from where you are.
What sort of work gets someone promoted here, and what gets overlooked?
Why ask it
The half about overlooked work is the real question. Launches are easy to see, while maintenance, cleanup and problems prevented are not, so ask how that quieter work gets noticed where you are. If there is no clear answer, describe your own work by what it stopped from going wrong.
How does someone get noticed by senior leaders here without turning into a self-promoter?
Why ask it
It admits the awkwardness, which most leaders appreciate. Practical answers include presenting your own work, writing the short summary other people forward, or taking on a problem that crosses teams. If the reply is simply to do good work, ask how that work would reach them.
Leadership
How would you describe your leadership style, and how has it changed?
Why ask it
The description on its own is rarely worth much, because nearly everyone says they are collaborative. The change is the real answer. What they stopped doing, and what made them stop, tells you more about working under them than any label.
What is the hardest part of your job right now?
Why ask it
Asked plainly, with no agenda, it tends to get a straight answer. It is often about people: a senior hire that is not working, two teams that will not cooperate, a decision that keeps getting postponed. Do not offer a fix, because listening is the whole job here.
Roughly how does a normal week break down for you?
Why ask it
The split between outside meetings, internal reviews and time alone to decide is often not what people further down imagine. It explains slow replies, and it tells you whether a short note or ten minutes in person is the better way to reach them.
What feedback do you get most often, and what have you done about it?
Why ask it
The second half separates leaders who collect feedback from leaders who act on it. A specific change, even a small one, is a better signal than any statement about being open to input.
What do you look for when you hire someone who will report directly to you?
Why ask it
Their answer describes the people who run your part of the company. Notice whether it is about skills, about trust, or about someone who will argue with them. It is also what they would weigh if your name ever came up for a role near them.
How would you describe the culture here, and what would you change about it?
Why ask it
Without the second half you get the values page. A leader who names something they would change, such as meetings that decide nothing or a habit of saying yes and then not delivering, is describing the culture as it really is. Ask what is stopping them.
How do you deliver a message you know people will not like?
Why ask it
Layoffs, a cancelled project, a return-to-office rule: every senior leader has had to do it. Listen for whether they explain the reasoning or only the decision, and whether they take questions afterwards. It predicts how the next piece of hard news will reach you.
Which book would you hand to someone who wants your job one day?
Why ask it
The book question nearly every leader gets, narrowed so the answer is advice and not a reading list. Ask what they took from it, since the reason says more than the title. If they are not much of a reader, ask who they call when they are stuck.
How do you protect time for a life outside a job this big?
Why ask it
You will hear firm rules from some leaders and an admission from others that they never solved it. Both are useful if you are weighing whether you want a job like theirs. Keep it light and let them move on quickly if they choose, since family or health may sit behind the answer.
What has kept you at this company?
Why ask it
Best asked of someone with long service, who will give reasons that never appear in a job advert: a boss who backed them, a problem they have not finished solving, the people. If they joined recently, ask what made them say yes instead.
Closing
What should I take back to my team from this conversation?
Why ask it
It makes them say the one thing they most want repeated, in their own words. It also gives you an honest reason to share the meeting with colleagues and with your manager, which keeps a skip-level from looking like a private channel.
Who else in the company should I talk to about this?
Why ask it
One introduction from a senior leader opens a door that a cold message will not. Be ready to say what you want to learn, because they will ask. Follow up within a week and tell them how it went, or the offer will not be made twice.
Is there something you hoped I would ask and I have not?
Why ask it
Good for the last two minutes. It hands them the floor for whatever they came ready to say, and that is occasionally the real reason they agreed to meet. If they say you covered it, take that as the end and thank them.
Could I come back in a few months and tell you what I did with this?
Why ask it
Asking for a follow-up is easier when it comes with a promise to report back. Put the date in your own calendar, since they will not, and open the next conversation with the one thing you changed because of this one.
If we talk again in a year, what would tell you the year went well?
Why ask it
This is 'what does success look like' with a date on it, which tends to produce two or three outcomes you can check. Write them down and bring them to the next conversation, so the second meeting has somewhere to start.
Making a short meeting with a senior leader count
Practical guidance for the conversation itself
Before the meeting
Send one line about why you asked
A line such as 'I would like your view on where our team's work fits with the shift in priorities' gets a prepared answer. A request for a chat gets small talk and a glance at the clock.
Choose three questions and accept you will ask two
These conversations run short and get interrupted. Rank them, lead with the one that would change what you do next week, and leave the interesting-but-optional ones at the bottom.
Tell your own manager you are meeting them
Skip-levels read badly when they are discovered afterwards. A sentence beforehand removes the ambiguity and often gets you a useful briefing on what the leader cares about.
Bring one thing they will not already know
A pattern from customer conversations, a recurring failure, something that took your team three weeks and should have taken three days. Senior people remember whoever gave them information they could not get elsewhere.
Which questions suit which room
A skip-level or one-to-one
Open with one question from Priorities, then spend most of the time in Your team. This is the only setting where they can talk about your group in particular, so do not spend it on questions any employee could ask from the floor.
A town hall or all-hands Q&A
One question, short enough to say in a breath, whose answer helps everyone listening. Priorities and Decisions work best. Keep anything about your own career or your own team for a smaller room.
A coffee or a mentoring conversation
Career and Leadership are written for this. Ask about their path before you ask for advice on yours, and save one question from Closing for the end, because a second conversation is the point of the first.
A lunch or roundtable with colleagues
You will get one or two turns. Choose something nobody else has asked and that a leader can answer in front of a group: what they are excited about, what they want people to stop doing, how they deliver unwelcome news.
What the answers may be telling you
- They cannot name anything the company said no to: the choosing may not have happened yet, so expect priorities to shift.
- They describe what success looks like but no sign that the strategy is failing: ask who would raise the alarm, and how.
- The number they check each week is not one the published strategy mentions: plan around the number.
- The reorganisation is described with no downsides: ask someone who was moved by it before you take that as the whole story.
- They have no answer on which work gets overlooked: do not assume quiet work is seen, and say what yours prevented.
- They can list the feedback they get but not one thing they changed: take your manager's advice before you bring them a disagreement.
How these meetings get wasted
Using it to complain about your manager
Assume whatever you say will get back to them. If there is a serious problem, find out how a concern is raised where you work, which HR can tell you, and use that route. Otherwise leave it out of this meeting.
Asking questions answered in the last all-hands
It signals you did not attend or did not listen. Ask about the reasoning behind what was announced instead, which is the part that never gets said on stage.
Pitching for twenty minutes
If you want something, say it in two sentences and ask what would make it easier to approve. Long pitches get a polite yes and no follow-up.
Leaving with nothing written down
Send three lines the same day: what you heard, what you will do, what you will come back with. A leader who has that note has a reason to say yes when you ask for a second meeting.