Questions to Ask Senior Leadership
Questions to ask senior management at a skip-level meeting, a town hall Q&A, or in the ten minutes you get with an executive between sessions. Written for someone who already works there and wants a straight answer from the executive team about strategy, trade-offs, and how decisions get made, without sounding like a complaint. An intelligent question to senior leadership is rarely a clever one: it shows you know the plan has costs and asks which ones were chosen.
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The questions
Each question, and why to ask it
What are you spending most of your time on right now?
Why ask it
An easy opener that often lands somewhere unexpected: a lawsuit, an acquisition, a single unhappy customer. Whatever it is, it is the real priority regardless of what the published goals say.
What has surprised you most since you took this role?
Why ask it
Invites a story instead of a position, which relaxes the conversation. Leaders new to a seat tend to be candid here, and what surprised them tells you what the organization hides from the top.
When you look at our results, which number do you watch most closely?
Why ask it
There is usually one metric an executive checks before anything else. Knowing which one lets you frame your own work in terms they already care about instead of terms you have to explain.
What are you hearing from customers that most of us never hear?
Why ask it
Executives sit in conversations that never get written down. The answer often contradicts the internal story, and the gap between the two is where the next strategy change comes from.
What are we deliberately choosing not to do this year?
Why ask it
A clear answer means real prioritization happened. If nothing was cut, the plan is additive, and the shortfall will land on teams like yours as overtime rather than as a decision.
Six months from now, how will you know whether this year's priorities were the right ones?
Why ask it
Forces the leap from goals to evidence. If they cannot describe what a wrong call would look like, the priorities cannot be evaluated, only defended.
What does the board push you hardest on?
Why ask it
Pressure from above becomes pressure on you within a quarter or two. It also tells you which requests will be approved quickly and which will die no matter how good the case is.
If we come in under plan this year, what gets protected and what gets cut?
Why ask it
Blunt, and worth asking anyway. The honest version of the answer tells you which teams are considered core, and hesitation tells you the question has not been thought through yet.
Which part of the business do you worry about most?
Why ask it
Notice whether they name a product, a market, or a team. Leaders who only name external forces may not be looking closely enough at what is inside their control.
What is the strongest argument against our current strategy?
Why ask it
A leader who can state the counter-case has stress-tested the plan and will listen when you raise a problem. One who cannot has probably surrounded themselves with agreement.
Can you walk us through how the last big decision was made, and what the other options were?
Why ask it
The rejected options are the interesting part. They show what constraints are real, and they explain far more of the eventual outcome than the announcement ever does.
What kind of information reaches you too late?
Why ask it
Gives you something concrete to fix, and it is a rare question that helps them rather than tests them. Common answers are bad news from the field and slippage nobody wanted to report.
Who outside the leadership team do you go to for an honest read on how things are going?
Why ask it
If they can name people at several levels, information moves in the building. If they name only their direct reports, they are seeing a filtered version and probably know it.
Where does the executive team disagree most right now?
Why ask it
Asked of one executive, this shows which debates are still open above you. A reply that everyone is fully aligned is either caution in front of an audience or a room where nobody argues.
When two people on the executive team want different things, how does it get settled?
Why ask it
You are asking for the company's tie-break: the chief executive rules, the budget owner wins, or it waits until someone gives up. Knowing which one saves you from lobbying the wrong person.
What does the weekly senior management meeting spend most of its time on?
Why ask it
That agenda is a truer list of priorities than any slide. If most of the hour goes to one account or one overdue project, you have found what is crowding everything else out.
Which decisions does the executive team keep for itself, and which do you want made lower down?
Why ask it
Worth asking if you have ever waited weeks for an approval. A clear line lets you stop escalating things that were yours to decide, and a fuzzy one explains the queue.
What message from senior management got lost on its way down?
Why ask it
Most leaders can think of an announcement that reached the floor meaning something else. Their example shows how they believe messages travel, and it opens the door for you to say what your team heard.
What is the executive team trying to get better at as a group?
Why ask it
People at the top are seldom asked about their own teamwork. Something specific, such as fewer reversals or clearer notes after a meeting, means they examine how they work together and not only the results.
What would you like to hear more of from teams like mine?
Why ask it
Turns the meeting into an exchange instead of an audit, and the answer is usually specific and actionable: earlier warnings, shorter updates, more about customers, less about process.
What do you wish people would stop doing in meetings with you?
Why ask it
You get the unwritten rules of executive communication: no forty-slide preambles, no surprises, no asking for a decision without a recommendation. Cheap to learn, expensive to learn the hard way.
How do you decide who moves into leadership roles here?
Why ask it
Compare the answer to who was actually promoted recently. When the stated criteria and the visible pattern do not match, the pattern is the real system.
What did leadership get wrong last year, and what changed because of it?
Why ask it
The second half matters more. Admitting a mistake with no resulting change is performance; naming a mistake and the process that changed after it is the thing you were hoping to hear.
What advice would you give someone who wants to be doing your job in ten years?
Why ask it
Flattering enough to answer honestly, and specific advice about which experience to seek beats any published competency framework. Vague answers about hard work suggest they are not sure how they got there either.
What is the hardest part of your job that people here probably don't see?
Why ask it
Builds some mutual understanding, and it often explains behavior that reads as indecision from below: legal constraints, board politics, commitments made years ago.
What is the one thing you wish everyone here understood about where we're headed?
Why ask it
A good closing question because it makes them summarize. If the answer differs from the last all-hands message, the strategy has not landed, and that gap is worth knowing about.
If this year goes the way you want, what will be different by next summer?
Why ask it
Strategy stated as outcomes is checkable later; strategy stated as themes is not. Note whether the answer includes anything you could observe from your own desk, because that is the part that will actually reach your team.
Which part of this year's plan are you least confident about?
Why ask it
You are asking a leader to name a risk in public, which is a real test. Good answers identify a dependency or an assumption. Answers that reframe every risk as an opportunity tell you the culture punishes people who flag problems early.
What do our competitors do better than we do?
Why ask it
Leaders who cannot name a single competitor strength are either performing confidence or are not looking. The useful version of this answer includes what the company has decided to tolerate about that gap and why.
Where do you think we are slower than we should be?
Why ask it
Executives usually know exactly which handoff or approval step frustrates them, and naming it gives you cover to work on it. If the answer is that everyone needs to move faster in general, no one is accountable and nothing will change.
How do you decide whether to fund something for three years rather than three months?
Why ask it
This gets at how the company treats work whose payoff arrives after the current planning cycle. Listen for whether long-horizon projects have a protected budget line or are funded from whatever is left over, because the second kind gets canceled first.
How do you tell the difference between a project that needs more time and one that should be stopped?
Why ask it
Watch for whether they can describe a stopping rule set in advance or only judgement applied after the fact. Companies without stopping rules tend to keep projects alive until someone senior loses patience, which makes planning around them impossible.
Whose work does this year depend on more than people realize?
Why ask it
The answer names the team carrying hidden load: an infrastructure group, a compliance function, one salesperson with a key account. That is both a good place to offer help and a good indicator of where the company is single-threaded.
What is something you changed your mind about in the last year?
Why ask it
Reversals are specific and hard to invent on the spot, so this question usually produces a real story. It also shows you how new information travels: whether they changed course because of data, a customer, or someone junior pushing back.
What behavior do you see rewarded here that you wish were not?
Why ask it
This is the sharpest question on the list and the one most likely to get a real answer, because leaders notice the mismatch between stated values and who gets promoted. If the reply is that the culture is working well, you have learned something else.
What would make you say the culture was drifting in the wrong direction?
Why ask it
It asks for a leading indicator rather than a values statement. Concrete answers, attrition in a specific function, meetings getting larger, decisions taking longer, are things you can watch for yourself over the following year.
If you were in my role today, what would you spend your time on?
Why ask it
This converts a vague offer of mentorship into one actionable answer, and it forces them to translate strategy down to the level you work at. If they cannot, that is a signal about how well the strategy connects to daily work.
Asking questions upward without paying for it
Practical guidance for the conversation itself
Choose the right setting
Town hall Q&A
Whatever you ask is heard by everyone, including your manager. Keep it forward-looking and about the business, not about your own grievance. Anything that names a person or a team should not be asked here.
Skip-level meetings
You usually get thirty minutes and they will spend part of it asking about you. Bring three questions, not ten, and lead with the one you most want answered in case time disappears.
Hallway and travel moments
One question, no preamble. These are for the short, memorable ones, and they are how executives form an impression of you when nothing is at stake.
How to phrase it so you get an answer
- Ask about the decision, not the decider. 'How did we land on this?' gets an explanation; 'why did you decide that?' gets a defense.
- Give them a way to answer at their own altitude. Adding 'as much as you can share' lets them tell you something true rather than refuse the whole question.
- Skip the multi-part question. Executives answer the last clause and the rest evaporates.
- Do not smuggle in a proposal. If you want a decision on something, ask for that separately and come with a recommendation.
Listening for what matters
- Note which questions get a specific number and which get a story. Numbers usually mean the topic is being managed; stories often mean it is not yet.
- Watch for the phrase 'we're looking at that,' which frequently means nobody owns it. Following up in a month tells you which it was.
- If two executives give you different answers to the same question, that disagreement is real and is probably being worked out above you.
What to avoid
Questions that are really complaints
'Why is our tooling so bad?' invites a defense of the tooling. Describing the cost in hours and asking what it would take to change the plan gets a different conversation.
Asking for confidential detail in public
Headcount plans, individual departures, and acquisition rumors cannot be answered in a room of two hundred people, and asking puts the leader in an awkward position everyone notices.
Going around your manager
If a skip-level surfaces something your manager should have heard first, tell them about it yourself afterwards. It costs you nothing and it prevents the version where they hear it secondhand.
Afterwards
- 1Write down what you were told, in their words. Six months later this is how you will know whether the plan changed or your memory did.
- 2If they asked you for something, send it within two days. Following through once is worth more than any question you asked.
- 3Share the useful parts with your team. People who bring information back from these meetings get invited to more of them.