Good Questions to Ask Senior Leadership
Questions for a skip-level, an all-hands Q and A, or a fireside chat with an executive. They cover what leadership is worried about, what the company is choosing not to do, how bad news travels upward, how long-term bets get funded, and how promotion decisions are really made.
The questions
Open any question for the note
What has been on your mind most this quarter?
Why ask it
Executives have a polished list of priorities ready and will recite it if you ask about priorities. Asking what occupies them gets past the list. If they name nothing specific, they are either far from the work or unwilling to be candid in front of this audience.
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.
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.
What are we deliberately not doing right now?
Why ask it
A strategy is defined by its exclusions, and most people never ask for them. A leader who can name the abandoned market, the deferred product or the customer segment they are willing to lose is making real choices. A leader who says the company is doing all of it is describing a wish list.
Which number do you look at first on a Monday morning?
Why ask it
Whatever they check first is what the organization is actually optimizing for, regardless of what the goals document says. If it does not match the metric your team is measured on, that gap is worth understanding before your next review cycle.
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 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.
How does bad news from the front line actually reach you?
Why ask it
Ask for the mechanism, not the intention. Skip-levels, support ticket reviews and reading customer complaints directly are mechanisms. An open door policy is not, because it depends entirely on someone junior deciding to walk through it.
What do you hear from customers that you wish more of us heard?
Why ask it
This surfaces the complaint or request that leadership finds most persuasive, which is often not the one being discussed internally. It also tells you whether they are still in customer conversations or only reading summaries of them.
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.
Which part of our strategy do you think is most often misunderstood inside the company?
Why ask it
Leaders find this easier to answer than a direct question about communication failures, and the answer is usually specific. It also gives you the one explanation they most want repeated, which is genuinely useful if you manage people.
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.
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.
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.
How are decisions about promotions into leadership actually made?
Why ask it
Ask about the mechanics: who is in the room, what evidence is used, how long before the decision the candidate knows they are being considered. The published framework and the actual process are rarely the same, and the difference is what determines your path.
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.
What did you try early in your career that failed, and what did you take from it?
Why ask it
Career advice from executives is usually generic because the question was generic. Asking about a specific failure gets a story with detail in it, and the lesson they draw tells you what they still believe about how work gets done.
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.
What question do you wish people here asked you more often?
Why ask it
A closing question that costs the leader nothing and often produces the most candid moment of the conversation. It tends to reveal the topic they feel is under-discussed, which is useful to know before the next planning round.
Talking with senior leadership
Practical guidance for the conversation itself
Match the question to the setting
All-hands Q and A
Everything you say is on the record with the whole company listening. Ask about strategy, exclusions and what the year is meant to produce. Save anything that could embarrass a named team or person.
Skip-level one to one
This is where the sharper questions belong: rewarded behavior, promotion mechanics, where the company is slow. You have privacy and time for a follow-up, which is what these questions need.
Fireside chat or panel
The format rewards questions that make a good answer easy to give. Reversals, career failures and what they wish people asked all work well because they invite a story rather than a position statement.
Chance encounter
Ask one question, not three. What has been on their mind, or what they are least confident about, both work in ninety seconds and neither requires preamble.
Handling the answer
Ask one follow-up, then stop
The first answer is usually the prepared one. A single specific follow-up, what did that look like most recently, gets past it. A second follow-up in a group setting turns into an interrogation and costs you the room.
Do not argue the answer
If you disagree, note it and take it up later with your own manager or in writing. Debating an executive in front of an audience makes the disagreement about status rather than about the point.
Write down what you can check
Most of these answers contain a claim that will be true or false in six months. Keeping a note makes your next conversation much better informed than everyone else's.
Close the loop
If you act on something they said, tell them briefly. Executives get very little feedback that their answers landed anywhere, and it is the cheapest way to be remembered.
Common mistakes
Asking something the last earnings call answered
Anything published in results, a shareholder letter or an internal strategy deck is a wasted turn. Read those first and ask about what they leave out.
Turning the question into a speech
Long preambles are the most common failure in all-hands questions. State the question in one sentence and let them fill the time.
Using the slot to raise your own grievance
A specific complaint about your team or your compensation belongs in a private conversation. Raising it here rarely resolves it and usually reads as an ambush.
Asking only about your own advancement
One career question is reasonable. If all of them are about your path, the leader learns nothing about you except that you were not curious about the business.