Questions to Ask Executive Leadership
Questions for a town hall, an ask-me-anything, or a skip-level with the leadership team: what the strategy actually commits to, what got dropped, how decisions are made, and what leadership is worried about. Written for employees who want a real answer rather than a restatement of the slide deck.
The questions
Open any question for the note
If the company only achieves one thing this year, what should it be?
Why ask it
Forcing a single answer separates a strategy from a wish list. Leaders who name one thing have made choices; leaders who name five have not, and the five will compete for the same engineers and the same budget until one wins by accident.
What are we deliberately not doing this year that we could have?
Why ask it
Every real plan has a discard pile. This is the question that reveals whether trade-offs were made on purpose or whether everything is still nominally alive. If nothing was cut, expect the cutting to happen quietly at team level in about two months.
How would you describe the strategy in a sentence someone in support could repeat to a customer?
Why ask it
Strategy that cannot survive compression into one sentence does not reach the people who talk to customers. Listen for whether the sentence contains an actual choice about who we serve, or only adjectives about being the best at something.
Which bets from last year did not work, and what did you change because of them?
Why ask it
The second half of the question is the point. Naming a failure is easy in retrospect; naming the resulting decision is not. If the answer is that they learned a lot, the postmortem never reached a conclusion, and the same bet is probably running again under a new name.
What does the leadership team disagree about most right now?
Why ask it
Executives usually present a united front, so an honest answer here tells you where the organization is genuinely unresolved, which is where your own work is most likely to get reversed. A claim of total alignment among a dozen senior people is not credible.
Which numbers do you personally look at every week?
Why ask it
This is the most reliable way to learn what actually counts, and it often differs from the published goals. If the weekly numbers are all revenue and pipeline while the stated priority is product quality, you now know which one is real.
Where does most of our revenue come from today, and is that mix changing?
Why ask it
Concentration determines fragility. Answers that reveal one segment, one contract, or one channel carrying the business explain a great deal about why leadership behaves the way it does, and why some requests get instant approval.
What would have to be true for this plan to fail?
Why ask it
You are asking them to state the assumptions the plan rests on: a hiring rate, a renewal rate, a partner shipping on time. Leaders who have stress-tested the plan answer quickly and concretely. Leaders who describe only external risks like the economy have not.
For a decision at that scale, who actually decides and who gets consulted?
Why ask it
Knowing the real path is worth more than any org chart, because it tells you whom to convince and in what order. Vague answers about consensus and collaboration usually mean the decision happens somewhere informal that nobody wants to name.
When priorities shift mid-quarter, how is a team on the ground supposed to find out?
Why ask it
This surfaces whether there is a mechanism or just word of mouth. The gap between when leadership changes direction and when the work changes is where months get wasted, and most executives have never measured it.
Which team is carrying more than it has the people to do?
Why ask it
Executives know, and saying it out loud commits them to either fixing it or explaining why not. If the answer is that everyone is stretched, that is a signal the company has more approved projects than staff, which is a decision nobody made explicitly.
What did you hear in the last employee survey that you have not acted on yet?
Why ask it
Everyone reports the encouraging results. Asking for the unaddressed part shows whether leadership is sitting on something knowingly, and whether they can say plainly that they read a complaint and chose not to fix it, which is a more useful answer than a promise.
What behavior actually gets someone promoted here?
Why ask it
Compare the answer to the written competencies. Real answers describe specific behavior, taking on a bad project, moving to a hard team, delivering something visible. If you hear only the values as printed, promotions are being decided on relationships nobody will describe.
Which competitor do you think about most, and why that one?
Why ask it
The reason matters more than the name. Watching a competitor's pricing, their hiring, or their newest product tells you which axis leadership thinks the market is competing on, and whether your team's work sits on that axis at all.
What are you personally spending most of your time on this quarter?
Why ask it
An executive's calendar is their real strategy. If most of it goes to fundraising, a single account, or an acquisition, that explains delays elsewhere, and it also tells you what they will and will not have attention for if you bring them a problem.
How do you decide when to reorganize versus leave a structure alone?
Why ask it
Reorgs cost roughly a quarter of productivity and are often the only lever an executive feels able to pull. Someone with a considered answer can name what a reorg is meant to fix and how they will know if it worked.
What is the biggest call you got wrong in the last couple of years?
Why ask it
Ask it late, once the conversation has warmed. You are testing whether it is safe to be wrong at senior level here, because that sets the tone for everyone below. A polished answer about a lesson learned early in their career is a dodge, and worth noticing.
How would you know the culture was getting worse before it showed up in people quitting?
Why ask it
Attrition is a lagging indicator; by the time it moves, the causes are a year old. Good answers name earlier signals leadership actually watches: internal transfer requests, who stops speaking up, how long roles stay open, referral rates.
What is the thing you most want us to push back on?
Why ask it
It gives explicit permission and reveals where they suspect they are wrong. It also tests the invitation to challenge that most leaders extend in the abstract. If nothing comes to mind, the invitation to speak up is decorative.
What question do you wish people asked you and never do?
Why ask it
A good closing question, because it hands the agenda back and usually produces the most candid minute of the session. What they volunteer is generally the thing they have been trying to communicate and failing to land.
Asking leadership a real question
Practical guidance for the conversation itself
Getting a real answer
Ask about a decision, not an opinion
Questions framed as views on a topic get you the company line, because they can be answered without disclosing anything. Questions about a specific decision, what was cut, who decided, what changed after, require actual information to answer.
Do the reading first
If the answer is in the last earnings call, the strategy deck, or a memo already sent, asking wastes your one turn and signals you have not been paying attention. Reference the material and ask what it left out.
Ask one question, then stop
Multi-part questions let the answerer pick the easiest part and leave the rest. Ask the single hardest version, then use silence. The follow-on detail after the first pause is usually the useful part.
Keep it about the work, not about you
In a group setting, a question that is really a personal grievance costs you credibility and gets a deflecting answer. Save individual issues for your manager or a one-on-one, and use the group forum for things everyone needs to hear.
Reading the answer
- A precise answer with a number, a name, or a date is usually true. Fluency without specifics often means the decision has not been made.
- Redirecting to process, that a working group is looking at it, generally means there is no decision and no owner yet.
- Everything is a priority means nothing has been sequenced, and your team will end up choosing for them.
- Watch for what they cannot say. Public companies have quiet periods, and pending deals, layoffs, and personnel matters are genuinely off limits. A refusal to answer is not always evasion.
- Notice which executive answers. If one person fields every question outside their area, decision-making is more concentrated than the org chart suggests.
- Compare the answer to what you were told last quarter. Quiet reversals with no acknowledgment are the clearest sign that plans are not being tracked.
Common pitfalls
Asking a question you already know the answer to
Rhetorical questions designed to make a point in front of an audience read as an ambush, and the answer will be defensive and useless. If you want to make an argument, make it directly and in writing.
Confusing seniority with omniscience
Executives are often several layers away from your specifics and will answer generally because that is all they have. Ask about direction, resourcing, and trade-offs, which are theirs, rather than implementation detail, which is not.
Letting a non-answer stand without a follow-up
One polite follow-up is acceptable and expected: who owns that, or by when. Asking it calmly is the difference between a question that changes something and a question that fills airtime.
Treating candor as a personal reward
If an executive tells you something unflattering and it circulates as gossip the same week, candor stops. Handle what you hear the way you would want your own half-formed thinking handled.