Questions to Ask Senior Leadership
Questions for a skip-level meeting, a town hall Q&A, or the ten minutes you get with an executive between sessions. Written for someone who already works there and wants a straight answer about strategy, trade-offs, and how decisions get made, without sounding like a complaint.
The questions
Open any question for the note
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.
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.
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.