Good Questions to Ask an Executive
Questions for a skip-level, an all-hands Q and A, or ten minutes in a hallway with someone several levels above you. They cover how decisions actually get made, which bets the company is least sure about, how executives learn that something is going wrong, and what they are worried about that has not reached a dashboard yet.
The questions
Open any question for the note
What are you spending most of your time on right now?
Why ask it
Calendars are more honest than strategy decks. Board prep and recruiting means a raise or a scaling push; one customer or one product line named repeatedly means that is where the risk sits. An answer like 'a bit of everything' usually means they have never audited their own week.
Which numbers do you look at first on a Monday morning?
Why ask it
Whatever they name first is what your team will eventually be measured against, whether or not anyone has told you. Note whether it is a lagging financial figure or a leading operational one, and whether it is a number your team even reports.
What has changed in your thinking about the business over the past year?
Why ask it
Executives who cannot name a single revision are either coasting or performing certainty. The useful version names a belief they held, what contradicted it, and what they do differently now. Ask what convinced them, because that shows you what evidence carries weight with them.
How much of next year's plan is settled, and how much is still open?
Why ask it
This tells you whether there is any point pushing an idea upward this quarter. It also flushes out a common gap: the plan is treated as fixed at the top and as negotiable in the middle, and nobody has said which.
Which customer conversation has stuck with you most recently?
Why ask it
Whether they have one at hand tells you if they still talk to customers directly or only see them summarized. A specific story with a name and a complaint is a good sign. A generic answer about 'customer feedback themes' means they are two layers removed from the customer.
When a decision reaches you, what usually makes it hard?
Why ask it
The honest answers are narrow: missing data, two good teams wanting the same headcount, or a promise made to someone outside the company. This names the real bottleneck, which is often not analysis but an unresolved political tradeoff.
How do you find out when something is going wrong three levels below you?
Why ask it
Most executives have exactly one channel, and it is usually a person rather than a system. If they cannot name the channel, bad news reaches them late, which tells you how to escalate and how much to put in writing.
What do you wish people further down understood about how decisions get made here?
Why ask it
This invites them to correct a misconception rather than defend a policy, so it tends to get a real answer. Expect to learn about a constraint nobody announced, like a contractual commitment or a cost ceiling that explains decisions that looked arbitrary.
When you and another executive disagree, how does that usually get settled?
Why ask it
Answers cluster into three types: escalate to the CEO, whoever owns the number decides, or it stalls until circumstances resolve it. The third is the most common and the least often admitted, and it explains projects that quietly never start.
What is a project you killed, and what tipped it?
Why ask it
The tipping point matters more than the project. Killed on a metric threshold means the company runs on evidence; killed because a senior person lost interest means it runs on sponsorship. Someone who has never killed anything is either new or not deciding much.
Where do you think we are slower than we should be?
Why ask it
Executives usually have a specific answer to this and rarely get asked for it. Notice whether they name a process, a team, or themselves. The last is rare and worth trusting.
What is the bet we are making that you are least sure about?
Why ask it
Asking for the weakest bet rather than the biggest one gets past the pitch. The answer tells you which roadmap items could vanish, which is directly useful if you are deciding what to attach your own work to.
What would have to be true for this business to double?
Why ask it
Forces them to state preconditions instead of ambitions. Good answers are uncomfortably concrete: a hiring rate, a pricing change, one channel working. If the answer is just 'execution,' the growth plan has not been thought through past the top line.
What did the company decide not to do that you think was the right call?
Why ask it
Restraint is where strategy actually lives, and it never shows up in an all-hands deck. This also surfaces near-misses, markets or acquisitions that were seriously considered, which tells you what the company thinks it is and is not.
How do you decide who gets the next big role?
Why ask it
Listen for whether they describe a process or a set of people they already have in mind. If it is the latter, internal promotion runs on visibility to a handful of executives, and that changes how you should spend your effort.
What do you hear from the board that does not make it down to us?
Why ask it
Usually pressure on a specific number, or impatience with a timeline. They will not repeat anything confidential, but the shape of what they can say tells you which constraint is really driving the next two quarters.
What is the hardest piece of feedback you have gotten in this job?
Why ask it
A real answer is specific and slightly unflattering, and it signals that feedback travels upward here. A polished answer about 'learning to delegate' means it does not, or at least not to them.
If you could reverse one decision from the last few years, which one?
Why ask it
The interesting part is whether they name a decision or a piece of timing. Naming a decision means they hold themselves accountable for judgment; naming timing means they attribute outcomes to circumstance, which predicts how they will treat your misses too.
What are you worried about that is not on anyone's dashboard?
Why ask it
Every executive has one of these and most are not asked. The answer is often a dependency, a key person, or a quiet erosion in something nobody instrumented, and it is frequently the most useful thing you will hear all year.
What should someone who wants your job be doing now that they probably are not?
Why ask it
Phrasing it as a gap rather than a path gets past the standard advice about hard work. Expect something specific about reading financials, owning a P and L, or managing sideways rather than down.
Working with limited executive time
Practical guidance for the conversation itself
Match the question to the setting
Skip-level, thirty minutes, just the two of you
This is the only setting where the searching questions near the end of the list work. Pick two, not ten. Send them the night before if you want considered answers rather than reflexes.
Town hall or panel, public and recorded
Anything that could embarrass a named team will get a non-answer, and you will have spent your credibility to get it. Ask about direction, tradeoffs and constraints, which they can answer honestly in public.
Two minutes in a hallway or after a talk
One question, no preamble. The time-and-attention questions work best here because they can be answered in a sentence and often lead to a longer conversation later.
Make the question easy to answer well
- Ask for the weakest version, not the biggest: the bet they are least sure about, the place the company is slowest. Superlatives invite pitches, uncertainties invite thinking.
- Anchor to a time window. 'Over the past year' or 'this quarter' produces specifics; open-ended questions produce philosophy.
- Ask about one decision rather than a category of decisions. 'A project you killed' gets a story; 'your approach to prioritization' gets a framework you could have read anywhere.
- Leave the follow-up unasked and let silence do it. Executives are used to being interrupted and often say the more interesting half second.
- Write down the numbers and names they mention. Repeating one back in a later conversation is the cheapest way to be remembered.
Common pitfalls
- Asking about their leadership philosophy. It produces a rehearsed paragraph that tells you nothing about how the company actually runs.
- Using the time to raise a grievance about your own team. Even a fair complaint reads as a complaint, and it usually gets routed straight back to your manager.
- Asking something they cannot legally or contractually answer, like details on an acquisition or someone's compensation. It wastes the slot and makes the rest of the conversation cautious.
- Stacking three questions into one sentence. They will answer the easiest and you will lose the other two.
- Treating the answer as a commitment. Executives think aloud, and something described as likely is not a plan you can safely build on.
Afterwards
- Send three sentences the same day: what you took away, and what you will do differently. Short beats thorough.
- If they named a worry, look for a small piece of it you can actually address, then report back in a month without asking for anything.
- Do not broadcast quotes from a skip-level. The fastest way to lose access is for your reading of the conversation to reach them secondhand.