Questions to Ask an Executive
Questions for the rare half hour with a senior executive: a skip-level meeting, an internal fireside chat, a panel, or a coffee you asked for. They aim at how decisions actually get made rather than the version in the strategy deck.
The questions
Open any question for the note
What has your attention this quarter that was not on your list a year ago?
Why ask it
Opens on something concrete and current, and it exposes the gap between the published strategy and what is actually consuming leadership time. The new items are usually the honest ones.
What does a normal week look like for you now compared with five years ago?
Why ask it
Easy for them to answer and unusually informative, because the shift from doing work to reviewing work is the part of senior roles nobody describes accurately from the outside.
What is true about this business that is not obvious from the outside?
Why ask it
Invites them to correct a public narrative they are probably tired of. The correction often points at a cost structure, a customer concentration, or a dependency the marketing never mentions.
Where does the money actually come from, and is that where you expect it to come from in three years?
Why ask it
Most people cannot answer this about their own employer. The gap between the two halves of the answer is the strategy, stated more plainly than any deck will state it.
What are we deliberately choosing not to do?
Why ask it
Strategy is mostly refusal, and executives who cannot name a rejected option are describing a wish list. The rejected options also tell you which internal arguments have already been settled.
What is the constraint on growth right now: people, cash, product, or demand?
Why ask it
Forces one answer instead of four. Whichever they name is where budget and attention will go next, which is useful if you are deciding what to work on.
What would make you say this year went badly?
Why ask it
Inverting the usual goals question gets past rehearsed targets to the specific failure they are actively steering away from. Vague answers here suggest the targets are not really operative.
Which number do you look at first on a Monday?
Why ask it
The metric they check by reflex outranks whatever the company officially reports. It also tells you what evidence would change their mind in a meeting.
How do you decide what to say no to?
Why ask it
Reveals their filter: financial thresholds, gut feel, deference to whoever asked most recently, or an explicit set of priorities. The answer predicts how a proposal from you would be received.
What risk do you think about that we do not discuss publicly?
Why ask it
Phrased so they can decline gracefully, and what they choose to share signals how much candor is normal at their level. Refusing to name any risk is itself an answer.
How do you find out when something is going wrong three levels below you?
Why ask it
Tests whether they have real channels or rely on a filtered reporting line. Executives who name specific practices, such as reading support tickets or skip-levels, tend to be harder to surprise.
What kind of information stops reaching you, and how do you compensate?
Why ask it
Asks them to describe their own blind spot, which most senior people have thought about and rarely get asked. Watch for anyone who claims nothing gets filtered.
What do you wish people brought to you sooner?
Why ask it
Practical and immediately usable: it tells you the threshold at which escalation is welcome rather than resented, which is normally learned by getting it wrong.
What made you promote the last person you promoted?
Why ask it
A specific case beats any list of stated values. If the reasons are visibility and tenure rather than judgment or results, that is the real promotion standard.
What advice did you get early on that turned out to be wrong?
Why ask it
Gets a reflective answer without asking them to criticize anyone present, and it often surfaces the conventional career wisdom they now think is useless.
What part of this job did nobody warn you about?
Why ask it
Usually produces something about isolation, the loss of direct work, or the weight of decisions about people. It is the most human question on the list and it rarely gets a rehearsed answer.
Who taught you the most about running something, and what did they do differently?
Why ask it
Specific behavior they copied is more instructive than a list of admired traits, and the story shows what they are still trying to imitate.
What is the hardest decision you have made about a person, and what did you learn?
Why ask it
Places the question late, when there is enough trust for a real answer. Leaders who describe only the outcome and none of the difficulty are telling you how they handle these decisions now.
From where I sit, what could I be doing that would actually be useful to you?
Why ask it
Turns a networking conversation into a working one, and the answer is often narrower and more actionable than anything in your objectives document.
What are you still trying to get better at?
Why ask it
A closing question that invites candor without pressure. A specific, current answer suggests someone still learning; a polished non-answer tells you the conversation was performance throughout.
Making Use of Time With an Executive
Practical guidance for the conversation itself
Before the Meeting
Read What They Have Already Said
Check the latest earnings call, all-hands recording, or public interview. Asking something they answered in detail last month wastes the slot and signals you did not prepare. Their own words also give you a specific thing to follow up on.
Pick Three Questions, Not Twenty
Half an hour holds about three real questions with follow-ups. Choose which one you would ask if the meeting were cut to five minutes, and lead with it.
Know What Sits Inside Their Remit
A chief financial officer and a chief operating officer will give very different quality answers about the same problem. Aim your questions where they hold actual authority, and you get decisions rather than opinions.
Decide What You Want to Leave With
An introduction, a decision, permission, or simply a better mental model of the business. Being clear stops the conversation ending pleasantly with nothing to act on.
During the Conversation
- Ask one question at a time. Stacked questions get answered at the easiest one.
- When you get an abstract answer, ask for the most recent example.
- Do not fill silence. Senior people often pause before the useful part.
- Take notes on paper if you can, and write down the exact numbers they mention.
- Skip questions whose answer you could look up in the annual report.
- If they say something surprising, stay there instead of moving to your next item.
Common Pitfalls
Using the Slot to Present Yourself
Long preambles about your own work eat the time and rarely land. If you want them to know something about you, put it in one sentence and get back to the question.
Asking Only Strategy Questions
Executives answer strategy questions all day and have polished versions ready. Questions about how they work, what they missed, and what they refused produce fresher material.
Raising a Grievance Out of Nowhere
A skip-level is a poor venue for a complaint your own manager has not heard yet. It usually travels back down the chain and costs you more than it gains.
Not Following Up
If they offered an introduction or a document, send a short message within two days referencing the specific thing. Offers made in the room expire quickly.