Questions to Ask Senior Executives
Questions for a skip-level meeting, a fireside chat, or a short coffee with a senior executive, covering where their time actually goes, decisions they are unsure about, how promotions are decided, and what they see that you do not.
The questions
Open any question for the note
What are you spending most of your own time on this quarter?
Why ask it
Calendar reality beats stated strategy. When the hours do not match the priorities that were announced, you have learned what the organization actually rewards.
What has changed in your priorities since the start of the year?
Why ask it
Shifts since January show whether the plan is holding. An executive who says nothing has changed is either unusually disciplined or not watching the market closely.
Which decision are you least sure about right now?
Why ask it
Naming an uncertain decision takes confidence, and the answer usually points at a live internal argument. It is also the question most likely to get you invited into that argument.
What does your boss or the board ask you about most?
Why ask it
The questions above them shape the questions that come down. Knowing what the board presses on explains apparently arbitrary requests for data three levels below.
What do you know about the business that most employees do not, but could?
Why ask it
Executives usually know one or two things they could share more widely and have not, often about margins, customers, or timing. Asking gives them a reason to release it.
Where is the company weaker than people outside it assume?
Why ask it
Weakness relative to outside perception is something they can answer without disloyalty, and it is far more revealing than asking about challenges. Note whether they name something structural or blame execution.
What is a project you killed, and how did you decide?
Why ask it
Killed projects show how decisions really get made here: whether evidence, politics, or exhaustion ended it. A leader who cannot name one has probably let things fade out instead.
What news reaches you too late, and how would you rather hear it?
Why ask it
Every senior leader has been surprised late by something their organization knew early. Their preferred channel is a practical instruction you can use the next time you spot a problem.
What do you wish managers a level or two below you did differently?
Why ask it
This surfaces the gap between what leadership thinks it asked for and what the middle layer actually does. If you manage anyone, the answer is directly usable on Monday.
When you and your leadership team disagree, how does that get settled?
Why ask it
Conflict resolution at the top sets the tone everywhere below it. An answer describing a forum and a decision rule is very different from one describing alignment, which usually means the loudest voice wins.
What is the first thing you look at on a Monday morning?
Why ask it
The first thing they check is their real dashboard, whatever the official one says. It tells you which number your own work is expected to move.
What did you get wrong in the last two years that you have since corrected?
Why ask it
Corrected mistakes are safer to discuss than current ones, and the correction shows how fast this organization changes course. No examples means either a short memory or a defensive culture.
Which part of your job did you have to learn the hard way?
Why ask it
Executives are rarely trained for the parts of the job that break people: firing, managing a board, being the only person who cannot show doubt. This is the most transferable thing in the conversation.
What would you do in my role if you had it now?
Why ask it
Asking them to occupy your job gets specific advice instead of general encouragement, and the differences between their answer and your current plan are the part worth writing down.
Who taught you the most, and what did they do differently?
Why ask it
Naming a person and a behavior makes influence concrete. It also tells you what they consider good management, which is how they will judge you.
How do you decide who gets promoted at the level above mine?
Why ask it
Promotion criteria one level up are usually unwritten and applied inconsistently. Hearing them from the person who signs off matters more than the published competency framework.
What tells you a team is in trouble before the numbers show it?
Why ask it
Early-warning signals are craft knowledge: attrition in one team, silence in meetings, small commitments slipping. Few leaders have written these down and most enjoy explaining them.
What do you say no to, and how do you say it?
Why ask it
How they decline requests is the skill most people below them lack. Both the criteria and the exact wording are worth copying.
What would you want to be true here in three years that is not on any slide yet?
Why ask it
This gets past the strategy deck to what they personally want and have not yet won support for. It is also where you find work worth volunteering for.
What should I be asking you that nobody does?
Why ask it
It hands them the floor and often produces the best material of the meeting, because senior people notice which subjects never come up. Have a notebook open when you ask it.
Using time with a senior executive
Practical guidance for the conversation itself
Before the meeting
Read what they have already said in public
The last all-hands, an earnings call, a conference talk, or an internal post tells you their current language and priorities. Asking something they answered publicly last month wastes the slot.
Bring three questions, not twenty
A thirty-minute meeting supports three real questions with follow-ups. Choose them for what you cannot learn anywhere else, and let the rest go.
Know what you want out of it
Advice, visibility, a decision, or context are different goals and lead to different questions. Deciding in advance stops the meeting becoming a pleasant conversation you cannot act on.
In the room
- Open with your sharpest question rather than saving it for the end.
- Skip the status update unless they ask. They have access to your numbers.
- Ask one question at a time and let the answer finish before adding a second.
- Take notes visibly. It slows you down and signals that the answers will be used.
- When an answer is general, ask for one example, once.
- End on time, or slightly early, and say what you will do with what they told you.
Common mistakes
Asking about strategy in general terms
Questions about vision and the future of the industry get the prepared answer. Questions about a specific decision, tradeoff, or number get a real one.
Using the time to complain
Raising a grievance about your manager or a peer team in a skip-level puts the executive in an awkward position and rarely fixes anything. Bring the problem as a question about how such issues get handled here.
Asking them to sponsor you in the first meeting
Requests for promotion support before they know your work read as transactional. Ask for their read on what the next level requires, then come back having done it.
Afterwards
- Send four or five lines the same day: what you took away and the one thing you will do.
- Do that thing, then report back briefly. That is what turns a single meeting into a relationship.
- Do not forward their candid comments. Anything shared in confidence closes the door on the next conversation.
- Pass on anything useful in general terms to your own team, without attributing quotes.
- Ask for the next meeting only when you have something to show or a genuinely new question.