Questions to Ask the President of a Company
Good questions to ask the president of your company at a town hall, a skip-level, a lunch or a chance minute in the corridor. They start with the big picture, then move to customers and risks, how the president leads, the culture, their own path and where your work fits in.
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The questions
Each question, and why to ask it
Big picture
Where do you want this company to be three years from now?
Why ask it
The staple opener, and worth asking because the answer becomes the yardstick for everything else you hear. Listen for something you could check later, such as a market, a size or a product, then ask what has to be true by next year for it to happen.
What is the biggest challenge the company faces over the next year?
Why ask it
The classic town hall question, and it earns a rehearsed answer unless you narrow it. Follow up by asking who owns that challenge and what they have been given to fix it, which is where a slogan and a plan part ways.
What is the one thing the company most needs to get right this year?
Why ask it
Company plans tend to list several priorities side by side, and this asks which one the others are allowed to lose to. If you still get three, ask which of them keeps its people when budgets tighten.
What has the company done in the past year that you are proudest of?
Why ask it
An easy question for a nervous asker and a welcome one for the president, which makes it a good first question from the floor. What gets picked, a number, a product or the way a hard stretch was handled, shows what counts as a win at the top.
What do you think this company does better than anyone else?
Why ask it
It sounds like an invitation to boast, yet it shows what the president believes the company is for. If the strength they name is not where the investment is going, that gap is your follow-up.
What would count as a good year, and what would count as a bad one?
Why ask it
The bad year is the part that matters, since company updates rarely say out loud what failing would look like. Ask for the number or the event that would mark each, so that in December you can tell which year you had.
What are you most excited about for the company right now?
Why ask it
Suits a first meeting or a new-hire welcome, where a hard question would feel out of place. Notice whether the answer is a product, a customer, a deal or a group of people, then ask what has to go right for the rest of the company to feel it too.
Where is most of your own time going this quarter?
Why ask it
A calendar is harder to dress up than a strategy slide. If two or three things come back, such as a new market, a hire or a difficult customer, those are the live priorities. A list of everything means you are hearing the org chart.
What is the company deliberately choosing not to do right now?
Why ask it
You are asking for something tempting that was turned down: a market, a product line, a big customer's request. A named example tells your team what it can stop being asked for. If nothing comes to mind, ask what was last cut to make room for the top priority.
What has changed about the plan since you last presented it to us?
Why ask it
Best asked a few months after a strategy presentation, with one point from it in mind. Hearing what moved and why is more useful than the original slides were. A flat 'nothing has changed' is worth testing against what your own team has since been told to do differently.
How is the company doing financially, in terms all of us can follow?
Why ask it
Plenty of people in the room want to know and feel they should not ask. How much a president can say depends on the company: at a publicly traded one they may only be able to repeat what has been published, and private owners choose how much to share. A trend and the reason behind it is a fair thing to hope for.
Market and risks
What are customers telling you lately that surprised you?
Why ask it
The answer shows how close the president still is to the people who pay. A recent conversation with one particular customer is a strong answer. A satisfaction score recited from memory suggests the news is arriving second-hand.
How much of next year's growth do you expect from existing customers rather than new ones?
Why ask it
Growing through the customers you already have leans on service, renewals and the product, while winning new ones leans on sales and marketing. You do not need an exact split. Which way it tilts is a hint about where hiring and attention will go.
Where is a competitor genuinely better than us?
Why ask it
Asking about competitors in general invites a boast, so this takes only the uncomfortable half. A precise answer, such as their pricing, their delivery times or one feature, means someone is studying them closely. Then ask whether the plan is to catch up or to compete on something else.
How do you expect AI and automation to change the work we do here?
Why ask it
Leaders get asked this a lot now, so expect a prepared answer and listen past it. The useful part is what has a budget and a date, and what the plan is for people whose tasks change. Ask which team goes first.
What is the biggest bet on the roadmap, and what happens if it does not work?
Why ask it
Naming the bet is the easy part, and what happens if it misses is the real question. A thought-through answer covers who is running it, when they will know, and what gets scaled back. Listen for whether your own team's work depends on it.
What worries you that the rest of us are not worried about yet?
Why ask it
This is 'what keeps you up at night' with a narrower target: the concern that has not reached a slide yet. It might be a supplier, a hire they cannot make or a contract coming up for renewal. If they share one, ask what the rest of you could do about it.
What outside the company's control could hurt us most?
Why ask it
Regulation, a supplier, interest rates, one very large customer: the answer is different at every company. You are listening for whether a response is ready, or whether the plan is to hope it does not happen.
If revenue came in well under plan, what would you protect first?
Why ask it
A calmer way into the subject of cuts than asking about layoffs, which a president often cannot discuss. What they would shield is what they see as the core of the company, and a considered answer suggests the scenario has already been worked through.
How you lead
How would the people who report to you describe your leadership style?
Why ask it
Asked straight, the leadership style question gets adjectives like 'collaborative'. Borrowing their direct reports' point of view makes them think about how they come across on a hard day. For a second question, try what those same people would say needs work.
Which decisions do you want made without you?
Why ask it
The examples show how much room people further down really have: a discount, a hire, a refund, a launch date. If they struggle to name any, a good share of the company's decisions may be waiting in one inbox. Ask where the line sits for someone at your level.
What happens when your leadership team disagrees with you?
Why ask it
Almost any leader will say they welcome debate, so ask for the last time it happened. You want to know whether the argument took place in the meeting or in the corridor afterwards, and whether anything changed because of it.
What was the hardest call you have had to make in this job?
Why ask it
At this level a hard call often means choosing between two groups of people. Notice whether those who lost out appear in the story at all, and whether the reasoning would have made sense to them.
Which of the past year's decisions would you reverse if you could?
Why ask it
'What did you learn' gets a lesson, and this gets a decision. Watch whether the example is small and safe or one that cost the company something. An honest one from the top makes it easier for everyone else to own up to a mistake.
How do you decide when to stop funding something that is not working?
Why ask it
Have in mind a project you have watched limp along, without naming it. A clear answer has a trigger in it: a date, a number, or a person whose job is to make the call. 'We review things regularly' leaves open how anything ever gets stopped, so ask for the last project that was.
Which numbers do you actually look at every week?
Why ask it
The handful they check weekly is what the company is steered by, whatever the annual report leads with. Three or four numbers is a clear answer. Find out which of them your own team moves, and whether you can see it too.
How do you find out when something is going badly?
Why ask it
By the time a problem reaches the top it has usually passed through several careful summaries. Listen for a route around that: customer calls they sit in on, support tickets they read, regular skip-levels, one person who says it plainly. An open door on its own depends on somebody being brave enough to walk through it.
Which parts of the business do you only hear about when something breaks?
Why ask it
It lets them admit a blind spot without it sounding like a failing, since nobody can watch everything. The teams they name, often quiet ones like payroll, IT or a small regional office, get attention only on their worst day. If yours is on the list, ask what a useful update from you would look like.
How do you and the CEO divide the job between you?
Why ask it
Only for companies that have both: in some the president is also the CEO or the owner, so check before you ask. Where the roles are separate, the split is different at every company. One may run the day-to-day while the other deals with investors and long-range plans, and the answer tells you whose desk a given decision lands on.
How do the board or the owners shape what you can and cannot do?
Why ask it
A president answers to someone: a board, a parent company, a founder, a family. Knowing what those people are asking for explains decisions that look odd from the floor. Some of it will be confidential, so accept a general answer.
Culture
How would you describe the culture here to someone outside the company?
Why ask it
Compare the description with your own week. Where the two match, the culture is real. Where they do not, you have found a blind spot or a polite fiction, and one specific example of the gap makes a fair follow-up.
Which of the company's values is hardest to live up to?
Why ask it
It only works if the company has written values, so have them in front of you. Naming one, say putting the customer first in a quarter when margins are tight, shows the list is used for real decisions. If every value is said to be going well, ask for a time one of them cost the company money.
What behaviour gets someone promoted here, and what quietly stalls a career?
Why ask it
The first half tends to get the official answer and the second half the candid one. Whatever they name as a career-staller, whether it is surprising your boss, hoarding information or missing a number quietly, is a rule of the place that no handbook prints.
Why do good people leave this company?
Why ask it
Direct, so ask it evenly and keep any particular departure out of it. Someone who has read the exit interviews will give a specific reason, such as pay in one function or a slow path to promotion, and can say what is being done about it.
What is one thing about how this company works that you would change tomorrow if you could?
Why ask it
People at the top get frustrated by the place too, and this gives them leave to say so. Follow the wish with what has stopped the change so far. Cost, habit or one old system: the obstacle is the part you learn from.
When did someone far from the top last change your mind?
Why ask it
The words far from the top matter, because being persuaded by a peer is easy to recall. A story about an engineer, a store manager or a new hire shows that ideas can travel upward here, and tells you how that person got heard.
How can people here raise an idea so that it gets a real hearing?
Why ask it
This asks for the route, because plenty of companies have a suggestion box nobody trusts. If the answer names a person, a forum or a small budget for trying things, write it down and use it.
How would you like us to bring you bad news?
Why ask it
Treat the answer as instructions: early or once it is confirmed, by message or in person, with a proposed fix or without. Once the answer has been given in front of a room, the next person who has to deliver bad news can point back to it.
What is your thinking on remote and office work over the next year?
Why ask it
Policies on this keep moving, so ask for the reasoning as well as the rule. Hearing what they are trying to protect, whether that is training new staff or the speed of decisions, gives you something to plan around even if the rule changes again.
Their path
What was your path to this job, and which move mattered most?
Why ask it
People tend to enjoy telling this story, so it warms up a lunch or a small group. Pay attention to the move they single out. If it was a sideways step or an unglamorous posting, that is worth knowing when you are weighing one yourself.
Why did you join this company, and what has kept you here?
Why ask it
The joining story is history. What has kept them is current, and it doubles as their view of what the company offers everyone else. If the president founded the business or grew up in it, ask what has kept them at it.
What was your first job, and what did it teach you that you still use?
Why ask it
A good one for interns and new graduates, because it puts the president back at the bottom of a ladder. Answers tend to be warm and long, so keep it for a setting with time to spare.
Who shaped the way you lead?
Why ask it
Expect a former boss, a parent or a coach, with a story attached. What that person actually did, whether it was backing them after a mistake or telling them a hard truth, is likely to be the standard they now hold their own managers to.
What is the best piece of advice anyone has given you about work?
Why ask it
A staple, and a better one if you also ask who said it and when they came to believe it. If they ignored the advice at first, that story is the part worth hearing.
What is the most useful piece of critical feedback you have had in this role?
Why ask it
Better in a small group than from the floor of a town hall, where it can sound like a challenge. A specific example, with who said it and what changed afterwards, shows that someone is still able to tell them. A long pause is worth noticing too, without reading too much into it.
What part of the job do you still find hard?
Why ask it
When the person at the top admits something is hard, it gets easier for everyone else to. Whatever they name, whether it is letting people go, speaking in public or staying patient, is something they will understand when you struggle with it too.
What do you read or listen to in order to keep learning?
Why ask it
Light enough for a corridor or a lunch queue. You get a sense of where their ideas come from, and if they name something specific, reading it gives you a reason to follow up later.
How do you switch off from a job like this?
Why ask it
Friendly more than probing, and it often turns up a hobby or a family routine you can ask about next time. It also opens the way to a practical follow-up: what they expect from others in the evening and at weekends, and whether a late email from them needs an answer that night.
What do you hope people say about your time in this job after you have left?
Why ask it
Legacy questions draw grand answers, so follow with what would have to happen in the next year for it to come true. That pulls the answer back to something the company is doing now.
What do you wish people asked you about more often?
Why ask it
A good last question when the room has run out of them, because it hands over the agenda. The subject they pick is often one they feel is misunderstood, so ask what people tend to get wrong about it.
Your part
How does the work my team does connect to the goals you are measured on?
Why ask it
Name your team when you ask. If the president can draw the line straight away, your work is visible at the top. If the answer is vague, someone needs to make the case for it, and that may be you.
What should someone in my role understand about the business that we usually do not?
Why ask it
Each function sees a slice: sales sees deals, engineering sees the product, finance sees the cost. The answer names what your slice hides, such as how the company actually gets paid or what a late delivery costs, and it is worth asking who could teach you the rest.
What skills will this company need more of in the next few years?
Why ask it
A career question that is safe to ask in front of a room. The answer points to where training budgets and new roles are likely to appear, and you can ask how someone already here would go about building those skills.
What do you know now that you wish you had known at my stage?
Why ask it
Say what your stage is when you ask, since the advice for a first-year analyst and for a new manager is not the same. If the answer is general, ask what they would have done differently in the first year of the job you have now.
If you were joining this company today in a junior role, where would you want to work?
Why ask it
A sideways way of asking where the interesting work is. The president's pick shows which part of the company they think has the most ahead of it, without anyone having to rank departments out loud.
How could someone at my level see more of how the business is run?
Why ask it
This is a request for access, so make it easy to grant. Sitting in on a quarterly review, shadowing another team for a day or joining a customer visit are things a president can often approve on the spot. Have one ready in case the reply is 'what did you have in mind?'
If I want to be useful to you over the next six months, where should I put my effort?
Why ask it
The closer for a one-to-one, because it ends on an offer instead of a request. At a town hall, ask it for the whole room: what is one thing each of us could do this month? Either way, write the answer down and report back once you have done it.
Getting something out of five minutes with the president
Practical guidance for the conversation itself
Before the conversation
Read the last two company updates first
The last all-hands, the most recent company letter, or the earnings commentary if the company publishes results. Asking something already answered there wastes the one question you get and signals that you have not been paying attention.
Match the question to the room
The big picture and risk questions suit a town hall, where the answer is useful to everyone listening. The ones about the president's own path belong at a lunch or in a small group, where there is time for a story. Keep the questions about your own role for a skip-level or a one-to-one.
Pick two questions, not ten
You will realistically get one question and a follow-up. Choose one about the big picture and one about how the president leads, and hold the rest in reserve.
Decide what you want to leave with
A clearer view of priorities, a decision you need unblocked, or visibility for your team are three different aims, and they need different questions. Vague admiration gets you nothing.
In the room
Ask one question and stop
Stacked questions get answered at the easiest part. Ask the single sentence, let the pause happen, and use your follow-up on whatever they skipped.
Follow the number, not the adjective
When an answer includes a metric, ask what it was last year. When it includes an adjective, ask for an example. That is where the interesting part of the answer lives.
Do not turn a question into a complaint
A grievance dressed as a question is obvious to everyone listening and gets a defensive answer. If you want a problem fixed, describe the problem plainly and ask who owns it.
Write down the answer, not your reaction
Note the actual words on priorities and thresholds. You will want them in three months when a decision seems to contradict them, and an accurate quote gets a better hearing than a paraphrase.
Afterwards
Send one short message
After a one-to-one or a skip-level, three lines will do: what you took from the answer, what you are going to do about it, nothing else. A long thank-you note is easy to skim past, and a request tacked on the end can undo the good impression.
Do the thing you said you would
If they told you where effort would help, report back once you have done it. One completed loop is worth more than a dozen further questions.
What lands badly
Asking for information they cannot give
Anything touching unannounced results, acquisitions, or individual pay puts them in an awkward position and burns the exchange. If layoffs are what you want to know about, ask about hiring plans, or what they would protect first if revenue fell short.
Asking a question designed to show off
Everyone in the room can tell the difference between curiosity and performance, including the president. The showy question also tends to get the shortest answer.
Accepting the first abstraction
Culture, focus, and alignment are not answers. One polite follow-up asking what that looks like in practice is where the conversation actually starts.