Questions to Ask Business Leaders
Questions to ask business leaders when you get time with one: an interview for a newsletter or a podcast, a panel of industry leaders, a town hall, a mentoring coffee, or a class assignment to interview a business professional. The 60 here are grouped by career path, the job, decisions, the business, people and advice. The familiar ones are all here, on how they got started, their hardest decision, hiring, culture and success, worded to draw one specific story in place of the answer they have given many times. Not every one suits a stage, and the notes say which to keep for a private conversation.
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The questions
Each question, and why to ask it
Career path
How did you get to where you are now, and which step was never part of the plan?
Why ask it
The career question every leader expects, with a tail that stops it turning into a recital of job titles. The unplanned step, whether a layoff, a favour for a friend or a move nobody else wanted, is usually where the real story sits, so follow that one.
What is the best piece of advice you have been given, and how long did it take you to act on it?
Why ask it
On its own the first half gets a slogan. The second half gets the story, because plenty of people sit on their best advice for years, and the reason they finally acted on it is the bit you can use.
What is the biggest risk you took in your career, and what made you willing to take it?
Why ask it
The risk matters less than the sums behind it: what they stood to lose, who they talked to, what the fallback was. If it only sounds brave in hindsight, ask how it felt the week before they decided.
Who taught you the most, and what specifically did they teach you?
Why ask it
This is the mentor question with the name made secondary. A tribute to an old boss is pleasant and no use to you, so hold out for the small thing they copied: the way that person ran a meeting, or broke bad news.
What are you proudest of in your career so far, and who else deserves credit for it?
Why ask it
Pride is easy to talk about, so the second half does the work. Listen for names and for what each person did, which shows how they see the people around them. If the answer is a revenue figure, ask what it took to get there.
What was your first job, and what habit from it have you kept?
Why ask it
Nobody polishes the story of a first job, since there was nothing glamorous in it. Listen for whether the lesson is about the work or about how they were treated, then ask whether it changed how they deal with their own newest staff.
The job
What does a typical week look like for you now, and how has it changed in five years?
Why ask it
Calendars are not something people rehearse, which makes this an easy way in. Ask roughly how the hours split between meetings, travel and time alone, and which of those they would cut. The five-year comparison shows how the role grew.
What does your job title leave out about what you actually do all day?
Why ask it
A good opener with a business professional whose title gives little away: an analyst, an account manager, a controller. The gap between the title and the day is where the detail for a class write-up comes from, so ask which part takes the most hours.
What caught you off guard in your first year in this role?
Why ask it
Admitting a surprise costs nothing, so the answer tends to be frank. If it is about workload, ask for the one that was not about hours: who stopped being straight with them, or which decisions turned out not to be theirs to make.
What were you good at on the way up that you have since let go rusty?
Why ask it
Writing code, selling, closing the books: many senior people left a craft behind, and naming it takes some honesty. Ask whether they miss it and who does that work now. A quick 'nothing' means they have not thought about it, or would rather not say.
Which skill do you use every day that no course or training ever covered?
Why ask it
Students tend to ask what to study, and this gets the other half. Writing a short email, reading a room and chasing a late payment politely are the sort of thing that comes back. Ask how they picked it up, since that is the bit you can copy.
Who outside your own company do you rely on to do your job well?
Why ask it
A supplier, a banker, an auditor, a recruiter, an old colleague at a competitor: the answer draws a map of the business that no organisation chart shows. It works at any level of seniority, and it hands you a list of roles you may not have known existed.
What still excites you about the work, after this long doing it?
Why ask it
Aimed at now, not at the start of the career, which is the version they have told before. 'The people' and 'the challenge' are placeholders, so ask about the last day they went home pleased and what had happened. If nothing recent comes to mind, do not press it in front of an audience.
If I asked your direct reports how you lead, what would they tell me?
Why ask it
Ask about leadership style head on and you get adjectives. Routed through the team's eyes, the answer has to include the unflattering part. If all they can picture is praise, ask when they last put the question to the team.
What keeps you up at night at the moment?
Why ask it
It is a stock question, so lean on 'at the moment' and wait for something current. The useful replies name one thing, a customer, a successor, a loan coming due, and the evasive ones blame the economy.
What do you do on the days when the pressure is getting to you?
Why ask it
A run, a walk round the block or a call to someone outside the company are all real answers, and more use to you than a line about staying calm. Then ask whether anyone at work gets to see the bad day, and what they say to the team when it shows.
How do you protect time to think when your calendar fills itself?
Why ask it
Some block a morning, some leave the building, some admit they have given up. Whichever it is, you find out whether the strategy you hear about gets made on purpose or in the gaps between meetings.
How do you keep the job from swallowing the rest of your life?
Why ask it
Balance tips are not what you are after, which is why it is put as a problem. Expect rules, not philosophy, such as no email at the dinner table, and treat 'I don't, really' as an honest answer that deserves a follow-up about what they would change.
Decisions
What is the hardest decision you have had to make in this role?
Why ask it
Often it involves people: a closure, a layoff, a parting with a co-founder. Ask what the alternatives were and who they talked it over with, because the bare decision tells you far less than the route to it.
What kind of decision is sitting on your desk this month?
Why ask it
Worded so they can answer without giving away anything confidential: the kind of decision, not the names in it. It moves the talk from history to a live problem, and people reason out loud about those in a way they rarely do about settled ones.
Tell me about a decision you had to make with far less information than you wanted. How did it turn out?
Why ask it
The outcome half keeps this from being a story about decisiveness. Listen for whether they separate a good decision from a lucky one. 'It worked, but I would not make the call that way again' is about as good as this answer gets.
Which of your decisions took longest to reveal whether it was right?
Why ask it
Hires, acquisitions and new markets can take years to prove out. Ask what they watched in the meantime and at what point they would have called it a mistake. If there was no such point, they were waiting, not judging.
When you face a big call, who is in the room and who has the final say?
Why ask it
This is the mechanics behind every general answer about decision making. Notice whether the people in the room are there to shape the call or to ratify it, and whether anybody is invited specifically to disagree.
When did your instinct disagree with the numbers, and which one did you follow?
Why ask it
Anyone who has run something for a while has a story on each side, so ask for the one that went badly as well. What you are after is their rule for when gut feeling gets a vote, not a claim that the data always wins.
What is your biggest failure in business so far, and what did you change because of it?
Why ask it
The failure question is a staple, and what counts is whether anything changed. A lesson with no new behaviour attached is a story they tell. A clause they now insist on, or a kind of deal they refuse, is a lesson they learned.
What did you get wrong the last time the business hit a rough stretch?
Why ask it
Crisis questions tend to get the heroic version, and asking for the mistake changes the register. Cutting too late, cutting the wrong thing and saying too little to staff are all answers worth a follow-up. If the company is in a rough stretch right now, keep this for a private conversation.
How do you decide when to shut down something that is working, but only a little?
Why ask it
A failing project makes its own case for closure. The half-working one has customers, a team and a sponsor, so ask about the last one they ended: how long it took and who argued to keep it.
What do you say no to most often?
Why ask it
Strategy shows up more clearly in refusals than in plans. A ready answer, such as a type of customer, a standing meeting or a product people keep proposing, means the priorities are narrow enough to act on. Ask who was last disappointed by it.
When has doing the right thing cost the business money?
Why ask it
Values are easy to state until they have a price attached. A real example has a figure or a lost customer in it, and somebody who argued the other way. Do not push for names: the story works without them, and they may not be free to give them.
The business
What do you look at first in the morning, and what number would ruin your week?
Why ask it
The figure they check before anything else tells you what they treat as the priority, whatever the strategy slide says: cash, orders, cancellations, a safety count. If nothing specific comes, ask what their finance lead sends them without being asked.
What do outsiders get wrong about how this business makes its money?
Why ask it
Plenty of companies earn their margin somewhere other than the product on the sign: servicing, renewals, financing, one unglamorous line. It works well on a panel because it invites them to correct the record. At a listed company, expect only what is already in the published accounts.
What is holding growth back most right now: demand, money, hiring or something else?
Why ask it
Offering a menu heads off the reply that everything matters. Whichever they pick, ask what has been tried already. If they add a fifth option of their own, that is the one to spend your follow-up on.
What does your industry broadly believe that you think is wrong?
Why ask it
This asks for a position, and it is often the most quotable answer of an interview. Have a follow-up ready on what they do differently because of it, since a contrarian view with nothing done about it is only an opinion. On a stage some people will play it safe, which is fair.
Where do you want the company to be in five years, and what has to go right for that to happen?
Why ask it
The vision half you could find in a press release. The conditions are the real answer: someone who can list three things that must go right, and admit which is least in their control, has a plan as well as a destination.
Which change in your industry are you watching most closely right now?
Why ask it
A good answer is narrower than 'technology' or 'regulation': one rule under review, one competitor's pricing, one shift in what customers will pay for. Follow up with what they would do differently the day it arrives.
Where has AI actually changed how your people work, and where has it made no difference yet?
Why ask it
Asking for both sides gets you past the announcement. A named task that is done differently now is evidence, and an honest 'nowhere much yet' is more credible than a list of pilots.
Who do you actually lose business to, and is it who outsiders would guess?
Why ask it
The obvious rival is often not the answer. You may hear a spreadsheet, a customer doing the work in-house, or people simply doing nothing, and each of those tells you what they think they are really selling.
When did you last talk to a customer yourself, and what did you hear?
Why ask it
The date matters as much as the story. A conversation from last week with a detail that surprised them means they still hear the market first-hand, while 'all the time' with no example usually means through a slide.
Which company in your industry do you learn the most from, and what have you borrowed from them?
Why ask it
Naming a rival they respect is safe on a stage, and it tells you who sets the standard in the field. The borrowed thing, a pricing model or a way of training new staff, is the part to write down. If the firm they pick is outside the industry, ask what made them look there.
What would it take for a newcomer to win a real share of your industry?
Why ask it
It asks about barriers without using the word. Capital, licences, long relationships and a trusted name are the common ones, and the one they reach for is the one they think protects them. Then ask whether anyone is trying.
What will someone joining your industry in five years need to know that you never had to learn?
Why ask it
A forecast put as a syllabus, which is easier to answer honestly than a prediction about where the whole field is heading. With a panel of industry leaders, put it to each in turn: the places where they disagree are your story.
People
What do you look for when you hire that a CV cannot show you?
Why ask it
Everyone says attitude, so ask how they test for it. The interview question they always use, or the thing that makes them end an interview early, is far more revealing than the trait they name.
How do you keep good people motivated when you cannot offer more money or a promotion?
Why ask it
Taking pay and titles off the table forces out the actual practice: harder problems, public credit, room to run something. It is also the position most managers are really in, so the answer is one you can borrow.
How would you describe the culture here, and what do you personally do that keeps it that way?
Why ask it
The description will sound like the careers page. What they do about it is where it gets real, because a culture somebody maintains has behaviour attached: who they promote, what they walk past, what they will stop a meeting for.
What is the last thing you changed your mind about because someone junior pushed back?
Why ask it
Welcoming dissent is easy to claim. An instance with a topic, a rough date and what changed afterwards is the evidence. It is worth asking whether the junior person ever found out they had won the argument.
When two of your senior people cannot work together, what do you do?
Why ask it
Putting both in a room, redrawing the jobs and letting one go are the usual options, and the one they reach for first says a lot about how conflict is handled lower down. Ask how long they waited before stepping in. Keep it general enough that no colleague can be picked out from the answer.
How do you find out something is going wrong before it reaches you through official channels?
Why ask it
Reports get tidied on the way up, so the useful answer is a habit: walking the floor, lunch with people two levels down, reading the complaints inbox, an old colleague who rings. 'My door is always open' is a hope. Ask when that door last brought bad news in.
What do you do once you realise you have the wrong person in a senior role?
Why ask it
The thing to listen for is time. Ask how long passed between knowing and acting, and what they told themselves in between. An admission that they waited too long is more believable than a clean process.
How do you spot someone who could run a team before they have the title?
Why ask it
Useful twice over if you work for them, since it describes what gets noticed. Good answers point at things seen in passing, who others go to for help, who brings a fix along with the complaint, and not at performance ratings.
What makes you lose confidence in someone who works for you?
Why ask it
Usually it is something small and repeated: a surprise that should have been a warning, a deadline that slid without a word. Ask how they raise it too, because some will admit they go quiet instead of saying so.
Advice
What did you believe about running a company ten years ago that you no longer believe?
Why ask it
It asks for one belief they dropped, which is harder to dodge than a question about growth. A good answer has a before and an after, such as once assuming every strong employee wants to manage. Ask what happened to change it.
If you were starting your career again today, what would you do differently?
Why ask it
Adding 'today' moves this from nostalgia to a view on the job market you are actually in. Notice whether the regret is a choice, like staying too long somewhere safe, or a habit, since a habit is something you can work on this year.
Which qualification, licence or course was worth the time, and which could you have skipped?
Why ask it
Worth asking if you are choosing a degree or a certificate. What counts differs by country, field and employer, so take the answer as one person's experience and ask how it works where you plan to work.
Which qualities matter most in a business leader, and which of them can be learned?
Why ask it
A staple that tends to get a list: integrity, communication, resilience. The second half is the useful one, so ask how they learned one of those themselves and how long it took. For a class write-up, ask them to pick one and say who they saw it in.
What do you read, watch or listen to that has changed how you work?
Why ask it
This is the book recommendation question, tightened so that a title is not enough. Ask what they did differently afterwards. If nothing comes to mind, you have a reading list and not a recommendation.
What separates the people who rise quickly from others who are just as capable?
Why ask it
Career advice from someone who has sat in the promotion meetings. Answers tend to be about being visible, picking the right problems or being easy to hand things to, and each is something you can check yourself against.
How do you define success for yourself now, and how has that changed?
Why ask it
A common pattern is a title or a number early on and something closer to time or people later. The shift is worth more than either definition, particularly if they can say what caused it.
What should someone who wants your job one day be doing this year?
Why ask it
'Work hard and stay curious' does not survive the deadline in this one. The best replies are an assignment: run a budget, take the posting nobody wants, learn to read the accounts. Say what you do now and they can fit it to you.
What advice for people at my stage do you think is overrated?
Why ask it
Asking what to ignore gets an opinion, where a plain request for advice gets hard work and networking. It also shows what worked for them, which may not be what works for you.
What were you hoping I would ask today that I have not?
Why ask it
Save it for the last two minutes. It hands over the agenda, and leaders often use it to say the thing they came ready to say and were never asked, which can be the best material of the whole conversation.
Getting a Real Answer From Someone Senior
Practical guidance for the conversation itself
Preparation That Pays Off
Find their last two public appearances, not only their bio
Knowing what they said on a podcast, at a conference or on an earnings call lets you skip the answers they have already given this month. It also lets you open with a follow-up to something they said, which shows you did the reading.
Bring five questions, not the whole list
In twenty minutes you will probably get through four or five, and fewer if the answers are good. Choose the ones only this person can answer, take them from more than one group, and keep two spare in case an answer runs short.
Match the questions to the setting
On a panel or at a town hall, the groups on decisions and the business travel well, because the whole room gains from the answer. One to one, career path and advice work better, and the questions about failure, pressure and the last rough stretch get fuller answers without an audience.
Interviewing a business professional for a class
Not every assignment puts you in front of a chief executive. With an accountant, a sales manager or a shop owner, the groups on career path, the job and advice carry over as written, and a question about direct reports or running the company can be put as 'your team' or left out. Open with career path and add two or three from the other groups so the write-up is more than a biography.
Ask for an instance, not a principle
Opening with 'tell me about', followed by a single event, produces detail. A question that begins 'what is your approach to' invites the version they have said before.
Decide what is on the record
If you are recording, publishing or writing anything up, settle it before the first question, including whether they will see their quotes first. Some companies want a press office involved and some do not, so ask how it works at theirs.
During the Conversation
- Ask one thing at a time. Where a question here has a second half, hold it back and use it as your follow-up if the first answer comes out rehearsed.
- When you get a rehearsed answer, follow with a concrete request: which year, who else was in the room, what did the number do afterwards.
- Leave a pause alone. Count to three before you speak, because what comes after a pause is often less polished than what came before it.
- Do not correct or debate them mid-answer, even when you disagree. Note it and come back once they have finished.
- Watch the clock and say when you are at your last question. It shows you respect their time, and they will know to make the answer count.
Common Mistakes
Asking what is already public
A question the annual report or the company website already answers tells them you did not prepare. Use the public material to build the question instead: last year you said the plan was this, so what has changed since?
Asking for the secret of success
You get a slogan, because nobody can cleanly separate what they did from what happened to them. Ask about one decision and how it turned out.
Turning it into a pitch
If you spend the conversation describing your own project, you get politeness and no information. Ask for their view first, and if it has gone well, ask for a second meeting at the end.
Fishing for confidential information
Asking about unannounced results, live deals or a named employee puts them in an awkward position and ends the candour. Frame questions so they can answer fully without disclosing anything.
Afterwards
- 1Write up the answers within a day, while you can still remember the phrasing.
- 2Send a short note that mentions one specific thing they said, not a general thank you.
- 3If they offered an introduction or a document, follow up within the week, while they still remember offering.
- 4Note the questions that produced nothing and swap them out before your next conversation of this kind.
- 5If you quote them, keep to whatever you agreed at the start about seeing the passage first. It is the main reason people say yes to a second conversation.