Questions to Ask a Managing Director
Questions to ask a managing director in an interview, a skip-level meeting, a town hall or a first coffee with the person who runs the business. They start with openers that suit any meeting, then cover the business and its money, how the managing director leads and decides, people and culture, and their own career, with a last group for job candidates, whether the managing director is the final round or, in a small company, the only one. Some belong in a private conversation and not in front of a room: a question about a mistake or a successor lands differently with the whole company listening.
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The questions
Each question, and why to ask it
Openers
What are your top priorities for the business this year?
Why ask it
Count what comes back. Two or three priorities, each with a number or a date on it, mean the year has been ranked and you can ask where your own work sits. Seven or eight mean the ranking has not been done, and the real order will show up in whatever gets funded.
What is the biggest challenge the business faces over the next twelve months?
Why ask it
A town hall regular, so the first reply is often the rehearsed one: the economy, hiring, costs. Ask which part of it sits inside the company's control, because that is the part that turns into work for the people in the room.
Where do you want the company to be in five years?
Why ask it
Size, markets and ownership are the three things to listen for. Doubling revenue, holding position and getting the company ready for a sale lead to very different jobs for everyone below. If the answer is plain about which one it is, ask whether the owners see it the same way.
How did you become a managing director, and which move mattered most?
Why ask it
Most people enjoy telling this story, which makes it a safe question for a nervous first meeting. The move they single out, whether a turnaround, a posting abroad or a spell in sales, shows what the company prizes in its leaders and what they may look for in you.
What do you actually spend a normal week doing?
Why ask it
An easy opener that gets past the job title. A managing director who lives in board papers and client dinners runs a different company from one who still sits in the weekly operating review, and the answer shows how close to your work they are likely to be.
What do you enjoy most about running this business?
Why ask it
A warm question for a coffee chat or the last minutes of an interview, and more revealing than it sounds. Notice whether they pick customers, the numbers, building a team or winning deals, because that is likely where their attention goes when the calendar is full.
What is one thing my team could do this year that would matter most to you?
Why ask it
Made for a skip-level or a site visit, when you already work there and want to know how your corner looks from the top. A precise answer shows they know what your team does. If you get thanks and encouragement and nothing else, your team's results are probably not reaching them, and that is the thing to fix first.
The business
What has changed in the business in the last year that an outsider would not notice?
Why ask it
This invites something real that is not in the press release: a lost account, a reorganization, a change in who has influence. If nothing has changed in a year, either the business is unusually stable or the answer is guarded.
Which two or three numbers do you look at first on a Monday morning?
Why ask it
Whatever they check without being asked is usually what everyone below gets managed on, whatever the strategy deck says. Ask who else sees those figures each week. If it is only the finance team, the people doing the work may not know how they are being judged.
Where does the revenue come from now, and where do you expect it to come from in three years?
Why ask it
You are checking whether the future depends on new customers, new products, price rises or acquisitions, since each means a different kind of work for you. If the three-year answer is the same as today's, ask what happens when the biggest line slows down.
Which customers would hurt most to lose, and how secure are they?
Why ask it
A company that leans on one or two accounts bends around keeping them happy: prices, staffing and deadlines get set by what those customers want. If the answer names an account, ask how long the contract runs and who holds the relationship. Some of this is confidential, so accept a general answer in an interview.
What do customers complain about most, and when did you last hear it firsthand?
Why ask it
The complaint shows where the product or the service is weakest. The date shows how far the managing director sits from customers: on a call last week is one kind of leader, and a quarterly satisfaction score is another.
What sets this company apart from its competitors, in your own words?
Why ask it
The website version is quality, service and people, which every rival claims too. Ask what a customer would say they get here and cannot get elsewhere, and whether it would still be true if two or three key people left.
Which competitor do you actually worry about?
Why ask it
Asking who worries them often gets a different name from asking who they compete with: a smaller or newer firm than the obvious rival. The reason they give, whether price, speed or a better product, shows where this company feels exposed. If nobody worries them, ask who they last lost a deal to.
What is changing in your market that the company is not ready for yet?
Why ask it
This asks them to admit a gap, so save it for a conversation that is going well. A named shift with a rough date beside it, such as a new entrant pricing lower, a change in how customers buy or a rule coming into force, shows someone is watching. Then ask who inside the company owns the response.
Where has AI or other new technology changed how the business runs, and where has it not lived up to the talk?
Why ask it
The second half is what lets them answer honestly. Look for one process that now works differently, with a result attached, and one experiment that was dropped. A reply made only of intentions means nothing has been tried yet.
What keeps you up at night about the business?
Why ask it
An old line, and still worth asking, because the worry that comes out is rarely the one in the annual report. It may be cash, one key person leaving or a decision that sits with a regulator. If the reply is that they sleep well, ask what last cost them a weekend.
What would have to go wrong for this year's plan to miss?
Why ask it
A plan that has been tested against a bad year comes with two or three named dependencies: a contract renewal, a hire that has to land by spring, a supplier holding its price. If nothing comes to mind, ask what happened the last time the plan was missed and what gave way first.
What are you spending money on that you would not start today?
Why ask it
This asks for a judgment made now and not a defense of the past, and it tends to bring up the project people inside already suspect is finished. Keep it for a one-to-one. In front of a room, the team running that project is listening.
Leadership
How would you describe your leadership style, and what would your direct reports add?
Why ask it
The label on its own (collaborative, direct, hands-off) tells you little. Asking what their own team would add often brings out the candid part, such as impatience, a habit of rewriting other people's work, or going quiet when unhappy.
Who did you learn to manage from, and what did you take from them?
Why ask it
People often manage the way a former boss managed them, or pointedly the opposite. Ask what that boss did that they still do, and what they promised themselves they never would. A reply made only of frameworks and book titles leaves you guessing how they behave on a bad day.
Which decisions do you keep for yourself, and which do you push down?
Why ask it
Ask about three in particular: how much someone can spend before it needs their signature, who approves a hire, and who can change a price. A managing director who says everything is delegated but still signs off every job advert is describing a bottleneck.
When the data points one way and your instinct points the other, which wins?
Why ask it
Ask for a case. A managing director who overrode the numbers once and can say how it turned out is describing judgment. One who says the data always wins is either running a very measurable business or leaving out the calls made on a hunch.
What is the biggest risk you have taken in this job, and would you take it again?
Why ask it
Whether it was a new site, a dropped product line or one very large contract, pay more attention to how they describe the downside than to how it ended. A leader who can say what they stood to lose weighed it beforehand.
Who here tells you things you do not want to hear?
Why ask it
A specific name is a good sign, and a long pause tells you something too. Talk of open doors with nobody named suggests bad news reaches this office late. Leave it out of a town hall, where the person they would name is sitting in the room.
What happens here when someone disagrees with you in a meeting?
Why ask it
The test is the last time it happened. A managing director who can describe being talked out of something, and by whom, runs meetings where people speak up. Generalities about welcoming challenge are not evidence.
What did you get wrong in the last year, and what did you do about it?
Why ask it
Naming a mistake is the easy part. Listen for the correction: what they changed, what it cost, and whether they told the people it affected. An answer that blames the market or a predecessor shows where accountability stops.
How do you handle it when the board or the parent company wants something you think is wrong?
Why ask it
Managing directors sit between owners and staff, and this reveals which way they lean under pressure. It also tells you how much of what arrives as strategy is negotiable at their level.
How do you decide between fixing a struggling team and changing its leader?
Why ask it
The answer predicts what happens if your own team hits a bad quarter. Listen for how long people get, what evidence is used, and whether anyone is ever moved sideways rather than out.
How do you find out what is really happening two or three levels below you?
Why ask it
Walking the floor, a monthly lunch with no managers present, reading the customer complaints personally: any habit counts as long as it is regular. Without one, the managing director knows the company through slides, and your work will reach them the same way.
What decision have you been putting off?
Why ask it
A candid answer is unusual and worth a lot, because the delayed decision is often the one that would disrupt your first year: a restructure, a site closure, a system replacement. Even a deflection shows where the discomfort is.
People
How would you describe the culture here, and what are you still trying to change?
Why ask it
Listen to the second answer more closely than the first. A managing director who can say what frustrates them about how the place works (slow sign-offs, departments that guard their turf, staying late to be seen) has looked at it squarely. Later, put the same question to someone two levels down and compare.
Which of the company's values has cost you something to keep?
Why ask it
Values on a wall are free. Turning down a profitable client, parting with a high performer who treated people badly or paying to fix a mistake the customer never noticed are what a value looks like once it has been tested. A struggle to find an example is an answer too.
What do the people who do best here have in common?
Why ask it
This is the unwritten job description for every role in the company. Set the traits they list against your own without flattering yourself, and if they describe someone who never switches off, believe them.
What does someone have to do to be promoted into your leadership group?
Why ask it
You want the last two examples, not the criteria. If the recent promotions all came from one function or one office, that is the real path, and it may not include yours.
What do new people here usually get wrong in their first six months?
Why ask it
The reply is usually concrete: moving too fast, skipping one particular stakeholder, sending long emails to someone who only reads the first line. Ask which of those cost the last newcomer most, then treat it as a checklist for your own first months.
When good people leave, where do they go and what do they say on the way out?
Why ask it
Leavers going to competitors for more money point to pay, and leavers going to a bigger title elsewhere point to a ceiling. A managing director who reads the exit interviews will know which it is. If you are told people rarely leave, ask how long the team you would join has been together.
What do you look for when you hire someone into a senior role?
Why ask it
Useful whether or not you are the candidate, because it shows what they think the company lacks. Notice whether they hire for years in the sector or for range, and ask how the last senior hire from outside has settled in.
How do you handle work-life balance, for yourself and for the people who work for you?
Why ask it
Policies are easy to list, so ask what they do themselves: when they send email, whether they take all their leave, what happened the last time a team was stretched for months. People copy the person at the top long before they copy the handbook.
How does the company develop people who are not yet ready for the next job?
Why ask it
Course budgets matter less than stretch assignments, temporary postings and who gets put in front of the board. Ask about someone who was given a role before they were ready and how it went, which shows whether the company grows its own leaders or buys them in.
Career
What surprised you most when you took over as managing director?
Why ask it
You may hear how lonely the seat is, how much time the owners take, or how slowly a decision travels down. Whatever it is marks the distance between the job as it looks from below and the job as it is, which matters if you want it one day.
What do you wish you had known at my stage of your career?
Why ask it
Best for a mentoring conversation or a networking coffee, since it turns the meeting toward advice they paid for with a mistake. Say briefly what stage you are at first, or the answer will be generic. Write it down in front of them.
Which skill mattered most in getting from senior manager to running the company?
Why ask it
Expect something other than technical ability: reading a balance sheet, handling a board, choosing people, saying no. Ask how they learned it, because the route (a mentor, a hard year, a course) is something you can copy.
What do you read, and who do you talk to, to keep your thinking fresh?
Why ask it
A trade title, a peer group of other managing directors, a former boss they still call: the sources show where their ideas come from. It also hands you something concrete to mention when you follow up.
What part of the job would you hand to someone else tomorrow if you could?
Why ask it
Asked lightly, it gets a laugh and then a true answer: the monthly reporting pack, a difficult shareholder, disciplinary hearings. If you are joining the leadership team, it is also a hint about work that may be heading your way.
How long do you expect to be in this seat, and who could do it after you?
Why ask it
Direct, so keep it for a private conversation once you know each other a little. If no successor comes to mind, there may be no succession plan, and any promise made to you about progression rests on this one person staying.
What would you like to be remembered for when you leave this role?
Why ask it
A legacy question sounds grand, so keep it for a relaxed moment. The answer is their private scorecard: a business that outlasts them, people they brought on, a number they hit. It often differs from the official priorities, and it explains decisions that otherwise look odd.
Interviews
What do you personally need from whoever takes this role?
Why ask it
In a large company the managing director may join only the interviews for roles they care about, and in a small one they may meet every hire, so it is fair to ask which this is. Their version of the brief sometimes differs from the hiring manager's. If it does, raise the difference politely before you accept anything.
What would you want me to have delivered by the end of my first year?
Why ask it
At this level expect an outcome more than a task list: a market opened, a cost taken out, a team rebuilt. Ask what they would stop or fund to make that outcome possible, since a target with no resources behind it is a wish.
How much freedom would I have to change how my area works?
Why ask it
Put it in terms of three things: people, budget and suppliers. Being told the area is yours to run means little if every replacement hire and every contract over a small sum goes back up for approval. What the last person in the job tried to change, and how far they got, is the fairest measure.
What should I leave alone in my first few months?
Why ask it
Most businesses have something that works for reasons nobody wrote down: a long-serving account manager, an old pricing arrangement, a Friday routine the team is attached to. A managing director who names one is sparing you an early mistake. It also shows what they would defend if you proposed changing it later.
Whose support on your leadership team would I need most, and what do they care about?
Why ask it
The names that come up are the people this job quietly depends on, often the finance director or whoever runs operations. If you have not met them during the process, say so and ask whether you can before an offer is made. Being hired by one person into a team that had no say is a hard way to start.
How would my work reach you, and how would you hear if it was going badly?
Why ask it
This tests whether there is a reporting line that functions or a game of telephone through two layers. If the only channel is your own manager, you will need to know that before something goes wrong.
What happened to the last person who held this job?
Why ask it
Promoted, moved on after a long run and gone within the year are three different stories about the same vacancy, and the managing director may tell it more bluntly than the recruiter did. If two people have left the seat in quick succession, ask what the company has changed since.
How is the company doing against this year's budget, and does that affect this hire?
Why ask it
A fair thing to raise in a final round, asked plainly. A business behind its numbers can freeze hiring or reshape the role after you have resigned from somewhere else, and the managing director is the person in the process most likely to know. A listed company may only be able to point you to what it has already published.
Is anything planned for the next year, such as a restructure or a change of owner, that would change this job?
Why ask it
They may not be free to say, and a careful non-answer is information in itself. What you can reasonably expect is a plain statement of who the role reports to and whether that is settled. If a sale or a merger is already public, ask directly how this team is meant to come through it.
What should a candidate know about this company before saying yes?
Why ask it
An open invitation to describe the downside, which recruiters are rarely briefed to give. Slow approvals from a parent company, a system everyone complains about, a busy season that eats December: an honest reply sounds like one of those. When the picture has no drawback in it at all, put the same question to whoever would be your peer.
What in my background made you want to meet me?
Why ask it
The reply shows which part of your record they are hiring: the sector you know, a turnaround you ran, the size of team you have led. That is the part they will expect to see at work first, so it tells you where to begin. If it is not the experience you would have picked yourself, say what else you bring while they are still deciding.
Having met me, do you have any doubts about my fit that I could answer now?
Why ask it
It takes some nerve with someone this senior, but it is your one chance to answer an objection before they carry it into the decision. If they name a gap, such as no experience in the sector or a smaller team than this one, agree with what is true in it and say how you would close it. If they say there are none, ask what would make you the first choice.
What are the next steps, and is the final decision yours?
Why ask it
When the managing director is in the room the process is usually near its end, but not always: a group HR sign-off, board approval for a senior hire or references may still follow. Ask for a date, and ask whether you may contact them or the recruiter if it passes.
Getting a useful conversation out of a managing director
Practical guidance for the conversation itself
First, work out what the title means here
Managing director is not one job. In the UK and a number of other countries it usually means the person who runs the company day to day, much like a chief executive elsewhere. In investment banks, consultancies and some other firms it is a senior rank that many people hold at once, often looking after clients and not running an operation. In a subsidiary of a foreign group it may mean the country head, with a parent company setting the strategy. Find out which it is before you choose your questions: the firm's website or the person's own profile usually shows it. This list is written mainly for the first kind. A banking managing director with a client book is better asked about clients, deals and the team than about company strategy, and a country head may have to pass anything about group strategy upward.
Preparation that pays
Read the last set of published results
Annual accounts, an investor call, a regulatory filing or trade press coverage, depending on what the company has to publish where it is based. Ten minutes with the actual numbers lets you ask about a specific line instead of strategy in general, and it shows in the question.
Pick three questions, not the whole list
Time with someone this senior is often short, and in an interview it may be the last few minutes. Choose one question about the business, one about how decisions get made, and one about what you would be measured on, and hold the rest in reserve.
Never ask what is on the website
Values, history, product lists and office locations are usually published. Asking about them suggests you did not look, and it uses up the little time you have.
Match the questions to the meeting
Meeting the managing director in an interview
Take one or two from Openers, one from The business and two or three from Interviews. When the managing director is the last person you meet, they are often judging whether you think about the company as a whole, so lead with the business and keep pay, hours and time off for the recruiter or the offer stage.
A skip-level or a first one-to-one
The business and People work best here, because you already know the day-to-day and want the view from above it. The opener about what your team could do belongs in this meeting. Tell your own manager it is happening, and give them the gist afterwards.
A town hall or all-hands
Choose something the whole room wants answered, from Openers or The business, and keep it to one sentence with no preamble. Questions about a managing director's mistakes, successor or delayed decisions belong in a private conversation, not in front of the whole company.
A coffee chat or mentoring conversation
Start in Career and let it run. People at this level are asked about the numbers all day and about themselves rarely, and the advice will be better if you first say where you are and what you are trying to decide.
If you are the one interviewing a managing director
Boards, owners and search panels ask many of the same things. Most of the Leadership and People questions work from that side of the table if you put them in the past tense and ask about the candidate's last company: the decision they delayed, who told them hard truths, what they stopped funding. Speak to people who reported to them as well, since a managing director's own account is only half of the evidence.
In the room
Ask for the most recent example
Almost every answer improves with "when did that last happen?" It moves the conversation from stated policy to what was actually done, and it works on nearly every question in the Leadership and People groups.
Let them finish, then take one thread
Resist cutting in to show what you know. One good follow-up on something they just said is worth more than three prepared questions in a row, and it is what makes the meeting feel like a conversation and not a questionnaire.
Do not use a skip-level to complain
If this is a meeting over your own manager's head, assume anything you say about them may get back to them. Keep it to the business, and take a problem with your manager through the route your employer has for that, such as HR or a formal grievance process.
Write down the numbers and names
The metrics, competitors and people they mention are a map of what matters here. If a follow-up note is appropriate, refer to one of them in it, which shows you listened and helps them remember the conversation.
Reading the answers
- Specific numbers, named people and recent dates suggest they are close to the operation
- Only frameworks and slogans may mean the detail sits with someone else, so find out who
- No mistake and no delayed decision they can name is a hint that bad news travels upward slowly
- Promotions that all come from one function or office show the path that has worked so far, whatever the policy says
- Discomfort at a question about the board or parent company shows where the constraints are