Questions to Ask a Managing Director
Twenty questions for a final-round interview, a skip-level meeting, or a first sit-down with a managing director, covering how the business makes money, who decides what, and how people get promoted.
The questions
Open any question for the note
How would you describe what you actually spend a normal week doing?
Why ask it
An easy opener that gets past the job title. Directors who are mostly in board packs and client dinners run very different organizations from those still in the weekly operating review, and you learn which kind of access you would have.
Who did you learn to manage from, and what did you take from them?
Why ask it
Most senior managers are running a copy of one or two former bosses. Naming that person tells you what will be rewarded here. An answer with no names, only frameworks, usually means the style came from books rather than practice.
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
The numbers a director checks unprompted are the ones the whole organization is actually managed by, whatever the strategy deck says. If the list is long or generic, decisions here are probably made on narrative rather than measurement.
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 implies a different kind of work for you. Vagueness at this level is a genuine warning sign about the plan.
Which decisions do you keep for yourself, and which do you push down?
Why ask it
This maps the real authority in the place. Watch for the spending threshold, hiring approvals, and pricing, which are the three that most often get pulled back up. A director who says everything is delegated but signs off on job ads is describing a bottleneck.
Who here tells you things you do not want to hear?
Why ask it
A specific name is a good sign, and a pause is informative. Answers about culture and open doors without a name usually mean bad news travels slowly, which is the condition most senior mistakes grow in.
What did you get wrong in the last year, and what did you do about it?
Why ask it
The useful part is the second half. Anyone can name a mistake, few can describe the correction and what it cost. An answer that blames the market or a predecessor tells you where accountability stops.
What would have to go wrong for this year's plan to miss?
Why ask it
Good operators can list their two or three real dependencies quickly: a single large client, one recruitment pipeline, a regulatory decision, a supplier. If nothing comes to mind, the plan has not been stress-tested.
Which competitor do you actually worry about?
Why ask it
The name they give when asked what worries them, rather than who the rivals are, tends to be the more honest read on the market. Dismissing all competitors is a well-documented prelude to losing share.
How much of your budget is already committed, and how much could you move if you had to?
Why ask it
Discretionary spend is where new initiatives, including anything you propose, will have to come from. A director who does not know their own flexible share is unlikely to be able to fund your idea mid-year.
What are you spending money on that you would not start today?
Why ask it
This asks for a live judgment rather than a defense of the past, and it usually surfaces the project everyone internally knows is dying. It also tells you how honestly the leadership talks about sunk costs.
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.
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
Directors see this pattern repeatedly and can rarely resist answering it: moving too fast, ignoring one particular stakeholder, sending long emails to someone who never reads them. It is the most practical answer you will get all meeting.
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 happens here when someone disagrees with you in a meeting?
Why ask it
Ask for the most recent instance. A director who can describe a time they were talked out of something, and by whom, is telling you the room is real. Generalities about welcoming challenge are not evidence.
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.
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 thing that will disrupt your first year: a restructure, an exit, a system replacement. Even a deflection tells you where the discomfort is.
How long do you expect to be in this seat, and who could do it after you?
Why ask it
Direct, and acceptable to ask once rapport exists. If there is no answer to the second half, the organization has no succession plan and any promise about your progression depends entirely on this one person staying.
Getting a useful conversation out of a director
Practical guidance for the conversation itself
First, work out what the title means here
Managing director is not one job. In UK and European companies it usually means the person running the company, equivalent to a chief executive. In investment banks, consultancies and some sales organizations it is a senior rank held by many people, often client-facing rather than running an operation. In a subsidiary of a foreign group it may mean the country head with limited autonomy and a parent company setting the strategy. Ask which it is before you choose your questions, because strategy questions are wasted on a banking MD who owns a client book, and client questions are wasted on a country head.
Preparation that pays
Read the last set of published results
Annual accounts, an investor call, a regulatory filing, or trade press coverage. Ten minutes with the actual numbers lets you ask about a specific line rather than about strategy in general, and directors notice the difference immediately.
Pick three questions, not twenty
You will usually get between five and fifteen minutes. Choose one 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 headcount are all published. Asking about them signals you did not look, and it burns the small amount of attention you have.
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 actual practice, and it is the single most useful follow-up phrase for senior conversations.
Let them finish, then take one thread
Directors are used to being interrupted and remember people who listened. One good follow-up on something they said is worth more than three prepared questions in sequence.
Do not use a skip-level to complain
If this is a meeting over your own manager's head, raising a grievance will be relayed downwards. Keep it to the business, and take the manager problem through the proper route.
Write down the numbers and names
The metrics, competitors and people they mention are the map of what matters here. Send a short note afterwards referring to one of them, which is both a courtesy and a memory aid.
Reading the answers
- Specific numbers, named people, and recent dates mean they are close to the operation
- Only frameworks and slogans usually mean the detail sits with someone else, so find out who
- An inability to name a mistake or a delayed decision suggests bad news does not travel upwards
- Promotions that all come from one function or office are the real career path, regardless of policy
- Discomfort at a question about the board or parent company tells you where the constraints are