Questions to Ask a Director
Questions to ask a director of a company, sorted by what you want from the conversation. The first four groups are for a director you already work under, in a one-on-one, a skip-level or a coffee you asked for: their priorities, how they lead, the state of the team, and careers, theirs and yours. Most of those work in an interview too, and the first group closes with a few about the business as a whole, for a director met at an event, on a visit or for an assignment. A fifth group is for candidates being interviewed by a director, and the last is for anyone sitting down with a director of IT. There are 67 questions, each with a note on what a full or a thin answer tells you and what to ask next.
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The questions
Each question, and why to ask it
Priorities
What are your top priorities for the department this year?
Why ask it
The plainest question on the list and the one to start with, because every later answer makes more sense once you know the two or three things they are trying to get done. If you hear more than four, ask which one would survive a budget cut.
What is the biggest challenge the department is facing right now?
Why ask it
Many directors answer this more frankly than people expect, since naming a problem everyone can already see costs them little. Listen for whether it sits inside the department, where they can act on it, or outside it, where they can only lobby.
What does success look like for this team over the next twelve months?
Why ask it
A date, a number or a thing shipped means the target is agreed and you can aim at it. Words like stronger, better or more strategic mean nobody has written it down yet, which is worth knowing before you are measured against it.
Where do you want the department to be in three years?
Why ask it
The answer shows whether they are building something or holding a line: growing, merging with another group and handing work to software are very different futures. Ask what has to go right in the coming year for that picture to stay realistic.
How does this team's work connect to the company's goals?
Why ask it
You are asking for the line between the daily work and something the chief executive would recognize. A director who can draw it in a sentence is well placed to argue for the team's budget. If it takes a paragraph, ask which part of the work they find hardest to explain upstairs.
What does your own boss want most from the department this year?
Why ask it
This gets you the list as it looks from above, which is not always the one on the strategy slide. Where the two differ, the boss's version tends to win, so check how much of your own work is on it.
If you were handed one more person or a little more budget tomorrow, where would it go?
Why ask it
This is the priority that did not get funded, and it is often closer to what they care about than the official list. For anyone already on the team, it is also a hint about which work would get noticed if you picked it up.
What is coming in the next six months that the team should be getting ready for?
Why ask it
Best asked a few weeks before planning season, while the answer is still forming. Even a one-line reply, such as a system being replaced or a target moving, lets you start on the reading or the training before everyone else is told to.
Which number do you check first to see whether the department is on track?
Why ask it
Whatever they name is the thing to understand properly: how it is calculated, who reports it and what moves it. If your own work touches that number, say so, because nothing makes the work easier for them to see.
What changes in the industry are you watching most closely?
Why ask it
Good for a town hall or a coffee, where a question about internal plans might get a careful non-answer. A director who names a competitor's move, a new regulation or a shift in what customers ask for is telling you where next year's priorities will come from. Ask which of them the company is slowest to respond to.
What do people outside the company most often get wrong about it?
Why ask it
An easy opening with a director you have only just met, at a networking event or on a site visit. The correction they reach for first is usually the thing they are proudest of or the criticism that stings most, and either is worth a follow-up.
How does the company make most of its money, and which part of the business is growing?
Why ask it
Fair from a student, a new hire or a visitor, and something a director can answer without notes. When the part that is growing is not the part that pays the bills today, ask how long the company expects to carry both.
What does the company do better than its closest competitors?
Why ask it
Marketing has a line for this, so listen for the director's own: a cost kept lower, a customer understood better, an order delivered faster. If that half goes well, ask what a competitor does better, which is the answer you could not have read on the website.
Which of the company's decisions are yours to make, and which go to the board or the owners?
Why ask it
Director is a different job from place to place: a department head in a large firm, an owner or a member of the board in a small one, with duties that depend on the country and the company. Their reply tells you which kind you are talking to, and so how far their other answers reach.
Which risk to the company do you spend the most time thinking about?
Why ask it
Losing a large customer, a change in the rules, a rival with lower costs and a key person leaving are the usual candidates. Naming one and saying what is being done about it is a straighter picture than hearing that the company is well placed.
What was the hardest year the company has had, and what got it through?
Why ask it
This one asks for a story, and people tell stories more freely than they give assessments, which suits a school or university assignment. Whatever they credit, whether cash in reserve, one loyal customer or cutting early, is what the company would lean on next time.
Leadership
How would you describe your leadership style, and when do you depart from it?
Why ask it
The first half gets a label such as hands-off or direct. The second half gets closer to the truth: many directors step in when a deadline is at risk or a customer is angry, and that is the version of them you would meet in a bad week.
How do you like to be kept up to date, and how much detail do you want?
Why ask it
Some directors want three lines on a Friday and others want to be copied on everything. Getting this wrong makes good work invisible or makes you look as if you need supervising, so write the answer down and follow it.
When something is going wrong, how early do you want to hear about it?
Why ask it
Almost every director says straight away. The follow-up is the useful part: ask what happened the last time someone brought them a problem with no solution attached, and whether they would rather get a message or a conversation.
How do decisions get made in your area when people disagree?
Why ask it
A useful answer names who breaks the tie and how long they let an argument run first. If all you hear is consensus and alignment, ask about the last disagreement that did not settle itself and how it ended.
How do you want people to disagree with you?
Why ask it
In the meeting, in private afterwards and in writing are three different answers, and choosing the wrong one can lose you the argument before it starts. A director who says they love being challenged should be able to recall the last time it changed the outcome.
What was the last project you stopped, and how did you make the call?
Why ask it
Stopping work is harder than starting it, because somebody senior usually asked for it. A director who can name the project, who had to be told and what the team did with the freed time has done it for real. If they cannot think of one, expect your own list to keep growing.
What do you do when priorities change above you in the middle of a quarter?
Why ask it
The last time it happened is the thing to hear about. Some directors take the change, re-plan and tell the team what has been dropped to make room. Others pass it straight down on top of everything else, and that second habit is where the late evenings come from.
What do you stay close to yourself, and what do you hand over completely?
Why ask it
Hiring, budgets and anything that reaches a customer are the usual things a director keeps hold of. If your work is in the kept pile, expect their comments on drafts. If it is in the other, expect to be left alone, which suits some people better than others.
Which decision in this job have you found hardest to make?
Why ask it
Ask this only once the conversation has relaxed, because a rushed director will give a tidy answer about trade-offs. A real one has a date, other people in it and something they would do differently, and it shows what they will not compromise on.
The team
What does your department own, and where does that stop?
Why ask it
The edges tell you more than the middle. Ask what sits just outside their remit and who has it, because work that crosses that line needs a second director to agree before anything moves.
How would you describe the culture on your teams, and what would you change about it?
Why ask it
The description alone will be warm and of little use. The part they would change is the honest half: long hours, people who avoid conflict, too many meetings. Compare it with what someone on the team tells you.
What holds this team back most: budget, headcount or waiting on other teams?
Why ask it
Offering three choices makes it easy to pick one, and the pick changes what the job is. Short of budget means making the case upstairs, short of people means choosing what not to do, and waiting on others means much of the week goes on chasing.
How much of the work is planned, and how much arrives unexpectedly?
Why ask it
Push for a rough split, such as seventy to thirty, and then ask where the unplanned part comes from. If most of it is urgent requests from one other department, you have found out who really sets the team's week.
How do you decide which projects get people and which ones wait?
Why ask it
A written ranking that is revisited each quarter is the good answer. Where the ranking lives only in the director's head, work gets reshuffled each time a senior person asks for a favor, and a project can lose its people without warning.
What has your team tried that did not work?
Why ask it
Listen for a named initiative, what it cost and what the team does differently because of it. If the story ends with somebody being blamed, that is a fair guide to how the next failed experiment will be handled.
Which other team do you depend on most, and how is that relationship?
Why ask it
Every department waits on another one: finance for sign-off, IT for access, sales for a forecast. A candid director names the team and the sticking point. If it is all described as a great partnership, ask how long a typical request to them takes.
What is the department's reputation in the rest of the company, and is it fair?
Why ask it
Slow, expensive, helpful, hard to reach: most departments have a one-word reputation, and the director has heard it. Whether they think it is deserved tells you if they plan to fix the work or the story told about it.
What is the team doing well right now, and where are we falling short?
Why ask it
Meant for your own director, and a way to get the view from one level up without making it about you. Set both answers against what your manager has been telling the team. If the director's worry is one nobody on the team has heard, mention it to your manager in the same words.
How do you find out what the team really thinks?
Why ask it
News has usually been tidied up by the time it reaches a director. Regular skip-level conversations, a survey they read themselves or a habit of sitting with the team are real answers. A claim that their door is always open leaves the effort with the people least likely to make it.
What has turnover been like on this team over the last two years?
Why ask it
Mostly a candidate's question, and a fair one. The count matters less than where people went: a bigger job elsewhere is a compliment to the team, while the same job at a competitor raises a question about pay or management. Expect an outline only, since most directors will not discuss individuals.
Careers
What was your path to becoming a director?
Why ask it
Easy to ask, and most directors enjoy answering it. Pay attention to the moves that were sideways or accidental, since a career plan would never have included them, and ask which job taught them the most.
What surprised you most when you went from managing a team to running a department?
Why ask it
Common answers are how little of the hands-on work they still see and how much time goes on budgets and on peers. If you want that job one day, this is a cheap preview of whether you would enjoy it.
What does a typical week look like for you?
Why ask it
Ask about last week and not an average one. The share that went to their own boss, to hiring and to problems tells you what the job is, and it explains why a reply to your message can take three days.
What do you enjoy most about working here, and what has kept you?
Why ask it
Put to someone who has stayed for years, this is really a question about why. The work, the people and the freedom to run things their own way are three different reasons, and each says something about what the company gives its senior people. If the answer is all in the past tense, ask what keeps them there now.
What do you wish someone had told you before your first director role?
Why ask it
Advice asked for this way comes tied to a mistake they remember, which makes it more specific than advice in general. Thank them for it and do not argue, even where it would not fit your situation.
How do you keep the job from taking over the rest of your life?
Why ask it
Better in a coffee or a mentoring chat than in an interview, where it can sound like a question about hours. Some directors have firm rules, such as no email after dinner, and others will admit they have not solved it. Both answers show you what the level above yours costs.
What should I be getting better at now if I want to move up a level?
Why ask it
Ask for one skill, not a list, and ask what doing it well looks like one level up. Then tell your own manager what you heard, so the advice turns into work you are given and not a note on your phone.
Who at my level has been promoted recently, and what did that take?
Why ask it
A name and a rough timeline show that the ladder works and what it rewarded. If no recent example comes to mind, promotion there may depend on somebody leaving, so ask what would have to open up.
What do you look for when you decide who gets the important work?
Why ask it
Promotion criteria are written down, and this is the unwritten version. Reliability, judgment on thin information and being easy to work with under pressure come up often. The one they name first is usually the one they find rarest.
What is one thing I could do differently that would help the most?
Why ask it
Only for a director who has seen your work. Asking for a single thing makes an honest answer easy to give, and the right reply is a thank you and a question about what better would look like, never a defense.
What could I or my team do that would make your job easier?
Why ask it
It sounds like flattery and works as intelligence: the answer names whatever is costing them time, often a report they have to chase or a question that keeps arriving from above. Offer only what you can deliver, because they will remember the offer.
Is there a problem nobody owns that I could help with?
Why ask it
Most directors carry a short list of these. Taking one on gets your work seen outside your own team, but agree it with your manager first so it does not look as though you went around them, and be honest about the hours you can spare.
Interviews
Is this a new position, or did someone leave it?
Why ask it
A new position, a replacement and a seat that has emptied twice in two years are three different situations. If someone left, ask how long they stayed and where they went. Few directors volunteer that, and most will answer when asked directly.
Who would be my manager day to day, and how long have they been in the job?
Why ask it
For when the director is not the hiring manager. A manager who started last month, or a seat above you that is still empty, means accepting the job without having met the person who will shape most of your days. Ask to meet them before you decide.
What do you need from this role that you are not getting today?
Why ask it
A second way into what the job is for. The gap might be a skill, spare capacity or someone to take a difficult client off the director's hands, and the rest of the interview gets easier once you can speak to that gap directly.
What does the first ninety days look like, and what would tell you it went well?
Why ask it
A director who lists who you would meet, what you would take over and one thing to deliver by the third month has planned for the hire. Being told to come in and see what you find means you would be writing the job yourself. Some people want exactly that, so decide which kind you are before you hear the answer.
How often would you and I meet, and what are those meetings like?
Why ask it
A weekly one-on-one, a skip-level every couple of months and contact only at a monthly review are very different amounts of access. Ask what has happened with their current reports in the last month, since the calendar is more reliable than the intention.
How is performance reviewed here, and when is the next cycle?
Why ask it
Review calendars differ from one employer to the next, and the date matters: join just after a cycle closes and the wait for a first formal review or raise can be long. Ask whether new hires are handled off-cycle, what the review weighs and who else has a say.
What would you want me to change, and what should I leave alone?
Why ask it
Directors hire to fix something, so the first half comes easily. Pay closer attention to the second: a process the team built and is quietly proud of is the easiest thing for a newcomer to trample in the first month.
What is the part of this job you would not put in the posting?
Why ask it
Asked plainly, this often gets a real answer: a difficult stakeholder, a reporting burden, a system nobody wants to maintain. If they claim there is nothing, you have learned how candid the working relationship will be.
What would make you say in a year that this hire worked?
Why ask it
The answer is the job description as the director sees it. Compare it with what the earlier interviewers told you, and raise any mismatch before you accept.
Is there anything about my background you are unsure about?
Why ask it
Uncomfortable to ask and worth it, because it is the last point at which you can answer an objection in person. Reply briefly and with an example, not a defense. If they say there is nothing, take that at face value and move on.
What happens next, and who else has a say in the decision?
Why ask it
Directors often make the final call but seldom make it alone. Hearing that a peer, a vice president or the team still has to weigh in tells you who to prepare for, and the timeline gives you a date after which a follow-up is reasonable.
IT director
What is on the IT roadmap for the coming year, and what was left off it?
Why ask it
For a director of IT, the roadmap is the priority list in its most concrete form: a migration, a security program, a new finance or HR system. What was left off tells you which departments will be waiting, and whether yours is one of them.
How much of your team's time goes to support tickets, and how much to project work?
Why ask it
A team that spends most of its week on password resets and broken laptops has little left for anything new, however good the plan. Candidates should ask which side of that split the role sits on, because the two are different jobs.
Who decides which department's request gets worked on first?
Why ask it
A steering group, a ranked queue and the director's own judgment are all workable. With no clear answer, requests get done in order of who complains loudest, which matters whether you are about to join the team or about to ask it for something.
What is the oldest system the business still depends on, and what is the plan for it?
Why ask it
Most IT departments have one: the server nobody dares restart, or the database only one person understands. A director with a dated plan to replace it is managing the risk. One who laughs and changes the subject is probably hoping it outlasts them.
How was the last major outage or security incident handled, and what changed afterwards?
Why ask it
You want a timeline, who was told, and one specific change that followed, such as a new backup test or a tighter login rule. Details of a security incident may be off limits, so accept an outline and ask about the lessons.
What do you run in house, and what goes to vendors or a managed service provider?
Why ask it
The split decides what the team does all day. Heavily outsourced departments manage contracts and escalations, and in-house ones build and fix. Ask when the largest contract comes up for renewal, since that is when the split is most likely to move.
Where do you stand on staff using AI tools, and who made that call?
Why ask it
Policies range from a ban to an approved list to nothing written at all, and they are changing quickly. The answer shows how the director weighs data risk against people getting on with their work, and whether legal or security has the last word.
What can people outside IT do to make a project with your team go well?
Why ask it
Meant for anyone who has to ask IT for something. Expect to hear about requirements that arrive late, testers who never turn up and tools bought without telling anyone, and treat the list as instructions.
Getting the most from time with a director
Practical guidance for the conversation itself
Pick the questions for the meeting you are in
A one-on-one or skip-level with your own director
Start in Priorities and take one or two from Leadership. Tell your manager beforehand that the meeting is happening and afterwards what you learned, since the director may well mention it to them anyway. Three questions are plenty for half an hour if you follow up on the answers.
A coffee chat or a mentoring conversation
Use the Careers group and let them talk. Ask about their path before you ask about yours, and leave with one piece of advice you will act on, so that you have something to report the next time you meet.
A town hall or a team Q&A
One question, asked on behalf of the room. Priorities, the biggest challenge, changes in the industry and what is coming next all work in public. Anything about your own career, your pay or a named colleague does not.
A director of a company you do not work for
At a networking event, on a site visit or for a school or university assignment, use the company questions that close the Priorities group, then ask about their path from Careers. Find out early what director means there: a department head in a large firm, often an owner or a board member in a small one, with duties that depend on the country. Leave the promotion and interview questions out.
An interview
Begin with the Interviews group, then borrow from The team and Leadership. The next section is about choosing between them, depending on whether the director would be your manager.
A director of IT
The last group is written for IT. Coming from another department, ask about the roadmap, whose request comes first and what makes a project go well. As a candidate, ask about the split between tickets and projects, the oldest system and the last outage.
In an interview, match the question to the seat
If the director would be your manager
Put first how often the two of you would meet, the first ninety days, what they would want changed, and what they do when priorities change above them. You are interviewing a working relationship as much as a company.
If the director is a level above the role
Put first what their own boss wants from the department, how disagreements get settled, and which other teams they depend on. Go light on the day-to-day, which a director one level removed can only describe from a distance, and save those questions for the hiring manager.
Save two questions for the end
The part of the job that is not in the posting and the question about their doubts both land best when the conversation has already gone well. Asked in the first five minutes, they can sound defensive.
Check what you are told
- Ask a prospective peer the same question about unplanned work, and compare the two answers.
- Ask the recruiter when the last person in this role left, then ask the director where they went.
- Ask two different interviewers what success in the first year looks like. If the answers differ, the role is not yet agreed internally.
- Look up whether the team has been reorganized recently, and ask what problem that was solving.
- If a promotion path is described, ask who took it last and how long it took them.
- If you already work there, compare the director's stated priorities with what your own manager is asking of you this month. Raise a gap between the two with your manager first.
What to avoid
Asking what you could have looked up
Questions about the company's products, funding or public strategy use up time with someone who is hard to get time with. Ask about the things that are not written down.
Stopping at the leadership style
On its own, the style question gets a prepared paragraph, which is why it comes with a second half on this page. A specific event, such as the last project they stopped or the last priority that changed, gives you the same information in a form you can check.
Leading with pay and title
In an interview, both are worth settling, but usually with the recruiter or HR and not in the middle of a conversation with the person deciding whether they want you. With your own director, take pay to your manager first.
Asking only friendly questions
Turnover, what holds the team back and what did not work are fair things for a candidate to ask, and many directors take them as a sign of interest. Asked politely, they show you are weighing the job and not only hoping for it.
Using the meeting to go around your manager
A complaint about your manager made to their boss rarely stays between the two of you, and it changes how both of them see you. Bring the director questions and take ordinary grievances to your manager. Something serious, such as harassment or a safety problem, is different: ask HR how reporting works at your employer.