Questions to Ask an Executive Director
These are questions to ask an executive director of a nonprofit when you get time alone with one: as a board member before a meeting, a candidate in a final interview, a new hire in a first one-on-one, a funder on a site visit or a volunteer offered half an hour. The first group suits anyone and covers priorities, the money and what worries them; the groups after it are sorted by who is asking, because a board chair and a weekend volunteer are owed different answers. Start with your own group and borrow from the first.
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The questions
Each question, and why to ask it
Anyone
What are your top priorities for the coming year, and what did you set aside to make room for them?
Why ask it
A director who names two or three has chosen; a list of eight means the choosing has not happened yet. The second half is the test, because a priority that displaced nothing is only a hope. Where there is a written strategic plan, it is fair to ask which of these came out of it.
What keeps you up at night?
Why ask it
The phrase is worn, but most directors still answer it straight because so few people ask them. Cash, a key person leaving and a contract up for renewal are the usual answers. Whichever one they name, ask what would have to happen for it to stop being the worry.
What is working best right now, and how do you know?
Why ask it
Directors are asked for good news all day, so the second half is the real question. Listen for something that could be checked: a waiting list that shrank, families who came back, a partner who asked for more. One story about one person is a start, and the fuller answer is what happened across everyone served last year.
Where does the money come from, and which source would hurt most to lose?
Why ask it
Ask for rough shares: grants, government contracts, individual donors, fees, events. The source they would miss most is not always the largest, since money that can be spent on anything is worth more than its size. The date that source next comes up for renewal is the other thing to leave the room knowing.
What do you need from someone in my position that you are not getting?
Why ask it
Say what your position is first, because the answer for a board member is nothing like the answer for a volunteer. Directors spend their days being asked what they can do for other people and seldom hear this one. If they name something, tell them before you leave whether you can do it, and by when.
What drew you to this work, and what has kept you in it?
Why ask it
It costs the director nothing to answer and shows what they care about before any numbers come out. Someone who came up through the programs tells a different story from someone hired in to steady the finances, and that difference colors the rest of what you hear.
How would you explain what this organization does to someone who has never heard of it?
Why ask it
You want the plain version, without the mission statement: who walks in, what happens to them and what is different when they leave. A director who can do that in three sentences has usually settled what the organization is for. When the answer wanders across six programs, the follow-up is which one they would keep if they could keep only one.
Which part of the job takes most of your week, and is it the part that should?
Why ask it
Fundraising, staff problems, the board and compliance paperwork compete for the same hours, and the split is seldom the one the director would choose. The gap between the two halves of the answer is where they need help. A board member can act on it; anyone else can at least avoid adding to the wrong pile.
What did you inherit when you took this job, and what have you changed since?
Why ask it
A director in the first couple of years is often still working through someone else's budget, staff and promises, and what they chose to keep tells you as much as what they changed. With a founder, turn it around and ask what they would set up differently if they were starting today.
What is the hardest decision on your desk at the moment?
Why ask it
It brings up the live problem instead of last year's: a program that no longer pays for itself, a hire they cannot afford, a lease. Hold back any solution unless they ask for one. Asking who else is helping them think it through is more use, and the answer tells you how alone they are with it.
What do the people you serve tell you that is hard to hear?
Why ask it
This checks whether criticism travels from the front desk to the director's office at all. A specific complaint, such as opening hours that do not suit people who work or a form that takes too long, means someone is listening. A blank is worth one follow-up: how would a client raise a concern, and who would read it?
If the next three years go the way you hope, what will be different for the people you serve?
Why ask it
Growth plans tend to be described in budgets and buildings. This asks for the change on the ground, which is harder to answer and more revealing. Ask next what is most likely to get in the way, and listen for whether it is money, people or something outside their control.
Board members
What do you wish the board asked you about more, and what do you wish we would leave to you?
Why ask it
Two lists come back: the big questions that never reach the agenda, and the details the board keeps reaching into. Take both to the chair as themes, not as quotes. If the second list is long, the board may be managing where it should be governing.
How many months could we keep the doors open on what is in the bank today, and what would you cut first?
Why ask it
The director should know the first number without looking it up, or be able to say who does. The second half matters as much, because a director who has already thought through the order of cuts will not be deciding it in a panic. What counts as a healthy reserve depends on the kind of organization, so ask what target they are working toward and why.
Which line in this year's budget are you least sure of?
Why ask it
Every budget holds at least one hopeful number, often a grant not yet awarded or an event expected to beat last year. Naming it lets the board watch that line each month instead of finding out at year end, and settle in advance what happens if it comes in at half.
When something goes wrong, how soon do you tell the board, and who do you call first?
Why ask it
You are agreeing a rule before it is needed. Many directors wait until they have a fix, which means the board hears late and has no chance to help. Settle together what counts as news for the chair the same day: a lost grant, a staff complaint, a safety incident, a letter from a regulator.
When was your own performance last reviewed, and what would make the next review useful to you?
Why ask it
On many boards the review slips for years because nobody owns it. Asking the director what they want from it, such as clear goals, frank feedback or a conversation about pay, turns a chore into something they will prepare for. If there has been no review lately, raise it with the chair this month.
If you were suddenly out for three months, who would run payroll, approve spending and talk to the funders?
Why ask it
This is the emergency version of succession, and it is less awkward to raise than retirement. You are listening for names, and for passwords and bank authority that sit with more than one person. If the answer is that nobody could step in, a short written plan is a fair thing for the board to ask for.
How are you holding up, and when did you last take a full week away?
Why ask it
Ask it one to one, never in a meeting, and leave a pause after it. A director who cannot remember the last week off, or who answered email all through it, is telling you the organization leans too hard on one person. The board can fix part of that by approving cover and insisting the leave is taken.
How is the staff doing, and who are you most worried about losing?
Why ask it
A board sees the staff mostly through the director, so this is your main view of morale. Listen for particular people and reasons, such as pay that has fallen behind or someone covering two jobs. Do not approach that staff member afterwards; ask the director what would keep them and whether it needs a board decision.
How much of your time goes to raising money, and which part of it could board members take on?
Why ask it
Directors often want introductions, thank-you calls or company at a donor meeting, and feel unable to ask a volunteer board for them. Get a specific task with a date instead of a general wish for more help with fundraising. Then do it, because a board member who offers and disappears is worse than one who never offered.
What makes a board member useful to you between meetings?
Why ask it
The answer is usually modest: someone who reads the packet, replies within a day and can be called with a half-formed idea. It also tells you, politely, what the unhelpful ones do. Pick one habit from that list and start before the next meeting.
Job candidates
What would you want the person in this role to have done a year from now?
Why ask it
In a small organization the answer is often two jobs in one, say running a program and writing its grant reports. Hear which half the director would judge you on. If the list could not be done by one person in a year, say so now, kindly, and watch how that lands.
What is on your own desk today that this role would take over?
Why ask it
In a small nonprofit the director has often been doing part of the job being hired for. Whatever they name is what they know best and will watch most closely in your first months. Ask what handing it over would look like, since some directors find it hard to let go of work they built.
How is this position paid for, and how far ahead is that money secure?
Why ask it
A role may sit on general funds, on one grant or on a mix, and the director is the person who knows. An end date is no reason to walk away, but you should hear it now and not in month ten. Ask what happened to the last person whose grant ran out.
How much would I work with you directly, and what would a normal week of that look like?
Why ask it
In an organization with few layers you may deal with the director daily even when you report to someone else. Ask for the detail: a standing meeting, messages as things come up, or contact only when something has gone wrong. If you are told the door is always open, ask how often people on the staff walk through it.
How would the people who report to you describe working for you?
Why ask it
This is the management-style question with the self-portrait taken out. Listen for a criticism they have plainly heard before, such as being slow to decide or hard to reach in grant season, because a director who can repeat one has been listening. When you meet staff later in the process, their version is the one to weigh.
How would you describe your relationship with the board, and would I ever present to them?
Why ask it
A director who describes the board as a help has room to make decisions and keep promises to staff. One who describes a struggle may be spending energy upward that you would feel as delay. For a role that does present to the board, find out how it went the last time a staff member did.
Who has left in the last two years, and what did you change because of it?
Why ask it
Turnover alone tells you little, since people leave small organizations for pay a nonprofit cannot always match. The second half is the test: a departure that led to a lighter workload, a raised pay band or a different manager shows a director who learns from it. Where nothing changed, what those people said on their way out is the next thing to find out.
The last time money was tight, what did you protect and what did you cut?
Why ask it
Past choices are a better guide than a promise about the future. Listen for where staff pay, hours and training sat in the order, and how early people were told. A director who has never had a tight year can still say what the plan would be.
What do you turn down so that the staff are not stretched too thin?
Why ask it
Nonprofits are offered more good work than they can do, and every yes lands on someone's week. A director who can name a grant not applied for or a partnership declined is managing workload on purpose. With no example to give, how the last new project was staffed answers the same question.
What do you still want to get done here before you would think about moving on?
Why ask it
You would be joining a leader as much as an organization, and a new director can bring new priorities and a new team. Hardly anyone announces a departure in an interview, so this asks about unfinished work instead, and a list that runs several years out is the reassuring answer. Save it for a final round.
New staff
What do you wish every new hire understood about this place in their first month?
Why ask it
You will get the thing earlier newcomers got wrong: a funder relationship handled carelessly, a shortcut that upset a partner, a piece of history nobody explained. Write it down. It is the director's short list of what matters, and it rarely matches the handbook.
Which of the things you are working on this year does my job touch?
Why ask it
New staff tend to learn their tasks long before they learn why those tasks matter this year. The director can tie your work to a grant deliverable, a board goal or a program being rebuilt, and that tells you which requests to drop everything for.
Which three people, inside or outside the organization, should I meet early?
Why ask it
The outside names, such as a program officer, a partner agency or a long-time donor, show you who the organization depends on. Ask whether the director would make the introduction, since a note from them opens the door faster than one from you.
What should I know about the history before I suggest changing anything?
Why ask it
Most odd-looking arrangements have a reason: a grant condition, a past crisis, a promise made to a community group. The director can save you from proposing something that was tried and went badly.
How do you want to hear bad news from me: at once, in writing, or with a fix attached?
Why ask it
Each director has a preference and few state it until someone gets it wrong. Some want a message the minute a funder is unhappy, others a short written note with options once you have the facts. An example of bad news that reached them the right way will be clearer than any rule.
Which decisions can I make without checking with anyone, and which should always come to you?
Why ask it
In a small organization the lines are often unwritten, and the ones worth pinning down are spending above a set amount, anything said to the press, and commitments to funders or partners. Hearing a limit now is easier than learning it by crossing it.
When I notice a problem outside my own job, who do you want me to tell?
Why ask it
New people see things the long-serving staff have stopped noticing, and that only helps if there is somewhere to take it. Some directors want it brought straight to them and others want it to go through your manager. Ask too how a concern about safety or money should be raised, since that often has its own route and it differs between organizations.
What would you like me to have learned by the end of my third month, apart from the job itself?
Why ask it
The director's answer is usually about the organization: who the funders are, how the budget year runs, what the board cares about. It gives you a reading list and a set of meetings to sit in on. Bring it back at the three-month mark and ask how you did.
Funders
If this grant came with no restrictions, what would you spend it on?
Why ask it
The answer shows the needs no project budget has room for: a finance hire, a database that works, a raise for the people doing the frontline work. Ask it only if you are willing to hear the answer and, at least sometimes, to fund it. A director who says they would spend it exactly as proposed may not yet believe the question is safe.
What does this program cost to run once rent, finance, supervision and your own time are counted?
Why ask it
Project budgets are often trimmed to what the applicant thinks a funder will pay, with the shortfall covered from somewhere else. Asking for the full figure invites the director to say what that somewhere else is. Where your grant covers less than the true cost, someone else is paying the difference, and you should know who and for how long.
How many staff hours does our reporting take, and which parts of it are of no use to you?
Why ask it
If the report wants numbers the organization would never otherwise collect, someone is being paid out of general funds to produce them. Take what you hear back to whoever designs your forms.
What is not going the way the proposal said it would?
Why ask it
Something always differs from the plan, and a director who trusts you will say what. Make it easier by saying first that a change of plan does not put the grant at risk, if that is true. Hearing only good news on every visit means the relationship is not yet one where problems get mentioned.
What happens to this work, and to the people hired for it, when our funding ends?
Why ask it
Ask early in the grant, not in its last quarter. A realistic answer names another funder being approached, a plan to shrink the program or a plain statement that it would close. Whatever you intend about renewal, give as much notice as you can, because notice is what lets the director plan.
How much of next year's budget is already committed, and how much still has to be raised?
Why ask it
This is the cash picture a year out, and it shows how much of the director's time will go to chasing money instead of running programs. Ask which months are tightest. A payment made early in their year, or a pledge that runs over several years, can matter more to them than the size of the check.
If demand doubled next year, what would give way first?
Why ask it
The reply shows where the organization is thinnest: space, trained staff, a manager's attention, cash to pay bills before a reimbursement arrives. It is a good question to ask before offering money to expand. Growth that is paid for without that weak point fixed tends to strain the program you liked in the first place.
Apart from money, what could we do that would help?
Why ask it
A funder can often give an introduction to another funder, a letter of support, a meeting room or a longer timeline. Offer two or three examples so the director does not have to guess what is on the table. Ask it last, once the money conversation is done, so it is not heard as a substitute.
Volunteers
Where does volunteer time make the biggest difference to what the staff can get done?
Why ask it
The useful jobs are not always the visible ones: data entry, driving or a regular reception shift may free more staff hours than a big one-day event. If the answer surprises you, ask whether that is where the next opening is.
What should I understand about the people you serve before my first shift?
Why ask it
Directors have watched new volunteers arrive with assumptions, about why people need the service or how grateful they will be, and can correct them in two minutes. Listen for the practical parts too: what not to ask a client, which words the staff avoid, when to step back and fetch a staff member.
What do volunteers do, meaning well, that makes more work for the staff?
Why ask it
Canceling late, reorganizing a system nobody asked to have reorganized and making promises to clients are the common ones. A director will only tell you if you ask in a way that shows you can take it. Whatever they list, treat it as the house rules.
What should I do if someone I am helping tells me something that worries me?
Why ask it
Every organization that works with people needs an answer to this, and the rules on reporting and confidentiality vary by place and by the kind of work. Ask who you tell, how quickly, and what you should and should not say to the person in the moment. If the director has no clear answer, ask who does before your next shift.
What may I say about the organization in public, and what should I leave to you?
Why ask it
Volunteers post photos, talk to neighbors and are sometimes asked questions by a reporter or a donor. Most directors are glad of the word of mouth and have two or three firm limits: clients' faces and names, funding news, anything political. Get the limits one at a time, since 'use your judgment' will not help when a reporter rings.
Is there a skill you need and cannot afford to hire?
Why ask it
Bookkeeping, design, translation, grant writing and fixing the printer all come up. Offer only what you would do reliably for months, because a half-finished website is a new problem for the director. If your skill is on the list, agree on a small first piece of work and a date.
What has made your longest-serving volunteers stay?
Why ask it
The reasons, such as a fixed shift, a staff member who thanks people or seeing the same families each week, tell you how the place treats its volunteers. They also show you what to look for in your own role. Being paired with one of those volunteers for your first few sessions is a fair thing to request.
How to get a straight conversation with an executive director
Practical guidance for the conversation itself
Getting ready for the conversation
Say who you are and why you are asking
An executive director hears questions about reserves from a board treasurer, a foundation and a curious neighbor, and owes each a different level of detail. Open by saying which seat you are in and what you plan to do with the answers. A director who knows the purpose can decide how candid to be, and most choose more candor than you would expect.
Read what is already published
The website, the latest annual report and any financial filing the organization has to make public will answer the basic questions about programs and income. What must be published, and where, depends on the country, so ask the organization or look up the regulator there. Arrive with questions that build on what you read, such as why one income line fell, and the director will treat you as someone worth a real answer.
Give notice of anything with a number in it
Few directors carry last year's fundraising cost or the exact reserve figure in their heads. Email those questions a few days ahead so the finance person can pull the figures, and keep the meeting for the questions that need a conversation. The exception is a board member checking whether the director knows the cash position: there, asking cold is the point.
Choose a few and decide the order
Half an hour is room for five or six questions with follow-ups. Take two from the group marked Anyone, the rest from your own, and put the one whose answer would change what you do next near the start. Leave the question about what they need from you until the end, when they know you well enough to answer it.
What changes with the seat you are in
Board members
You are one of the director's employers and also one of the few people they can lean on, and the same question lands differently depending on which of the two they hear. Ask the personal and the financial questions one to one or in a closed session, not across the table at a full meeting with staff present. On most boards one member acting alone cannot instruct the director, so say plainly when you are asking out of interest and when you are asking for the board.
Job candidates
An interview with the executive director is often the last round, and they are judging you while you judge them. Keep the first questions close to the role, then ask about funding and turnover once the conversation has warmed up. Questions about money are ordinary in this sector, and a director who resents them is giving you an answer of a kind.
New staff and volunteers
You are there to learn the place, not to audit it. Stay with the questions about history, limits and where you can be useful, and leave the budget alone unless the director brings it up. Thank them for the time, since a first one-on-one with the person at the top is not something every organization offers.
Funders
The director needs your money and knows it, which bends every answer toward what you seem to want to hear. Say what will not happen as a result of a frank answer, if you can promise that, and mean it. One visit where bad news was met calmly does more for the next conversation than any wording of the question.
What to listen for in the answers
Figures given without a pause
A director who can say roughly how many months of cash are in the bank, what share the biggest funder provides and how many posts are vacant is running the organization from the numbers. Rounding is fine. 'I would have to ask our bookkeeper' is fine once and a concern as the answer to everything.
Problems named before you find them
Every nonprofit has a weak spot, and the director knows where it is. One who brings it up unprompted, along with what they are doing about it, is safer to back than one whose account has no difficulties in it. Treat a spotless picture as a reason to ask one more question.
Who gets the credit and who gets the blame
Notice whether successes belong to named staff and whether failures belong to the previous director, the funders or the board. Some of that blame will be fair. A pattern in which nothing was ever the speaker's own doing tells you how a setback would be described to you later.
The same question put to someone else
Where you have the standing, ask one of your questions of a second person: the board chair, the finance lead, a program manager. You are not trying to catch the director out. Two accounts that match mean the picture is shared, and two that differ show where the organization has not yet talked to itself.
Ways this conversation goes wrong
Turning a coffee into an inspection
A volunteer or a new hire who works through a list of financial questions will get short answers and a wary director. Match the depth of the questions to the reason for the meeting. If you find you need the harder ones, say so and ask for a second conversation.
Advice dressed as a question
'Have you thought about a gala?' is a suggestion, and the director has heard it many times. If you have an idea, ask first what has been tried, then offer it once, along with what you would do to help make it happen.
Asking what they need and then vanishing
The question about what the director needs from you creates a small debt. If they name something, reply within a week with a yes, a no or a smaller version you can manage. Silence after that question teaches them not to answer it next time.
Passing on what was said in confidence
Directors say more in a one-to-one than they would in a report, about staff, about board members, about funders. Before you repeat any of it, ask whether you may. A board member with a real concern takes it to the chair, not to the staff or to another funder.