Questions to Ask a President
Questions for a town hall, an all-hands, a student newspaper interview, or a board Q&A with the president of a company, college or university, association, or country. They ask about specific decisions rather than leadership in the abstract. The closing group is questions to ask a college president about enrollment, tuition and the faculty, with two for a job candidate who meets the president during an interview.
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The questions
Each question, and why to ask it
Which part of this job turned out to be nothing like you expected?
Why ask it
An opener that gets a real answer because it invites candour without cost. Most presidents name the volume of internal arbitration or how little of their week they control.
What did you inherit that you wouldn't have chosen?
Why ask it
Distinguishes the problems they created from the ones they were handed, which is information you cannot get from the annual report. Watch whether they blame a person or describe a constraint.
What's on your desk this month that most people here haven't heard about yet?
Why ask it
Asks for news rather than a summary, and the refusal is informative too: a president who cannot name anything is either not deciding much or does not trust the room.
What decision from this year do you expect to be judged on?
Why ask it
Forces a ranking, which prepared talking points never do. If the answer is a list of five priorities, you are being handed the communications plan rather than their own view.
Which commitment from when you took office is behind schedule?
Why ask it
Everyone in the role has one, so a claim that everything is on track is a claim not to be tracking. A specific delay with a specific reason is a good sign about internal reporting.
What are you not going to do, even though people keep asking for it?
Why ask it
Real strategy shows up as refusals. A president who can name the request they keep declining, and why, has actually made a choice rather than accumulated initiatives.
How do you usually hear about a problem before it becomes a crisis?
Why ask it
Listen for a mechanism, not a sentiment. "People know they can come to me" is not a mechanism, and it is the standard answer in organizations where bad news travels slowly.
What reaches you only after three other people have filtered it?
Why ask it
Tests whether they understand their own blind spot. Presidents who have thought about this can usually name the exact layer where candour dies.
Who tells you when you're wrong, and when did they last do it?
Why ask it
The date matters more than the name. If the example is months old or has to be searched for, the answer is that nobody currently does it.
Where do you disagree with your own senior team at the moment?
Why ask it
A president who says there is no daylight is either not consulting or not listening. Naming a live disagreement, without naming the loser, is a sign of a functioning cabinet.
Which budget line has grown fastest over the last three years, and why?
Why ask it
Where the money moves is the strategy, whatever the mission statement says. Read the published accounts first so you can ask about a figure they cannot recharacterize.
If you had to cut five percent this year, what would go?
Why ask it
The hypothetical version gets an honest answer where the direct question would not. What they name first is what they privately consider least defensible.
Who benefits least from the current strategy?
Why ask it
Every plan has a group it quietly deprioritizes. Whether the president can name that group, and whether they seem to have thought about it before, tells you a lot.
What would have to happen for you to conclude that your flagship program isn't working?
Why ask it
Asks for the exit condition in advance, which is when it is still cheap to say. No stated condition usually means the program will outlive its results.
What's the last thing you changed your mind about after someone pushed back?
Why ask it
Concrete and dated, so it cannot be answered with a general commitment to listening. A trivial example, such as a venue or a date, is itself the answer.
Which of your predecessor's decisions have you quietly kept?
Why ask it
New leaders advertise their changes and stay silent about their continuities. The continuities show what they judged sound, and often what is too costly to unwind.
What conversation are you currently putting off?
Why ask it
Almost always the real bottleneck: a funder, a division that needs closing, a colleague who is not working out. Expect a pause, and let it run rather than filling it.
What do you know now that would have changed your first hundred days?
Why ask it
Reflection with a specific object, so it resists the stock answer about moving faster. Useful for anyone who might take a similar role later.
What do you want your successor to inherit that you didn't?
Why ask it
Shifts the frame from legacy to handover, which is more concrete and harder to answer with slogans. Answers tend to name a reserve fund, a working process, or a settled dispute.
Which question do you get at every one of these, and what's the answer you don't usually give?
Why ask it
Best saved for last, when the guard is lowest. It sometimes gets nothing, and when it works it produces the only unrehearsed minute of the session.
What are you spending most of your own time on this quarter?
Why ask it
Where a president's hours actually go is a better guide to real priorities than any stated strategy. If the answer is mostly external work such as fundraising, the board and regulators, that tells you who is really running the inside.
What would you most want to be true about this place in three years?
Why ask it
Asking for one thing forces a choice among the four or five items in the strategy deck. A president who cannot narrow it down is describing ambitions rather than a plan.
Where are we strongest, and where are we thinnest?
Why ask it
The second half is the useful one, and presidents are often more candid about it than middle managers, who have reputations attached to the gaps. It also tells you where a contribution would be noticed.
Where do you think we are slowest, and what have you tried about it?
Why ask it
Naming a bottleneck is easy; the second half is where you learn whether anything was actually attempted. An answer with a failed attempt in it is more credible than a fluent diagnosis.
Which number do you check first in the morning?
Why ask it
The metric a leader watches personally shapes what the whole organization optimizes for, whether or not it appears in the goals. If it differs from the metric your team is measured on, that gap is worth understanding.
What do you wish people raised with you more often?
Why ask it
This is an invitation, and the answer tells you what will be welcomed rather than tolerated. It also frequently reveals that the president feels insulated, which is a common and rarely admitted problem at that level.
How do decisions get made when your leadership team disagrees?
Why ask it
Some presidents decide, some require consensus, some let disputes sit unresolved. The third is the one that stalls work several layers down, and you can usually tell which you have from how they describe a recent disagreement.
Who outside the organization do you take advice from?
Why ask it
Presidents with no outside counsel tend to hear only what their own team tells them. The answer also tells you whose thinking is likely to be shaping decisions you see from a distance.
Which decision from the last year would you make differently?
Why ask it
Willingness to name one, with detail, is the clearest available signal of how mistakes are treated in the organization. A president who says none is either newly appointed or setting the tone for everyone below them.
What is the strongest case against our current strategy?
Why ask it
You are asking them to argue against themselves, which is a fair test at this level. Note whether they can state the objection in a form its holders would recognize, or only a version convenient to dismiss.
How would you know if the culture here were getting worse?
Why ask it
Culture answers are usually the vaguest part of any leadership conversation. Asking for the warning signal forces something measurable: attrition in a particular group, who stops speaking in meetings, what exit interviews say.
What keeps you awake about the next twelve months?
Why ask it
This works better than asking about challenges, which invites a rehearsed list. What you want is the risk that is specific and near: a funding gap, a contract renewal, a key person about to leave. A general market observation is a way of not answering.
What should a new person understand in their first month that is written down nowhere?
Why ask it
The answer is usually about history: a failed project everyone still flinches at, a rivalry between two functions, a founder's rule nobody will break. It is the most practical thing a president can give a newcomer.
What could I do that would actually be useful to you?
Why ask it
The word actually matters, since the polite version of this question gets a polite answer. Presidents asked directly will sometimes name something small and specific, which is worth far more than a general offer to help.
What does the enrollment forecast for the next five years assume, and what happens if it is wrong?
Why ask it
At a tuition-dependent college, enrollment is the budget, so this sits behind most other answers you will get. A college president who can name the assumption, such as transfer numbers holding or a new program filling, has read the model and not only its summary.
When tuition goes up, who decides where the added money goes?
Why ask it
Students hear the size of an increase and rarely its destination. The reply shows whether there is a process with names in it, and it hands a student reporter the next person to call.
How would the faculty describe shared governance here, and would you agree with them?
Why ask it
Asking for the faculty's version first makes the handbook definition hard to fall back on. Any gap between their description and the president's is a fair guess at where the next campus dispute starts.
Which academic program would you keep even if it never paid for itself?
Why ask it
Colleges often carry programs that cost more than they bring in, and say so quietly. The one a president would protect anyway shows what they think the place is for.
What would you want the person in this role to have changed by the end of the first year?
Why ask it
One for a candidate: a dean, director or faculty finalist whose campus visit ends in the president's office. It turns the job description into a single priority, which you can then compare with what the search committee told you.
What do you need from this office that you are not getting now?
Why ask it
Also for a candidate, and the closest you will come to hearing why the post is open. Notice whether the gap is about information, speed or trust, since each of those is a different job.
Questioning Someone Who Does This Every Week
Practical guidance for the conversation itself
Preparation That Changes the Answer
Read the published numbers first
The annual report, the budget, the strategic plan, the last three press releases. A question that cites a specific figure cannot be answered with a general aspiration, which is the whole difficulty of interviewing someone at this level.
Ask about a decision, not a philosophy
"What is your leadership style" has a pre-written answer. "Walk me through how you decided to close the branch" does not, and it produces the same information with evidence attached.
Ask for a number, a date, or a name
Requesting one concrete detail turns a smooth answer into a checkable one. If the detail never arrives after two attempts, that is your finding.
Spend your one question well
In a town hall you may get a single turn. Pick the question only you are placed to ask, and do not use it on something the last three questioners already circled.
Where These Conversations Go Wrong
Accepting the bridge
Trained speakers acknowledge your question and pivot to their message. The repair is one sentence: "That's helpful, but the part I asked about was the timeline." Said once, politely, it usually works.
Making a speech
Staff and members often use their turn to register a grievance. It feels satisfying and it gets a thank-you rather than an answer. If you want the answer, ask a question.
Asking something that cannot be answered in public
Personnel matters, live litigation, and unannounced deals will be declined regardless of how you phrase them, and the decline burns your turn. Ask about process instead: how such decisions get made, and who reviews them.
Softening the question into nothing
Adding "I'm sure there are good reasons, but" hands them the answer. State the question plainly. Politeness lives in your tone, not in hedges.
Sequences by Setting
Staff all-hands
- 1"Which commitment from last year is behind schedule?"
- 2"What reaches you only after three people have filtered it?"
- 3"What are you not going to do, even though people keep asking?"
Press or student newspaper interview
- 1"What decision this year do you expect to be judged on?"
- 2"Which budget line grew fastest, and why?"
- 3"Who benefits least from the current strategy?"
- 4"What would have to happen for you to call the flagship program a failure?"
Board or governance review
- 1"Where do you disagree with your senior team right now?"
- 2"Who tells you when you're wrong, and when did they last do it?"
- 3"What conversation are you putting off?"
- 4"What do you want your successor to inherit that you didn't?"
Job interview with a college president
- 1"What would you want the person in this role to have changed by the end of the first year?"
- 2"What do you need from this office that you are not getting now?"
- 3"How would the faculty describe shared governance here, and would you agree with them?"