Questions to Ask President
Questions for a conversation with the president of your company, university or nonprofit, covering what they are spending time on, what the organization is deliberately not doing, how bad news reaches them, and what they would change.
The questions
Open any question for the note
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.
What are we deliberately not doing?
Why ask it
Every real strategy has abandoned options, and naming them is harder than naming goals. A blank answer usually means the organization is trying to do everything, which employees experience as constant reprioritization.
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.
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 look at to know how we are doing, and how often?
Why ask it
Weekly figures produce a different management style than quarterly board packs. This also reveals whether they see anything directly, such as customer calls or classroom visits, or only summaries prepared by others.
How do you want bad news to reach you?
Why ask it
Most senior leaders say they want it early and few describe a route. Listen for something concrete: a named person, a standing item, a threshold. Without one, bad news travels slowly no matter what is said publicly.
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.
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.
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.
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 has changed your mind recently?
Why ask it
Ask for the thing itself, not the process. Leaders who can point to a specific reversal and what caused it tend to run organizations where evidence beats seniority, and that is hard to fake in an answer.
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 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.
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.
What are we likely to look back on as the mistake of this period?
Why ask it
This is the same question as asking about risk, but framed in hindsight, which people answer more honestly. It often produces the concern they have not yet been willing to raise with the board.
What would you want to be remembered for here?
Why ask it
Best kept for the end, and better asked of a president several years into the role than a new one. The answer tends to explain which projects get their personal attention and which quietly do not.
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.
Talking with the Head of Your Organization
Practical guidance for the conversation itself
Match the Question to the Setting
At an all-hands or town hall
Ask something the whole room benefits from hearing answered: what the organization is not doing, where it is slowest, how bad news should travel. Save anything that concerns only your team for later.
In a scheduled one to one
You will realistically get through two or three questions. Choose ones that need candor rather than information, since the informational answers are usually available elsewhere.
In a chance encounter
One question, brief, and no request attached. What they are spending time on, or what changed their mind recently, both work in ninety seconds and are easy to pick up on later.
As a candidate or new joiner
The questions about what is written down nowhere, and about the case against the strategy, tell you most about what you are joining. Asking what they would change also lets you gauge how mistakes are handled.
How to Ask
- Ask for a specific instance rather than a policy. "When did that last happen?" turns a statement of values into something checkable.
- Do not use the slot to report your own achievements. If you want credit, send the update separately and use the conversation for the questions.
- Take the answer at face value in the moment and check it later against what people two levels down say. Contradictions are information, not grounds for confrontation.
- Watch for the question they turn toward something more comfortable. What they steer away from is often the more interesting subject.
- Follow up in writing on anything they offered, whether an introduction, a document or a decision. Presidents make offers in conversation and forget them by the afternoon.
Common Mistakes
Asking what could be answered by anyone
Questions about process, headcount or last quarter's numbers waste rare access. Use the time for judgment, reasoning and history that only they hold.
Raising a grievance without a request
A complaint delivered to the president usually returns to your manager. If you have a real problem, bring the specific decision you want made rather than the frustration.
Treating agreement as a commitment
Senior leaders sound supportive in conversation and are constrained afterwards. Ask what would have to be true for it to happen, and who else would need to agree.
Flattery in the question itself
Loading a question with praise makes the honest answer harder to give. Ask plainly, and let the substance carry the respect.