Questions to Ask the President of a Company
Questions for a skip-level, a town hall, or a short one-off conversation with a company president, aimed at priorities, risk, and how decisions actually get made rather than at what is already in the all-hands deck.
The questions
Open any question for the note
What are you spending most of your own time on this quarter?
Why ask it
Time is the one resource a president cannot delegate, so where it goes is the real strategy. If the answer is a list of everything, you are hearing the org chart rather than a priority.
What has changed about the plan since you last presented it to us?
Why ask it
The plan on the slide and the plan being executed drift apart quietly. Someone who can name what changed and why is running the plan; someone who repeats the slide is presenting it.
What is the company deliberately choosing not to do right now?
Why ask it
Strategy is mostly refusal. Leaders who cannot name a rejected option usually have not made one, which means the teams below them are quietly funding everything at once.
Which decision from the last year would you make differently now?
Why ask it
Asks for a specific reversal rather than a lesson. Watch whether the example is small and safe or one that cost the company something, because that tells you how honest post-mortems are here.
How do you find out when something is going badly?
Why ask it
Bad news travels slowly upwards. A useful answer names a mechanism: a metric they check themselves, a channel they read, a specific person who will say it plainly.
Where do you get information that does not come up through your leadership team?
Why ask it
Tests whether they have any unfiltered view of the company. Customer calls, support tickets, and standing skip-levels are answers; an open-door policy is not one.
What would count as a good year, and what would count as a bad one?
Why ask it
Forces a definition of failure, which public messaging almost always avoids. If a bad year cannot be described, nobody below can tell whether they are on track.
Which numbers do you actually look at every week?
Why ask it
Weekly numbers reveal what leadership steers by, as opposed to what appears in the annual review. If the list runs to ten items, none of them is a priority.
What is the biggest bet on the roadmap, and what happens if it does not work?
Why ask it
Puts a name on the one thing that has to land. Vagueness here often means the bet has no single owner, and a real answer includes what gets cut to pay for the failure.
What worries you that the rest of us are not worried about yet?
Why ask it
Invites an unpolished concern, and presidents usually have one. It is often a dependency, a key hire, or a contract renewal that has not been discussed publicly.
Where is a competitor genuinely better than us?
Why ask it
Competitive questions are easy to boast through, so this one only asks for the uncomfortable half. Leaders who can answer precisely are the ones tracking rivals at all.
How much of next year's growth do you expect from existing customers rather than new ones?
Why ask it
Those two paths need different companies behind them. The split tells you which teams are about to be resourced and which are about to be squeezed.
How do you decide when to stop funding something that is not working?
Why ask it
Stopping is the hardest discipline in any company. A real answer has a trigger, a threshold, or a date; regular review means projects here die of neglect instead.
What behaviour gets someone promoted here, and what quietly stalls a career?
Why ask it
The promotion half is often aspirational and the stalling half rarely is. What they name as career-limiting is the most accurate description of the culture you will get in one sentence.
What happens when your leadership team disagrees with you?
Why ask it
Reveals whether disagreement happens in the room or in the corridor afterwards. Push for a recent example, because the stated philosophy is always healthy.
What is the most useful piece of critical feedback you have had in this role?
Why ask it
Turns the conversation towards them without flattery. Someone who cannot recall recent critical feedback is probably not receiving any.
Which parts of the business do you only hear about when something breaks?
Why ask it
Every president has blind spots and most know roughly where they are. Naming them shows you where attention and budget are thin, which is often where the next problem starts.
How would you like us to bring you bad news?
Why ask it
A practical question with a practical answer you can use next week. Ambiguity is a warning sign: it usually means bad news has been punished here before.
What do you wish people asked you about more often?
Why ask it
Gives them room to raise the subject they think is misunderstood, which is often the thing the company explains worst. It also tends to get a longer and less rehearsed answer than anything else on this list.
If I want to be useful to you over the next six months, where should I put my effort?
Why ask it
Ends with an offer rather than a request, and gives you something specific to act on. An answer that stays generic suggests the priorities above you are not settled either.
Getting something out of five minutes with the president
Practical guidance for the conversation itself
Before the conversation
Read the last two public updates first
Earnings commentary, the last all-hands, or the most recent company letter. Asking something already answered there wastes the one question you get and signals that you have not been paying attention.
Pick two questions, not ten
You will realistically get one question and a follow-up. Choose one about direction and one about how decisions get made, and hold the rest in reserve.
Decide what you want to leave with
A clearer view of priorities, a decision you need unblocked, or visibility for your team are three different aims, and they need different questions. Vague admiration gets you nothing.
In the room
Ask one question and stop
Stacked questions get answered at the easiest part. Ask the single sentence, let the pause happen, and use your follow-up on whatever they skipped.
Follow the number, not the adjective
When an answer includes a metric, ask what it was last year. When it includes an adjective, ask for an example. That is where the interesting part of the answer lives.
Do not turn a question into a complaint
A grievance dressed as a question is obvious to everyone listening and gets a defensive answer. If you want a problem fixed, describe the problem plainly and ask who owns it.
Write down the answer, not your reaction
Note the actual words on priorities and thresholds. You will want them in three months when a decision contradicts them, and being able to quote a president accurately carries weight.
Afterwards
Send one short message
Three lines: what you took from the answer, what you are going to do about it, nothing else. Long thank-you notes go unread and requests attached to them go unanswered.
Do the thing you said you would
If they told you where effort would help, report back once you have done it. One completed loop is worth more than a dozen further questions.
What lands badly
Asking for information they cannot give
Anything touching unannounced results, acquisitions, or individual pay puts them in an awkward position and burns the exchange. If you want to know about layoffs, ask about hiring plans and headcount assumptions instead.
Asking a question designed to show off
Everyone in the room can tell the difference between curiosity and performance, including the president. The showy question also tends to get the shortest answer.
Accepting the first abstraction
Culture, focus, and alignment are not answers. One polite follow-up asking what that looks like in practice is where the conversation actually starts.