Questions to Ask Executives at Your Company
Questions for an employee who has an executive's attention at an all-hands, an offsite, or a coffee: where your team's work sits in the plan, what constrains the company, how budget and decisions really get set, and what it takes to move up or across. Written for people who work there, not for candidates.
The questions
Open any question for the note
When you look at the plan for this year, where does my team's work fit into it?
Why ask it
You will learn whether your work is load-bearing, useful but optional, or invisible at their level. Hearing that an executive cannot place your team is uncomfortable and worth knowing early, because that is the work that disappears first when budgets tighten.
What do you hear about my team from other parts of the company?
Why ask it
Executives receive a version of your team assembled from complaints and escalations, and it is often years out of date. Getting it stated plainly is the only way to correct it, and the specific gripe they repeat is usually the one you can fix in a month.
What is the real constraint on us right now: money, people, customers, or attention?
Why ask it
Forcing a choice among four gets you a straighter answer than asking about challenges. It also tells you which arguments will work: pitching something that needs headcount when the constraint is management attention will fail no matter how good the case is.
How does budget get set for a team like mine, and what time of year is it actually decided?
Why ask it
Most people discover the planning calendar after missing it. Learning that next year's headcount is settled in October means a request made in January was never going to land, whatever the merits, and it tells you when your manager needs your case in hand.
How much of next year is already committed to existing customers versus new bets?
Why ask it
The ratio explains the tone of the whole company. Heavily committed capacity means most requests will be declined regardless of quality, and it also predicts whether ambitious internal proposals have any room to exist.
What is the fastest way to get a decision here when two teams disagree?
Why ask it
Every company has a real escalation path, and it is rarely written down. Getting the honest version, escalate to a named person, put it in a specific forum, get one executive to sponsor it, saves months of polite stalemate.
If a project of mine is going to be cancelled, when and how would I find out?
Why ask it
Asking before it happens is much easier than asking after. Good answers describe a checkpoint and an owner. If the honest answer is that people usually find out late or by rumor, you know to build your own early warning by asking your manager quarterly.
Which internal process do you wish someone would just fix?
Why ask it
Executives carry a list of small, tractable irritations they have no time to address, and adopting one is the cheapest way to become visibly useful. It also tells you what they consider fixable, which is a decent proxy for how much slack the organization has.
How do you find out whether something we shipped actually worked?
Why ask it
Answers ranging from a dashboard to a customer email to nothing tell you the maturity of the company's feedback loop. If nobody checks, the incentive is to keep launching, which explains a lot about why unfinished work gets abandoned rather than improved.
What is the company noticeably worse at now than it was two years ago?
Why ask it
Growth trades speed for coordination and companies rarely say so out loud. An executive who can name the loss is watching the organization honestly; one who insists everything is improving is either new or not looking.
Which roles are hardest to hire for, and what does that do to the plan?
Why ask it
Open positions that stay open for six months quietly reshape strategy, because the work gets absorbed by whoever is already there. This is also where you find out whether an internal move of yours would be welcomed or blocked.
If I wanted to move into a different part of the company, what actually happens?
Why ask it
Policy says one thing and practice says another. Listen for whether a manager can veto, whether there is a waiting period, and whether anyone has actually done it recently. If nobody can name a person who moved, the internal mobility policy is decorative.
What has someone at the level above mine typically done before they got there?
Why ask it
Asking what people did, rather than what the competencies say, produces concrete answers: ran a launch, fixed a failing project, took the unpopular assignment. That list is a plan; a rubric is not.
What do you wish people told you directly rather than through a survey?
Why ask it
It gives you permission and shows what kinds of message get through. It also reveals whether they know they are hard to reach. An executive who says the survey is fine as it is has probably not read the free-text answers.
What are we saying externally that you think we have not fully earned yet?
Why ask it
Marketing usually runs ahead of the product, and the gap is where support tickets and unhappy customers come from. An executive willing to name it is telling you which promises your team may be asked to make good on next.
What do new people misunderstand about how this place works?
Why ask it
The answer is a description of the unwritten rules: which meetings matter, whose sign-off is real, what gets decided in writing versus in hallways. Useful even years in, because most people learn these by breaking them.
Which customer conversation has changed your thinking most recently?
Why ask it
This tells you whether they are still hearing from customers directly and which segment they are listening to. If the last example is old or secondhand, decisions upstairs are being made on internal summaries, which is worth knowing when you present data.
If we had to stop a third of what we are doing, what would you protect?
Why ask it
A hypothetical cut gets you a ranking that no roadmap will state. Whatever they protect is the actual core of the company, and if your work is not near it, that is useful information about where to spend the next two years.
What have you stopped measuring, and why?
Why ask it
Retired metrics are more revealing than current ones. A number dropped because it stopped mattering shows judgment; a number dropped because it looked bad shows something else. Either way you learn which targets are still live.
What should we be worrying about that most people here are not?
Why ask it
Executives see the threat before the rest of the company does and often soften it in public forums. Asked directly and in private, many will name it, and it is the single most useful thing you can know when deciding what to work on next.
Talking to leadership where you work
Practical guidance for the conversation itself
Choosing the moment
Match the question to the forum
A recorded all-hands gets you the company position, no matter how good the question is. Sensitive topics belong in a small room or a hallway. Save the questions everyone needs answered for the public forum and the ones you personally need for a one-on-one.
Tell your manager first
If you plan to ask an executive something about your team's direction or resourcing, mention it to your manager beforehand. It costs nothing and prevents the version where they hear about it secondhand and read it as going around them.
Ask about the plan, then say what you can do about it
The follow-up is where the value is. Once you know the constraint, offering something concrete, a report you can produce, a task you can absorb, is how you become the person leadership remembers when a decision affects your area.
Prefer this year to five years
Long-horizon questions produce vision statements. Questions about this quarter's trade-offs produce information you can use, and executives are usually more candid about the near term because they are living in it.
What they usually cannot answer
- Anything about a specific person's performance, pay, or departure, including your own manager's.
- Pending layoffs or restructuring before it is announced. Asking in public forces a non-answer that then sounds like a denial.
- Unannounced financial results at a public company, and anything material during a quiet period.
- Acquisitions, funding, or partner deals under a signed agreement.
- Individual customer contract terms, which are commonly under confidentiality.
- Legal disputes in progress, where even a candid aside creates exposure for the company.
Common pitfalls
Turning a grievance into a question
A question that is really an accusation gets a defensive, generic answer and costs you the room's goodwill. If you want something changed, write the case out, name what you want decided, and hand it to whoever owns it.
Asking what you could have looked up
Read the last all-hands notes, the strategy memo, and the earnings summary if there is one. Executives notice the difference between someone building on what has been shared and someone who has not been paying attention.
Treating an offhand answer as a commitment
An executive thinking aloud in a hallway has not authorized anything. Before you tell your team that a plan changed, confirm in writing with the person who owns the decision, or you will have created a rumor with your name on it.
Only surfacing when you need something
If the only time leadership hears from you is when you want headcount or an exception, the request carries less weight. Send the occasional short, useful note with no ask attached and the relationship is there when you do need it.