Questions to Ask Your Leadership Team
Questions for the executive team at an all-hands, a town hall, or a small-group session, covering strategy, the tradeoffs behind it, how success will be measured, whether stated values match daily practice, and how the team itself decides and disagrees. For employees who want substance rather than reassurance, and for a new joiner or a candidate meeting the whole team.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
What is your vision for the company over the next three to five years?
Why ask it
A useful opener because it is easy to answer well and revealing when answered badly. Listen for whether the picture includes specific customers, products, and choices, or only adjectives about growth and being a leader in the space.
What are the biggest challenges facing the organisation right now?
Why ask it
How candid they are in front of a whole company tells you how much bad news is allowed to circulate here. A leader who names competition and the economy is avoiding the question; internal challenges are the ones with information in them.
Which numbers do you look at first when you want to know how we are doing?
Why ask it
Asking what they check, rather than how they define success, gets you the short list that actually drives decisions instead of the full scorecard. If every number named is a lagging financial one, nobody upstairs is watching the operational measures your team is being asked to move.
What are the key priorities for this quarter, and what did you decide not to do?
Why ask it
The second half is the real question, because a priority list with nothing dropped is not a plan. What was cut also tells you which teams are about to have a difficult few months.
How do you make a decision when two things you care about are in direct conflict?
Why ask it
Asking for the method rather than the outcome gets you something you can apply to your own decisions. Ask for a recent example, since the abstract answer is always that they balance both.
How do you balance short-term results against longer-term investment?
Why ask it
Reveals what happens in a bad quarter, which is when this tension is actually resolved. If they cannot name something long-term that survived pressure, the answer in practice is short-term.
What feedback do you hear most often from employees, and what have you changed because of it?
Why ask it
The change is the part that matters. Themes without a corresponding action means the survey is being read but not acted on, and that is worth knowing before you invest effort in the next one.
How do you see our industry changing, and what are we doing now to prepare?
Why ask it
Separates leaders who can describe a shift from leaders who have committed resources to it. Ask what we have started or stopped as a result, since a plan with no reallocation behind it is a forecast.
How does customer feedback reach you, and when did it last change a decision?
Why ask it
Every company claims to be customer-led, so the test is whether a specific instance comes to mind. If the answer is entirely about dashboards, ask when they last spoke to a customer directly.
What could someone in a role like mine do this quarter that would actually help?
Why ask it
Narrowing it to one quarter and one role makes it much harder to answer with ownership and passion. If nothing concrete comes back, the strategy has not been translated below the leadership layer yet, and you can stop waiting for a plan that has not been written.
What is your philosophy on workload and hours, and how does it show up in practice?
Why ask it
Stated policy and lived reality diverge here more than on almost any other topic. Ask what happens when a deadline and the policy conflict, because that is the only version of the answer that matters.
How does a new idea from outside the leadership team actually get funded?
Why ask it
Much better than asking whether the company values innovation. You want the mechanism, the person who says yes, and the last thing that made it through that route.
How do you make sure our stated values show up in day-to-day decisions?
Why ask it
Look for an example of a decision that cost the company something because of a value, since that is the only real evidence a value is operative. Without one, the values are a description of how people would like to be seen.
What is one thing you would change about the organisation if you could do it immediately?
Why ask it
Reveals what they think is broken and, by omission, what they consider untouchable. If the answer is entirely about other people's behaviour rather than structure or their own decisions, that is worth noting.
How are we investing in employee development, and what is the actual budget for it?
Why ask it
Development commitments are cheap to state and easy to check: a budget, a number of hours, a named programme. Ask who approves it, because a shared pool with no owner is usually spent elsewhere.
What would make you reconsider the current strategy?
Why ask it
A strategy with no conditions for change is a conviction rather than a plan. The answer also tells you which signals the leadership team is genuinely watching.
Where do you think we are ahead of our competitors, and where are we behind?
Why ask it
The behind half is the informative one, and how freely it is discussed in public says a lot about internal candour. Vague answers here often mean the comparison has not been done recently.
What advice would you give someone trying to build a career here?
Why ask it
The specifics reveal what leadership actually notices: visibility, particular functions, willingness to move. Compare it against the promotion criteria on paper, since the difference is where people get stuck.
How will we know in a year whether this plan worked?
Why ask it
Asks for a test with a date, which is harder to give than a goal. It also gives everyone in the room a shared way to check back without it becoming an argument.
What question do you wish employees would ask you more often?
Why ask it
A good closer that hands them the topic they came prepared for and rarely get asked about. Whatever they name is usually the thing they feel has been misunderstood.
How long has this group worked together, and who joined most recently?
Why ask it
A team formed six months ago behaves nothing like one that has been through a bad year together. The most recent arrival is also the person most likely to still see the organization clearly, which is worth knowing before you pick who to follow up with.
What is each of you accountable for that nobody else here is?
Why ask it
Asked around the table, this exposes overlaps and gaps quickly. Two people describing the same territory predicts turf friction; an area nobody claims predicts something being dropped quietly for months.
Which decisions come to this team, and which ones deliberately do not?
Why ask it
The second half is the useful half: it shows where authority genuinely sits lower down. If everything comes to this room, people below them are waiting a lot, and that shows up as slowness nobody can locate.
What does this team spend most of its meeting time on?
Why ask it
The answer is usually reporting rather than deciding, and hearing that said out loud tells you where the group's real bottleneck is. Leadership teams that mostly review status are not steering anything, whatever the agenda is titled.
When this group commits to something, who communicates it and how?
Why ask it
Decisions that arrive through five different voices arrive as five different decisions. Listen for whether one person owns the message or whether each leader relays their own version to their own organization.
How much of what you decide here reaches the front line as you intended?
Why ask it
Honest estimates from experienced leaders tend to be sobering, and the reasons they give, layers of translation, competing messages, no follow-through, tell you where communication actually breaks in this specific organization.
What was the last thing you could not agree on, and how did it get settled?
Why ask it
How disagreement resolves is the most informative fact about any leadership team. Listen for whether it went to whoever owns the area, to whoever argued longest, or to the most senior person in the room, because that pattern repeats everywhere.
Where are two of your areas pulling in different directions right now?
Why ask it
Every organization has live tensions, sales against delivery, growth against reliability, and they are managed rather than solved. A team that can name theirs openly is much less likely to be passing that conflict down to their staff unresolved.
What happens in this room when someone brings bad news early?
Why ask it
The question is not whether they say they want bad news, but what happened the last time. Watch whether anyone can point to an example of someone raising a problem early and being glad they did.
What did this team get wrong last year, and what changed because of it?
Why ask it
The second clause is the test. Plenty of teams can name a mistake; far fewer can point to a process, a hiring decision or a meeting that exists differently now as a consequence.
What decision are you currently putting off?
Why ask it
Deferral is the most common form of leadership-team failure and the least discussed. Even a partial answer tells you what the group finds too costly or too contentious to face, which is often the thing employees are waiting on.
What do you not talk about in this room?
Why ask it
Every group has subjects that are out of bounds by habit rather than by rule: a founder's pet project, an underperforming peer, a customer nobody wants to lose. Naming one is a strong sign of a team that can handle discomfort.
Which of you would tell me if I were getting an optimistic version of this company?
Why ask it
Useful when you are a candidate or a new joiner. Someone will usually be volunteered or volunteer themselves, and the reaction of the rest of the group to that offer is as informative as the answer.
What would you want employees to bring straight to you rather than to their manager?
Why ask it
This draws a practical line most organizations never state, and the answers differ by leader in ways worth noting. It also tells you whether they expect to be reachable or expect the hierarchy to be respected.
What question do you get asked most often that you still cannot answer well?
Why ask it
Placed at the end, this surfaces the unresolved thing sitting under everything else, often compensation, restructuring, or a strategy that has not been decided. Hearing it named plainly is more useful than another confident non-answer.
Engaging with a leadership team
Practical guidance for the conversation itself
Choosing the moment
Public forums reward answerable questions
At an all-hands, a leader will answer generously anything they can say to everyone. Save the questions that require a leader to name a weakness or a disagreement for a small-group session or a skip-level.
One sentence, no preamble
Long setups in front of a company read as a speech and get a procedural reply. Ask the question, then let them ask you for context if they want it.
Ask for the example, not the position
Nearly every question here has a stock answer available. Adding when did that last happen, or can you give a recent example, is what turns a stock answer into information.
Reference something real
Tying your question to a specific announcement, a customer, or a number that was published shows you have been paying attention and makes a vague reply harder to give.
Send a short note afterwards
Two or three lines with what you took from the answer. It is the difference between having asked a question and being remembered as the person who asked it.
What to listen for in the answer
- Whether a specific example appears, or only principles and adjectives
- Whether anything was given up: a project dropped, a budget moved, a customer turned down
- Whether the challenges named are internal or safely external, such as the market or competitors
- Whether the same theme is described differently by two different leaders
- Whether there is any condition under which they would change course
- Who they credit, and whether it is a function nobody in the room belongs to
Common pitfalls
A complaint in the shape of a question
Everyone present can tell, and the reply will be defensive and procedural. If you want something fixed, use the route that can fix it and ask leadership about the pattern instead of the incident.
Asking what has already been published
Numbers from the last results, a strategy stated in the previous all-hands, or a policy on the intranet. You usually get one question, so do not spend it on something you could have read.
Putting a leader on the spot about a named person
No honest answer is available in public, and the cost lands on you. Ask about the process or the incentive rather than the individual.
Asking a question you will not follow up
An answer nobody returns to teaches the room that these sessions are theatre. Note what was promised and ask about it next quarter, plainly and without an edge.