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, and whether stated values match daily practice. For employees who want substance rather than reassurance.
The questions
Open any question for the note
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.
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.