Questions to Ask Your Leaders
Questions for senior leaders you do not work with daily, in a skip-level, an office hour, or a few minutes after an all-hands. Aimed at what they are actually working on, what they are least sure about, and what gets rewarded here.
The questions
Open any question for the note
What are you personally spending most of your time on this quarter?
Why ask it
Their calendar is a better guide to real priorities than any strategy deck, and the answer often differs from the stated top priority. It also gives you a low-risk opening that does not require them to disclose anything sensitive.
What are you hearing from customers that has not made it into our plans yet?
Why ask it
Senior leaders see accounts and complaints that never reach individual teams. Asking what has not been acted on yet tends to produce something concrete, and occasionally something you could pick up.
Which of this year's goals are you least confident about?
Why ask it
Most leaders will answer this honestly if asked in a small setting, and the answer tells you where help is genuinely wanted. A claim that they are equally confident about all of them usually means the goals were never ranked.
What does the leadership team disagree about most?
Why ask it
Unresolved disagreement upstairs is the reason work downstairs keeps changing direction. Even a general answer explains a lot about why two departments are pulling against each other.
Which decision from the last year would you make differently now?
Why ask it
Asks for reflection without demanding an admission of failure, and how they answer says as much as what they say. A leader who cannot name one either is not looking back or is not being straight with you.
Where do you think we are strongest, and where do you think we are flattering ourselves?
Why ask it
The second half is what makes this worth asking, and pairing it with the first makes it answerable in public. Listen for whether the weakness they name is one anyone is actually addressing.
What information do you wish reached you faster from teams like mine?
Why ask it
Turns a vague desire to be visible into a specific request you can act on next week. It also reveals where reporting is being smoothed out on the way up, which is worth knowing.
What would you want escalated to you, and what would you rather we handled ourselves?
Why ask it
Removes the guesswork about when contacting a senior leader is welcome. Their examples are the useful part, because everyone claims to have an open door and few mean it without qualification.
What gets someone noticed here in a good way?
Why ask it
The honest answer is often about visibility, timing, or a particular kind of problem-solving rather than output. Compare it with the stated promotion criteria, since the gap between the two is where careers stall.
What behaviour do you see rewarded here that you wish were not?
Why ask it
Asks a leader to criticise the system they run, so expect either a considered answer or a deflection, and both tell you something. It is also the fastest way to learn what the culture actually selects for.
Who do you go to when you need the unvarnished version of something?
Why ask it
Names a real channel of influence that no organisation chart shows. It also tells you whether they have anyone who will contradict them, which is a fair indicator of how decisions get made.
What did you believe when you started this job that turned out to be wrong?
Why ask it
Gets past the polished version of a leadership story to something specific. If the answer is about how long things take or how hard it is to change behaviour, ask what they do differently now.
How do you decide when to keep funding something that has not worked yet?
Why ask it
This is one of the hardest judgements they make, and their answer reveals whether the organisation kills projects on evidence, on politics, or not at all. Useful before you propose anything new.
What is one thing my team could stop doing that nobody would miss?
Why ask it
Invites them to name work with no audience, which is more common than most teams believe. Even an inaccurate answer tells you what your team is known for at their level.
How will we know in twelve months whether this year's strategy worked?
Why ask it
A strategy with no failure condition is a set of intentions. Asking for the test forces specifics and gives you something to measure the year against without having to argue about it.
What part of the business worries you that most employees never think about?
Why ask it
Often produces something structural: a single large customer, a supplier, a regulatory change, a key dependency. It is the kind of context that changes how you read the next round of decisions.
What is the hardest part of your job that people do not see?
Why ask it
Asked with genuine curiosity, this tends to get a real answer rather than a polished one. It also builds the kind of goodwill that makes a later, more pointed question land better.
If you could remove one constraint we are living with, which would it be?
Why ask it
Directs the conversation at the limit rather than the complaint, and names something you may be able to work around now that you know about it. Constraints named here are frequently budget or headcount decisions made above them.
What is the case against the direction we have chosen?
Why ask it
Asks whether the strategy was stress-tested and whether the leader can articulate the other side. An inability to state the opposing case is a reasonable warning sign about how the decision was made.
What question do you wish people in my role would ask you?
Why ask it
A good closer, because it hands them the topic they came prepared to discuss and rarely get asked about. Whatever they name is worth following up on in writing afterwards.
Talking to senior leaders
Practical guidance for the conversation itself
How to ask
Match the question to the setting
An all-hands microphone is for questions a leader can answer generously in public. Questions about disagreement upstairs, rewarded behaviour, or the case against the strategy belong in a skip-level or a small room.
Ask one question, not a preamble with a question attached
Long setups in a public forum read as a speech and get a polite non-answer. State the question in one sentence and let them ask you for context if they want it.
Give them an easy exit
Adding as much as you can say about it, or if that is shareable, makes a candid partial answer possible instead of a flat deflection. You usually learn more from the qualified version than from nothing.
Follow up in writing the same day
Two or three lines thanking them and confirming what you took from it. This is what turns a conversation into being remembered, and it gives them a chance to correct anything you misread.
Bring something, not just questions
One observation from the front line, stated briefly, changes the exchange from an interview to a trade. Senior leaders are short of unfiltered ground-level detail and know it.
What goes wrong
A complaint dressed as a question
Everyone in the room can tell, including the leader, and the answer will be procedural. If you have a grievance, raise it as a grievance through a route that can act on it.
Asking something you could look up
Numbers already published, a strategy stated in the last all-hands, or a policy on the intranet. It uses up the one exchange you get and suggests you have not been paying attention.
Naming individuals in public
A question that requires a leader to criticise a named person or team in front of an audience will not be answered honestly and may cost you goodwill. Ask about the system instead.
Treating the answer as confidential when it is not, or public when it is
If you are unsure whether something said in a skip-level can be repeated, ask before you leave the room. Getting this wrong once ends your access to that channel.