Leadership Questions to Ask Your Team
Leadership questions to ask your team, for a manager or team lead talking to the people who report to them. Most are questions to ask team members one at a time, and the Team group ends with a handful written for the whole room at a staff meeting. The 61 questions run from a weekly check-in through the work itself, growth, feedback on you and how the team operates, to what keeps someone here and what would make them look elsewhere. A manager after questions to ask employees to improve morale should start in the Team group, which asks what is wearing people down before it asks what would lift them. This is the leader's side of the table: questions to put to an executive team at an all-hands are a different list.
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The questions
Each question, and why to ask it
Check-in
What is in your way this week that I could clear?
Why ask it
Naming the week keeps the answer concrete. If you hear 'nothing' three times running, it may be that an earlier request went nowhere, so ask what they raised last month and what became of it.
What has gone well since we last talked?
Why ask it
Opening on a win is more than politeness: it shows what this person counts as progress, which may not be what you count. If every answer is a finished task and never something learned or a colleague helped, ask about those separately.
What do you see as your top priorities right now?
Why ask it
Let them list theirs before you say yours. Where the two lists differ, the gap is in how you explained the plan, and it is far cheaper to find it here than at the end of the quarter.
Is your workload sustainable for the next three months?
Why ask it
The time frame heads off the reflexive 'busy but fine'. A yes with a caveat is the useful answer. Watch for someone who is coping only by working evenings, and ask about that pattern directly instead of about hours in general.
What could I do differently that would make your job easier?
Why ask it
'How can I support you?' tends to get 'nothing, all fine'. Asking for a change in your own behavior gets real requests: reply faster, stop changing the brief, come to fewer of their meetings. Choose one, and say out loud that you will do it before you next meet.
What do you most want us to cover today?
Why ask it
Asked in the first minute, it gets their agenda on the table before yours crowds it out. Someone who never has an item may need the question a day ahead, or may have concluded the meeting is for your benefit.
Is there a decision sitting with me that you are blocked on?
Why ask it
You can be the bottleneck without anyone having told you: an approval unread, a hire unsigned, a 'let me think about it' from two weeks ago. Ask for the list and put a date on each item before the meeting ends, since 'I will get to it' is what built the backlog.
Is there anything going on outside work that I should know about? Only as much as you want to say.
Why ask it
The second sentence is what makes this askable. You are not owed the details, only a signal that some flexibility is needed. If they do share something serious, offer something specific, such as a later start or a lighter fortnight, and find out what your employer's leave policy allows before you promise more.
What should I have asked you today that I did not?
Why ask it
Save it for the last five minutes, where it often brings out the thing they came in carrying. Leave real time for it, because asked with your laptop half shut it gets a no. If something large arrives with two minutes left, book the follow-up before either of you stands up.
The work
What part of your work takes longer than it should?
Why ask it
You will hear about a slow laptop, a manual export, an approval that needs four signatures. People stop mentioning these once they have accepted them, so treat a shrug as a sign the annoyance has become permanent, not that it is absent.
Is there anything on your plate you think is not worth doing?
Why ask it
The person doing a pointless task tends to notice first and say nothing, because someone senior asked for it. Expect the answer to implicate a report you request yourself, and be ready either to explain who reads it or to stop it.
Which of our meetings would you drop if it were your call?
Why ask it
Almost everyone has an answer, and having asked makes the rest of the conversation more honest. If they name a meeting you run, find out what they would need from it instead before you defend it.
What tool, access or information are you missing to do this job properly?
Why ask it
Name the three categories and people find one: a software license, a login, a dataset another team is sitting on. Some of it you cannot get, so say on the spot which requests you will chase and which are a no.
How do you see your work connecting to the company's goals this year?
Why ask it
You are testing your own explanation here, not their commitment. A halting or generic answer means the goals arrived as slogans, so take one current project and trace it to a goal together. If you cannot make the connection either, that is a question to carry upward.
Which decisions do you wish you could make without checking with me?
Why ask it
The answer marks where your sign-off has become habit instead of a safeguard. Hand one over on the spot, with its limits stated: a spending ceiling, who needs to be told. Autonomy promised in general terms rarely arrives.
What work here are you proudest of?
Why ask it
The project they pick shows what they think their best work looks like: careful craft, speed, a rescue, teaching someone. Steer assignments toward it where you can. If the example is more than a year old, ask what has changed since.
What risk in our current work do you think I am underestimating?
Why ask it
The people doing the work see a slip weeks before the plan shows one. Framing it as your blind spot, not their worry, makes it safer to say. Ask what they would do about it and what it would cost, then either make room for the fix or explain why you are accepting the risk.
What are you hearing from customers, or from whoever uses our work, that I am not hearing?
Why ask it
Whoever is nearest the customer hears the complaint before it turns into a number on a report. On an internal team, swap in the departments that depend on you. Ask for the words the person actually used, since a summary smooths off the part you need.
What idea do you have that we have never given a fair try?
Why ask it
Plenty of people are carrying one: a different rota, a tool from their last job, a customer nobody is calling. Ask what the smallest test would look like and who would run it. If the idea was raised before and turned down, give the reason now, because a no with no reason is how ideas stop arriving.
Growth
What do you want to be doing more of, and less of, six months from now?
Why ask it
Six months is close enough to plan around, so the answer can shape how you hand out the next round of work. The 'less of' half is where you learn what they are quietly dreading. Do not promise it will go away, only that you now know.
What do you want to get better at this year, and what would you need from me?
Why ask it
Attaching the ask to you turns an aspiration into a plan: a project, an introduction, time protected in the week. If they cannot say what they need, offer two concrete options and let them choose.
Where would you like your career to go in the next few years, even if that is not on this team?
Why ask it
The last clause is the important part, because people hide ambitions that point away from their manager. Hearing that someone wants to manage, move into another function or stay exactly where they are changes which work you give them now. 'I like what I do' is a legitimate answer, not a lack of drive.
Which of your strengths are we not using?
Why ask it
Most roles draw on a slice of what a person can do. Expect a second language, an earlier career, a knack for writing or for calming an angry customer. You cannot always make room for it, though one project or one presentation can be enough to change how the job feels.
How do you think I judge whether you are doing a good job?
Why ask it
Here you find out whether your expectations ever landed. People often describe a standard stricter or vaguer than the one you hold: every ticket closed, never being wrong in front of a client. Correct it there and then, and note what you said so the review later in the year matches it.
What have you done lately that you wish someone had noticed?
Why ask it
This brings out the quiet work: a fix nobody asked for, a difficult customer calmed down, a new starter shown the ropes. How they tell it also shows the kind of recognition they want. Say it back where others can hear, unless they are someone who would hate that.
When did you last feel stretched by your work, in a good way?
Why ask it
A recent example means the job is still teaching them something. If they have to reach back a year or more, boredom may be setting in, and people volunteer that far less readily than overwork. Follow up with what kind of problem they would like next.
Who on the team, or outside it, would you like to learn from?
Why ask it
A name gives you something to arrange: a pairing, a shadowing day, a joint project. It costs almost nothing. You also learn whose judgment the team rates, which is not always the person with the senior title.
Feedback on you
What is one thing I should start doing, one I should stop, and one I should keep?
Why ask it
Three slots make criticism feel like filling in a form instead of passing a verdict. 'Stop' will be the thinnest of the three. If it comes back blank, ask again next month and do not push: people fill it in after they have seen what you did with 'start'.
What did the best manager you have had do that you would like me to do?
Why ask it
Useful in the first month with a new report, or a team you have just taken over, when they have little to say about you yet. The answer is usually a habit, such as shielding the team from last-minute requests or giving credit by name, and you can start it that week. The worst-manager version works too, once there is some trust.
When was the last time feedback from me was useful, and what made it useful?
Why ask it
If they cannot recall an instance, you are probably giving encouragement and calling it feedback. If they can, the details are your template: how soon after the event it came, whether it was written down, how specific it was.
How do you prefer to get feedback: in the moment, in writing, or saved for our one-on-one?
Why ask it
Preferences here run firmer than you might guess. One person wants the correction straight away, another hears nothing after being corrected in front of colleagues. Honor the channel they choose, and keep the content just as direct whichever it is.
What have I asked you to do that you disagreed with?
Why ask it
The wording takes it as given that there was a disagreement, which makes one easier to admit. Whatever they name, your first response decides whether you ever hear another, so acknowledge before you explain, and do not reargue the decision in the same breath.
What do you need from me that you have stopped asking for?
Why ask it
This is the one that brings back the abandoned request: equipment, a promotion conversation, cover for a recurring commitment. If something comes up, say plainly what you can and cannot do about it instead of promising to look into it.
Am I too involved in your work, not involved enough, or about right?
Why ask it
The right distance differs by person and by project, and it is easy to run one setting for everybody. Ask which piece of work they want you closer to and which they want you out of. Then stay out of that one, visibly.
When have I been unclear lately about what I wanted?
Why ask it
Rework after a vague brief tends to get pinned on whoever did the work, and this hands it back to you. Take the example without defending it, then ask which one sentence from you at the start would have saved the time.
What do you tend to find out later than you should?
Why ask it
Common answers: a change of priority, someone leaving, a decision taken in a room they were not in. You will not be able to share everything early. Say which kinds of news you have to hold back, and set a routine for passing on the rest.
Team
What is this team best at, and where do we let ourselves down?
Why ask it
Works in a team meeting if everyone writes an answer first and you read them out unattributed. A strength the whole room names is your culture. A weakness only one person names is either a blind spot or a private grievance, and a one-on-one will tell you which.
If you were leading this team, what is the first thing you would change?
Why ask it
Notice whether the change is to a process or to a person. A process answer you can often act on within the month, so pick it up and credit them when you announce it. An answer about a colleague may point to a friction nobody has told you about: ask for an example, and neither agree nor disagree on the spot.
How would you describe the mood on the team right now?
Why ask it
Asking about the team lets someone report low morale without owning it. Go after what sits behind the word they choose, since 'tired' after a launch is not the same as tired of a reorganization rumor. Do not ask who feels that way.
What is wearing people down at the moment that I could do something about?
Why ask it
Morale asked about in the abstract gets abstract answers, so this one points at causes and at you. Expect a deadline that keeps moving, a system that fails daily, or weeks of uncertain news. Sort what you hear into what you can change and what you can only explain, and tell them which is which.
Which recent change has been hardest on the team, and what was missing from how it was explained?
Why ask it
A new system, a restructure or a colleague who was never replaced can sit badly for months. The second half separates the change itself from the way people learned of it, and the telling is the part still open to repair. Go back and give the missing reasons, even late.
Think of a time when this team was at its best. What was different then?
Why ask it
A memory comes with details a wish list lacks: a smaller group, one clear deadline, a customer who wrote to say thank you. Some of it cannot be brought back. Pick the piece that can, such as fewer projects running at once, and say what you will try.
What would lift morale here that costs little or nothing?
Why ask it
The limit keeps the answers practical and stops the talk turning into a pay negotiation, which needs its own conversation. Listen for requests about predictability and respect: rotas published earlier, no meetings on Friday afternoon, thanks that names what was done. Do one within a fortnight, and do not swap it for a social event nobody asked for.
Who has helped you recently that I would not know about?
Why ask it
You get a picture of how the team runs day to day, which the org chart does not show. A name that comes up in several one-on-ones belongs to someone holding the team together, so check whether that person is getting any credit for it.
When did you last hold back an opinion in one of our meetings, and why?
Why ask it
'Do you feel safe speaking up?' gets a yes from exactly the people who do not. An instance comes with a reason: the decision already looked made, the last objection was brushed aside, someone senior had spoken first. Each of those has a different fix, and most of them are yours.
What is the conversation this team keeps not having?
Why ask it
Typical answers are a deadline everyone has privately written off, a colleague who is not pulling their weight, or a plan nobody believes in. Ask it in private first. If two or three people name the same subject, raise it with the group yourself so that nobody has to be the one who said it.
Which other team is hardest for us to work with, and what makes it hard?
Why ask it
Trouble across a boundary is often structural: targets that conflict, a handoff nobody owns, two priority lists. Your report cannot fix that alone, which makes it your job. Get one recent example you can take to the other manager without it sounding like a complaint about individuals.
What did we do well on the last project that we should make a habit?
Why ask it
Reviews drift toward what went wrong, so the things that worked stay accidental. Saying them aloud makes them repeatable: a one-page kickoff note, a short daily call during the crunch. Find out who started it and credit them by name.
What would surprise someone joining this team tomorrow?
Why ask it
A newcomer sees the unwritten rules at once, and this asks the people who have stopped seeing them to look again: nobody takes lunch, decisions get made in a side chat, cameras stay off. Some answers you will be proud of. For the rest, check whether you set the example.
What did we agree at the last staff meeting that has not happened yet?
Why ask it
Open with it and begin with your own actions, since yours are the ones people are watching. For anything still undone, either set a new date with a name against it or drop it out loud. A meeting whose decisions quietly evaporate teaches the room to stop bringing things.
Which recent decision would you like explained more fully?
Why ask it
Decisions often reach a team as one line in an email, with the reasoning left in the room where they were made. Give the reasons you know and the trade-off that was accepted. Where you do not know, say so and name the day you will come back with an answer.
Where did work get stuck between two of us this month?
Why ask it
Put to the group, this is about the handoff and not about either person. Have each side say what they expected to receive and when. The fix can be as small as a shared checklist or a named owner for the step in the middle, and you can agree it before the meeting ends.
What is coming in the next month that we are not ready for?
Why ask it
One person knows about the audit, another about the school holidays, a third that the system upgrade lands the same week. Only with everyone present do the clashes show up. Write the dates where all can see them and decide who is covering what.
What question about where the company is heading should I take upward for you?
Why ask it
Rumors fill the space where information should be, and a staff meeting is a good place to learn which ones are going round. You will not have every answer, and some you may not be free to give. Collect the questions, say when you will report back, and do it even if the answer is 'I was not told'.
What would make this meeting more useful to you?
Why ask it
Worth asking two or three times a year, with examples to get it going: a shorter agenda, updates sent in writing beforehand, a different day. Change one thing by the next meeting. If the honest answer is that it should be fortnightly, that is a result too.
Staying
What keeps you in this job?
Why ask it
A stay-interview question, and comfortable to ask long before anyone is thinking of leaving. Pay may be part of the answer, but listen for the rest: particular colleagues, flexible hours, a problem they find interesting. Once you know it, take care not to remove it by accident in the next reshuffle.
What would make you start looking at other jobs?
Why ask it
Direct, and best asked while the answer is still hypothetical. People tend to name one thing: a manager, a ceiling, a commute, a salary gap. That is a specific risk you can work on. Leave it alone during a round of job cuts, when it sounds like a loyalty test.
How has your energy for this job been over the past month?
Why ask it
Energy is easier to report than happiness and less loaded than the word burnout. A dip that follows one hard project is normal and lifts when it ends. A slow slide with nothing to point at is the one to act on, so ask what a good week used to look like.
When did you last take a proper break, and if it has been a while, what got in the way?
Why ask it
Look at the leave calendar before you ask so the conversation starts from facts. The reasons you hear tend to be no cover, a deadline that keeps moving, or a sense that you would disapprove, and a manager can do something about each. Leave entitlements differ by country and employer, so check your own policy before promising anything.
Does anything about your pay, title or level feel out of step with the work you do?
Why ask it
Uncomfortable to ask because the answer may be outside your control, but they are having this conversation with somebody, and better you than a recruiter. Promise no outcome. Explain how the review process works where you are, when the next one is, and what you will take to whoever decides.
Would you recommend this team to a friend, and what would you warn them about?
Why ask it
The warning is the real answer. A recommendation alone gets a polite yes, while the caveat, 'great people, but expect the deadlines to move', is a description of the team you could not get by asking for one.
Running the conversation
Practical guidance for the conversation itself
How to use the list
Two or three per one-on-one
The whole list in one sitting is an interrogation and produces short answers. Keep one recurring opener from Check-in, then rotate one from The work or Growth and one from Feedback on you.
Match the question to the relationship
Questions about disagreement, the mood on the team, pay and looking for other jobs need trust already in place. With a new report, or a team you have just taken over, spend the first weeks on Check-in and The work, ask what their best manager did, and come back to the rest.
Keep the group and private versions separate
Process, meetings, customers and new ideas can be discussed as a team, and most of the Team group works in a meeting if people write their answers before anyone speaks. Recognition, career plans, feedback about you, pay and anything personal belong in a one-on-one, where nobody is performing for colleagues.
One or two at a staff meeting
The Team group ends with six questions written to be asked of everyone at once. Good questions to ask your staff as a group are ones nobody loses face by answering in front of colleagues: handoffs, dates, decisions, habits. One or two per meeting is plenty, with the agreed-actions question as a standing opener.
When the aim is to improve morale
Asking does not raise morale; what you do with the answers does. Start with what is wearing people down, act on one thing where the team can see it, and say plainly what you cannot change. A survey or a social event offered in place of that reads as not having listened.
Give the Staying group its own conversation
Pay, energy, time off and what would make someone leave land badly in the last five minutes of a weekly catch-up. Book a separate slot once or twice a year, say beforehand what it is for, and keep it apart from the performance review, where people are busy defending their rating.
Getting past 'all good'
- 1Ask about a period, not in general. 'This week' and 'in the last three months' get real answers where 'usually' does not.
- 2Send the harder question in advance. Feedback about you, or a career direction, is better answered with a day to think.
- 3Assume the problem exists. 'What did I get wrong there?' is easier to answer than 'did I get anything wrong?'.
- 4Sit with the silence for a few seconds. Fill it yourself and you end up answering your own question.
- 5Do not defend yourself in the moment. Write it down, say thank you, and come back with what you plan to do.
Follow-through is the whole thing
- Track what each person raised and close the loop out loud: what you did, what you could not do, and why.
- Fix one small annoyance quickly. A license approved or a meeting deleted buys more candor than any statement about open doors.
- When the answer is no, say no. Requests that get no answer teach people to stop asking, and then a resignation comes as a surprise.
- Look across the team for repeats. Three people naming the same blocker is a systems problem you own, not three individual issues.
- Keep what you are told to yourself, your own manager included, unless it is something you are obliged to report. What that covers depends on your employer and where you work, so find out, and say up front which subjects you would have to pass on.
Common mistakes
Asking for feedback you are not ready to hear
Requesting criticism and then explaining why the criticism is mistaken is worse than not asking. If you are not in the mood for it that day, ask a different question.
Turning the one-on-one into a status meeting
If the whole slot goes on project updates, none of these questions fit. Get status in writing beforehand and keep this time for the things that only a conversation brings out.
Treating quiet as contentment
Someone who never raises anything may be content, or may have stopped expecting anything to change. With a reserved report, ask narrower questions, and ask more than once.
Collecting problems you never resolve
A list of blockers with no action makes the next conversation shorter. If capacity is the real constraint, say so plainly instead of gathering more requests you cannot meet.