Leadership Questions to Ask Your Team
Twenty questions for a manager to bring to one-on-ones, covering what is blocking someone this week, work that is not worth doing, workload over the next few months, what they want to get better at, feedback on you, and what would make them start looking elsewhere.
The questions
Open any question for the note
What is in your way this week that I could clear?
Why ask it
Naming the week keeps the answer concrete and answerable. If you get 'nothing' three times in a row, the problem is usually that a previous request went nowhere, so ask what they raised last month and what happened to it.
Where are you waiting on someone else, and how long has it been?
Why ask it
Waiting time is invisible in most status reports and it is often the largest part of a delay. The duration is what makes it actionable: a two-day wait is a nudge, a three-week wait is yours to escalate.
What part of your work takes longer than it should?
Why ask it
You will hear about a slow environment, a manual export, an approval chain. People stop mentioning these once they have accepted them, so treat a shrug as a sign the annoyance has become permanent rather than absent.
What did you spend real time on last week that I probably do not know about?
Why ask it
Surfaces the invisible load: onboarding someone, fixing another team's problem, interviews, incident cover. Managers routinely rate people against a workload they can only half see, and this is how you correct that before review season.
Which of our meetings would you drop if it were your call?
Why ask it
Almost everyone has an answer, and the fact you asked makes the rest of the conversation more honest. If they name your own meeting, you have learned something worth more than the meeting.
Is there anything on your plate you think is not worth doing?
Why ask it
People notice pointless work long before managers do, and usually keep quiet because someone senior asked for it. Expect the answer to implicate a report you request, and be ready to either explain who reads it or stop it.
Is your workload sustainable for the next three months?
Why ask it
The time frame stops the reflexive 'busy but fine'. A yes with a caveat is the useful answer. Watch for someone who is coping only because they are working evenings, and ask directly about that pattern rather than about hours in general.
What do you want to be doing more of, and less of, six months from now?
Why ask it
More concrete than asking about career goals, and it gives you something you can act on when you next allocate work. The 'less of' half is where you learn what they are quietly dreading.
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 rather than leaving it open.
What do you think the bar is for your work here? Tell me how you believe it is judged.
Why ask it
You find out whether your expectations ever actually landed. Hearing a version that is stricter or vaguer than the real one is common, and correcting it is one of the highest-value things you can do in a one-to-one.
What have you done lately that you wish someone had noticed?
Why ask it
Easier to answer than asking how they like to be recognized, and it tends to produce the invisible work: a quiet fix, a difficult conversation handled well. Then say it back to them in front of other people, not just here.
Who has helped you recently that I would not know about?
Why ask it
Builds a picture of how the team actually functions rather than how the org chart says it does. The names that come up repeatedly across several one-to-ones are the people holding the team together, and they are usually under-recognized.
When was the last time feedback from me was useful, and what made it useful?
Why ask it
Sharper than asking whether your feedback is helpful. If they cannot recall an instance, you are probably giving encouragement rather than feedback, and the specifics in their example tell you what format to repeat.
What have I asked you to do that you disagreed with?
Why ask it
Assumes the disagreement exists, which makes it easier to admit. Whatever they name, your first response decides whether you ever hear another one, so acknowledge before you explain, and do not relitigate the decision in the same breath.
What do you need from me that you have stopped asking for?
Why ask it
This is the question that surfaces 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 rather than promising to look into it.
Is there a decision sitting with me that you are blocked on?
Why ask it
Managers are a common bottleneck and rarely told. Ask for the list and put a date on each item in the meeting, since 'I will get to it' is what created the backlog in the first place.
Is anything going on in the team that I am probably the last to hear about?
Why ask it
Phrased to admit you are outside things, which makes it answerable without anyone feeling like an informant. Expect frictions between colleagues or a rumor from elsewhere in the organization, and do not press for names.
If it were your call, what would you change about how we work?
Why ask it
Look for whether the suggestion is about process or about people, since the second usually means there is a conflict you have not been told about. Pick one suggestion, implement it, and credit them when you announce it.
What would make you start looking at other jobs?
Why ask it
Direct, and better asked while the answer is hypothetical. People generally name one thing: a manager, a ceiling, a commute, a salary gap. That gives you a specific risk to work on instead of a resignation to react to.
Is there anything happening outside work I should be aware of? Only what you want to tell me.
Why ask it
The opt-out clause is what makes this askable. You are not entitled to the details, only to know if flexibility is needed. If they do share something serious, state what you can offer, in specifics, rather than saying to let you know if they need anything.
Running the conversation
Practical guidance for the conversation itself
How to use the list
Two or three per one-to-one
Twenty questions in one sitting is an interrogation and produces short answers. Keep one recurring opener about blockers, then rotate one from the development section and one about how you are doing.
Match the question to the relationship
Questions about disagreement, team gossip and looking for other jobs need trust already in place. With a new report, spend the first weeks on blockers, workload and expectations, and come back to the rest.
Keep the group and private versions separate
Process, meetings and workload can be discussed as a team. Recognition, career plans, feedback about you and anything personal belong in a one-to-one, where nobody is performing for colleagues.
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. Filling it yourself is how managers accidentally answer their own question.
- 5Never react defensively 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 licence approved or a meeting deleted buys more candor than any statement about open doors.
- When the answer is no, say no. Unanswered requests teach people to stop asking, which is what produces the manager who is surprised by a resignation.
- Look across the team for repeats. Three people naming the same blocker is a systems problem you own, not three individual issues.
- Keep confidences absolutely, including from your own manager, except where you have a duty to escalate. 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-to-one into a status meeting
If the whole slot goes on project updates, none of these questions fit. Get status from your tracking tool and keep this time for the things that only a conversation surfaces.
Treating quiet as contentment
The person who never raises anything is often the one closest to leaving. 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 rather than gathering more requests you cannot meet.