Questions to Ask a New Direct Report
For a manager's first few one-to-ones with someone new: a new hire, or a person you inherited when you took over a team. They also serve as questions to ask your new team when everyone on it is new to you: put them to one person at a time, and spend longest in the group called The team. The 57 questions follow the order those first meetings tend to take: how they work, what they want from a manager, the work itself, the team, where they want to grow, and a few to close on.
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The questions
Each question, and why to ask it
How you work
What should I know about how you work that will not show up on your calendar?
Why ask it
Invites the practical detail people rarely volunteer: a school run, a commute they dread, headphones meaning do not interrupt. You get more usable material than from asking about working style in the abstract.
When in the day do you do your best thinking, and when should I leave you alone?
Why ask it
The answer lets you put the one-to-one, and any hard conversation, at an hour that suits them instead of you. If their best hours are swallowed by a standing team meeting, find that out before you pick up the habit of scheduling over them.
What does a good week look like for you?
Why ask it
You are listening for the shape of work that suits them: long stretches of focus, lots of people, finishing things, starting things. It tells you more about which assignments will suit them than a list of their skills does.
How do you want to use our one-to-one time?
Why ask it
Left to itself a one-to-one drifts into a status meeting, and a status update could have been a message. Ask them to name what they want the time for and hold that shape for at least a couple of months.
What does it look like from the outside when you are overloaded?
Why ask it
One person goes quiet, another gets short in messages, a third starts sending emails at midnight. Ask what they would want you to do when you spot it, because 'leave me to it' and 'come and ask' are both common answers.
How do you prefer to be reached: a message, a call, or a walk over to your desk?
Why ask it
Follow up by asking what counts as urgent enough to break the rule. Someone who checks chat twice a day and a manager who expects a reply in ten minutes will each decide the other is being difficult.
Do you like to think out loud, or would you rather see a question before you answer it?
Why ask it
People who need time to think get mistaken for people with no opinion, especially in fast meetings. If they want notice, send the one or two things you most want to discuss the day before.
Which days are you usually in the office, and what do you save for them?
Why ask it
One for a team that splits its week between home and the office. Someone who saves office days for talking to people will want the one-to-one then, and someone who comes in for a quiet desk will not. If they ask to change their days, check what your employer's policy allows before you agree.
Is there anything outside work you would like me to take into account when I plan your work?
Why ask it
The wording leaves it to them what to share, so say plainly that no is a complete answer. Do not follow up with questions about health or family: what a manager may ask, and what has to go to HR, depends on the country and the employer, so find out how it works at yours.
From a manager
What did your last manager do that you would like me to keep doing?
Why ask it
Easier to answer than a question about what they want from a manager in general, because they are describing something that actually happened. You also learn what standard you are being measured against.
What did your last manager do that you would rather I did not?
Why ask it
Pair it with the question about what to keep, so the two read as a comparison and not as an invitation to complain. The answers are usually small and specific: skipped one-to-ones, rewritten work, a copied-in boss.
How much involvement do you want from me: daily, weekly, or only when you flag something?
Why ask it
Both micromanagement and abandonment come from a manager guessing at this. Ask them to pick a level, and agree that either of you can change it later without it being read as a judgment.
When I have criticism of your work, how do you want to hear it?
Why ask it
Ask in week one, before you need it. Some people want it at once and without padding, others need a minute of context first, and guessing wrong in the first hard conversation colors every one after it.
How do you want to be recognized when something goes well?
Why ask it
Public praise is a reward for some people and a penalty for others. Settling this early stops you thanking someone in an all-hands and wondering why they looked stricken.
When you bring me a problem, do you want a suggestion, a decision, or someone to think it through with?
Why ask it
Managers reach for a fix by habit, and often the person already had one and wanted to test it aloud. Agree a short way of saying which of the three you are after, so either of you can ask in the middle of a conversation.
Which decisions do you expect to make yourself, and which would you bring to me?
Why ask it
New hires tend to guess low, and people you inherited are still working to the last manager's line. Test it on two or three real cases, such as moving a deadline or saying no to another team, and say where you would draw it.
How will I know when you disagree with me?
Why ask it
Some people say so in the meeting, some send a careful message the next morning, and some simply go quiet. Once you know which, you can tell silent agreement from silent objection. Tell them in return how you like to be told you are wrong.
What have I said that has not made sense to you?
Why ask it
Every team runs on shorthand and new people nod through it for weeks. Asking directly gives them permission to admit they have been guessing at three acronyms since they started.
What was agreed with you before I arrived that I should know about?
Why ask it
A promotion timeline, a place on a project, a day working from home or a training course may have been settled in a conversation that left no record. Do not say yes on the spot: write it down, check what you are able to honor, and come back with a straight answer.
What were you told about the change of manager, and who told you?
Why ask it
Someone handed to a new manager is often carrying a version of events you have never heard: a promise, a rumor, a reason that was never official. Hear theirs before you give yours, then fill in what you honestly can.
What would you like to know about me and how I manage?
Why ask it
A new report is working you out as well, and rarely has a polite opening to ask. Answer plainly, including the habit of yours that people find hardest, since they will meet it soon enough.
The work
Can you walk me through everything on your plate this month, and tell me which piece matters most?
Why ask it
A plain tour of their work, taken before you have opinions about it. Set the piece they call most important beside what you were told the priorities are, because a mismatch there is the first thing to straighten out.
What are you working on right now that you are least sure about?
Why ask it
A status update covers what is on track, and this asks for the part that is not. Whether a new report keeps answering it honestly depends on how you react the first time, so thank them before you start solving.
What does good work look like in your role, as you understand it?
Why ask it
If their picture of a job well done differs from yours, every piece of feedback this year will arrive as a surprise. Say back what you heard, then add the one or two things you would weigh more heavily.
What should I not expect from you yet?
Why ask it
A new starter needs to hear that being slow in the first month is allowed, and naming what is not expected often reassures more than a list of goals. From someone you inherited, the answer may be a skill everyone had assumed they already had.
How does the job so far compare with what you were told in the interviews?
Why ask it
For a new hire, the advert, the interviews and the first fortnight can describe three different jobs. Hearing about the gap early lets you change either the work or the expectation while it is still a small disappointment.
What part of your job would you hand to someone else if you could?
Why ask it
The answer is often something that is nobody's real job and has quietly attached itself to them. Some of it can be removed, and removing it early buys a great deal of goodwill.
Who do you depend on to get your work done?
Why ask it
Their list becomes yours, since a delay from any of those people lands on your report and it is your job to chase it. A new starter who cannot name anyone yet has just told you which introductions to make this week.
What is the slowest or most irritating step in getting your work finished?
Why ask it
Expect an approval that sits for days, a tool that needs three workarounds or a report copied across by hand. Fixing one of these in the first month shows that telling you things has an effect.
What access, equipment or training are you still waiting for?
Why ask it
New starters will go weeks without a login or a walkthrough before mentioning it, because asking feels like complaining. Chase the missing item yourself the same day: it is a short errand for you and a stalled week for them.
Which piece of your past work are you proudest of, and why that one?
Why ask it
The reason matters more than the project. 'It was hard', 'the customer wrote to thank us' and 'I did it my own way' point to three different things that keep a person going.
Where do you feel you are measured on the wrong thing?
Why ask it
You may learn that a target punishes careful work, or that their best work is invisible because it prevents problems. You cannot always change the measure, but you can change how you describe them to the people above you.
What have you asked for in this job that never arrived?
Why ask it
An old request is an easy win when you can grant it and a test of trust when you cannot. Close each one with a yes, a no or a date, since being ignored a second time is worse than being refused.
The team
What is working well on this team that I should be careful not to break?
Why ask it
The first thing to ask each person when the whole team is new to you, and best asked before anything about problems. Whatever three people name without prompting should be left alone for a good while.
What is broken here that people have stopped mentioning?
Why ask it
Fresh eyes do not last: within a few months a newcomer adapts and stops seeing it, so ask now and write the answers down. A long-serving person you inherited gives you the other half, the things they gave up raising.
If you were sitting in my chair, what would you do first?
Why ask it
It hands them the manager's view for a moment, and the reply shows what they think the team's real problem is. Do not commit to it in the room. Say you are asking everyone and will share what you heard.
Who on the team do you go to when you are stuck?
Why ask it
Collected from everyone, the answers draw the team's real map, which seldom matches the org chart. The name that keeps coming up is carrying work nobody has counted, and should hear that you noticed.
How do decisions really get made on this team?
Why ask it
The official answer is that the manager decides, and the true one tends to involve a senior colleague, a group chat or whoever speaks last. You need the true one before you change anything.
What happened the last time something went badly wrong on this team?
Why ask it
The story shows whether mistakes here get examined or pinned on someone. Listen for who is named, who is left out, and whether anything was done differently afterwards.
Which of the team's regular meetings would you miss if it vanished?
Why ask it
Asking what they would miss is gentler than asking what to cut, and gives you the same list in reverse. Sit through each meeting at least twice before you cancel one.
What does the rest of the organization get wrong about this team?
Why ask it
Most teams have a grievance about how they are seen: slow, expensive, a help desk for everyone else. You will be speaking for them in rooms they are not in, so you need both the reputation and their answer to it.
Who should I talk to early, in the team or outside it, to understand how things work here?
Why ask it
You come away with a list of people to meet and a view of who this person trusts. A name from another department often explains more of the team's history than a week of reading documents.
What worries you most about a new manager coming in?
Why ask it
Every new manager is assumed to have a plan, and people brace for a reorganization, for losing a project they fought for, or for a flexible arrangement being withdrawn. Say which worries you can rule out and which you do not know about yet, and do not reassure past what you know.
Growth
Where do you want to be stretched this year?
Why ask it
Ask for an area rather than a title. The distance between what they name and what the team actually needs is the thing you will spend the year managing.
What do you want to learn in this job that you could not learn in your last one?
Why ask it
For a new hire this is often the real reason they accepted the offer, and it is rarely in the job description. With someone you inherited, change the wording to what they have wanted to learn here and never had the chance to.
What are you good at that this job does not currently ask for?
Why ask it
People arrive with skills their job description never mentioned: a second language, a knack for spreadsheets, years of running a volunteer rota. A manager who never asks tends to hear about it in the leaving speech, when they go to a role that uses it.
When were you last bored at work, and what were you doing?
Why ask it
Boredom is hard to admit to a new boss, so the question asks about a past case. The task they describe is the kind to keep small in their week, or to share around the team.
What kind of feedback has helped you improve most in the past?
Why ask it
They will describe a particular moment: a marked-up draft, one blunt sentence after a presentation, a senior colleague sitting beside them while they worked. Borrow the format as well as the content, since it has already worked once.
Do you know how pay rises and promotions are decided here?
Why ask it
Plenty of people do not, and a new hire almost never does. The process differs from one employer to the next, so if you are new yourself, ask HR or your own manager how it works there before you explain it, and do not guess at a timeline.
What do you want to be doing in two years, here or somewhere else?
Why ask it
Including somewhere else is what makes it answerable. Managers who insist the answer must involve the company get a rehearsed reply and learn nothing from it.
What would make this the best job you have had?
Why ask it
The mirror image of asking what would make them leave, and easier to answer early on. Replies are often modest: a say in what they work on, a team that laughs, a boss who turns up to the one-to-one.
What would make you start looking for something else?
Why ask it
Managers usually hear this answer in a resignation meeting, when it is too late to use. Asked while things are fine, the replies are concrete: no route upward, one specific person, being too far from the work they care about.
To close
What do you need from me in the next month, specifically?
Why ask it
It turns a friendly hour into one request with a deadline on it. If the answer is nothing, offer two or three concrete options and let them choose, because new people rarely feel entitled to ask.
How often should we meet for now, and what would make you want to change that?
Why ask it
Weekly is a sensible place to start with someone new, but ask anyway. Agree that either of you can propose a change, so that moving to every other week later reads as trust and not as neglect.
Is there anything we talked about today that you would like kept between us?
Why ask it
A new report does not yet know what you repeat to your own boss or to their colleagues. Keep to whatever they say, and be honest that a few things, a safety or harassment concern for one, you may be required to pass on under your employer's rules.
How did this conversation compare with what you expected?
Why ask it
A light way to ask for feedback on yourself before they know you well enough to give it straight. 'More questions than I expected' and 'I thought you would tell me the plan' each say something about how the last manager ran these meetings.
What should I have asked you that I did not?
Why ask it
Most people walk in with one thing they meant to say and never find the opening for it. Sit through the silence after you ask, because the real answer tends to come after a pause you would normally fill.
The first month
Practical guidance for the conversation itself
Running the first few one-to-ones
- 1Start weekly unless they ask for something else, even if you intend to move to fortnightly later. Meeting often at the start is what lets you meet less later without it looking like lost interest.
- 2Spread the groups across four or five conversations: How you work and From a manager in the first, The work in the second, The team and Growth once they have seen how you react to an honest answer. Six questions in a row is an interview, not a one-to-one.
- 3Answer the same question yourself first where you can. Telling them how you like to receive bad news makes it much easier for them to tell you theirs.
- 4Take notes in front of them and read the previous week's notes back at the start of the next meeting.
- 5Close every one of these conversations with one thing you will do before the next, and then do it.
Things to do rather than ask
- For someone you inherited, read two or three recent pieces of their work before the first meeting so your questions are about something real. For a new hire, reread the application and your interview notes.
- Introduce them to the people their work depends on, rather than waiting for them to find those people.
- Remove one obvious blocker in week one. It establishes that saying something out loud leads to something changing.
- Give them something finishable in the first fortnight. A completed piece of work does more for confidence than any amount of encouragement.
- Tell them explicitly what you do not need to see. New reports over-report by default and then feel watched.
If you inherited them
- Ask the outgoing manager for a handover on each person if you can, and treat it as one opinion. Then ask the person the same things and note where the two accounts differ.
- Do not promise to be different from the last manager. Say what you will do and let them draw the comparison.
- Take any commitment made before you arrived to your own manager or HR before you answer. Whether an unrecorded promise of a promotion or a flexible arrangement can be honored depends on the employer, and a quick yes you later withdraw does more damage than a slow answer.
- If your employer lets you see their last review, read it, but ask them what they thought of it before you decide what it means.
- Hold off on conclusions about their performance for as long as you reasonably can; a full quarter is a fair rule of thumb. Much of what you see in month one is the handover, not the person.
If the whole team is new to you
- Meet every person individually inside your first two weeks, and tell the team beforehand that you are doing it. A manager who has sat down with three people out of eight is assumed to have chosen favorites.
- Put the same four or five questions from The team to each person, in the same words. Answers can only be compared, and a pattern only shows, when the question did not change between meetings.
- Hold the group conversation after the individual ones. Tell the room what you heard in general terms, with no names attached, and what you have decided to leave alone.
- Make the small fixes people asked for and hold back anything structural for the first month. A reorganization announced before you have finished listening tells the team the listening was for show.
- Ask your own manager what they expect of the team this quarter before the first one-to-one, so you can tell which of the hopes you hear are possible.