Questions to Ask a New Direct Report
Questions for a manager's first few one-to-ones with someone new on the team, whether they have just joined the company or you have inherited them from another manager. Covers how they work, what they want from you, what they can already see that you cannot, and how they want to hear bad news.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
What should I know about how you work that will not show up on your calendar?
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.
- 2
How do you want to hear it when something is wrong?
Ask in week one, before you need it. Preferences split cleanly between people who want it immediately and directly and people who need a minute of context first, and getting it wrong once can cost you months.
- 3
How do you want to be recognized when something goes well?
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.
- 4
What did your last manager do that you would like me to keep doing?
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.
- 5
What did your last manager do that you would rather I did not?
Ask straight after the previous question so the two read as a pair rather than as an invitation to complain. The answers are usually small and specific: skipped one-to-ones, rewritten work, a copied-in boss.
- 6
How much involvement do you want from me: daily, weekly, or only when you flag something?
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.
- 7
What are you working on right now that you are least sure about?
More productive than a status update, because it asks for the uncomfortable part. Whether a new report answers honestly in month one depends almost entirely on how you react the first time.
- 8
What part of your job would you hand to someone else if you could?
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.
- 9
What are you good at that this job does not currently ask for?
People arrive with skills their job description never mentioned. If you do not ask in the first month you tend to find out two years later, when they leave for a role that uses it.
- 10
Where do you want to be stretched this year?
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.
- 11
What does a good week look like for you?
You are listening for the shape of work that suits them: long stretches of focus, lots of people, finishing things, starting things. It predicts which assignments go well better than any competency framework.
- 12
Who do you depend on to get your work done?
Maps the dependencies you are responsible for unblocking. A new report who cannot yet name any is telling you who they still need to be introduced to.
- 13
What is broken here that people have stopped mentioning?
New eyes expire in about three months. Ask now and write the answers down, because they will stop being able to see it once they have adapted to it.
- 14
Is there anything going on in your life I should know when I plan your work?
Phrased so that nobody has to disclose anything. Say plainly that no is a complete answer, and that whatever they do say stays with you unless they ask otherwise.
- 15
How do you want to use our one-to-one time?
The default in most teams is a status meeting, which is the least valuable thing you could do with it. Ask them to name what they want it for and hold that shape for at least a couple of months.
- 16
What do you want to be doing in two years, here or somewhere else?
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.
- 17
What have I said that has not made sense to you?
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.
- 18
What would make you start looking for something else?
Far better asked while things are fine than during a resignation conversation. Most answers are concrete and fixable: no route upward, one specific person, being too far from the work they care about.
- 19
What do you need from me in the next month, specifically?
Forces something actionable out of the conversation. If the answer is nothing, offer two or three concrete options and let them choose, because new people rarely feel entitled to ask.
- 20
What should I have asked you that I did not?
Catches whatever they walked in wanting to say. It works only if you then sit through the pause rather than filling it.
The first month
Practical guidance for the conversation itself.
Running the first few one-to-ones
Running the first few one-to-ones
- 1Book them weekly for the first two months, even if you intend to move to fortnightly later. Frequency early is what makes the later cadence safe.
- 2Spread these questions across four or five conversations. Six 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
Things to do rather than ask
- Read their last three pieces of work before the first meeting so your questions are about something real.
- Introduce them to the three 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
If you inherited them
- Ask what they were told about the change, and by whom. People are often managing a story you have not heard.
- Do not promise to be different from the last manager. Say what you will do and let them draw the comparison.
- Find out what commitments were made to them before you arrived, including promotions, projects, and flexible arrangements.
- Read their last review, but ask them what they thought of it before you decide what it means.
- Give it a full quarter before you conclude anything about their performance. Most of what you see in month one is the handover, not the person.