Questions to Ask a New Employee After 30 Days
These are for a manager or HR partner deciding what questions to ask on a 30-day review, or holding a looser check-in with a new employee after 30 days in the job. The 56 questions follow the order the meeting usually takes: the job so far, onboarding, role and goals, the team and you as their manager, what they notice with fresh eyes, and what comes next. Choose eight to ten, send two or three of them ahead, and always finish on the last one, because it is the question that leaves you with something to do.
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The questions
Each question, and why to ask it
The job so far
How would you say your first month went?
Why ask it
In a 30-day review, hear their account before you give yours, because once they know your verdict they will trim their own to match. The places where the two versions differ are what the rest of the meeting is for.
Is the job what the job description said it was?
Why ask it
Ask it flatly. Gaps between the posting and the reality are common and usually correctable, and at one month a new hire can still name them without sounding like a complainer.
What surprised you in the first month?
Why ask it
Deliberately wide, and it catches things you would never have thought to ask about, from how loud the office is to how many approvals a two-hundred-dollar decision needs.
Have you finished anything yet that you were pleased with?
Why ask it
A first completed piece of work is what makes someone feel they belong here. If the answer is no at thirty days, find them something finishable rather than something impressive.
Which part of the work has turned out harder than you expected?
Why ask it
Harder than expected is a safer thing to admit than struggling, so this covers the same ground without the word. Ask whether the difficulty is the task itself, the tools, or not knowing who to ask.
Where have most of your hours gone these first four weeks?
Why ask it
Compare the answer with what you thought you had assigned. A month spent mostly on setup, shadowing or waiting is information about your planning, not a mark against them.
What does a good day here look like so far, and how many have you had?
Why ask it
The description tells you which part of the work they like, and the count tells you how the month really went. If good days have been rare, ask what the last one had that the others were missing.
Which part has come more easily than you thought it would?
Why ask it
The easy part is usually a strength you hired without noticing. Write it down, because it shows where they could take on more before the ninety-day mark.
What made you say yes to this job, and has the first month backed that up?
Why ask it
Their reason for joining is the promise they are quietly checking you against. Whether it was the people, the project or the chance to learn something, you now know which thing not to take away.
Is there anything we promised you during hiring that has not happened yet?
Why ask it
Think of the laptop, the parking space, the training course or the day at home that somebody mentioned at interview. Small promises like these are easy to keep once you hear about them, and a forgotten one tells a new hire how much the rest of what they were told is worth.
How are the hours, the commute or the home setup working out?
Why ask it
Practical strain shows up within weeks and seldom gets raised in a work meeting. Listen before you offer anything, and find out from HR what flexibility your employer allows before you promise a change.
Onboarding
What part of onboarding actually helped?
Why ask it
Ask what worked before what did not, or you will only collect complaints. Whatever they name is the part to protect the next time somebody proposes redesigning the whole program.
What did you have to work out alone that somebody should have told you?
Why ask it
This is the real onboarding gap list. The answers are usually unglamorous: where expenses go, which channel matters, who actually signs things off.
What took the longest to get access to?
Why ask it
Waiting for a login or a permission can swallow much of a new hire's first two weeks and often goes unreported, because the new person assumes the wait is normal here. Ask which request is still open today and chase that one yourself.
Did it feel as if we were expecting you on your first day?
Why ask it
A desk that was not ready, lunch alone or a manager who was away that week shapes how the whole first month is remembered. You cannot give them the day again, but you can apologize for it and put it right before the next person starts.
Which training session or document could we have skipped?
Why ask it
Asking what to cut gets a more honest review of the program than asking what to add. If hire after hire names the same session, it is probably there for the person who runs it.
Is there a tool or system you still do not feel comfortable in?
Why ask it
If they hesitate, name the two or three systems the job depends on. An hour beside someone who uses the tool every day usually does more than repeating the training course.
What words or acronyms do people use that nobody has explained?
Why ask it
Ask for the list. They will have been nodding along for a month, and it tends to be longer than you would guess and quick to clear up.
When you get stuck, where do you look first: a person, a document or a search?
Why ask it
The answer shows what your written documentation is really worth. If it is always the same colleague, that colleague is the onboarding program and deserves to hear that you know it.
Is anything about pay, benefits or paperwork still unsettled?
Why ask it
A first payslip that looks wrong or an enrolment form with a deadline can sit on a new hire's mind all month. Do not answer from memory: the rules and dates differ by employer and country, so take the question to HR or payroll and come back with an answer.
What would you tell yourself on day one, knowing what you know now?
Why ask it
Turns criticism into advice, which is much easier to give. Collect these answers across several hires and you have written the onboarding guide from the only useful point of view.
Role and goals
How clear are you on what you are accountable for?
Why ask it
Have them list it in their own words instead of answering yes. Anything on your list that is missing from theirs is work that nobody is doing at the moment.
Do you know what the team is trying to get done this quarter, and where your work fits in?
Why ask it
A month spent learning tasks one at a time leaves little room for the larger picture. If they cannot say, give it five minutes now: priorities are hard to follow for someone who does not know what the work is for.
Which of the goals we set for the first month did you reach, and which are still open?
Why ask it
Bring the list you gave them in week one so neither of you is relying on memory. If there never was a list, say so, and make writing the next one together the main result of this review.
What do you think success at ninety days looks like?
Why ask it
A new hire who pictures day ninety as still learning and a manager who pictures it as running the work alone are heading for a hard review. Put your picture beside theirs and agree on one version before the meeting ends.
How is your workload: too light, about right, or underwater?
Why ask it
New hires almost never volunteer that they have too little to do, because it sounds like an admission. Offering the three options is what makes the light answer sayable.
What feedback have you had on your work so far, and who gave it?
Why ask it
If the answer is none, this meeting is the first, and you should say that it came late. If all of it came from peers, check that it matches what you would have told them, since early habits form around whoever comments first.
Do you know how I will decide whether a piece of your work is good?
Why ask it
Most new hires are guessing at the standard from whatever gets praised in meetings. Describe one finished example you would call good and say why, which teaches more than a list of criteria.
Is there a task you keep doing without being sure you are doing it right?
Why ask it
Nobody corrects a new person on routine things, so small errors settle in unnoticed. Offer to watch them do it once, or pair them with whoever does it best.
Which decisions do you think you can make without checking with me?
Why ask it
Have them list a few, then correct the list in both directions. New hires tend to ask permission for too much, and the cure is one clear sentence from you.
When two people ask you for things at the same time, how do you decide which comes first?
Why ask it
A month in, requests are arriving from people whose seniority and urgency they cannot yet read. If the rule turns out to be whoever asked last, give them a better one and tell them to send real conflicts to you.
Which of your skills have we not used yet?
Why ask it
You hired a whole CV and the first month uses a corner of it. The unused skill is often the one they were proudest of at interview, and finding a place for it costs little.
Is there anything about the probation period or the next review that you would like explained?
Why ask it
Ask this only if your employer has such a period, and have the facts in front of you. What probation means for notice, pay or benefits depends on the contract, the employer and the country, so confirm it with HR before you explain it.
Team and manager
How has the team been with you, honestly?
Why ask it
The word honestly matters, and so does not filling the pause. A warm answer that arrives at once is probably true; after a hesitation, ask what a better first month with the team would have looked like.
Who has been most helpful, and did anyone point you to them?
Why ask it
You find out who is absorbing onboarding work informally, which is worth recognizing and sometimes worth reducing. If nobody pointed them there, whatever buddy system you have is not working.
Is there anyone you have not met who you think you should have?
Why ask it
New hires build their map of the organization from whoever happens to speak to them first. Any obvious gap is cheap to fix this week and expensive to fix in six months.
Whose work does yours depend on most, and how is that going?
Why ask it
This one is about handoffs, not friendships. A slow or unclear handoff is easier to raise in the first month, before it has hardened into a grievance between two people.
Which regular meeting do you still not see the point of?
Why ask it
They may be right, or they may be missing background that nobody gave them. You gain something in both cases: explain the meeting, or release them from it.
Have you disagreed with anything yet, and did you say so?
Why ask it
A new person who has found nothing to disagree with in four weeks is probably being polite. The second half matters more: if they kept quiet, ask what would have made it easier to speak.
Have you had the right amount of time with me?
Why ask it
Give three options: more, less, or a different kind. Most new hires will never tell you unprompted that your one-to-ones are the wrong shape.
When I have a correction for you, how would you like to get it?
Why ask it
Some people want it on the spot, some in private at the end of the day, and a few in writing so they can reread it. Ask before you have a correction to give, so the first one is not also the experiment.
Is there anything I do that makes your work harder?
Why ask it
Expect a small answer first, such as slow replies or a brief that changed at the last minute. Thank them and fix it where they can see, and a bigger one may follow at the sixty-day meeting.
Fresh eyes
Has anything happened that struck you as odd?
Why ask it
Vague on purpose, so it can catch anything from a strange meeting norm to something you would want to hear about immediately. Ask it late, once they are talking freely.
What is still confusing about how decisions get made?
Why ask it
Every organization has an official process and a real one. What a new person finds confusing is usually the gap between them, and they can still describe it before they learn to stop noticing.
What did your last workplace do better than we do?
Why ask it
Give explicit permission for the comparison, since most new hires have learned not to begin a sentence with 'at my old job'. You are after one practice worth borrowing, not a verdict on the company.
What works well here that you had not seen done before?
Why ask it
This is not fishing for praise: it shows you what people who have been here for years have stopped noticing. Pass the answer on to whoever built the thing they name.
Which rule or process have you been asked to follow without seeing the reason for it?
Why ask it
Some rules have a sound reason that nobody remembered to give, and explaining it takes a minute. If you cannot find the reason either, you have a candidate for removal.
If you could fix one small thing about how this team works, what would it be?
Why ask it
The word small keeps the answer practical and safe to give. If it really is small, let them make the fix themselves, which works as a first piece of ownership.
What have you heard customers or other teams say about us?
Why ask it
New people get told things in corridors and on calls that nobody would say to the manager. Take it as a report, not a complaint, and do not ask who said it.
Looking ahead
What is one thing you want to have finished by this time next month?
Why ask it
One finished thing is easier to hold both of you to than a list of intentions. Put it in writing where you can each see it, and open the sixty-day check-in by asking how it went.
What would you like to learn or get better at over the next two months?
Why ask it
Push for one skill with a name, such as running the weekly report alone or presenting to a client. Agree who will teach it and by when, or it stays a wish.
Is there a project or part of the business you would like to get closer to?
Why ask it
Curiosity at thirty days is worth using while it lasts. A seat in one meeting or an afternoon of shadowing costs little and shows that the interest was heard.
What do you want to be doing here in a year?
Why ask it
Asked at thirty days the answer is still ambitious rather than shaped by what they have since learned is possible. Write it down and reread it before their first annual review.
Has anything this month given you second thoughts about taking the job?
Why ask it
Say first that you would sooner hear it now than read it in a resignation letter. Do not argue with what comes back: ask what would need to change, and be straight about which parts you can affect.
Is there anything I have not asked that you were hoping I would?
Why ask it
Leave a real silence after this one. The thing a new hire was saving for the end of the meeting is often the thing they walked in with.
What do you need from me over the next month?
Why ask it
Ends with something you can act on. Attach a date to it, because the value of a thirty-day check-in is entirely in what has visibly changed by day sixty.
Running a 30-day check-in or review
Practical guidance for the conversation itself
Setting it up
- 1Tell them in advance what the meeting is: a check-in on how the first month and onboarding went, or a 30-day review that includes an assessment. Left to guess, they will assume the second and spend it defending themselves.
- 2Book forty-five minutes of its own, outside your usual one-to-one slot, so it does not get eaten by the week's business.
- 3Choose about ten questions, which is roughly what forty-five minutes holds once the follow-ups are counted. Take one or two from each group, leaning on Role and goals for a formal review and on Onboarding and Fresh eyes for a check-in. The first question on the page and the last one are worth asking every time.
- 4In the same room, leave the laptop shut and write on paper. On a video call, say that you are taking notes, so the typing is not mistaken for email.
- 5Ask the questions in roughly the order given: The job so far and Onboarding first, Role and goals next, then Team and manager, with Fresh eyes held back until they are talking freely and Looking ahead to close.
- 6Say at the start that you are going to ask what went badly and that you want the real answer, then wait longer than is comfortable after each one.
When it is a formal 30-day review
Keep the assessment and the listening apart
Some employers hold a 30-day review with a form, a rating or a note for the file, and others only expect the manager to check in. If yours has an assessment, give it in its own part of the meeting, after the questions under The job so far, and say who will read what is written down. Then make clear that the Onboarding and Fresh eyes answers are not going on the form, or a new hire will treat every honest answer as evidence.
Find out what the 30-day point means where you work
If the first months are a probation or introductory period, ask HR before the meeting whether anything is decided at thirty days, what has to be recorded, and what you may say about the sixty-day and ninety-day reviews. Those rules differ by employer, contract and country, so do not explain them from memory.
If you are the one being reviewed
A new employee preparing for their own 30-day review can turn the page around. Arrive with your answers to the Role and goals group already thought through, and ask your manager three things in return: what they would like to see from you by day ninety, what they would change about your first month, and who you should have met by now.
What to do with the answers
- Split the list into things you can fix this week, things that belong to onboarding generally, and things that are just how the company is.
- Fix one thing from the first pile straight away and tell them you did. Nothing else you do will convince them the meeting was real.
- Keep a running file across hires. A single new person's complaint is an anecdote; the same complaint from four is a broken process.
- Do not pass an individual's comments about a colleague upward without telling them first.
- Close the loop on anything you cannot change, and say why. Silence gets read as the question having been unwelcome.
Signs the first month has gone wrong
- They cannot describe what they are accountable for, or describe something different from what you would say.
- They have not completed a single piece of work, and cannot name what they are waiting on.
- They still lack access to a system central to the job.
- Every helpful person they name sits outside their own team.
- They answer every question with a version of fine, including the ones that have no fine answer.
- Something they were promised during hiring has not happened and nobody has acknowledged it.