Questions to Ask New Hires After 30 Days
Questions for a manager's one to one with someone who has been in the job a month, covering what the work turned out to be, where onboarding left gaps, what they still cannot access, what they can see with fresh eyes, and what they need from you next.
The questions
Open any question for the note
How is the job different from what you expected when you accepted it?
Why ask it
The gap between the offer and the reality is where early resignations begin, and at thirty days it is still fresh enough to be described honestly. A large gap is worth treating as a recruiting problem, not just a personal adjustment.
What did you actually spend most of your time on this month?
Why ask it
Compare their answer with what you intended their first month to be. New hires routinely lose weeks to setup, training that was not relevant, or covering for someone who left, and nobody notices until you ask.
What is still unclear about what you are responsible for?
Why ask it
Asking what is unclear gets you further than asking whether things are clear, because it assumes there is something. Anything named here is usually a documentation gap that affects every new starter after them.
Where do you get stuck, and what do you do when that happens?
Why ask it
The second half is the important one: whether they ask, wait, or guess. Someone who has been quietly stuck for three days each week has a problem you can fix immediately.
Who have you relied on most, and is there anyone you should have met by now and have not?
Why ask it
Identifies who is quietly carrying your onboarding, which is worth acknowledging, and the introductions that were never made. Missing relationships are the most common invisible cause of a slow start.
What took you longest to find or work out that should have been written down?
Why ask it
Turns their frustration into an asset, and a new hire is the only person who can see this clearly. Ask them to write it up while they still remember, then use it for the next hire.
Is there anything you still cannot do because of missing access, tools or permissions?
Why ask it
Access requests fall through the cracks constantly, and people stop chasing after the second attempt. This question regularly turns up something that has been blocking work for weeks.
Was anything said during interviews that has not matched what you have found?
Why ask it
Uncomfortable but valuable: it tells you what your hiring process is promising. Expect small mismatches, and take a large one seriously, because it will be repeated to every candidate they know.
What is this team better at than you expected?
Why ask it
Balances the conversation and tells you which strengths are visible from outside. It is also worth passing back to the team, because praise from a new colleague lands differently.
What have you seen us do that looks strange or inefficient to you?
Why ask it
Ask this now, because in three months they will have stopped noticing. If they hedge, say plainly that you want the version they would tell a friend, and be prepared not to defend anything they name.
What are you least confident about right now?
Why ask it
More answerable than asking how confident they feel, and it produces something specific you can act on. If the answer is nothing, ask what they would need to do tomorrow that they would rather not.
Can you tell me in your own words how your work will be judged at six months?
Why ask it
Asking them to say it back reveals what actually landed, which is often not what you said. Any mismatch is far cheaper to correct now than at a review.
Which meetings are you in that you do not think you need to be in?
Why ask it
New hires are added to calendars generously and removed from them never. Cutting two recurring meetings is one of the fastest useful things a manager can do at thirty days.
Have you had enough time with me, and would you want it differently?
Why ask it
Asked directly, most people will tell you if a weekly slot keeps being cancelled or if they need less structure. Being willing to hear that your own cadence is not working sets the tone for the rest of the relationship.
Has anyone here treated you in a way you did not expect?
Why ask it
Deliberately open, so that it covers unusual kindness as well as rudeness or exclusion. Ask it while they are still willing to say something, because after a few months people assume it is normal and stop mentioning it.
What would have made your first two weeks easier?
Why ask it
Narrowing to the first two weeks gets specific answers, where asking about onboarding in general gets a shrug. Answers tend to be small and fixable: a seating plan, a glossary, someone to eat lunch with.
What are you working on right now, and does it feel like the right thing?
Why ask it
Checks alignment and gives them a sanctioned way to say that their current task feels pointless. If they cannot connect it to anything, that is your gap to close, not theirs.
What would you like to be doing in six months that you are not doing now?
Why ask it
Signals that development is on the agenda before the first review, and tells you what they came here for. A vague answer is fine at thirty days; note it and ask again later.
What would you tell a friend who asked about working here?
Why ask it
The referral version of their experience, which is usually more candid than a direct question about satisfaction. It is also a fair predictor of whether they will still be here in a year.
What do you need from me in the next month?
Why ask it
Ends with a request rather than an assessment, and puts the next step on you. Write down what they say, then reference it at the next check-in so they know the question was real.
Running a thirty-day check-in
Practical guidance for the conversation itself
Setting it up
- 1Book it as a longer conversation with the purpose stated in the invitation, so it is not mistaken for a performance review.
- 2Say at the start that you are asking about the onboarding and about them, and that nothing here feeds into an assessment.
- 3Choose six or seven questions rather than the whole list. A month in, people tire quickly of being interviewed.
- 4Have it privately, and not in a room with glass walls onto their new team.
- 5If you are the person who hired them, consider asking a peer or another manager to have a second, separate conversation. Some feedback will not come to you.
What to listen for
Everything is fine usually means not yet
At thirty days most people are still deciding how safe candor is. Follow a positive answer with a specific prompt: name one thing that was harder than it needed to be. Silence after that tells you far more than silence before it.
Time is the most honest measure
What they spent hours on tells you more than how they say they feel. If most of the month went to setup and waiting, the onboarding failed regardless of how positive they sound.
Distinguish induction gaps from role problems
Missing access, absent documentation and unmade introductions are fixable this week. A role that turns out to be different from the one advertised is a longer conversation, and worth having explicitly.
Their comparisons are data
New hires are the only people who can compare you with somewhere else from recent memory. When they say we did this differently, ask how, before they lose the habit of noticing.
Afterwards
- 1Pick one thing they raised and fix it within a week, then tell them it is done. This is what determines whether the next check-in gets honest answers.
- 2Be straight about anything you cannot change and say why. Unexplained inaction reads as indifference.
- 3Add anything about missing documentation to the onboarding checklist immediately, while their notes are still fresh.
- 4Book the sixty or ninety day conversation now, and reference what they asked for in this one.
- 5If several new hires raise the same issue, treat it as a process problem and take it to whoever owns onboarding.
What goes wrong
- Running it as a survey. Reading twenty questions in order gets shorter answers with every one.
- Defending the team when they name a problem. Explain later if you must, but not in the moment they took a risk.
- Asking for feedback and doing nothing with it, which is worse than not asking.
- Leaving the conversation until ninety days. By then they have adapted to the problems and can no longer see them.
- Treating the check-in as the whole relationship. What matters is whether they can raise things in an ordinary week.