Questions to Ask a New Employee After 30 Days
Questions for a thirty-day check-in with someone you hired: what onboarding missed, whether the job matches what they were sold in interviews, who they still have not met, and what they can see that nobody who has been here two years can see any more.
20 questions, each with the reason to ask it · includes a conversation guide
The questions
Open any question to see why it works.
- 1
Is the job what the job description said it was?
Ask it flatly. Gaps between the posting and the reality are common and usually correctable, and month one is the only point at which a new hire will name them without feeling like a complainer.
- 2
What surprised you in the first month?
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.
- 3
What part of onboarding actually helped?
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.
- 4
What did you have to work out alone that somebody should have told you?
This is the real onboarding gap list. The answers are usually unglamorous: where expenses go, which channel matters, who actually signs things off.
- 5
What took the longest to get access to?
Access delays quietly waste most of a new hire's first two weeks and are almost never reported, because the new person assumes the wait is normal here.
- 6
Who has been most helpful, and did anyone point you to them?
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.
- 7
Is there anyone you have not met who you think you should have?
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.
- 8
How clear are you on what you are accountable for?
Ask them to say it back in their own words rather than to answer yes. The mismatch between their version and yours is the most common reason a first review goes badly.
- 9
What do you think success at ninety days looks like?
Let them answer first, then say whether you agree. In that order you surface the mismatch; the other way round you simply get agreement with whatever you said.
- 10
How is your workload: too light, about right, or underwater?
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.
- 11
Have you finished anything yet that you were pleased with?
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.
- 12
What is still confusing about how decisions get made?
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.
- 13
What words or acronyms do people use that nobody has explained?
Ask for the list. They will have been nodding along for a month, and the answer often runs to ten items and takes five minutes to clear up.
- 14
Has anything happened that made you think, that is odd?
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.
- 15
How has the team been with you, honestly?
The word honestly matters, and so does not filling the pause. A warm answer that arrives instantly is probably true; a hesitation is worth following up on privately.
- 16
Have you had the right amount of time with me?
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.
- 17
Was anything you were told during hiring not true?
Uncomfortable and worth asking anyway. Interview panels oversell, and the specific oversold thing is often what makes this person leave in year two.
- 18
What would you tell yourself on day one, knowing what you know now?
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.
- 19
What do you want to be doing here in a year?
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 review.
- 20
What do you need from me over the next month?
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 thirty-day check-in
Practical guidance for the conversation itself.
Setting it up
Setting it up
- 1Tell them in advance that the meeting is about how onboarding went, not about how they are performing. Otherwise they will spend it defending themselves.
- 2Book forty-five minutes somewhere other than your usual one-to-one slot, so it does not get eaten by the week's business.
- 3Do not bring a laptop. Write on paper, or type up afterwards.
- 4Ask the questions in roughly the order given: onboarding first, clarity second, people third, and the harder ones about honesty last.
- 5Say 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.
What to do with the answers
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 of the week-one items immediately 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
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 told in interviews has turned out to be untrue and nobody has acknowledged it.