30-60-90 Day Check-In Questions for New Hires: 30 Examples

BambooHR’s 2025 onboarding benchmark found that 39% of new hires have second thoughts during onboarding, and Enboarder’s 2025 HR leader survey found that 86% decide how long they will stay within six months. The 30-60-90 day check-in questions below help managers learn what a new hire is actually thinking at each mark, while there is still time to act.

What Are 30-60-90 Day Check-In Questions?

30-60-90 day check-in questions are the prompts a manager uses in three conversations with a new hire, at the end of their first, second, and third month. Each conversation has a different job: the 30-day check-in tests expectations against reality, the 60-day check-in tests for real work and real feedback, and the 90-day check-in tests for ramp and what comes next.

Check-in	What the conversation needs to uncover	Questions
30-day	Expectations vs. reality, access, early relationships	1-10
60-day	Real ownership, feedback received, blockers	11-20
90-day	Ramp against the plan, confidence, next six months	21-30

If the 30-60-90 plan itself is not written down yet, start with our guide to the five stages of the employee onboarding process.

30-Day Check-In Questions

The 30-day check-in is a reality check. Its job is to find the gap between what the new hire was told during hiring and what they have experienced since, and to clear anything still blocking them from doing real work. Ask about expectations directly.

Enboarder puts misaligned job expectations at 30.3% of early exits, ahead of every other cause, and BambooHR found that 42% of new hires felt overwhelmed by too much content at once. Both are fixable at day 30 and expensive at day 90.

How does the role compare to what you expected when you accepted the offer?
What has been the most confusing part of your first month?
Do you have the access, tools, and information you need to do your work?
Is there anything you are still waiting on from IT, HR, or me?
Who have you worked with so far, and who do you still need to meet?
How clear are your goals for the next 30 days?
What do you wish someone had told you in week one?
Have you gotten feedback on your work yet? Was it useful?
What is one thing that would make next month easier?
Is there anything you have been hesitant to ask?

60-Day Check-In Questions

The 60-day check-in tests whether onboarding has turned into a job. By now a new hire should own at least one real deliverable, have received specific feedback on it, and be working with people beyond their immediate team. If any of those three is missing, the ramp has stalled, and this conversation is where you find out.

It is also the check-in most likely to be skipped, because the structured first-month content is over and nothing forces the conversation to happen.

What is the first piece of work you have felt real ownership over?
Which parts of the job feel solid now, and which still feel shaky?
Where are you spending time that does not feel like the real job?
What feedback have you received in the last month, and what did you do with it?
Is anything blocking you that you have not been able to clear on your own?
How well do you understand how your work connects to the team’s goals?
Who outside our team do you work with regularly, and is that working?
Are our 1:1s useful? What would make them more useful?
What would you like to be doing more of by day 90?
What is one thing I could do differently as your manager?

90-Day Check-In Questions

The 90-day check-in closes formal onboarding and opens the regular performance rhythm. It looks backward at the 30-60-90 plan, forward at the next six months, and inward at whether the new hire has the confidence and relationships to succeed. It is also the last low-stakes moment to catch a hire who is quietly reconsidering.

Many companies fold this into a formal 90-day review, which works if the new hire knows in advance. Our manager review template includes a 90-day new hire version.

Looking at your 30-60-90 plan, where did you land against it?
What are you most proud of from your first three months?
Where do you still feel like a new hire, and where do you feel fully up to speed?
How would you describe this job to a friend now, versus at the offer stage?
What part of onboarding should we change for the next person we hire?
What do you want to own over the next six months?
What do you want to learn or get better at?
How would you like to receive feedback going forward?
Is anything about the role, the team, or the company making you reconsider?
What questions do you still have that nobody has answered?

How to Run 30-60-90 Check-Ins So They Actually Happen

Check-in programs rarely fail because the questions are bad. They fail because the later conversations quietly stop happening. The 60- and 90-day check-ins are the easiest meetings to cancel and the most expensive to skip. Schedule all three by start date on day one, put HR in charge of the cadence, and the manager in charge of the conversation.

Pick six to eight questions, not all ten. Reciting a list kills the conversation.
Pair each check-in with a short survey. It gives HR comparable data across hires and catches what people will not say to a manager’s face. Our pulse survey questions include check-in formats.
Write the answers down and compare across hires. One confused person is a coaching moment. Five is a broken step.
Know the red flags. Day 30: still waiting on access, no real work. Day 60: no owned work, no feedback received. Day 90: describes the job exactly as at the offer stage, or hesitates on question 29.

Running New Hire Check-Ins With Windmill

Windmill’s Pulse Surveys include a New Hire schedule: set the number of days after start date once, and Windy, Windmill’s AI agent, reaches out to every new hire at 30, 60, and 90 days through a short Slack conversation. Results go to the pulse’s owners, so HR and managers see the pattern across hires without a spreadsheet.

Windy also builds 1:1 agendas from a new hire’s recent work across Slack, GitHub, Jira, and 20+ other tools, so each conversation starts from evidence, and it can nudge anyone who has not responded.

Book a Windmill demo

Good questions are cheap. Asking them consistently is the hard part.

Frequently Asked Questions

What are 30-60-90 day check-in questions?

They are the questions a manager asks a new hire at the 30, 60, and 90-day marks of onboarding. Each conversation has a different job: the 30-day check-in tests expectations against reality, the 60-day check-in tests whether the new hire has real work and real feedback, and the 90-day check-in tests whether they are ramped and where they go next.

Who should run new hire check-ins, HR or the manager?

The manager should run the conversation, because the questions are about the role and the work. HR should own the cadence: scheduling the three check-ins by start date, making sure they happen, and reviewing patterns across new hires. When HR runs the conversation instead, managers disengage and the answers get generic.

How long should a 30-60-90 day check-in take?

Thirty minutes is enough for each check-in if it is separate from the weekly 1:1. Pick six to eight questions from the list rather than asking all ten, and leave the last five minutes for the new hire to raise anything they have been holding back.

What is the difference between a 90-day check-in and a 90-day review?

A 90-day check-in is a conversation about how onboarding went and what comes next. A 90-day review is a formal evaluation of performance against the 30-60-90 plan, usually documented. Many companies combine them into one meeting, which works as long as the new hire knows in advance that it is a review.

Should new hire check-in questions be a survey or a conversation?

Both, in that order. A short survey at each mark gives HR comparable data across every new hire and catches problems people will not raise face to face. The conversation is where the manager acts on what the survey surfaced. Skipping the survey loses the pattern; skipping the conversation loses the hire.