50+ New Hire Check-In Questions by Timeline

Most new hires who quit do so silently. They smile in meetings, say everything is fine, and then give two weeks notice. By the time you realize something was wrong, it is too late.

The fix is simple: ask better questions, earlier. Regular check-ins catch problems when they are still fixable. They show new employees you care about their experience. And they give you the feedback you need to improve onboarding for everyone who comes after.

This guide gives you 50+ questions organized by timeline: from week one through six months. Use them as a menu, not a checklist. Pick the questions that fit your situation and skip the rest.

Why Check-Ins Matter

The numbers are stark. Over half of employees who voluntarily leave say their manager or company could have done something to prevent it. The most common response? Nobody asked how things were going.

New hires are especially vulnerable. They are still figuring out if they made the right choice. Small frustrations feel bigger because they do not have context. Without regular check-ins, these frustrations compound until leaving seems like the only option. This is one of the most common onboarding mistakes small businesses make.

Employees who receive weekly feedback are five times more likely to be engaged than those who receive annual reviews only. For new hires still forming their opinion of your company, this matters even more.

When to Check In

Check-in frequency should start high and taper off as the employee settles in. The first week is critical. By six months, monthly conversations are usually enough.

These are guidelines, not rules. A senior hire who has done similar work before might need less handholding. A junior employee in their first professional role might need more. Adjust based on what you observe.

Week 1 Questions

The first week is about comfort and clarity. New hires are overwhelmed with information, new faces, and unfamiliar systems. Your job is to make sure they have what they need to do basic work and feel welcome enough to ask questions.

Day One and Two

How was your first day? Open-ended on purpose. Let them tell you what stood out, good or bad. Listen more than you talk.

Do you have everything you need to start working? Computer, passwords, access to systems, basic supplies. Forty-three percent of new hires wait over a week for basic tools. Do not let yours be one of them.

Is there anything that surprised you so far? Surprises can be positive or negative. Either way, they reveal gaps between expectations and reality.

End of Week One

Have you met everyone on your immediate team? If not, arrange introductions. Feeling isolated in week one is a major red flag. Consider pairing them with an onboarding buddy who can help with informal introductions.

Do you feel comfortable asking questions when you are stuck? This reveals whether they feel psychologically safe. If they hesitate, probe deeper.

What could we have done to make your first week better? Ask this while the experience is fresh. You will get more honest answers now than in a survey three months later.

Is the role what you expected based on the interview process? Misalignment between job descriptions and actual work is a top reason new hires quit. Catch this early.

30-Day Questions

By day thirty, the honeymoon period is ending. Initial excitement fades. New hires start seeing how things really work, not just how they were described. This is when doubts creep in.

Progress and Fit

Do you feel you made the right choice coming here? Direct and important. If they hesitate, dig into why.

What progress have you made in the last 30 days? Helps them recognize their own growth, which builds confidence.

Is the job what you expected it to be? Similar to week one, but now they have real data to compare against expectations.

Are you feeling challenged by the position? Too easy is just as bad as too hard. Both lead to disengagement.

Support and Resources

What tools or resources do you need that we have not provided? Sometimes they need software, sometimes training, sometimes just clearer documentation.

Do you have adequate access to your supervisor? If they feel their manager is unavailable, address this immediately.

Do you feel like you are integrating well with your team? Social connection predicts retention. Isolated employees leave faster.

Looking Ahead

What would you like to focus on in the next 30 days? Encourages goal-setting and gives you alignment on priorities.

Which aspects of your role are you most excited about? Most anxious about? Both answers are valuable. Excitement shows engagement. Anxiety shows where to provide more support.

60-Day Questions

Two months in, new hires should be contributing meaningfully. The questions shift from survival to growth. You are checking whether they can work independently and whether they see a future here.

Independence and Performance

Do you have everything you need to perform your job? By now, any remaining gaps in tools or training should be obvious.

Are you getting constructive and timely feedback on your performance? Feedback-starved employees cannot improve. And they often leave because they assume silence means disapproval.

Do you find your position challenging but not overwhelming? The sweet spot is stretch without stress.

Relationships and Culture

Have you had meaningful one-on-one meetings with your supervisor? Not just status updates, but real conversations about growth and goals.

Do you feel respected and valued by your coworkers? Feeling undervalued kills engagement faster than almost anything else.

Are you creating a healthy work-life balance? Some new hires overwork to prove themselves. This is not sustainable.

Growth and Development

What are you most proud of having done in the last 60 days? Reflecting on wins builds confidence and momentum.

Are there any skills you need to learn to improve? Shows initiative if they can identify gaps themselves.

How can we help you grow professionally over the next few months? Signals that you are invested in their long-term development, not just their current output.

90-Day Questions

Ninety days is the traditional end of onboarding. By now, you should know if this hire is going to work out. The questions get more direct about satisfaction and retention.

Satisfaction and Retention

Are you happy with your decision to accept this job? The most direct question you can ask. Their answer tells you a lot.

Is there any reason you would consider leaving? Uncomfortable to ask, but necessary. Better to hear it now than in an exit interview.

What would make your job more satisfying? Often reveals small changes that have big impact.

Role and Fit

What do you look forward to when you come to work each day? If they struggle to answer, that is a problem.

What talents do you have that are not being used? Underutilized skills lead to boredom and disengagement.

If you could change something about your job, what would it be? Gives them permission to be honest about frustrations.

Manager and Team

What can your manager do to support you better? Actionable feedback for the direct supervisor.

Who has been most helpful during the learning process? Identifies informal mentors and strong team players.

How do you fit in with the team? Social integration is critical for retention.

Looking Forward

Have you set any personal goals for yourself? Self-directed goals show engagement and initiative.

Do you feel prepared and supported to meet your performance goals? Aligns expectations between you and the employee.

What can we do to make training more streamlined for future new hires? Turns their experience into process improvement.

6-Month Questions

Six months is when new hires become regular employees. The questions shift from onboarding to ongoing engagement and career development.

Reflection and Performance

Tell me about your best week and your worst week since starting. The stories they choose reveal what matters to them.

On a scale of 1 to 10, how would you rate your performance and why? Self-assessment shows how accurately they evaluate their own work.

Where have you excelled and where can you continue to improve? Balanced question that acknowledges growth while identifying development areas.

Expectations and Career

Does the role meet your expectations? By now, they know the real job, not just the job description.

Do your expectations of the work change in the next six months? Reveals whether they see a future or are already thinking about what comes next.

Are the company values aligned with your own? Cultural fit becomes clearer over time. Misalignment eventually causes friction.

Support and Growth

How can I help you succeed over the next six months? Demonstrates ongoing investment in their development.

What is your greatest challenge at the moment? Opens the door for problem-solving together.

Are there specific skill sets or extra training you would recommend? Identifies development opportunities they have noticed.

Remote Employee Questions

Remote employees face unique challenges. They miss informal interactions, struggle with isolation, and often feel disconnected from company culture. Add these questions to your regular check-ins if you have remote or hybrid team members.

Connection and Isolation

Do you feel connected to your team despite working remotely? Connection does not happen automatically through Slack and Zoom.

Have you had opportunities to meet team members socially? Virtual coffee chats, online games, or video happy hours all count.

Do you feel equally included whether you are in the office or working remotely? Hybrid environments often favor in-office employees unintentionally.

Work Environment

Do you have all the technical equipment you need to work effectively from home? Monitor, keyboard, chair, reliable internet. Small investments make big differences.

Are you able to maintain healthy boundaries between work and personal time? Remote work blurs these lines. Some people overwork. Others struggle to stay focused.

Do you feel pressure to be always on? This leads to burnout. Address it directly if they say yes.

How to Conduct Effective Check-Ins

Having good questions is only half the battle. How you ask matters just as much as what you ask.

Create Psychological Safety

New hires will not share problems if they fear consequences. Start check-ins by reminding them that honest feedback helps you help them. Never punish someone for telling you something is wrong.

Listen More Than You Talk

Aim for an 80/20 split. They talk 80 percent of the time. You talk 20 percent. Your job is to ask good questions and then get out of the way.

Take Notes and Follow Up

Write down what they tell you. If they mention a problem, follow up on it at the next check-in. Nothing kills trust faster than asking for feedback and then ignoring it.

Schedule Consistently

Put check-ins on the calendar as recurring events. Treat them as non-negotiable. Canceling or rescheduling sends a message that these conversations are not important.

Frequently Asked Questions

How many questions should I ask in one check-in?

Three to five is usually right for a 20-minute conversation. Pick the most relevant questions from each timeline rather than trying to cover everything. Quality over quantity.

What if the employee says everything is fine but seems unhappy?

Trust your instincts. Try asking the question differently: "If you had to change one thing about your experience so far, what would it be?" Sometimes rephrasing helps people open up.

Should HR or the manager lead these check-ins?

The direct manager should lead most check-ins because they have the best context and the ability to make immediate changes. HR can do a separate check-in at 30 and 90 days to catch issues employees might not share with their boss.

How do I handle negative feedback?

Thank them for being honest. Ask clarifying questions to understand the root cause. Tell them what you will do about it and when. Then actually do it. Nothing builds trust faster than taking action on feedback.

What if I do not have time for all these check-ins?

You do not have time not to. The cost of replacing an employee who quits in the first year is 50 to 200 percent of their annual salary. Fifteen minutes of conversation is a small investment against that risk. If you want to measure whether your check-ins are working, track your onboarding KPIs like 90-day retention and time-to-productivity.

Start This Week

You do not need a formal program to start. Pick your newest hire. Schedule a 15-minute conversation. Ask three questions from the list that matches their timeline.

The goal is not perfection. It is consistent, genuine interest in how they are doing. New hires who feel heard and supported stay longer, perform better, and become advocates for your company.

At FirstHR, we built check-in reminders and question templates into the platform because we know how easy it is to let these conversations slip. But even without software, you can start today. Your new hires will notice the difference.