30-60-90 Check-In Questions

An effective performance management strategy is one that’s continuous. These frequent evaluations at regular intervals provide necessary support to help your people achieve their goals and problem solve issues.

While this is important for all employees, constant check-ins are critical for new hires. In the first 90 days, employees are learning about your company, taking on new responsibilities, and discovering opportunities within their role. During this time, they may require a lot of hands-on engagement from their managers. With new AI-powered tools, HR teams can now analyze early-tenure feedback more effectively and give managers deeper insight into how new hires are adjusting.

It’s best practice for managers to have proactive check-ins with their new direct reports at the 30-day, 60-day, and 90-day marks.

These 30-60-90 check-in meetings should have clearly defined agendas that cover all areas of the new hire's work-life, reflection, feedback, and goal-setting. Every company has unique contexts to consider, but here's a list to get you started building out your questions to best support your people.

30-Day Check-In: The Discovery Phase

The 30-day review is beneficial for the new hire, manager, and company as a whole. It allows the employee to reflect on their first 30 days and ask any questions about the company or role. This check-in also gives managers the time to restate expectations and better understand the employees’ strengths and weaknesses so far. AI summaries can help HR spot early patterns in new-hire feedback—such as common onboarding gaps or recurring pain points.

Additionally, 30-day check-ins provide insights as to the effectiveness of your organization’s onboarding process. If employees are confused or overwhelmed, it may be time to reconfigure your onboarding strategy.

Reflection Questions

• How do you feel after your first month?
• So far, is your role what you expected it to be?
• Have you felt welcomed by your new team?

Planning Questions

• What was your biggest time waster?
• What accomplishment would make you happy?
• What was your biggest challenge this past month?

60-Day Check-In: The Ownership Phase

During the ownership phase, employees are better able to discuss their day-to-day tasks and relationships within the team. They’ll now have more experience to dive deeper into the following questions. At this stage, AI-generated insights can show whether new hires are ramping as expected or where additional support may be needed.

Reflection Questions

• How do you feel after your second month with the company?
• What's something you discovered recently that you wish you would have known sooner in your onboarding process?
• How well positioned did you feel to accomplish your 60-day goals?

Planning Questions

• What are some of the missing pieces to the puzzle you'd like to learn in the next 30 days?
• What goals do you feel like should be your priority?
• What would make the next 30 days feel like an accomplishment?

90-Day Check-In: The Growth Phase

Now that your employee is three months in, you can work together to set long-term goals, identify professional development opportunities, and ramp up responsibilities. By this point, it’s also easier to recognize if this person is a strong fit for the position and company, or if they’re better suited elsewhere. Looking across many 90-day reviews, AI can identify what predicts long-term success and help you continuously refine your onboarding process.

Reflection Questions

• How do you feel after being with the company for 3 months?
• What have you enjoyed most in your first 90 days?
• Do you feel that your onboarding process was successful?
• What has been the most surprising about your role? The company?

Planning Questions

• How do you see your role progressing from now on?
• Is there anything you need more time on in terms of onboarding?
• What from your onboarding experience should we change to better help new hires get acclimated?

How AI Helps You Run Better 30-60-90 Day Check-Ins

While nothing replaces thoughtful conversations between managers and new hires, AI can make your 30-60-90 day process more efficient and insightful. With ChartHop’s AI capabilities built directly into your HRIS, managers and People teams can uncover patterns, prepare for check-ins faster, and support new employees with data-backed decisions.

1. Spot Themes Faster with AI Summaries

If your check-ins include written feedback, ChartHop AI can analyze all responses across new hires and summarize what’s working and what needs attention.
It surfaces common themes, recurring challenges, onboarding gaps, and bright spots so you don’t miss critical insights hiding in individual responses.

2. Turn Check-In Data Into Meaningful Insights

ChartHop AI can also analyze quantitative data from your 30-60-90 check-ins, including:

• Performance ratings
• Engagement scores
• Time-to-productivity metrics
• Skill development progress

It then provides concise summaries so managers can quickly understand how new hires are progressing and how onboarding is performing across the organization.

3. Use Conversational AI to Prepare for Manager 1:1s

Managers can “Ask ChartHop” questions before check-ins, such as:

• “How is my new hire progressing compared to their peers at 60 days?”
• “Have they hit their onboarding milestones?”
• “Show me their goals and any outstanding tasks for our next meeting.”

This gives managers the context they need to have more supportive, productive conversations.

4. Filter New-Hire Data in Plain Language

No spreadsheets. No complicated reporting. With natural language filtering in ChartHop, you can ask:

• “Show me all 30-day check-ins where onboarding satisfaction was under 4.”
• “Compare 60-day feedback across departments.”
• “Which new hires may need extra support based on early feedback?”

AI instantly produces the answer, grounded in your real HRIS data and permissions.

5. Improve Onboarding Over Time with Trend Analysis

Because ChartHop keeps historical data, AI can highlight:

• Long-term onboarding trends
• Turnover patterns in early tenure
• Recurring challenges at the 30, 60, and 90-day marks

This helps HR continuously refine the onboarding program—not just reactively.

Make the Most of Your 30-60-90 Check-Ins

Your people should feel supported no matter how many days, months, or years they’ve worked at your company. However, those first 90 days are crucial to employee success (and, in fact, retention), so it’s important to schedule check-ins to ensure they understand role expectations and are meeting their goals. With the support o AI tools, managers and HR teams can keep a better pulse on these early experiences through trend summaries and real-time insights based on your HRIS data.