Beyond "How's It Going?": Onboarding questions managers should ask

3 Key takeaways from this blog:

1. Move beyond small talk: Learn the crucial questions to ask at each onboarding phase (Pre-Day 1, day 30, day 60, day 90) to replace unproductive "check-ins" with conversations that give you real insights.
2. Build a framework for success: Discover how to use different tools - from 1-on-1s and anonymous surveys to quick chats - to create a structured (and flexible) strategy for your onboarding conversations. 
3. Act on feedback: Always translate feedback into concrete improvements and follow up with the new employee.

The onboarding black hole

A new hire’s first 100 days are a critical period. They’re excited, nervous, and full of potential. Yet, so often, this potential is squandered. Managers are busy with their own workloads and can fall into a common trap: they assume no news is good news. A quick hallway check-in ("Everything going okay?") met with a nod and a smile, feels sufficient. But beneath the surface, uncertainty builds.

New hires, eager to make a good impression, are often reluctant to admit confusion or ask for help. They might quietly struggle with unclear tasks, new ways of working, or feeling alone. By the time you notice - through missed deadlines or lower motivation - it's often too late to easily fix. If you don't have clear and regular check-ins, these small problems can grow into bigger ones, like disengagement, poor performance, or the employee leaving.

The solution: Structured, intentional conversations

The antidote to the onboarding black hole isn't a grand gesture; it's a consistent practice. Onboarding thrives on regular, meaningful dialogue. By replacing superficial check-ins with a framework of structured conversations, you can:

• Uncover knowledge gaps before they become risks.
• Clarify expectations and ensure everyone is aligned on goals and success metrics.
• Create a safe space for honest feedback, showing you are invested in your employees’ success.
• Help new hires move from being an outsider to a connected, engaged team member.
• Identify and remove roadblocks, providing extra guidance where needed.

Questions to ask your new hire during different onboarding phases

As you now know, structured conversations are the key to successful onboarding. By using a mix of one-on-one meetings, quick chats, and anonymous feedback tools, you can gather honest insights at every stage. Here you will find example questions for each stage:

Pre-Day 1 (Preboarding): Build excitement & reduce anxiety

This phase is about keeping the excitement alive, making new hires feel welcome, and calming any nerves before day one. 

A quick welcome call, a friendly email, or a message in your onboarding app can answer their questions and start building a connection early.

Example questions to check if everything is clear:

• "What questions do you have about your first day that we haven't covered yet?"
• "What are you most looking forward to about diving into your new role?"
• "Is there anything that would help you feel more prepared and confident on Day One?"
• "Thinking about your first week, what does a successful start look like to you?"

Best practice: gather info via your onboarding app
A survey in your onboarding app is perfect for gathering fun facts to personalize your new hires’ experience. This shows you’re paying attention and - if you share the info - helps the team connect with the new hire on a human level.

You could ask:

• “What do you like for lunch?”
• “What’s a hobby or passion project you’re excited about?”
• “What’s one thing that makes your workspace comfortable or productive?”

Use this information to create a personalized welcome kit, plan their first team lunch (with their favourite food), or introduce them to colleagues with shared interests. 

[.callout-small]Check out more ideas for a creative welcome kit.[.callout-small]

The first 30 days: Foundation & connection

The goal here is acclimation and clarity. Establish a rhythm of weekly 1-on-1 meetings for deeper discussions, and use quick chat messages (Slack/Teams) for simple, non-intrusive check-ins on resources and access. 

You could also ask for onboarding improvements via a survey or feedback questions in your onboarding app.

Example questions to ask:

• "What part of the onboarding process has been most helpful so far? What’s been confusing?"
• "Do you have the tools and access you need to do your job effectively?"
• "How clear are you on your top priorities for these first few weeks?"
• "Who have you enjoyed connecting with so far? Is there anyone in the company you’d like an introduction to?"

Days 30-60: Contribution & applying knowledge

The focus now shifts to helping the new hire contribute effectively and build momentum. Support them as they apply their knowledge and make sure they have what they need to be effective in their core responsibilities.

Continue 1-on-1s to discuss progress and challenges. Introduce an anonymous survey to gather candid feedback on the onboarding process without putting the new hire on the spot.

Example questions to ask:

• “What’s a task or project you’ve started to own? How can I best support you?”
• “How are you settling into your role?”
• "What has been your biggest challenge in the last few weeks?”
• "How does the reality of the role so far match what we discussed during the interviews? Is there anything that seems different?"
• "Looking at your initial goals, what support do you anticipate needing from me or the team to meet them?"
• “Do you feel you have all the resources and tools you need to perform your job effectively?
• "Which part of your onboarding has been most useful in your day-to-day work?"
• “What’s one process you think could be improved?”

Days 60-100: Impact & confidence

The goal here is to solidify the new hire's confidence and help them see their growing impact. Use your 1-on-1s for more strategic conversations about impact and growth. An anonymous survey can also be a safe channel for them to provide feedback on your management style.

Example questions to ask:

• "What’s a recent win you’re proud of?"
• "How do you see your work contributing to larger company goals?"
• "What part of your role are you feeling most confident in now?"
• "Do you have everything you need to do your work effectively, or is anything still missing?”
• “What are the biggest barriers preventing you from being even more effective?”
• "How can I better support you in your day-to-day work?"
• “How comfortable do you feel with the team and the company culture?”

The 100-Day Evaluation: Look back & plan forward

This milestone marks the transition from onboarding to full contribution. Schedule a dedicated 1-on-1 meeting, separate from your regular catch-ups.

Frame this as a collaborative strategic conversation rather than a formal evaluation, focusing on reflection, alignment, and future growth.

Make sure you co-create the agenda. Share questions in advance and invite your employee to add their own topics. And don’t forget to document commitments. Capture agreed-upon goals and support measures.

Example questions to ask:

• "Looking back at your first 100 days, which accomplishments are you most proud of and why?"
• "What surprised you most about the role, our team, or how we work together?"
• "How does the reality of the role differ from your expectations?"
• “What are your professional goals for the next six months?”
• “What personal goals would you like to achieve in the coming months?”
• "What aspects of our culture have resonated with you most, and which have been most challenging to adapt to?"
• "What advice would you give me about managing someone in your role effectively?"
• "What resources, information, or support would help you maximize your impact in the next quarter?"
•  “What has been the most valuable part of your onboarding experience?"
• "Based on your experience, how can we improve onboarding for the next person?"

Best practice: Make it a celebration

Mark this milestone by explicitly acknowledging their progress and officially welcoming them as a fully integrated team member. To make it memorable, establish a small tradition that fits your culture.

For example, at Appical, new hires receive a special sweater after 100 days. Or, take inspiration from Personio: let the employee choose the restaurant for their review, turning the conversation into a special occasion.

Turn feedback into action

Asking good questions is important, but what you do with the answers matters most. If a new hire shares feedback and nothing changes, it can break trust faster than not asking at all.

The key is to show you’re listening by taking visible action. Start by simply thanking them for their input. Then, prioritize their feedback: address quick fixes immediately, such as a missing software login, and schedule time to discuss larger issues later. 

Most importantly, always close the loop.  A simple follow-up like, "Thanks for mentioning that, here's what we'll do," shows their voice is heard and builds trust.

Conclusion

The difference between a new hire who struggles and one who thrives often comes down to consistent, meaningful support. By replacing superficial check-ins with intentional dialogue, you build the trust and clarity needed for long-term success. So, the next time you meet, skip the “How’s it going?” and ask one intentional question instead. You might be surprised just how much you both stand to gain.