30 impactful questions to ask during employee 1-on-1s

Employee 1-on-1s are one of the most overlooked tools for improving both wellbeing and performance. When they’re done right, they become more than just monotonous meetings. They turn into a reliable source of insight on how people are really doing and what they need to thrive.

Due to the hustle and bustle of day-to-day operations, it’s easy for managers to slip into a routine where 1-on-1s are treated as simple status updates, quick task reviews, or surface-level check-ins that miss the deeper conversations employees actually need.  

Worse yet, some managers begin replacing 1-on-1s with group standup meetings or simply cancel them altogether. At first, it might seem like a practical decision. Cutting a recurring meeting can feel like a win for efficiency, especially on a packed calendar. But 1-on-1s serve a purpose that no group meeting can replicate. They offer a private space for open conversation, honest feedback, and individual support. When that space disappears, so does the opportunity to catch issues early, build trust, and stay closely connected to what employees need to do their best work.

Below is a categorized set of questions designed to support more meaningful, well-rounded 1-on-1 conversations that strengthen both individual wellbeing and team performance. These conversations can surface misalignment, catch signs of burnout early, and help people feel seen, supported, and set up to succeed. 

Building a culture of listening

Regular 1-on-1s aren't just a time slot on the calendar. They reflect a deeper cultural mindset that values listening as a strategic asset. Listening builds trust. It shows that each employee's experience matters and that their input isn’t just tolerated, but welcomed. For leadership, it’s also one of the most effective ways to stay connected to reality on the ground.

But this kind of listening takes intention. Let employees lead when they’re ready to. Encourage them to bring topics, questions, or challenges to the table. The role of the manager is to make space, ask thoughtful questions, and respond with full attention.

It’s also important not to confuse listening with agreeing. Sometimes what’s needed most is a willingness to hear tough feedback or hard truths without defensiveness. That openness sets the tone for a culture where ideas and concerns can be aired early, before they grow into problems.  

It’s also important to note that listening requires follow-through. If someone shares something vulnerable or makes a request, track it, follow up, and close the loop. That’s what turns a good conversation into real progress.

If you’re looking for ways to build a culture of listening at your organization, the Navigate platform features streamlined communication tools that make it easy to gather valuable feedback. Use our list of employee engagement survey questions to gain real-time insights into how teams are feeling, helping leaders identify strengths, address concerns, and take action before small issues grow into larger challenges.  

Core categories of questions to ask during 1-on-1s

Below are six categories of questions to help structure more meaningful and productive 1-on-1s. You don’t need to ask every question each time. Use them as a guide, rotating focus depending on what feels most relevant. 

Workload and priorities

An employee’s workload has a direct impact on both performance and wellbeing. When priorities are clear and responsibilities feel manageable, people are more likely to stay engaged and deliver high-quality work. On the other hand, if the workload is overwhelming or misaligned, it can quickly lead to burnout, disengagement, and missed deadlines. These questions help you understand what your employee is focused on, how sustainable their workload feels, and whether they’re running into friction that needs to be addressed.

• Is your current workload sustainable?

• Do you feel you have the support you need to manage your workload?

• Do you feel like your current deadlines are reasonable?

• What resources would be helpful to manage your workload?

• Are there any roadblocks currently standing in your way?

These kinds of questions can flag misalignment early and reveal hidden obstacles that might otherwise go unspoken. 

Wellbeing and stress levels

Employee wellbeing is foundational to both productivity and long-term retention. When people feel supported and balanced, they bring more energy, focus, and creativity to their work. If stress or burnout goes unnoticed, it not only impacts the individual but also the team around them. These questions invite openness without prying, helping surface signals that may point to stress, overwork, or disengagement.

• How have you been feeling lately, in and out of work?

• What’s energizing you right now? What’s draining you?

• Are you getting enough time to recharge during the week?

• Is anything outside of work affecting your focus or energy?

• Do you feel comfortable speaking up if you’re feeling overextended?

Even if an employee chooses not to go into detail, the act of asking reinforces that their wellbeing matters. Of course, employee wellbeing goes far beyond asking your team a few poignant questions. Navigate’s employee wellbeing platform seamlessly integrates physical, mental, financial, and social wellbeing initiatives, creating a culture of holistic health that not only enhances individual lives but also drives organizational success.  

Growth and development

Opportunities to grow are one of the strongest drivers of engagement and retention. When employees see a path forward and feel they are building new skills, they are more likely to stay motivated and committed to the organization. Growth can take many forms, from learning new capabilities to taking on stretch projects or preparing for leadership roles. These questions help clarify whether the employee feels they’re learning, progressing, and building a meaningful future within the company.

• Are there career paths or roles within the company that interest you for the future?

• Are there any skills you’d like to develop or sharpen?

• Do you feel you're growing in your role? Why or why not?

• Is there a type of project you’d love to get involved in?

• Are there mentors or colleagues you’d like to learn from more closely?

Development doesn’t have to mean promotion. It can mean more learning resources, different challenges, or a shift in focus. What matters is showing that growth is on the table. 

Manager support and team dynamics

The relationship between employees, their manager, and their team has a direct influence on day-to-day performance and overall job satisfaction. When people feel supported by their manager and connected to a healthy team environment, they are more likely to collaborate effectively and stay engaged. Without this foundation, even the most talented individuals can struggle to thrive. This is where you open the door to feedback on your leadership style and the broader team environment. Done well, these questions build transparency and uncover opportunities to lead more effectively.

• Is there anything I can do to support you better?

• Do you feel your contributions are recognized?

• How is collaboration going within the team?

• Are there any team dynamics you'd like to see improved?

• What’s something we could do differently that would make your work easier?

These conversations are where psychological safety really gets tested. Making space for honest input, even when it’s uncomfortable, signals real trust to your team. 

Purpose and motivation

A sense of purpose is one of the strongest predictors of employee engagement. When people understand how their work connects to something larger, they are more motivated and resilient in the face of challenges. Without that connection, tasks can start to feel routine and uninspiring, which leads to disengagement over time. These questions help employees reconnect with the meaning behind their work and highlight what drives their motivation on a daily basis.

• What are your goals over the next year, and how can I help support them?

• What part of your work feels most meaningful right now?

• When do you feel most motivated at work?

• Do you feel connected to the broader mission?

• Do you feel that you can effectively utilize your strengths in your current role?

Motivation isn’t a fixed trait. It’s influenced by environment, recognition, challenge, and connection. Understanding what lights people up helps you keep that flame going. 

Feedback and communication

Open communication is the backbone of a healthy workplace. Employees need to know they can share ideas, raise concerns, and give feedback without fear of being dismissed or overlooked. Likewise, managers need clarity on how their communication is being received and what adjustments might help build stronger connections. These questions help strengthen two-way communication, uncover unspoken issues, and create space for dialogue that builds trust.

• Do you feel comfortable sharing feedback with both leadership and peers?

• Is there anything you’ve been wanting to bring up that we haven’t discussed yet?

• How do you prefer to receive feedback?

• Do you feel like everyone on the team is on the same page?

• What’s one thing I could be doing differently to support clearer communication?

Sometimes these questions will open the door to direct feedback. Other times, they’ll reveal that people aren’t sure where or how to speak up. Both are worth knowing. 

Putting it into practice

You don’t need a script to run a good 1-on-1. You need presence, consistency, and curiosity.

Use these questions as a toolkit, not a checklist. Some meetings may stay focused on one category. Others might move across several. What matters is that employees leave the conversation feeling heard and supported.

Take notes during or after each meeting so you can follow up later. Whether it’s a development goal, a stressor, or a suggestion, looping back shows that what’s said in the 1-on-1 doesn’t disappear. You don’t have to have all the answers immediately. Just being there, asking the right questions, and listening carefully goes further than most realize.

Ready to build a culture of listening in your organization? Book a personalized demo of the Navigate platform today to see how we can transform employee wellbeing.