Check-in questions for meetings: How to get employees to open up

Employee check-in meetings are a great way to regularly touch base with your team members. But despite the best intentions, they can also become one-sided or disengaging. You might find that your meetings with team members are shallow or unproductive. 

So how do you get your team members to feel comfortable and engage in productive conversations?

In this post, we'll guide you through the art of asking the right questions to make your meetings more impactful. We share effective check-in questions that encourage transparency and trust, plus actionable tips to foster a more open environment for honest conversation.

Why employees hold back during meetings

It’s important to understand why employees might hesitate to speak up in meetings. Here are a few common reasons why your team members may not be opening up. 

• Fear of judgment or repercussions: Employees may worry about how their feedback or ideas will be received.

• Lack of psychological safety: If the meeting environment feels hostile or overly critical, employees are less likely to share their true thoughts. 

• Meeting fatigue: Long, unstructured meetings can lead to disengagement, especially if employees don’t feel that their input will lead to meaningful change.

Creating a safe space for employees to express themselves is key. Teams with high psychological safety are more innovative and productive, as members feel more confident sharing ideas and concerns.

How to set the stage for open communication

Before diving into specific check-in questions, create the right environment for honest communication. By laying this groundwork, you’ll set the stage for a more open and investing conversation.

1. Start with trust

Open communication begins with trust. As a leader, you can set the tone by being transparent about your own challenges or doubts. When employees see you as being vulnerable, they’re more likely to reciprocate.

2. Clarify the purpose of check-ins

Employees are more likely to engage if they understand the “why” behind ‌check-ins. Provide context on why you’re asking specific questions. Clarify that your questions are meant to create a dialogue, gather feedback, and make their work experience better.

3. Use positive language

Avoid framing check-in questions in a way that feels confrontational. Use positive, non-judgmental language, and ensure your tone is warm and supportive. You’re offering a place for honest conversation, not criticism.

The best check-in questions to encourage open dialogue

Now that you’ve created a supportive environment, let’s explore some of the best check-in questions to ask during your meetings. Tailor these questions depending on the topic of the meeting with your team members.

1. Personal well-being

Employees’ personal well-being directly impacts their performance. Use these questions to check in on how they’re doing physically, emotionally, and mentally.

• How are you feeling today or recently? How is your health overall?

• How are you spending your time outside of work? Did anything interesting happen? 

• Do you need any support to improve on any area outside of work?  

These questions help you understand employees beyond their work tasks, which fosters a more human connection.

2. Work progress and challenges

Understanding how employees feel about their work helps identify any roadblocks or problems. Helpful questions to understand whether your employees have work challenges include: 

• Are there any work challenges you are facing right now? Is there any way I can support you with that? 

• I noticed your progress on task X, which is very impressive. Is there anything you want to share on the task or any possible blockers on completing this task? 

• Is there a project or task where you’d like more support?

These questions let employees voice their accomplishments and challenges, making it easier for you to offer help where needed.

3. Team dynamics and feedback

For a stronger team, you need to know how employees feel about the group’s overall dynamics. Here are some questions to help you understand how your employees feel about their teams.

• Do you think there are any ways we can support each other better? 

• Is there something you need from me or your teammates to be more effective?

• How do you feel about the way our team collaborates?

Encouraging feedback on team collaboration helps you build teams that are supportive, kind, and work together efficiently.

4. Personal development and career paths  

Encouraging conversations around personal growth and development can help individuals reflect on their own journey, skills, and goals. These discussions not only inspire self-awareness but also provide opportunities for feedback, mentorship, and mutual support. Here’s how you can expand on this topic:

• Is there a particular area you’re passionate about that you’d like to explore more?

• I see you made major progress on area X. Is this field still where you want to focus on? 

• Are there any new skills or areas you’d like to develop in the future? Is there anything you want to change about your career path? 

These questions not only open up dialogue but also help create an environment where continuous learning and growth are prioritized, both individually and collectively.

Tips for arranging check-in meetings

Asking the right questions is important, but so is facilitating the meeting in a way that invites participation. Here are a few key tips on arranging check-in meetings to make your employees comfortable to open up. 

1. Timing and frequency matter

Keep check-ins regular but short. Regular, brief meetings are often more productive than infrequent, long meetings. Timely meetings help your employees feel secure that they have regular opportunities to voice their thoughts without feeling overwhelmed.

2. Be inclusive

Not everyone feels comfortable speaking up. Start by framing questions that invite participation without putting individuals on the spot. Use open-ended questions that allow employees to share as much or as little as they feel comfortable with, and avoid questions that might make people feel singled out or pressured. 

Recognize that different employees may communicate in various ways, so offering multiple ways to respond (verbally, in chat, or through follow-up messages) ensures that everyone’s voice can be heard.

3. Follow up on feedback

Employees who feel their voice is heard are 4.6 times more likely to feel empowered to do their best work. So make sure to follow up on the feedback you receive. 

If employees don’t see any changes after they share their observations, they may stop engaging in honest conversations with you. Take notes and commit to action, even if it’s something small, to show that their input has real value.

4. Active listening 

When an employee offers feedback, acknowledge their perspective without interrupting or rushing to solutions. Show genuine interest in what they’ve shared. This encourages people to feel comfortable sharing, knowing their thoughts will be heard and respected.

If you’re holding group meetings, rotate who gets to speak first or to ask questions in a way that doesn’t always favor the more vocal participants. By making space for quieter or more introverted employees, and by considering diverse perspectives‌ — ‌cultural, gender, or neurodiverse backgrounds‌ — ‌you create a more welcoming environment where employees feel empowered to open up in a way that feels authentic to them.

Remote HR Management to improve team check-ins 

For distributed or remote teams, check-ins can become even more challenging. You don’t have the in-person cues and informal interactions that naturally build rapport and trust. Without the non-verbal feedback that comes from face-to-face interactions, it can feel more difficult for remote employees to open up or share honest feedback. 

That’s why Remote HR Management offers streamlined solutions for running remote check-ins, tracking feedback, and fostering engagement in digital settings. With a single HR platform, you can maintain meaningful connections with employees no matter where they are in the world, ensuring that check-ins are insightful and effective.

Plus, empower your employees with self-service capabilities to access data, manage expenses, and document their thoughts for meetings. To see how Remote HR Management can help you connect with your remote team, create your free account today.