The Best Check-in Questions for Meetings: Building Stronger Connections with Your Team

Teams aren't just about tasks and timelines. They're ecosystems thriving on rapport and understanding. And for managers, leaders, or anyone steering the ship, knowing your crew is crucial. 

But meetings are not everyone's cup of tea, especially when it comes to one-on-one sessions. 

So, how do you spark dialogues that create depth, insight, realness, and connection? That's the art of check-in questions.

For those seeking to transform meetings into melting pots of insights, for those aiming to know their team beyond the spreadsheets, this is your toolkit. 

🗣️ What do you talk about in a check-in?

Conducting check-ins is an excellent opportunity for you to get updates and connect with your employees. 

The discussions can vary from relationship-building with colleagues, sharing project updates or progress, reviewing goals and objectives, reporting employee performance, and offering support when needed.  

"A manager is in place to help clear roadblocks and help team members succeed. Therefore, the main purpose of a one-on-one meeting should be to expose what's getting in the way, help find a solution, and check in to make sure previous roadblocks have been cleared." Henry O'Loughlin at Buildremote.

📅 Check-in questions for weekly meetings

Preparing check-in questions for weekly meetings can be a great way to gauge team priorities and setbacks from the previous week and set expectations for the following week. 

When setting one-on-one meetings with your team members, it's important to talk about their current workload so you can offer support when needed. 

Your check-in questions for weekly meetings can include: 

Previous week's summary:

• What are your and your team's priorities from the previous week? 
• What accomplishments from the past week are you most proud of?
• What specific task has kept you preoccupied from last week? 
• What challenges and setbacks have you encountered? If none, what do you foresee as potential risks that can hinder your progress? 

Support or resources needed from the team:

• Using a percentage, how heavy is your workload at the moment? 
• How can we support you in ensuring the success of your project? 
• What resources or support do you need moving forward?

Projects or tasks in the pipeline for the current week:

• What upcoming projects or tasks are you looking to accomplish for this week? 
• What have you learned from our last check-in that you can apply moving forward? 

➡️ Not sure how to get started? Download this weekly one-on-one template for your next check-in. 

➡️ Start thinking ahead to empower your team. Use our monthly one-on-one template for a productive check-in meeting. 

🤝 Relationship check-in questions

Relationship check-in questions can be a great way to understand your employees better. Doing so allows them to foster transparent and open communication about their feelings about the management and the workplace. 

Relationship check-in questions can include the following: 

Seeking feedback from employees:

• What do you like most about our working relationship?
• Is there anything you would like to change about our working relationship?
• Do I meet your expectations as a manager?
• What improvements in our dynamics do you want to recommend?  
• On a scale of 1 to 10 (10 being the highest), what do you think is our level of trust from each other? 

Assessing the employees' career plans within the company:

• Are you satisfied with your current position? 
• What are your recent wins, both personally and professionally?
• Do you feel you are headed in the right direction regarding your career path? 
• What support do you need to help us achieve your career goals? 

📈 Performance check-in questions for meetings

You can use your check-ins with your direct reports to share feedback about their performance and work together to achieve specific goals and objectives in the workplace. This can be an excellent opportunity to conduct a performance review meeting where you discuss gaps in knowledge and current achievements and clarifications about the role if needed. 

Performance check-in questions can include the following:

Accomplishing a task or project: 

• What specific task helped you step up this week? 
• Can you share the report from your last project? 
• If successful, what was the most challenging task you encountered during this project? 
• If delayed, what do you think can be done moving forward? 
• What short-term and long-term goals would you like to share in achieving the success of this project? 
• How do you work towards achieving your goals? 
• Are there notable achievements about your current tasks or projects you would like to share? 

Overall performance of the employee: 

• How do you feel about your current job role? 
• What are your strengths and weaknesses as an employee? 
• Do you think you are maximizing your strengths enough?
• How are you working towards conquering your weaknesses? 
• Where do you see your role progressing in the next 1/3/5 years?
• Are there specific training or development opportunities you want us to support you with? 

👩‍⚕️ Mental health check-in questions

Mental health has been a top concern for most employees as it can affect their performance at work. In fact, according to a study, 92% of employees encounter mental health challenges that impact their work. 8 out of 10 employees consider mental health support when choosing employers. This means asking mental health-related questions during your check-ins is a great way to offer them the mental health support they need.

Some mental health check-in questions should include: 

• On a scale of 1 to 5 (5 being the highest), how high are your current stress levels? 
• What makes you feel stressed? 
• What makes you feel anxious, and how often do these feelings arise?
• Are you happy with your job? What would you like to change to make you happier? 
• What keeps you motivated at work and life in general? 
• What keeps you inspired at work and life in general? 
• How do you handle your emotions? 
• What helps you stay productive and focused at work? 
• What are the things you're grateful for?
• What do you do during your free time to relax? 
• How do you practice self-care? 

😊 Fun check-in questions

Some check-ins do not necessarily have to be serious. Sometimes, keeping things light at the beginning can be a great icebreaker to make employees feel comfortable opening up about their feelings at work. 

Some fun check-in questions to break the ice during meetings can include: 

• What was the first thing you thought about when you woke up today?
• What is one thing on top of your bucket list you would like to share? 
• What's something interesting about your family history? 
• What is your secret talent? 
• If you could choose any superpower, what would it be and why? 
• If you could say one thing to the entire world right now, what would you say? 
• What is your favorite or go-to film, and why? 
• What is your dream destination?
• Out of all the places you've been in, what's your favorite destination and why? 
• If time travel exists, do you wish to travel back in time or to the future? 

🖥️ Check-in questions for virtual meetings

The challenge with virtual meetings is getting your remote team to listen and focus. So, you have to make them as engaging as it is with face-to-face meetings. To do this, ensure the same level of engagement so your employees can be comfortable sharing during your check-ins. You can ask fun icebreaker questions or ask them to write written responses that you can discuss during the meeting.

Some check-in questions you can add to keep virtual meetings engaging include:

• What is the best part about working remotely? 
• What's your favorite space in your home office? 
• What's one thing you like to change about your home office? 
• How do you spend your day off? 
• How do you set boundaries after work hours when working remotely? 
• What would you like to change about the idea of working remotely?
• Are you as productive working from home as in an office?
• What would help make your work easier? 
• What challenges do you encounter in managing distractions? 
• How do you prevent burnout?
• Do virtual team meetings drain you? How can we manage it?
• What remote tools will help you? Are the current resources and tools you have enough? 

🗣️ Why are check-ins important? 

Improving team collaboration

When there is regular communication among your team members, it makes it easier to delegate or work together on a task. It also becomes easier for you and your colleagues to interact and bond over work, which can help foster team collaboration. 

Setting company and individual goals and objectives

During check-in meetings, managers can take this as a great opportunity to discuss the new goals and brainstorm on how to achieve your goals together.

Doing this can help employees know what to prioritize.

Plus, when you meet regularly, you can track progress and help set them in the right direction.

Identifying opportunities to solve a problem together

One of the skills managers should possess is learning to identify potential challenges that affect the quality or productivity of a project the team is currently working on. Having check-ins with your colleagues opens discussions on potential risks or challenges for certain tasks. 

Creating a sense of accountability

Check-in meetings allow employees to share updates on the progress of each project and open discussion for evaluation. This creates an opportunity for employees to take ownership of their projects and can increase their motivation to put in the effort to deliver a good quality output. 

🤩 How to improve meeting productivity and participant engagement with check-in questions: 6 Helpful tips

Check-in meetings are vital to foster team collaboration, communication, and alignment. However, keeping the meeting productive and making employees participate is a challenge.

Here are practical tips to help improve your check-in questions.

Set a clear agenda

Whether it's checking up on their performance, a project or task, or simply doing a general check-in, establishing the purpose of the meeting at the start of the call can help set expectations and prevent the discussion from getting derailed. 

➡️Come to your 1:1 check-ins prepared. Here are some one-on-one meeting templates to help you keep your meetings structured and organized. 

Start with simple questions

It's always a good idea to start with a simple question about how they're feeling to begin the conversation on a personal level. Then, ask if they need support at work to build rapport and make them feel cared for. 

Remember to let the employee drive the conversation so they can freely discuss any possible issues with you. ‍

"To keep employees engaged in these meetings, it's important to begin the check-in in a casual fashion and be open to sharing personal tidbits or using stories to show empathy or commiserate. Remain open and empathetic to situations that may arise in performance check-ins and listen actively." Jarir Mallah, HR Specialist and Hiring Manager at Ling App.

Ask open-ended questions

The best way to encourage participation is to leave open-ended questions that can open discussions, opinions, insights, or experiences.

For example, instead of asking, "Do you think this plan is good?" ask, "What are the pros and cons of this plan?" or "What do you like to change about this plan?". This stirs curiosity and critical thinking, allowing your employees to feel valued when heard.

Celebrate big and small wins

During your check-ins, ensure you allot time to acknowledge and appreciate big and small wins.

Express gratitude to your team members for sharing their thoughts, celebrate their accomplishments, and recognize their strengths. This allows you to encourage participation and make employees speak up during meetings to ask questions and offer recommendations or suggestions. 

Track progress and adjust as needed

Constantly monitor your check-in meetings' effectiveness and make the necessary adjustments to the agenda, frequency, format, or questions to make it more productive and effective. Keeping a pulse on the employees' preferences will align your check-in meetings more with your goals.

Seek feedback and recap 

Allow your team members to share how check-in meetings can be improved. Check patterns for the 1-on-1s and implement changes based on their suggestions. Doing so can help make your meetings both engaging and effective.

➡️ Conduct better check-in meetings with Zavvy

Structuring effective check-in meetings can help build better connections with your employees. The key is to ask the right check-in questions that drive consistency and accountability, making your meetings more engaging and dynamic.  

Zavvy can help you run productive meetings by: 

• Automatically creating calendar events for all participants to the meetings.
• Setting up different types of check-ins with the same employee (e.g., performance check-ins, developmental conversation, etc.)
• Creating pulse questions for meetings to check in on blockers, task load, employee well-being, and more.
• Setting a collaborative agenda that you and your team members can agree to discuss before the 1:1 check-ins to ensure alignment.
• Saving action items that you can keep track of and prioritize during your next check-in.
• Recording private notes to help you evaluate and improve check-ins continuously.

Zavvy's AI-powered one-on-one meeting software helps you transform boring and unproductive meetings into structured, organized, and interactive check-in meetings that can help engage team members and boost company performance.

📅 Book a demo now to see the power of Zavvy.

❓ FAQs

What types of check-in questions are suitable for different types of meetings?

Whether it's 1:1 meetings or group meetings, the right check-in questions would depend on the agenda for the meeting. Relationship and mental health check-in questions are ideally used during 1:1s, while performance check-in questions are often used for group meetings. Fun check-in questions can also be a good icebreaker for 1:1s or group meetings.

➡️ Wondering how you can effectively check in with the team about their manager? Try out these skip-level meeting questions to keep the discussion going. 

How do you have a good check-in meeting? 

Setting a clear agenda can help your check-in meetings become productive and engaging. Make it a point to start the check-in with casual questions and make room for sharing personal anecdotes. Also, show empathy for additional insights they might share. Ultimately, the key is to actively listen to better understand employee concerns. 

How do you ask questions about the employee's career plans?

It's essential to assess your employees' career goals so you can extend support as needed. Your questions should:

• Be open-ended to prompt a good amount of introspection.
• Help identify ambitious career goals by encouraging open and honest communication about their plans. 
• Align their personal goals with company objectives so you can help them achieve them. 

Asking the appropriate development conversation questions can help you assess the level of your employee's knowledge and skills to identify leadership opportunities in the future.