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85 Best Check-In Questions to Use At Meetings And Work

Using check-in questions can actually make your company more effective.

When employees are engaged, companies are more effective. Disengaged employees1 are 60% more likely to make errors, 37% more likely to skip work days, and 18% less productive.

The greatest indicator of employee engagement, according to a Gallup Poll2, is employee well-being. And as the Harvard Business Review1 puts it, “Well-being comes from one place, and one place only—a positive culture.”

In this article, we’ll show you how to make your work culture more positive—where employees feel supported and connected—using skillful check-in questions in your meetings.

What Are Check-In Questions?

Check-in questions are a communication tool to use with your employees to foster transparency, positive rapport, openness, and satisfaction. You can use them in-person or virtually and for one-on-ones or performance reviews.

They set the tone for a one-on-one or group meeting and ultimately contribute to the greater culture you are building in your workplace.

Check-in questions serve as prompts for team members to share any of the following:

  • Project updates
  • Personal updates
  • Concerns about the company or a project
  • Challenges or struggles in work
  • Feedback about management
  • Their career development

If you intentionally incorporate check-in questions into your workplace, you can build a culture where individuals feel heard, supported, and motivated. This will be a workplace where employees will do their best work, enjoy themselves the most, and want the company to succeed. 

Incorporating the right check-in questions can help build an office culture where your employees want to work.

Why Are Check-In Questions Important?

While check-in questions provide myriad benefits, their direct effects include the following:

  • Open communication. Check-in questions provide the structure for individuals to share updates, talk about their work-life balance, and seek feedback. This promotes better team coordination and trust. 
  • Engagement and well-being. Check-in questions demonstrate a genuine interest in how employees are doing. By asking about their progress, challenges, and aspirations, you show your employees that their opinions and experiences matter. This fosters a sense of belonging, boosts morale, and enhances job satisfaction. 
  • Growth and improvement. Check-in questions help identify obstacles, challenges, and areas for improvement. They create an opportunity to address issues proactively and collaboratively and support employees in growing their skillset. This promotes a culture of learning, growth, and collaboration.

How to Overcome Common Barriers to Using Check-In Questions

Below are three common barriers managers face that prevent them from incorporating check-in questions into their work culture and the solution to overcoming each barrier. 

Barrier 1: Time and prioritization

Managers often have busy schedules and no shortage of responsibilities, making it challenging to prioritize regular check-ins with team members. The perceived time investment required for effective check-ins may deter some managers from implementing them consistently.

How to overcome this barrier: Think long-term. 

Ultimately, you probably want to build a company where your employees want to work with you for a long time. You want employees who feel at home at your company and aren’t constantly seeking better opportunities. The best way to do this is to build a culture where people feel connected and like you are investing in them with care. 

You don’t want your employees to come to work each morning feeling like this cat.

Your company will benefit from an open connection with your employees. And check-in questions are one of the best tools to facilitate that open connection.

Barrier 2: Lack of awareness of the value of open communication.

Some managers may not be aware of the benefits of check-in questions. They may not recognize the value of open communication and employee engagement or underestimate the impact of regular check-ins on team performance.

How to overcome this barrier: Try out the mindset that employee engagement is the key to success. 

You can treat it like an experiment—introducing check-in questions at the start of your meeting agendas for one quarter. Measure any differences in employee engagement.

Gallup describes the gold standard of employee engagement2 as an employee who: 

  • Is fully involved in and enthusiastic about their work
  • Knows your expectations
  • Receives ongoing support and feedback
  • Feels cared for
  • Has a close friend at work.

Employee engagement helps revenue. Employees who are actively disengaged2 earn 28% less revenue than engaged employees. Further, in one study2, companies that improve their engagement scores two years in a row experienced a per-person revenue growth six times faster than companies whose engagement scores remain static or decline in a two-year period.

Barrier 3: Lack of communication training

Managers may lack the necessary training or guidance on effectively conducting check-in conversations. They may feel unsure about which questions to ask, how to handle difficult conversations, or how to provide constructive feedback. Such managers might feel awkward or tentative about creating open lines of communication.

How to overcome this barrier: Fail forward!

Communication is a challenging, life-long skill. Developing your communication skillset will benefit you at work, in your friendships, and your romantic partnerships. 

It’s okay if you try out check-in questions and more open communication, and it feels clunky or awkward at first. If that does happen, it’s just part of the learning curve!

If you follow the tips below, it’ll give you a massive headstart in your communication game.

Lots of people also feel tentative about how to run successful meetings over Zoom. If you’d like to learn how to thrive all around in the virtual workplace, this goodie might be for you.

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85 Best Check-In Questions

Try out any of the following ideas for different situations.

Project and progress check-ins

If your employee is undertaking a long-term project, it can be helpful to know how their progress is coming along and ways that the project is contributing to their growth or bringing forth challenges. Try any of these questions to dig deeper.

Starting a project check-in questions

  • At the end of this project, what would you look back on and feel like it was a success?
  • What resources or support do you need to effectively kick-start the project?
  • What possible roadblocks can you foresee on this project, and how might you overcome them?
  • How might working on this project contribute to your personal growth?
  • In what way does this project draw upon your strengths?

Project-specific check-in questions

  • What new skills or knowledge have you acquired during this project that you find valuable for your personal growth?
  • Have you faced any challenges or obstacles during the project that have pushed you out of your comfort zone? How did you handle them?
  • If you had to ask for support to help you on this project, what would you ask for?
  • How can we incorporate opportunities for your professional development into the remaining phases of this project?
  • What have been the most enjoyable and the least enjoyable parts of this project so far?

Questions for concluding a project

  • What are you most proud of in your work on this project?
  • What valuable lessons have you learned throughout this project that you can apply to future endeavors?
  • Were there any unexpected challenges or obstacles that arose during the project, and how did you overcome them?
  • How has this project contributed to your professional growth and development?
  • What feedback or suggestions do you have for improving similar future projects?

One-on-one check-in questions

One-on-one meetings are your best chance to form meaningful connections with your employees. If you can give them space to share openly and make yourself known as a great listener, then your employees will start to look forward to one-on-ones with you.

Questions to help your employee feel encouraged and supported

  • How do you feel about your overall work and job satisfaction?
  • What accomplishments or progress are you most proud of since our last meeting?
  • What are your short-term and long-term career goals, and how can we work together to help you achieve them?
  • Is there any specific feedback, recognition, or appreciation you would like to receive for your contributions or performance?
  • What can I do as your manager to ensure you feel valued, motivated, and engaged in your work?

Questions to build your employee’s confidence

  • If you were the CEO of this company, what changes would you make?
  • What recent accomplishments or successes are you proud of in your work?
  • If you were to describe yourself as a superhero at work, what superpower would you possess, and how does it contribute to your success?
  • Imagine you are presenting at a TED Talk. What topic would you choose to speak about, and why do you believe you would inspire and captivate the audience?
  • Think about a time when you faced a significant challenge at work and overcame it. What personal qualities or strategies did you tap into that demonstrated your resilience and ability to thrive?

Questions to elicit more transparent communication

  • What do you appreciate about my management style, and what could I shift to be more supportive of you?
  • What at work has caused you to feel frustration or stress?
  • Is there anything you haven’t shared with me that you’d like to get off your chest?
  • Is there anything in your personal life that would feel helpful or exciting to share?
  • How comfortable do you feel expressing your ideas and opinions openly within our team? Are there any suggestions on how we can foster a more inclusive communication environment?

Check-in questions for team meetings

If you open your team meeting with a question, you are directing the attention of all of the attendees toward the topic of the question. You can use this insight strategically depending on the type of meeting. 

For example, If it’s a brainstorming session, then it might be wise to open with a check-in question that stokes creativity and curiosity. Or if it’s a team bonding meeting, maybe you’d do well with a question that evokes a touch of vulnerable reflection.

Icebreaker questions to start a meeting

  • What is one thing you’re currently excited about, either personally or professionally?
  • What’s something you feel proud of?
  • What’s a hobby outside of work that’s bringing you joy? What do you enjoy about it?
  • Are there any recent books, TV shows, or podcasts that you’ve enjoyed, and what about it did you find interesting about them?
  • What is something you appreciate or admire about a fellow team member, and why?

If you’d like to use your icepick to dig a little deeper, here are a few more ideas on icebreakers.

Questions to check in on a project

  • How have you personally grown or developed from working on this project? 
  • In what ways has this project allowed us to strengthen our connections as a team? How can we continue to nurture those connections moving forward?
  • Do you have any ideas or suggestions for improving our collaboration and teamwork going forward?
  • How have we demonstrated our company’s core values throughout this project? Are there any opportunities to further embody those values moving forward?
  • Are there any ways in which we can foster more innovation, creativity, or out-of-the-box thinking within the team? How can we support each other in exploring new ideas and approaches?

Team-building questions

  • What strengths and qualities do you admire in your fellow team members, and how do they contribute to our overall success?
  • How can we create a more inclusive and supportive environment where everyone feels valued and heard?
  • What team-building activities or initiatives would you suggest to enhance our bond and cohesion?
  • How can we better communicate and collaborate across different roles or departments to ensure seamless teamwork?
  • Are there any team rituals or practices we can implement to celebrate achievements or boost team morale?

Performance and development questions

If your goal is to support an employee’s development, then think about questions that have them reflect on their growth and goals. When you ask these questions, you can accurately gauge how your employee is doing, and they will hugely benefit from the sense that you are there to support and believe in them.

Questions about an employee’s goals and development

  • Imagine yourself in your dream career path. What exciting milestones or achievements would you like to accomplish, and how can we collaborate to help you reach those heights?
  • If you had a magic wand to enhance any skills or abilities, which ones would you choose to develop further? 
  • If you had to pick one primary goal that you’d like to get out of working here, what would it be?
  • Think of a professional role model or mentor whose path inspires you. What lessons can we learn from their journey, and how can we integrate those insights into your development plan?
  • Imagine our company as a playground for innovation and experimentation. How can we create an environment that encourages calculated risks, creativity, and personal growth?

With your help, your employees will not feel like this baby!

Coaching questions

  • What’s the boldest, most audacious goal you could set for yourself right now? 
  • Imagine you have access to an unlimited reserve of courage and resilience. What courageous act would you take today that would transform your growth trajectory? 
  • Picture yourself one year from now feeling massively confident in your career, looking back at this moment. What is the one bold decision you made that accelerated your personal and professional growth? 
  • If you were to surround yourself with a powerful network of individuals who inspire and uplift you, who would be part of your dream team and why? 
  • Envision a scenario where you’ve overcome your deepest fears and self-doubts. What specific actions would you take in that fearless state? How can we unlock your inner power to take those actions now?

Performance questions

  • If you were to step into the shoes of an observer, how would you assess your own performance? What strengths and areas for improvement would you notice?
  • What specific accomplishments or milestones have you achieved since our last check-in? How do you feel about your progress?
  • If you were to write a headline about your performance over the last month that captures its essence, what would it say? 
  • What friction have you experienced around performing at your peak ability?
  • Imagine you have a mentor guiding your professional growth. What advice would they offer to enhance your performance? How can we infuse that wisdom into our collaboration?

Experience and culture questions

Many employees might feel tentative about giving honest feedback about their gripes on work culture. But if you can listen honestly to what your employees have to say and then strive to consider their feedback, it will create a positive ecosystem where your employees feel like they are building this company with you and that their voice matters.

Work culture questions

  • How do you feel about our office culture and the overall work environment? 
  • What aspects of our company culture do you appreciate the most, and what would you want to change?
  • In what ways does our office culture match your personal values? Which of your personal values don’t feel represented in our office?
  • How connected do you feel to your teammates? Are there any opportunities for increased collaboration or relationship-building that you would like to explore?
  • If you got to lead one meeting or activity a week whose sole purpose was to shift our office culture in some direction—it could be playful, sincere, collaborative, etc.—what would you lead and why?

Wellness questions

  • How would you rate your current level of well-being and mental health on a scale of 1 to 10? What factors contribute to your rating?
  • Are there any specific work stressors or challenges impacting your well-being and mental health? How can we address or alleviate those stressors?
  • What strategies or practices have you found effective in promoting your well-being and mental health?
  • How well do you feel connected to a support system within the workplace? Is there anything we can do to foster a culture of connection and support that promotes your well-being?
  • What is your current relationship with scarcity and abundance, and how is it affecting your overall well-being?

Work-life balance questions

  • How do you feel about your current work-life balance? 
  • How do you feel about your current workload?
  • What specific strategies or practices have you found effective in maintaining a healthy work-life balance?
  • How well do you feel supported by the organization in maintaining a healthy work-life balance? Are there any initiatives you believe would contribute to a better balance for all employees?
  • Are there any work-related responsibilities that are causing undue stress or encroaching on your personal time? How can we address those challenges and find solutions together?

Mindset questions

  • How would you describe your current mindset towards work-related challenges?
  • How does work fit into the landscape of your life?
  • How does work relate to your sense of purpose?
  • In what ways do you feel creatively expressed at work? 
  • Are there any thought patterns or beliefs that may be limiting your potential? 

Fun Check-In Questions

Sometimes, you might want to lead with a light and bright tone. Asking any of these fun questions might uplift a team meeting or spark an inspiring note for your one-on-one.

  • If you could plan any activity to help our whole team bond, what would you plan?
  • Envision our workplace as a theme park. Which attraction would best represent your work experience, and why?
  • What are you most excited about in your life right now? What about that? Have you excited?
  • What’s one thing nobody here knows about you?
  • Tell us about a moment when you felt inspired recently.

What Makes a Good Check-In Question?

When designing check-in questions to help foster more open communication, consider the following best practices.

Open-ended questions

The best questions will get people talking. An open-ended question is one that someone can’t answer with a single word or sentence.

These questions allow team members to provide thoughtful and meaningful responses, where they may learn something about themself while sharing.

Instead of

  • “Is the project going well?”

Try these three questions to start a check-in:

  1. “How have you felt the project has gone in the last few weeks?” or
  2. “Tell me about your major challenges and victories in the project so far.”
  3. “Update me on what’s happening with the project, including how you are feeling about everything?”

Growth questions

Questions are powerful because they direct the other person’s attention. Compare these two questions: “What is most exciting in your life right now?” versus “What is most difficult in your life right now?” 

They are both useful questions, but they orient your attention toward completely different aspects of your experience. When you understand the power of questions in commanding attention and setting a tone, you can bring more intentionality into your meetings.

Instead of, “How’s it going?”

Try these three questions at your next check-in:

  1.  “How are you feeling about your career development as it relates to your current role?”
  2. “What were your goals last month, and how do you feel about them now?”
  3. “Tell me about what you have learned on this project?”

Individualized questions

The more you personalize a question to an individual or a team, the more they’ll feel like you are keeping track of their progress.

Instead of, “How’s your progress coming along?”

Try these fill-in-the-blanks: 

  • “I remember last time you were feeling stuck with the _____ tasks; how’s that been coming along?”
  • “I know you were excited about learning ____. How has it been going?”
  • “Last time we talked about ____. Update me!”

Easy-to-understand questions

This tip is especially useful if you’re giving a check-in question as a round in a meeting for each team member to answer. 

If the question is too multi-faceted or convoluted, people’s responses will appear murky and unhelpful.

Instead of, “Given the recent project developments, the evolving market landscape, and the challenges we’ve encountered, could you please provide a comprehensive and detailed account of your progress, the strategies you’ve employed, the specific obstacles you’ve faced, and your plans for mitigating those challenges moving forward?”

Try, “What progress have you made on the project, and what challenges have you encountered?”

Create a supportive environment

From an employee’s perspective, it’s an amazing feeling to have a manager who believes in you, wants you to succeed, and helps you with your goals.

Try any question that starts with, “How can I support you with __________.”

Or ask, “What can I do to be a better teammate?”

Avoid giving advice or expressing reactive judgments

One primary purpose of check-in questions is to create a space for your employees to freely express what’s on their minds.

If they sense that what they share will be met with negative judgment or immediate advice, they may not feel free to share.

Let them know periodically that you want to hear what’s honestly going on for them, even if it feels scary for them to say.

And in general, if you’d like support preparing for a meeting and getting into the right headspace, you can read some tips here.

Frequently Asked Questions About Check-Ins

What are check-in questions?

Check-in questions are questions that a manager asks their employees to get a pulse on how things are going for them. These questions also contribute to a work culture that is open, trusting, and supportive. 

What do you say in a check-in meeting?

At a check-in meeting, it’s best to come in with a few questions to check in on different aspects of your employee’s experience. Three simple questions you could try at your next meeting might be: “How has your work-life balance felt?” “How inspired or uninspired have you felt at work recently?” and “What challenges have you been facing at work recently?

How do you do an effective check-in?

To do an effective check-in, first schedule the call and then come with a few pre-prepared questions. Scheduling the call will let the other person know what to expect. Two solid questions you could ask are “What’s been most exciting recently?” and “What’s been most challenging recently?” Then just listen without judgment and aspire to create a space that is supportive and encouraging.

What is the purpose of a check-in call?

The purpose of a check-in call is to help employees feel heard, cared about, and encouraged. On these calls, you can open up transparent lines of communication to get to know how the employee feels and what they think.

How do you do a fun check-in?

To do a fun check-in, ask a question that inspires creativity and reflection on positive emotions. An easy one is, “If you could plan our next team activity, what would you plan?”

How do you check in with team members?

One way to do check-ins with team members is to start the meeting agenda with a round where each person has 1-2 minutes to answer the same question. One question you can use is, “What is one thing you’re currently excited about, either personally or professionally?”

What are good check-in questions for meetings?

A good check-in question for a meeting could be, “Name one way in which you’ve grown from this project so far.” A good check-in question will create an open, non-judgmental space for your employees or colleagues to share what’s under the surface.

Incorporating Check-in Questions

I hope this article has inspired you to experiment with different check-in questions in your quest to create a positive work culture! 

Feel free to borrow any of the questions from this list, or just remember the following principles:

  • Ask open-ended questions that spur reflection
  • Use specific questions that intentionally explore some part of the employee’s experience
  • Ask questions individualized to the employee or team that shows you’ve been tracking their journey week to week
  • Use questions that are simple to understand
  • Ask questions that show you want to support and encourage your employees
  • When someone shares something, especially something scary, receive it without judgment.

While check-in questions are crucial to a strong meeting, you can check out this article for other key principles necessary for a fantastic meeting.

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