100 Check-In Questions for Every Occasion

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If you found this post, that means you know check-in questions are important. But do you realize how important they are?

Imagine that you’re a scuba instructor about to give your first lesson. Before you head out on the boat with the class, you want to ask check-in questions to your students. How much experience do they have? Do they all have the proper equipment? How are they feeling about diving?

Their answers will determine what you need to run a successful class. Even if they don’t change your plan, they will undoubtedly help you understand who you’re working with.

This same philosophy applies to pretty much any situation in life. We’ll be more successful if we check-in before diving into the ocean that is life, whether that’s checking in with other people or with ourselves.

Check-in questions will not only help you understand the needs of others. They will also offer valuable opportunities for reflection and connection.

Whether you’re about to start a meeting, begin a new personal project, or engage in a conversation with your partner, check-in questions can create a more positive and successful opportunity.

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Table of Contents: Check-In Questions for Every Occasion

• Check-In Questions as Fun Ice Breakers In a Group
• Check-In Questions to Build Trust
• Check-In Questions Before a Meeting with a Clear Objective
• Check-In Questions Before a Difficult/Controversial Discussion
• Check-In Questions for a Casual Conversation with Friends
• Check-In Questions Before a Deep Relationship Conversation with Your Partner
• Check-In Questions Before Taking on a New Goal as a Group
• Check-In Questions Before Individually Taking on a New Goal
• Check-In Questions if There’s a Conflict or Disagreement
• Check-In Questions As a Daily Habit

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The Purpose of Checking In

Check-in questions are much more than simple “small talk.” They help improve emotional intelligence, both collectively and individually. Additionally, they serve a valuable function in a multitude of situations.

For groups, check-in questions can:

• Create a moment for collective reflection
• “Break the ice” and make people feel more comfortable
• Help all parties identify and voice their emotions and feelings
• Allow everyone to understand the needs and concerns of others
• Make sure everyone is on the same page
• Create opportunities for greater connection

For private moments, check-in questions can:

• Create a moment for personal reflection
• Allow you to identify your current emotional state and what caused it
• Increase your personal accountability
• Allow you to better understand your biases, desires, and values
• Help you practice and improve your self-awareness skills

No matter what they are, these questions provide opportunities for us to be vulnerable. Vulnerability doesn’t come easy to many of us. On the contrary, our culture and personal fears discourage us from showing our true selves. You must create environments that encourage vulnerability, genuine connection, and acceptance.

Read more about How to Be Vulnerable and How To Be More Self-Aware.

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How These Questions Can Be Used

Your check-in questions will be dependent on the situation and objective. When choosing check-in questions to use, think about:

• How much time do you have?
• What is your objective for the check-in, as well as what comes after it?
• What would help achieve this objective?
• What tone are you trying to set?
• What are the needs of the audience?
• What is the current situation?
• What methods for answering can you employ?

It’s important to consider the objective of both the check-in and what comes after it. For example, if you’re about to start a 3-week workshop, you might want to dedicate a lot of time to check-in questions at the beginning of the workshop to really foster a sense of connection. However, if you’re about to start a 30-minute meeting with a clear goal, you might want to use one check-in question to help you accomplish that goal.

Conversely, if you’re using the check-in questions for personal discussions, you can drop some of the structure/rigidity and make the check-in questions more conversational in nature. Finally, check-in questions for yourself might come in the form of journaling, audio recordings, or quiet moments.

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100 Check-In Questions for Every Occasion

Check-In Questions as Fun Ice Breakers In a Group

1. What is a favorite childhood memory?
2. What does your ideal day off look like?
3. What is something fun on your bucket list?
4. If you could invent something, what would it be?
5. What is a TV show that you grew up watching?
6. If you could be a character in a book or movie, what would it be?
7. What is a silly fear or phobia that you have?
8. What famous person would you like to meet in real life?
9. If you could travel anywhere, where would you go?
10. What is something that defined you growing up?

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Check-In Questions to Build Trust

1. What is your reason for being here?
2. Who was an impactful adult in your life growing up, and why?
3. What is a powerful life lesson that has stuck with you?
4. What is a challenge that you’ve had to overcome in your life?
5. What are you most proud of in your life?
6. What is something in your life that gives you great joy and meaning?
7. How are you feeling about the state of the world?
8. What is a personal value that you stand by or something that motivates you?
9. How has your perspective on life changed as you’ve gotten older?
10. What is something hard for you to do?

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Check-In Questions Before a Meeting

1. What is your energy level today?
2. What is your focus level today?
3. How do you feel about what we need to accomplish today?
4. What is your vision for what needs to be accomplished?
5. What concerns do you have about the work we must complete?
6. What questions do you have about the work we must complete?
7. What support do you need to be able to do your job successfully?
8. How are your stress levels? What is currently causing you stress?
9. How do you feel working in this group?
10. What is something that could improve the dynamics of this group?

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Check-In Questions Before a Difficult/Controversial Discussion

1. How do you feel about having this discussion?
2. What worries you about having this discussion?
3. What are the potential benefits you see in having this discussion?
4. What do you need to feel supported and trusted in this discussion?
5. What emotions are you currently feeling? What is causing them?
6. How can we help make each other feel more comfortable?
7. What language will help make this discussion more effective?
8. What is our goal for this discussion?
9. What similarities are there between everyone involved in this discussion?
10. Why is it important to have this discussion?

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Check-In Questions for a Casual Conversation with Friends

1. How are you feeling?
2. What have you been spending most of your time doing?
3. How are your relationships going (other friends, family, coworkers, etc.)?
4. How is your partner/dating life?
5. How are you feeling about work/school/etc.?
6. How are you feeling about the state of the world?
7. What is something that is bothering you in life right now?
8. What is something that you’re really excited about?
9. What is something that you’re trying to change?
10. What is something that’s been giving you a lot of joy and purpose?

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Check-In Questions Before a Deep Relationship Conversation with Your Partner

1. How are you feeling right now?
2. Why is this conversation important to have?
3. What are the benefits you see of having this conversation?
4. What do you need to feel heard and respected in this conversation?
5. What language should we use to make this conversation most effective?
6. How much uncertainty do you feel around this topic or conversation?
7. What is one thing that we really appreciate and love about one another?
8. What can we do to stay calm or pause if our emotions become too intense?
9. What have we learned from previous hard conversations that would be helpful now?
10. What do we know about ourselves that might make it difficult to communicate?

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Check-In Questions Before Taking on a New Goal as a Group

1. How do you feel about this new goal?
2. What concerns do you have about this new goal?
3. What questions do you have about this new goal?
4. What will the positive outcomes be once this goal is accomplished?
5. What can you contribute to this group?
6. What do you need from this group to be able to be successful?
7. What challenges do you foresee that might work against our new goal?
8. What have you learned from previous experiences about this group?
9. What can you do to help support and encourage each other?
10. What will motivate you to accomplish this goal?

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Check-In Questions Before Individually Taking on a New Goal

1. How do I feel about this goal?
2. What made me want to pursue this goal in the first place?
3. What challenges do I foresee when pursuing this goal?
4. What will the outcome be if I accomplish this goal?
5. What do I need to keep myself motivated when pursuing this goal?
6. What have I learned about myself from similar experiences in the past?
7. What can I do to help keep myself inspired and accountable?
8. How much will other aspects of my life influence this goal?
9. How is my overall emotional well-being right now?
10. How can I remove possible barriers to accomplish my goal?

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Check-In Questions if There’s a Conflict or Disagreement

1. How are you feeling about the present situation?
2. Why is it important for this conflict to be resolved?
3. What do you think an ideal resolution looks like?
4. How have your actions or words influenced others?
5. What external factors have you allowed to control your emotions?
6. What do you need to feel heard and respected in this conversation?
7. What is common ground that everyone can start from?
8. What is something you appreciate about everyone involved?
9. What language will be important to use to resolve this conflict?
10. What is something that you can contribute to help resolve this conflict in a respectful manner?

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Check-In Questions As a Daily Habit

1. What emotions am I feeling right now?
2. What caused these emotions?
3. What is something that I did well today?
4. What is something that I could have done better today?
5. How am I feeling about the relationships in my life?
6. How am I feeling about the state of the world?
7. What is something that has been causing me stress?
8. What is something that I’m grateful for?
9. What is something that brought me joy today?
10. How well did I live by my values today?

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Conclusion

Check-in questions are valuable tools to help build connections, identify challenges, and develop self-awareness. Once you identify the needs and objectives for your check-in, choose which questions will help you achieve the positive outcome that you’re looking for.

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