One of the greatest challenges all leaders face is balancing employee autonomy with the need for structure and guidance.
A survey by senior analysts Priyanka Mehrotra and Stacia Grar highlights this tension—88% of respondents prefer a high-trust, low-micromanagement approach, but 70% still want regular check-ins with managers.
This brings us to the question: How can managers reconcile these seemingly contradictory needs and ensure employee satisfaction?
One way to do this is by regularly asking check-in questions focused on your team’s needs and career goals. By shifting the focus from outputs (task completion) to goal alignment, managers can maintain a sense of connection without micromanaging. Employees feel supported, yet they also maintain ownership over their work.
In this blog post, we’ll explore how to host employee-centered check-ins at meetings, along with 100 ready-to-use questions for various scenarios.
100 Engaging Check-In Questions to Transform Your Meetings
Summarize this article for me pleaseWhat Are Check-In Questions?
Check-in questions are open-ended or closed-ended questions used to assess individuals’ emotional, mental, and physical well-being, often in settings like team meetings or 1:1 performance reviews. Fun check-in questions are also a great way to build rapport and ease tension, especially in new team settings or during project meetings and kickoffs.
Here are some situations where you can use check-in questions.
Weekly check-ins
As a manager, staying in regular touch with your team members is crucial. A weekly check-in gives you a fair idea of what your team members are going through and how it may affect their work and productivity. Some ideas you can try out are:
- Motivated Mondays: Setting intentions and goals for the week
- Wellbeing Wednesday: Rotating stand-up questions to assess team members’ well-being
- Thursday Thankfulness: Ask teammates what they’re grateful for during Thursday standup meetings
Retrospective meetings
Retrospective meetings are structured sessions that allow teams to reflect on completed projects and determine areas for improvement. During these meetings, you can ask check-in questions while:
- Opening the meeting: Use check-in questions to create a safe space for honest feedback
- Closing the meeting: Reflect on learnings so you can apply them to future work
Workshops
When conducting workshops, many participants may be new to you and each other. Checking in with them can help make them feel comfortable and set the tone for the rest of the session. You can try the following:
- Pre-workshop check-in: Icebreakers to build rapport and assess participants’ mental capacity to absorb new information
- Post-workshop check-in: Get feedback from participants and evaluate the effectiveness of your workshop
Incorporating check-in questions in team meetings can help you get a pulse check of employee sentiments and create a supportive work environment.
Also Read: How To Say Just Checking In Professionally
Summarize this article for me pleaseBenefits of Using Check-In Questions
Let’s look at how exactly check-in questions and fun icebreakers can improve team dynamics, productivity, and overall job satisfaction. This is what they’re meant to achieve:
- Breaking down cliques: Regular check-ins can help remove hierarchical barriers and encourage cross-functional collaboration
- Encouraging vulnerability: By creating a safe space, team members can share their fears, doubts, and challenges without judgment
- Fostering empathy: By sharing personal experiences and challenges, team members can develop a deeper understanding of one another
- Increasing productivity: By addressing issues early on, teams can avoid potential bottlenecks and delays
- Reducing stress and anxiety: Sharing concerns and worries can alleviate stress and anxiety
- Strengthening team cohesion: Regular check-ins can build camaraderie and a sense of shared purpose, improving company culture
Summarize this article for me please100 Engaging Check-In Questions
Now for the best part: here are 100+ check-in questions for any type of team meeting. This includes questions for daily stand-ups, weekly check-ins, goals, one-on-one meetings, and many more.
Icebreakers and fun
The easiest way to avoid the inevitable awkwardness of meetings? Opening them with fun icebreakers and team-building activities before you transition to shop-talk. Here are some ideas to get you started:
- If your workday were filmed as a movie, who would star in it?
- If you could live someone else’s life for a day, whose life would you choose?
- Which emoji best represents your personality?
- Do you prefer silence, music, or background noise when working deeply?
- What’s the quirkiest or most unusual work experience you’ve had?
- What is your favorite work-appropriate GIF?
- What’s your fanciest work gadget or stationery?
- If you could invent a new holiday, what would it be?
- What’s the silliest thing you’ve ever done at work?
- Do you have a favorite office plant?
Personal wins and well-being
Who doesn’t like celebrating and talking about their wins? Even small wins can act as big motivators and set the tone right for those action-oriented meetings.
If you want to keep it simple but genuine, even asking people about their day and mood can go a long way and show your team you really care about them.
- What’s one positive thing that happened this week?
- What’s a personal goal you’re working towards?
- What non-work topic or hobby have you been interested in lately?
- How are you feeling today, physically and emotionally?
- What’s stressing you out lately?
- What are you doing to improve your work-life balance?
- When was the last time you took a break and really relaxed?
- How are you managing negative emotions?
- What’s your go-to workout routine?
- How present are you feeling right now?
- How connected do you feel to something larger than yourself?
- What’s one financial tip that’s made a big difference in your life?
Work progress and updates
It can be challenging to speak up about one’s struggles and problems at work. Open, empathetic check-ins around task progress and updates can act as a bridge and allow everyone to seek the support they need to do their best work. Here are some helpful questions:
- How are you prioritizing your workload?
- Do you feel more productive working from home or at the office?
- What strategies are you using to manage your time?
- What is working as expected, and what is not?
- What would you change if you could do this project over again?
- Are there any roadblocks preventing you from moving forward?
- Do you need any additional resources or support?
- What’s been consistently challenging for you at work?
- What’s one thing that would make your work life easier?
Team dynamics and collaboration
Team-oriented check-ins are a great way to forge stronger team dynamics and connect better with your colleagues. Try these questions to start with:
- Rate team morale on a scale of 1 to 10.
- Share a GIF to describe your team.
- What’s one thing we can do to create a more positive and inclusive team culture?
- Give a shoutout to someone on the team.
- Is there anything your team members can do to help you be more effective?
- Are we leveraging each team member’s strengths?
- Is everyone’s voice being heard?
- How can we celebrate successes together?
- How can we encourage diverse perspectives in our team?
- Do you feel valued by the team?
- How can we improve trust and respect among team members?
- Do you feel supported by your managers and leadership staff?
Goals and priorities
Align your top goals and priorities with your team with this list of handy questions:
- What are your top three priorities for this week?
- What’s a quick win that made you feel good?
- Are you making progress towards your long-term goals?
- How will you measure the success of your project?
- What’s something you would like to prioritize in the upcoming weeks?
- How can we better track our progress toward team goals?
- What’s holding you back from reaching your goals?
- How do you reward yourself for achieving your goals?
- How do you stay accountable to your goals?
- How do you ensure that ad-hoc tasks don’t derail your long-term goals?
Feedback and growth
Want yourself and your team to keep growing every day? Establish a regular feedback cycle. Check-ins during your daily, weekly, and monthly standups provide an excellent opportunity to do this.
- What are your preferred methods for giving and receiving feedback?
- Are you receiving enough feedback?
- What’s the most and least favorite part of your job?
- What’s one area where you can improve this week?
- What’s one thing you’d like to do differently next week?
- What’s one thing you’ve learned about yourself this week?
- Does your current role align with your career aspirations?
- What’s a skill you have that you don’t use at work but would like to?
- Did you feel like you failed at something recently? How can we help address that?
Task and deadline management
These check-in questions can be a godsend in foreseeing project hindrances and addressing risks that affect their timely completion.
- What is your workload like?
- Are there any tasks you can delegate or postpone?
- Are you on track to meet the deadline?
- Are your deadlines motivating (or demotivating) you?
- What’s one thing you can do to improve your productivity?
- What’s been taking the majority of your time?
- How are you balancing meetings with deep work?
- How are you avoiding multitasking?
- What’s preventing you from starting or finishing a task?
- What’s a task that’s been a big time-waster?
- What should we keep, pause, or stop doing in the project?
Innovation and creativity
Tired of saying: “Has anyone got any ideas?”
Spark creative brainstorming in your meetings with these new questions instead.
- What’s a campaign you’d run or feature you’d build if you had limitless resources?
- What’s one way to encourage a culture of innovation?
- What’s one experiment you’d like to try, even if the chances of failure are higher?
- What’s a brainstorming technique you find helpful?
- What’s your favorite creative outlet?
- What’s a future technology that excites you?
- What’s one thing we can do to disrupt the market?
- What’s a mindfulness exercise that’s improved your creativity?
- Is there a particular product or service offered by a competitor that you believe we could have introduced first?
- What’s one way we can differentiate us from our competitors?
Communication and collaboration
👀Did you know?
Workers are 12 times more likely to be engaged when they trust their team leaders?
These questions allow you to communicate with your team with greater empathy and build transparency and trust.
- Are there any communication breakdowns we need to address?
- What’s one way to improve our team’s brainstorming sessions?
- Do you prefer synchronous or asynchronous conversations?
- Are we addressing conflicts openly and honestly?
- What tools can we use to stay connected?
- How can we practice active listening?
- What’s your communication style—written, verbal, or visual?
- Are there any situations where you feel hesitant to speak up?
- What can we do to minimize distractions and maximize productivity during team meetings?
- Are there any specific team members you’d like to connect with more?
- How can we encourage everyone to participate in meetings?
Learning and development
Finally, employees really crave a chance to learn and grow. Investing in people—their aspirations and motivations—contributes to building bonds between team members, managers, and the organization.
So, you need to ask your employees:
- Which new skill would you like to learn?
- Are you seeking feedback and mentorship?
- What can you do to improve your knowledge and expertise?
- What’s something you’ve always wanted to try but haven’t?
- Where do you see yourself in five years?
- What are you currently reading or learning about?
- What’s something you recently learned?
- How are you staying up-to-date with the latest trends and technologies?
- Have you considered building a professional brand?
- What tools do you use to monitor your progress and stay accountable?
- Which online platform or community has been most helpful for your professional development?
- Have you ever set up a reward system or challenge to motivate yourself to learn?
- What’s your opinion on experiential learning? Is it overrated or useful?
💡Pro Tip: Be mindful of when and where to ask your check-in questions. Icebreaker check-ins, questions on work updates and communication, etc., may be asked in a group setting. In contrast, questions related to feedback and health must be asked in a private setting, one-on-one.
Summarize this article for me pleaseEnhance Check-ins and Meetings with Tools
With remote work (and online meetings) becoming increasingly common, technology can help combat virtual fatigue, improve team collaboration, and optimize meeting processes with tools such as AI-powered note-taking or agenda creation.
Let’s look at how you can use work management software like ClickUp to simplify meetings and check-ins and make conversations both organized and organic.
Increase collaboration with digital whiteboarding tools
If you host your brainstorming sessions online, whiteboarding tools can help you map out ideas visually, collaborate in real time, and spark creative thinking—whether that’s freehand drawing to explain a creative concept or flowcharts to design systematized workflows.
ClickUp Whiteboards, for example, allows you to draw figures, add shapes, create sticky notes, and link objects to visualize your thoughts. You can also add images, links, and documents from your ClickUp Workspace to your Whiteboards to have all your informational resources in one place when brainstorming.
The best part? Remote teams can work on the whiteboard together, making every meeting an interactive and collaborative experience.
Organize your meeting details
According to most surveys, employees attend an average of 10 to 15 meetings per week. For managers, this number can double, reaching up to 30 meetings weekly.
So, how do you keep track of your meetings? This includes participating in the actual meeting and managing all administrative work, such as meeting agendas, minutes, and notes.
The solution—a tool that helps you create a system to track and manage your meetings. For example, with ClickUp Meetings, you can set meeting agendas, document meeting summaries, and track action items—all from one place.
Some things you can do are:
- Organize your team meetings efficiently by creating separate Lists within the ‘Meetings’ folder
- Create a task for each Meeting List so you can directly track updates and meeting notes within that task
- Use Recurring Tasks for meetings that occur periodically, like daily standups and quarterly reviews
- Use the ClickUp Calendar View to visualize your meetings in the traditional calendar format
- Add your notes to a ClickUp Notepad so you can easily convert them into tasks or action items after the meeting
But that’s not all! You can use the ClickUp Agenda Template to set meeting goals, outline the agenda, track attendance, and document key decisions all in one place.
The ClickUp Agenda Template comes in three parts:
- Meeting information: Here, you outline the purpose of the meeting, logistics, and who’s participating in the meeting
- Agenda: Here, you’ll list out your talking points along with the name of the participant who will bring that point up during the meeting
- Post-meeting details: Here, you add a recording to the meeting and meeting notes, along with details on when the next meeting will be hosted
By duplicating this document and creating an agenda for each of your meetings—1:1 and group—you can save time and keep meetings focused.
Document your meeting minutes
With the number of meetings you attend every week, it’s inevitable that you’ll forget something. That’s why meeting minutes—a written record of what happened at the meeting—have become a standard meeting protocol.
Start with a template like ClickUp Meeting Minutes Template, so you have a standardized format for all your team meetings. This template allows you to create subpages for each meeting or have all your minutes in a running document—whatever your preferred method may be.
This template includes the following sections:
- Attendees: The participants who were present at the meeting
- Action items: Tasks that were confirmed along with the DRIs and deadlines
- Save for later: Topics or ideas that require further discussion
- General updates: Announcements made during the meeting
- Blockers: Any obstacles or challenges that might hinder project progress
By using a standardized format for your meeting minutes, you can ensure that all essential information, from action items to decisions, is easily accessible.
Speed up meeting ops with AI
As we already saw, AI meeting note-taking tools can jot down action items and create meeting summaries automatically. All you have to do is pull out important information and add it to your meeting minutes doc.
However, it doesn’t end there. You can use a GenAI engine like ClickUp Brain to summarize your meeting minutes or pull out specific action items. For example, if you run a lot of check-ins, then you can ask ClickUp Brain to give a one-line summary of the last five check-ins, so you have an overarching idea of team sentiments.
You can also use ClickUp Brain to brainstorm creative check-in questions for meetings or leverage AI prompts to create workflow automations for routine tasks like scheduling recurring meetings or inviting meeting participants.
Continue conversations outside your meeting tool
If important points couldn’t be fully discussed during the meeting, you can create a group conversation or add comments to the meeting notes doc to continue the dialogue. This also helps you share detailed information and have in-depth conversations asynchronously at your own convenience instead of running hours-long meetings.
For example, you can create a channel for each meeting in your team communication tool, such as ClickUp Chat, to share resources, track action items, and have ad-hoc conversations on the next steps.
ClickUp Chat really scores at helping you address issues instantaneously. Let’s say you simply ask someone on your team how their day is going, and they tell you they’re a bit rushed off their feet because some personal stuff came up.
Since ClickUp Chat is connected to their entire workflow in ClickUp, you can use AI summaries to go through their day’s workload, confer with other team members and/or stakeholders, reprioritize, reschedule, and/or reassign tasks—all of it from within Chat. Nothing can get missed out—because everything is connected. And it all began with a simple check-in.
The verdict? Let intelligent meeting tools take over the busy work for your check-in meetings so you can focus on the actual conversation and use it to drive impactful outcomes.
Summarize this article for me pleaseDos and Don’ts for Effective Check-ins
It’s now time for some check-in etiquette so your questions are more impactful during team meetings and don’t come across as insensitive or intrusive.
Let’s start with the dos:
- Frame questions positively to encourage open and honest communication
- Create a safe and supportive environment where team members feel comfortable sharing their thoughts and feelings
- Adapt your check-in style to the individual’s needs and preferences
- Keep check-ins concise and focused to avoid wasting time
- If necessary, follow up on any concerns or issues raised during the check-in
And now for some don’ts:
- Avoid asking overly detailed or intrusive questions
- Don’t focus solely on work. Include personal check-ins to foster stronger relationships and well-being
- Ensure that no one dominates the conversation and everyone is allowed to share their thoughts
- Don’t shy away from difficult conversations. Address conflicts directly and provide constructive feedback
- Don’t be dismissive and take team members’ concerns and ideas seriously
💡Pro tip:
Frame questions that help you check in with teammates, not check up on them.
Here’s how they differ:
- Check-ins are empathetic, non-judgmental, and team-focused: “How are you feeling about the project? Is there anything specific you’d like to discuss or any challenges you’re facing?”
- Check-ups are direct and output-focused: “What’s the current status of the project? Have you finished it?”
Summarize this article for me pleaseHumanize your Team Meetings with ClickUp
A well-crafted check-in question can revitalize team meetings, fostering a positive work environment and strong team dynamics. By asking thoughtful, non-judgmental questions, you can create a space for open communication, empathy, and genuine connection with each team member.
By combining team check-in questions with tools like whiteboards and note-taking apps, you can optimize meeting time, enhance collaboration, and drive better outcomes. That’s why we recommend trying out an all-in-one work management tool like ClickUp.
It helps you organize your meetings, make them collaborative, and automate meeting operations so you can focus on facilitating meaningful discussions and driving decisions.
Curious to learn more? Sign up to ClickUp for free and see how it simplifies meeting management.
Everything you need to stay organized and get work done.
