The first five minutes of your meeting can determine the success of the next fifty-five. A powerful check-in question does more than just break the ice, it builds psychological safety, boosts engagement, aligns your team before the agenda even begins.
Many managers either skip check-ins entirely or ask the same stale question (“How is everyone?”) that elicits one-word answers, wasting a crucial opportunity to connect. This is your definitive guide to mastering the art of the check-in, complete with 100+ check-in questions categorized for every possible scenari- from one-on-one meetings to daily stand-ups - fun icebreakers.
The Psychology of a Great Check-in: Why It Works
Beyond “How Are You?”: The Core Benefits
Building Psychological Safety: Check-ins create a safe space for team members to be authentic and vulnerable, establishing trust that carries throughout the meeting.
Increasing Engagement: Teams that begin meetings with purposeful check-ins report 39% higher engagement levels compared to those that dive straight into business.
Stimulating Creativity: Personal or creative questions prime the brain for innovative thinking by activating different neural pathways than typical work discussions.
Giving Everyone a Voice: Check-ins ensure that even the quietest members participate right from the start, setting an inclusive tone for the entire session.
How to Facilitate a Check-in Round for Maximum Impact
A Simple 4-Step Process
1. Set the Stage: Announce the check-in question clearly at the very beginning of the meeting. This signals intention and prepares participants mentally.
2. Lead by Example: As the manager, answer the question first to model vulnerability and set the tone. Your authenticity encourages others to open up.
3. Go Around the “Room”: Use a predictable order (clockwise, alphabetical, or screen order for virtual meetings) so everyone knows when their turn comes.
4. Listen Actively, Don’t Solve: Emphasize that the check-in is for sharing, not problem-solving. Acknowledge answers with a simple “Thanks for sharing” to maintain momentum.
15 Check-in Questions for High-Impact One-on-Ones
To Gauge Workload - Well-Being
- “What is your workload like right now? Are you feeling energized or drained?”
- “What’s one thing we could change about our team’s process to make your life easier?”
- “On a scale of 1-10, how supported do you feel in your current projects?”
- “What’s taking up the most mental space for you this week?”
- “What would help you feel more confident in your role right now?”
To Discuss Career Growth - Aspirations
- “Does your work here align with your long-term career aspirations?”
- “Which skill of yours do you feel is currently being underutilized?”
- “What’s one thing you’d like to learn that would excite you most?”
- “Where do you see yourself making the biggest impact next quarter?”
- “What kind of projects energize you versus drain your enthusiasm?”
To Strengthen Manager-Employee Connection
- “What’s one way I can better support you as your manager?”
- “Is there anything you’ve been hesitant to bring up that we should discuss?”
- “What feedback do you have about our communication style?”
- “What would make our one-on-ones even more valuable for you?”
- “How can I help remove obstacles that are slowing you down?“
18 Check-in Questions for More Engaging Team Meetings
To Align on Work - Priorities
- “What’s one thing you’ve accomplished this week that you’re proud of?”
- “What are the biggest time-wasters for you each week?”
- “What’s your main focus for the rest of the week?”
- “Where are you feeling most stuck right now?”
- “What’s one decision we made as a team that’s working really well?”
- “What would help you be more productive this week?”
To Strengthen Team Connection
- “Who in the team deserves a shoutout for something they did this week, and why?”
- “As a team, what’s one thing we did well last month, one thing we could do better?”
- “What’s one thing you’ve learned from a teammate recently?”
- “How would you describe our team’s energy level right now?”
- “What’s something you appreciate about working with this group?”
- “If our team had a theme song, what would it be why?”
To Foster Innovation - Problem-Solving
- “What’s an idea you’ve been sitting on that might help our team?”
- “If you could change one thing about how we work together, what would it be?”
- “What’s a challenge you’re facing that the team might help solve?”
- “What’s the best process or tool you’ve discovered lately?”
- “What would you do if budget wasn’t a constraint for our next project?”
- “What trends or changes in our industry are you most curious about?“
10 Check-in Questions for Remote and Hybrid Teams
- “What are the best and worst parts of working remotely for you this week?”
- “Do you feel you have the resources and tools you need to succeed from home?”
- “What’s something we can do to make our virtual collaboration more effective?”
- “How are you staying connected with the team while working remotely?”
- “What’s your biggest challenge with remote work right now?”
- “What part of your home workspace is working well, and what isn’t?”
- “How do you prefer to receive feedback when we’re not in person?”
- “What’s helping you maintain work-life balance while remote?”
- “What do you miss most about in-person collaboration?”
- “How can we make virtual meetings feel more engaging for you?”
Check-in Questions for Every Stage of a Project
At the Project Kickoff
- “What are you most looking forward to about this project?”
- “What do you need from me as a project manager to be successful?”
- “What concerns do you have about this project timeline?”
- “What’s your biggest hope for the outcome of this work?”
- “What skills are you excited to use or develop during this project?”
During Project Execution (Mid-Project Check-in)
- “What is working as expected, and what isn’t?”
- “Is everything on track, or are we behind schedule? What can we do to adjust?”
- “What’s been your biggest learning so far?”
- “Where do you need more support or resources?”
- “What would you change about our process if we started over?”
At the Project Retrospective
- “What is the single biggest lesson we can learn from this project?”
- “What will you do differently next time we have a project like this?”
- “What part of this project made you most proud?”
- “What process or decision helped us succeed?”
- “How has this project changed your perspective on our work?“
100+ Fun Check-in Questions - Icebreakers (Clustered by Theme)
Desert Island - Survival Scenarios
- “You’re stranded on a desert island. Which coworker do you want with you and why?”
- “What one kitchen utensil would you bring to a desert island?”
- “A mild-mannered animal is now your sworn enemy for life. Which animal is it?”
- “You have to build a fort using only office supplies. What’s your primary material?”
- “You can only listen to one song on repeat while stranded. What song do you choose to slowly drive you insane?”
- “You’ve just been made the leader of a new, tiny island nation. What’s the first law you enact?”
- “What is the most useless survival skill you possess?”
- “You have to survive a zombie apocalypse with the team. What role does everyone play?”
- “You can only eat one food for the rest of your life. It has to be something you currently hate. What is it?”
- “A friendly dolphin offers you a ride back to civilization, but you have to pay it with the most embarrassing story you have. What’s the story?”
- “You find a treasure chest, but it’s full of something incredibly inconvenient. What’s inside?”
- “Your only companion on the island is a parrot that only repeats one phrase you’ve said in a meeting. What’s the phrase?”
Food and Snack Absurdities
- “What is the most controversial food opinion you hold? (e.g., ‘Pineapple belongs on pizza.’)”
- “If you had to replace your hands with food items, what would you choose?”
- “What’s a food you could happily eat for a week straight?”
- “You’ve been hired to create a new, terrible flavor for a popular snack. What’s the flavor?”
- “If you were a potato, what way would you like to be cooked?”
- “What’s a ‘weird’ food combination you secretly love?”
- “You can only smell one food for the rest of your life. What is it?”
- “What is the absolute worst pizza topping imaginable?”
- “If fruits could talk, which one would be the rudest?”
- “You have to make a sandwich using only ingredients found in this room right now. What’s in your sandwich?”
- “What meal would you choose to eat for the rest of your life?”
- “You must rebrand a common vegetable to make it sound like a luxury item. What’s its new name?”
- “If you had a restaurant, what would its name be, what would be your signature dish?”
Superpowers, Sci-Fi - Fantasy
- “You get a superpower, but it’s incredibly inconvenient. What is it? (e.g., ‘The ability to fly, but only two inches off the ground.’)”
- “What would be the most boring superpower to have?”
- “If you were a wizard, what would be your most-used, mundane spell? (e.g., ‘Accio TV Remote!’)”
- “You’re a superhero. What’s your name and what’s your weakness?”
- “If you could have any mythical creature as a pet, what would it be?”
- “What sci-fi gadget do you wish existed in real life?”
- “You have to replace your legs with the legs of an animal. What animal do you choose?”
- “What would be your ‘walk-on’ song if you were a professional wrestler?”
- “You are a ghost. Who or what do you haunt and why?”
- “You can talk to one species of animal. Which one do you choose to talk to?”
- “You’re an evil genius. What’s your ridiculously petty evil plan?”
- “If you were a Dungeons and Dragons character, what would your primary stat be? (Strength, Dexterity, Constitution, Intelligence, Wisdom, or Charisma)”
- “You can teleport, but only to places you’ve been in the last 24 hours. Where are you going?”
Weird Talents and “Would You Rather”
- “What is your most useless talent?”
- “Would you rather have a permanent bad haircut or a permanent ‘hiccups’ sound effect after every sentence?”
- “What’s a strange skill you’d love to learn?”
- “Would you rather fight one horse-sized duck or one hundred duck-sized horses?”
- “What’s the weirdest thing you’re an expert on?”
- “Would you rather have everything you eat be slightly too salty or slightly too sweet for the rest of your life?”
- “What’s a completely false fact you could make up that sounds believable?”
- “Would you rather have fingers for toes or toes for fingers?”
- “What is the most ridiculous thing you’ve ever convinced someone to believe?”
- “Would you rather have the ability to talk to animals or speak every human language fluently?”
- “What’s a secret skill you have that would surprise the team?”
- “Would you rather have a theme song play every time you enter a room or a laugh track play after everything you say?”
Pop Culture and Nostalgia
- “What movie or TV show title best describes your last week?”
- “If your life was a movie, what genre would it be?”
- “What fictional character do you relate to the most?”
- “What 90s fashion trend do you secretly wish would make a comeback?”
- “You have to join the cast of a reality TV show. Which one is it?”
- “What’s a song you know all the lyrics to, but you’re slightly embarrassed about it?”
- “If you could live in any sitcom’s universe, which one would you choose?”
- “What movie villain do you secretly root for?”
- “What was your favorite childhood cartoon?”
- “If you could bring back one cancelled TV show, what would it be?”
- “What song would you choose for the final, epic scene of a movie about your life?”
- “You can only quote one movie for the rest of your life. Which movie is it?”
- “What’s a piece of old technology you miss?”
Work and Office Humor
- “What’s the most ridiculous ‘corporate speak’ phrase you’ve ever heard?”
- “If our company had a mascot, what would it be?”
- “What would be the title of your work-themed autobiography?”
- “If you could replace the hold music for our company’s phone line, what song would you choose?”
- “What’s the most creative way you’ve ever procrastinated?”
- “If you could have any celebrity narrate your workday, who would it be?”
- “What is your go-to ‘I’m paying attention’ face for long meetings?”
- “If you could add one ridiculous item to the office supply cabinet, what would it be?”
- “What’s the funniest thing you’ve overheard at work?”
- “If we had an office pet, what would it be and what would its job title be?”
- “What’s the title of a movie about our last major project?”
- “If you could only communicate using emojis for a full day, which three would you use the most?”
- “What’s the most bizarre dream you’ve had that involved work?”
Animal Kingdom Mayhem
- “If you were an animal, what animal would you be, based purely on your eating habits?”
- “What animal do you think is the most dramatic?”
- “If you could shrink any animal to the size of a cat, which one would you keep as a pet?”
- “What animal’s ‘special ability’ do you wish you had? (e.g., a cat’s ability to sleep anywhere)”
- “If you had to be a sidekick to an animal superhero, which animal would you choose?”
- “What animal would be the best at your job?”
- “You’re a zookeeper for a day. Which animal enclosure are you most excited about and which one are you dreading?”
- “If you had an army of squirrels at your command, how would you use them?”
- “What animal walks the weirdest?”
- “If you were a dog, what breed would you be?”
- “What animal would you least like to be reincarnated as?”
- “If you could crossbreed two animals to create the ultimate pet, what would they be?”
Everyday Absurdities and Musings
- “What’s a small, insignificant thing that makes you unreasonably happy?”
- “What’s a weird thing you do when no one is watching?”
- “If you could have a lifetime supply of anything, what would it be?”
- “What’s the most ridiculous purchase you’ve ever made?”
- “If you had to describe your current mood as a weather pattern, what would it be?”
- “What is something you are hilariously bad at?”
- “You can invent a new holiday. What is it called and how is it celebrated?”
- “If you could pick a new first name for yourself, what would it be?”
- “What’s the strangest compliment you’ve ever received?”
- “If you had to live without one of your five senses, which one would you give up?”
- “What’s a common saying that makes no sense to you?”
- “If you could ask your future self one question, what would it be?”
- “What’s the silliest thing you’ve had an argument about?”
- “If you could only use one condiment for the rest of your life, which one would it be?”
The “Check-Out” Question: How to End Meetings Effectively
Bookend Your Meeting with Intention
A “check-out” question helps summarize feelings and ensure alignment before everyone leaves. It creates closure and maintains the human connection established during check-in.
Sample Check-Out Questions
- “What’s your main takeaway from this meeting?”
- “On a scale of 1-5, how productive was this meeting for you?”
- “What’s one thing you’re committed to doing before our next meeting?”
- “How are you feeling as we wrap up today?”
- “What question are you leaving with that we should address next time?”
Leveraging Technology for Better Meeting Outcomes
While check-ins create human connection, technology can help you capture and act on the insights they generate. Meeting summarizers can automatically transcribe discussions and highlight key action items mentioned during check-ins, ensuring follow-through on commitments made.
For remote teams especially, having accurate meeting notes helps preserve the context and emotional tone established during your check-in round. The combination of intentional human connection and smart automation creates the foundation for highly effective team meetings.
Frequently Asked Questions
What do you talk about in a check-in?
Check-ins should focus on current state, feelings, energy levels, or fun icebreakers depending on your meeting’s purpose. The goal is connection, not problem-solving.
How long should a meeting check-in take?
Plan for 1-2 minutes per person maximum. For a team of 6, your check-in should take no more than 12 minutes to maintain meeting efficiency.
What do you do if a team member gives a concerning or negative answer?
Acknowledge their response during the meeting, then follow up privately afterward. The check-in isn’t the time to solve problems, but it’s crucial to address serious concerns one-on-one.
How often should you change the check-in questions?
Rotate questions every 2-3 meetings to maintain novelty. Having a few go-to questions is fine, but variety keeps engagement high.
What are good check-in questions for new employees?
Focus on comfort level, learning experiences, and what support they need. Avoid anything too personal until they’re more comfortable with the team.
Can check-ins work for large meetings?
For groups larger than 8-10 people, consider breakout rooms or alternative formats like polls to maintain efficiency while preserving connection.
Start Your Meetings with Purpose
Check-in questions are a simple but powerful tool for leaders to build connection, increase engagement, foster psychological safety. The best meetings start with a moment of genuine human connection. By thoughtfully choosing your check-in questions, you can transform your team’s culture, one meeting at a time.
Whether you opt for practical work-focused questions or dive into the fun & absurd options we’ve shared, remember that consistency matters more than perfection. Start small, observe what resonates with your team, adjust your approach based on what creates the most authentic engagement.
