141 Check-In Questions For Digital Teams Handpicked By Productivity Experts

Check-in questions are tricky.

Ideally, a check-in question must do three things at the same time: elicit an honest response, generate valuable data, and keep your employees engaged. 

But the payoff is there. 

Teams that regularly ask the right check-in questions at the right time experience higher productivity, unwavering team morale, and a strong bond between employees and managers. 

In this article, we gathered the most reliable check-in questions for every scenario: daily check-ins, weekly meetings, group check-ins, and check-ins for specific team setups. 

Tune in!

Daily Check-In Questions

Daily check-in questions are designed to align daily team efforts with broader goals while making sure not to interrupt daily operations. Ideally, daily check-in questions invoke collaboration between team members and help identify current roadblocks without putting pressure on individuals. 

Employees often are too shy to ask for help or express their current struggles, so a well-timed daily check-in can boost both trust and collaboration. Daily check-in questions share many characteristics with daily stand-up questions.

Good daily check-in questions:

  • Align workflows. Make sure team members are working in the right direction.  
  • Identifying immediate roadblocks. Fix small issues before they snowball into major delays. 
  • Spike collaboration. Team members can help when they know where they are needed. 

Not recommended during daily check-ins:

  • Putting constant pressure on progress. People stress out when they feel like they are monitored or judged on their performance. Ironically, stressed people are less productive.
  • Seeking improvement. The purpose of daily check-ins is not to improve processes, but to ensure their smooth operation. In other words, don’t try to improve what’s already working in the middle of the process, especially on a daily basis. Weekly and monthly check-ins are suited much better for strategic improvement. 

Examples of daily check-in questions: 

  1. What will you do today?
  2. What did you do yesterday?
  3. Anything blocking your progress?
  4. What distractions or interruptions prevent you from completing your work?
  5. How can we ensure that your projects and tasks are completed on time?
  6. Are there other projects or tasks that our team is responsible for that you could contribute to?
  7. Will you need to leave today at any point during the day?
  8. What information do you need to complete your tasks?
  9. Are there any resources you would find useful right now?
  10. Is anyone on the team can help you with overcoming roadblocks?
  11. Can you help anyone on your team overcome their roadblocks?

Weekly Check-In Questions

Weekly check-in questions offer unique opportunities to improve existing processes and perform a weekly touch base with your entire team. Employees still remember what they struggled with during the week, their highs and lows, but are not bogged down in immediate work and can answer more strategically.

Weekly check-in questions work similarly to Scrum retrospectives. The best weekly check-in questions help identify strategic opportunities for improving team productivity and team relationships in the long term. 

Tip: Try conducting regular weekly check-ins with your team directly in Slack or MS Teams because these can be automated and won’t distract your teammates from their work.

Good weekly check-in questions:

  • Inspire long-term improvement. 
  • Help identify significant inefficiencies. Recurring issues can plague productivity for months. Make sure to record your weekly check-in answers to spot negative patterns as soon as possible.

    Pro Tip: Learn how the Shopify team used Geekbot to identify trust problems within their team that led to reduced collaboration and miscommunication. 

Not recommended during weekly check-in questions:

  • Don’t be obsessed with details. Don’t fish for details during weekly check-ins. Our memory can be hazy, especially when people are trying to remember the nuances of the tasks they worked on almost a week ago.

    Instead, you can make sure you have a recorded history of all responses to daily check-in questions over the week. Tools like Geekbot can help you gather and store check-in responses automatically in Slack or MS Teams. 

Examples of weekly check-in questions:

  1. Each week, what are the biggest time wasters for you?
  2. Are there any major risks or issues we should address with our products or services?
  3. What constructive feedback have you received from your peers?
  4. Do you want more or less direction in your work? Why?
  5. What does your work-life balance look like right now?
  6. Is the type of work you are doing balanced?
  7. What will be the biggest challenge for you next week?
  8. What did you do last week that helped you reach your goals?
  9. What have you improved in your processes since last week?
  10. Were there any inefficiencies you’ve solved since last week? 
  11. What went wrong last week, and what can we learn from it?
  12. When it comes to your day or week, what activities take up the most time?
  13. When are you at your most focused and energetic during the week? Why
  14. What was the highlight of this week?
  15. What was the low point of this week?
  16. How could we improve these types of projects or tasks in the future?

Monthly or Quarterly Check-Ins

Monthly and quarterly check-ins work best when they focus on individuals rather than processes or workflows. Monthly check-in questions are a useful way to understand each employee’s struggles, how team members perceive their roles, how they communicate with a team or management, and so on. 

Regular monthly check-ins are a wonderful opportunity to identify any inner employee struggles such as the absence of praise, direction, motivation, and so on. Fixing these issues yields profound results for an individual’s productivity and the entire team’s well-being.

Great monthly check-in questions:

  • Identify employee struggles. Issues such as lack of motivation or purpose have dramatic effects on employee productivity, yet are notoriously hard to spot during daily or even weekly check-ins. Use monthly check-in questions to stay ahead of any deep-buried issues within your team. 
  • Forge strong connections between employees and managers. Successful managers know the immense value of monthly one-on-one sessions with employees, and monthly check-ins are a perfect addition to these. 

Pro Tip. Keep it light. We don’t recommend asking more than five questions during your monthly check-ins. 

Examples of monthly and quarterly check-in questions:

Have you made any progress on the three key areas we discussed in your last progress check?

Do you have clarity when it comes to your responsibilities?

What type of tasks could be shifted off your plate?

In the next four months, what do you think will be the keys to your success?

  1. What excites you most about your daily responsibilities?
  2. Which of your strengths is underutilized in your current role?
  3. In your role, what isn’t going well?
  4. What would you like to do more often?
  5. Where does this job fit within your future career goals?
  6. How does this job align with your personal values?
  7. Is your role fulfilling the responsibilities you expected? Why/why not?
  8. What new skills would you like to learn?
  9. What training is available internally that could assist you in your development?
  10. Do you face any obstacles to reaching your advancement goals?
  11. What other areas of the company would you like to learn about?
  12. Would you like to lead others?
  13. Are you worried about your ability to succeed in the coming months?
  14. What role/career would allow you to utilize your strengths every day?
  15. Why do you remain with this organization?
  16. Would it be possible to delegate some of your responsibilities to someone else so you can focus on new, more challenging tasks?
  17. Over the next two years, what would keep you at this job and in this organization? Five years? Ten years?
  18. Are there any projects or contributions you feel you should have been recognized for but haven’t been?
  19. In terms of recognition, what is more important to you: more responsibilities, more time off, cash, or job title?
  20. When you are at work, what makes you feel valued? Undervalued?
  21. Do you have any questions about the benefits you are currently receiving?

To make your one-on-one sessions even more effective, use Geekbot’s 1-on-1 feature that automatically gathers employee insights right before the 1-on-1 session with a manager. 

Developers Check-In Questions

In development teams, a great deal of success depends on the ability of managers to eliminate roadblocks that stand in the way of the development process and transfer knowledge from more experienced developers to junior ones.

The following check-in questions for developers will help you achieve both tasks. 

Examples of developer check-in questions:

  1. What bugs did you encounter this week and how did you resolve them?
  2. Is there anything you did yesterday that wasn’t planned?
  3. What unexpected coding issues did you encounter yesterday?
  4. What is your next step in the project?
  5. Was there anything you learned that will help you in the future?
  6. To help you reach your development goals, what can you start/stop/keep doing?
  7. How could you use your last professional experience to teach others?
  8. Does anyone in our organization appeal to you as a mentor?
  9. How would you like to benefit from a mentor?
  10. What new skills would you like to learn?

Marketing Check-In Questions

The success of any marketing team, whether it’s direct, inbound or outbound sales, will depend upon two factors:

  • How well do marketers understand their customer
  • How well the marketing team generates new opportunities for success. 

The following check-in questions for marketers will help you assess how well your team is doing in both. 

Examples of check-in questions for marketing and sales teams:

  1. Did you help your clients achieve the results they needed?
  2. How did you overcome a challenge by coming up with new ideas?
  3. What is the biggest obstacle to acquiring new customers?
  4. Which are your most and least significant opportunities?
  5. What are the things your customers want?
  6. What makes us different from our competitors?
  7. When was your last brainstorming session? 
  8. Are you confident in our marketing strategy?
  9. What are the current marketing department goals?
  10. Who are we targeting?
  11. How are we using our data?
  12. How are we tracking results?
  13. What is our strategy for retaining customers?
  14. How many referrals do you get?
  15. What are the most common sources of our leads?

Group Check-In Questions

Group check-in questions are designed to be asked and discussed within a team. These questions might focus on various aspects of team performance such as collaboration, organization, or team well-being. 

Group check-ins are best combined with team surveys, as surveys allow you to gather more elaborate data that you can use to better understand what to focus on during group check-ins.

Examples of group check-in questions

  1. Who would you turn to today for support?
  2. Are there any behaviors you bring to your work and to the team that make a positive difference?
  3. What areas of team collaboration are in need of improvement?
  4. What would you do differently if you managed our team?
  5. If you could change one thing about our team, what would it be?
  6. How could we be more creative or innovative as a team?
  7. How can we improve one of our products or services?
  8. What can we do to improve our teamwork?
  9. What kind of team-building activities would you like to see at work?
  10. How connected or disconnected do you feel with the team? Please elaborate.
  11. What do you admire about your team members?
  12. Is there a way to build trust among all our coworkers?
  13. What areas of our group performance are in need of improvement?
  14. What makes our team special from the ones you’ve worked with before?
  15. Are you satisfied with the level of support you receive?
  16. What was the latest useful thing you learned from a teammate?
  17. On a scale from 1 to 5, rate how often team problem-solving results in effective
  18. solutions. 
  19. On a scale from 1 to 5, rate the team skills we have to do our jobs
  20. effectively. 
  21. On a scale from 1 to 5, rate how attentive our team members are as listeners.
  22. On a scale from 1 to 5 rate how much everyone values what each member contributes
  23. to the team.
  24. On a scale from 1 to 5, rate how much members of our team trust each other.
  25. On a scale from 1 to 5, rate how productive our group meetings are.

Mindset Check-In Questions

Mindset check-in questions are used when you need to probe the level of motivation within a team and identify whether the current mindset is beneficial or detrimental to your project or company goals.

Mindset questions can also gauge employee well-being, especially in the connection with latest events such as recent sprints, change of work responsibilities, or team expansion. 

Examples of mindset check-in questions:

  1. Are there any mental blocks that prevent you from achieving success?
  2. When are you at your most focused and energetic during the day/week?
  3. How would you describe our team culture?
  4. Do you feel supported by your managers?
  5. Do you feel supported by your colleagues?
  6. Do you think our team culture actually helps us achieve our goals more efficiently? 
  7. How can we improve our team culture?
  8. What tasks push you outside of your comfort zone?
  9. What can we do to improve our company culture?
  10. Your current mindset: how would you describe it?
  11. What do you enjoy or dislike about working here?
  12. How does working here make you proud?
  13. On a scale from 1 to 5, evaluate the statement: my team has a strong sense of accomplishment
  14. relative to our work.
  15. On a scale from 1 to 5, evaluate the statement: people on my team are rewarded for being team players
  16. On a scale from 1 to 5, evaluate the statement: our team’s mission and goals are well aligned with the organization’s mission and goals.

Progress Check-In Questions

Use progress check-in questions when you need to learn about the current state of matters. Try mixing up various progress check-in questions to evaluate progress from different perspectives and keep things fresh. 

Examples of progress check-In questions:

  1. How are your projects or tasks coming along?
  2. Are the projects or tasks you are working on aligned with your goals?
  3. How do you prioritize your projects and tasks?
  4. How will this project or task benefit you, the team, and the company?
  5. How will you measure the success of this project or your work?
  6. What could you learn from this project? Have you learned anything so far?
  7. Are you having trouble completing your work? Is there anything preventing you from completing it?
  8. Is there anything that could prevent you from completing your projects or tasks on time?
  9. Which of the following would help you complete your tasks or projects: additional resources, mentoring, support, etc.?
  10. Was the project successful?
  11. Did you finish your part of the work successfully?
  12. Would you like to work on any other projects or tasks?
  13. On a scale from 1 to 5, evaluate the statement: we strive to integrate our plans with those of other work groups.

“Get to Know Your Employee” Check-In Questions

Check-in questions can be a great way to learn more about your employees and facilitate deeper bonds between team members. 

The following check-in questions are similar to icebreaker questions, so make sure to check our complete list of icebreaker questions if you want to find more examples of “get to know your employees” and team bonding questions. 

Examples of “get to know your employee” check-ins:

  1. Did you receive the name of someone special or does it have a special meaning?
  2. What is the scariest thing you’ve ever done?
  3. Do you have a favorite place in the world? 
  4. Which of your senses would you give up if you had to (hearing, seeing, feeling, smelling, tasting)? 
  5. What animal would you be and why?
  6. Would you prefer a cat or a dog as a pet?
  7. If you were an animal, what would you be and why?
  8. What is one goal you’d like to accomplish during your lifetime?
  9. Do you prefer the mornings or the evenings?
  10. Which Disney movie is your favorite, and why?
  11. What do you want to be famous for?
  12. What three words would you use to describe yourself?
  13. What kind of car do you drive? How do you choose a car?
  14. Do you have a secret vice?

Common Issues With Check-In Questions

The most effective check-in questions are specific, targeted, and well-timed.

And although check-in questions are a powerful tool that can alleviate many aspects of team performance, many teams struggle with harnessing their full potential.

Here are the common issues that greatly diminish the power of check-ins. 

  • Irregular check-ins. One-time check-ins won’t have much of an impact as their power comes from their regularity.

    When you regularly gather feedback from your team, you can spot recurring issues, track changes in team dynamics, and refine your approach.
  • No recorded history of answers. When you don’t have a recorded history of previous answers, you have two problems: no one remembers what was already said, and people forget valuable lessons of the past.

    Moreover, without a history, you can’t spot recurring patterns in team answers and will have the same issues affecting your performance over and over.
  • Hard or impossible to organize manually. There are different types of check-in questions, and each serves a valuable, yet unique purpose.

    But organizing responses to different types of check-ins, scheduling new sessions, and selecting participants can eat up lots of managers’ time, so managers stick to irregular check-ins or drop check-ins completely.

Fortunately, there’s a way to automate check-ins and automatically record and organize everyone’s responses. 

And that’s why we developed Geekbot.  

Using Geekbot, you can automatically send regular check-in questions to your team members in Slack or MS Teams. The bot will gather all the responses in the selected channel:

What’s important is that Geekbot was built to eliminate distraction. Instead of wasting hours in check-in meetings, team members spend less than a minute answering questions and can do that whenever they can. 

All the responses will be stored forever, meaning you will have a full history of previous responses and can go back to any point in the past.

You can pick how often you want to send check-in questions, what questions to send, and who will receive them. Use our default templates or add any check-in questions you want. 

Moreover, there are randomized templates like Pizza Toppings that will send random questions of each type if you want to keep your check-ins fresh and unique.

Geekbot can be used to conduct daily, weekly, and monthly check-ins directly in Slack or MS Teams. You can also use Geekbot to conduct standups, retrospectives, and surveys, and replace all ineffective and time-eating meetings. 
Best news? Geekbot is totally free for small teams with up to 10 members. For larger teams, we provide a 30-day free trial with no restrictions. Try Geekbot now and harness the full power of automated check-ins for your team.

Frequently asked questions

What’s the difference between check-in and icebreaker questions?

The difference between check-in questions and icebreaker questions lies in their purpose. Regular check-ins help you gather valuable data from the team to help you identify roadblocks and improve team productivity. Icebreaker questions facilitate team bonding and help employees learn more about each other.

How often should you ask check-in questions?

The frequency of asking check-in questions defines their effect. For example, daily check-in questions serve as a way to align team members and identify short-term roadblocks in the way of their productivity, while monthly check-ins are better suited for surfacing issues within employees such as morale and well-being.

What’s a good check-in question?

A good check-in question helps managers gather valuable info about employees without interrupting both parties from work. Such a question is designed to elicit an honest response while not confusing employees. Hence why the best check-in questions are designed to be short, yet have psychologically meaningful intent.

Leave a Reply

Your email address will not be published.