30 Great Check-In Questions for Managers to Drop in Meetings

Whether you're managing a small team, a whole department, or an entire company -- asking the right check-in questions can be the difference between a status update that could have been an email, and the opportunity to clear time-wasting blockers off your team's plate. But when busy professionals are hustling to stay on top of a never-ending task list, balancing 39.3 meetings/week on average, and trying to maintain their work-life balance, it's easy for proactive question planning to be put on the backburner when that check-in meeting rolls around.

And with a shocking 78.7% of professionals stressing about increasing workloads and less time to get everything accomplished -- it's more important than ever that managers check-in with their team to stay updated on progress, identify issues, and develop stronger relationships with your direct reports. 

So how do you start having better conversations with your team? In this blog post we're going to go over best practices for checking in with your team, and look at examples of great check-in questions to use in daily standups, one-on-one meetings, and team meetings, as well as mental health check-ins and fun icebreaker questions to build rapport with your team. 

How to (effectively) check in with your team 

The purpose of asking check-in questions in meetings is to keep team leaders up to speed on the progress of projects, examine blockers the team might be facing, realign direction with objectives, and get feedback on how to better support their work. But when asked without a purpose, check-ins can distract employees from their focus work, negatively affect team morale, and strain the relationship between managers and direct reports.

You're probably here because you want to avoid the latter scenario with your team, so let's look at some do's and don'ts for managers to facilitate productive check-ins. 

Dos for manager check-ins:

• Do respect everyone's time by upholding planned meetings.
• Do make it a safe space for your team to share ideas and concerns.
• Do be transparent about progress, expectations, and goals. 
• Do ask for feedback on how you can better support your team.
• Do help remove blockers that are preventing progress.
• Do use smart tools to automate and optimize check-ins.
• Do discuss career development on a regular cadence. 

Don'ts for manager check-ins: 

• Don't let a few dominate the conversation or interrupt others. 
• Don't turn a group meeting into a one-on-one.
• Don't make check-ins too formal that attendees feel stressed.
• Don't just focus on status updates that aren't relevant to everyone.
• Don't go off topic or consistently run over time. 
• Don't exclude remote team members in a hybrid work environment. 

Now that we've covered the basics of effective check-ins, how do we implement them in our meetings? Let's break down some of the most valuable types of check-in questions by meeting type, and walk through tips for each.

Daily standup check-in questions

Daily standups are a standard check-in meeting for many teams' day-to-day workflows. The purpose of standup meetings is to get a status update on daily progress and identify any blockers from the team. These should ideally be short and sweet - no more than a couple minute update per person - so that everyone can get back to more high-value task work for the day. 

Examples of standup check-in questions:

1. What did you accomplish yesterday?
2. What are you planning to accomplish today?
3. Do you have any blockers or concerns?

Tips: A few other pointers to make daily standups more productive include keeping your standup groups small so daily updates are agile, concise, and relevant to attendees -- ideally at a 9 person maximum, according to the Scrum Guide. Also consider automating standup meetings to be more flexible for bigger teams with tools like Standuply or Geekbot.

One-on-one meeting check-in questions

One-on-one meetings are a great opportunity to connect with individual team members, examine blockers more closely, realign priorities with company goals, build stronger interpersonal work relationships, and check in on employee job satisfaction. But unfortunately, more than 40% of one-on-ones are rescheduled every week because they often aren't prioritized highly enough by managers, and are considered 'moveable' meetings. In order to effectively lead your team, you need to make time to connect and discuss both challenges and opportunities with each individual team member so they can feel confident and supported in their role. 

Examples of one-on-one check-in questions:

1. What have you been working on since we last met?
2. What's been taking up most of your time?
3. What milestones have you hit?
4. What obstacles/blockers are you facing in your work?
5. What are your goals between now and our next meeting? 
6. How is work at the company aligning with your career goals?
7. How can I better support your work?

Tips: Of course, having more productive one-on-one check-ins starts with making sure they actually happen. Try using smart scheduling tools like Smart 1:1 Meetings at Reclaim to automatically find the best time for your meetings across both attendees schedules, and auto-reschedule when a conflict comes up to reduce cancellations by 83%.

Team meeting check-in questions

Team meeting check-ins can happen across staff meetings, cross-functional team meetings, leadership meetings, skip-level team meetings, even all-hands meetings -- allowing managers and executives to connect and facilitate conversation between relevant team members. Team check-ins can be especially valuable as groups come together to review performance against milestones, work through concerns, realign new objectives, and plan how to optimize collective progress moving forward. Since these check-ins usually involve more attendees and are thus longer, they should be kept agile to maximize value for everyone. 

Examples of team check-in questions:

1. What planned milestones did we meet in the last sprint, week, month, or quarter? 
2. How can we improve how we're approaching (insert specific launch/project/etc.)? 
3. Which tasks are taking up most of your time?
4. What are the biggest time wasters for you each week?
5. As a team, is there anything we should START/STOP doing?
6. Are there any blockers slowing down our progress?
7. What additional support can I provide to help us reach our team goals?
8. Who knocked it out of the park this week on the team?
9. Anything else you would like to share?

Tips: Team check-ins can be held at different intervals -- weekly, biweekly, monthly, and quarterly team meetings all serve different purposes for different teams (and should never be scheduled more than needed). One tip to avoid meeting conflicts across multiple busy schedules is to use an availability calendar to optimize the scheduling process, and eliminate the back-and-forth of finding a time that works for everyone. And, if you're working in a hybrid work setup, be inclusive of remote employees by using video conferencing to get everyone together. 

Wellness & mental health check-in questions 

Supporting employee mental wellness and offering a healthy work-life balance has become a top priority for organizations, with over 92% of companies adding support for new mental health programs since the pandemic started. And while programs are amazing additions at the organization-level, it's also up to managers to check in with direct reports to help prevent work-related mental health issues. Improving employee wellness at work isn't just the right thing to do for employees, it also benefits employers as positive job satisfaction actually improves employee productivity up to 30%. 

Examples of wellness and mental health check-in questions:

1. What is going well in your role? What have been some recent wins?
2. What is your biggest challenge right now?
3. How fulfilled are you by your role? What talents do you have that you would like to be using at work but aren't?
4. What resources would be helpful to you at this time?
5. How can I (as your manager) better support your work life? 

Tips: Mental health questions can apply in a one-on-one scenario, or on a team level, though if you think an individual is struggling, it's always best to check in individually. A good tip is to ask wellness questions regularly, and not just once you notice that a team member might need extra support. The key to preventing mental exhaustion and burnout in your team is to address issues proactively at the first signs. This creates a safe space and shows your team that you care, which also makes it easier for them to open up or approach you if something does come up in the future.

Ice breaker & fun check-in questions 

Let's wrap up this list of check-in questions on a fun note with some ice breaker questions you can bring to your next meeting. Including light-hearted check-in questions creates opportunities for your team to build rapport and connect on a personal level, especially for remote teams who only cross paths for specific work-related topics. Whether in a one-on-one, or a team meeting -- building interpersonal relationships with coworkers actually improves confidence in sharing opinions, brainstorming, and being enthusiastic about ideas from coworkers.

Examples of fun ice breaker check-in questions:

1. If you were going to cook for the whole team, what dish would you make?
2. If you had to perform karaoke right now, what song would you pick?
3. What is the most used emoji on your phone right now?
4. Do you have a favorite mug? Show-and-tell the team why it's the best.
5. What's a hobby or side project you've been meaning to take up?
6. What's something new or interesting you've learned recently?

Tips: As many of us have experienced working in remote, dispersed teams, we no longer have those easy 'water cooler' or 'break room' conversations, so these questions are really a great way to get everyone to open up and learn something new about each other. As for all check-in questions, it's important to be conscious and inclusive of everyone. Adding an ice breaker check-in at the beginning of a meeting can help set it up to be a more creative and productive session. Another tip is to implement a round-robin approach to answering fun questions to encourage involvement from the whole team and help take some of the pressure off more reserved members when it comes to their turn to answer.

Better check-in questions = better team productivity 🙌 

Check-in questions are a great way to stay updated on your team's status, track progress, and remove blockers, but taking full advantage of these opportunities to connect with your team is an effective approach to boosting productivity in and outside of meetings.

When it comes to check-in questions for any meeting scenario, it's important to prioritize inclusivity of all team members, facilitate support, and encourage feedback for management. And remember, it's important that work progress checks are also balanced with mental health check-ins and fun team building questions to maintain employee wellness and boost workplace culture. Try some of these example check-in questions at your next meeting to maximize insight and better connect with your team.

Pro tip - answer one of the ice breaker questions in the comments below just for fun!😜