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15 Check-In Questions That Won't Make Your Eyes Roll

Check-In QuestionsCheck-In Questions
min read
August 21, 2023

You want to know how your employees are doing. The easiest way to find out? Go ahead and ask them. 

Checking in with your co-workers, team members, and employees is the best way to get a feel for what’s going well within your business—and what isn't. But, it takes more than simply asking, "How are you doing?" If you really want to know how your workers are feeling about their jobs and your company as a whole, you’ll want to ask the right questions.

Stuck on how to get the conversation rolling? We're here to help with the best check-in questions to get the real lowdown on how your team is doing. 

What Makes the Best Meeting Check-In Question?

As a team leader, it’s your job to act as the meeting facilitator. That might seem like a fancy title, but all it means is that you’re in charge of keeping the meeting focused—and that includes putting together the questions that will get the most out of attendees.


The most effective check-in questions are:


They require a longer answer than simply "yes" or "no.”

Framed Positively

They don't use overly negative language.

Answered Quickly

They might be open-ended, but they're focused enough that they don't require an essay to answer.

An Opportunity to Share New Information

They ask about things you don’t have the answers to yet (otherwise, it can feel like you’re asking leading questions).


A check-in meeting should happen frequently—ideally every week or every other week. This isn’t a formal performance review or career conversation and is instead an informal and low-pressure chance to touch base with your employees


If you’re still not sure what type of questions to ask, here are a few check-in meeting templates to get the ball rolling.

Individual Check-In Questions

1. What are the top three things you’re working on this week?

This is a good question to help you and your employee get on the same page about what’s most important to focus on during the coming week. It also helps you make sure they’re meeting deadlines and figure out if they need help or are available to help others. If they clearly have a lot on their plate, others might be able to chip in and lighten the load. In turn, that will make your check-ins a positive and supportive experience for them.

2. What are some things that went super well this past week? 

This is a great check-in question to ask because it gives you a chance to recognize an employee for their solid work. What’s more, you don’t only have to focus on work achievements. Finding out more about people’s hobbies or accomplishments in their life outside of the office is just as important when it comes to team bonding. Plus, closer teams tend to collaborate better and more often, which boosts overall productivity.

3. How did any advice you were given this week affect your work?

Letting your employees know how they’re doing is one of the most important responsibilities of a manager. It’s not only great for employee engagement but also for your business’s bottom line. Studies have found that companies have a nearly 15 percent lower turnover rate when they regularly provide employees with feedback. This is a way for you to figure out if your feedback is helping your employees grow or if you need to tweak some things. 

4. Were you able to get everything done you wanted to this week?

It can be difficult for employees to approach leadership when they’re feeling overwhelmed. So take the lead here and ask the question directly. It’s important for you to know the bandwidth across the team so that you can make sure everyone has enough time for the work they’ve been given. 


This is also a good opportunity for employees to self-reflect on how they can improve their performance and where they may need support to achieve this. Areas like work environment, team collaboration, or a different work schedule could all come up in response to this question.

5. What’s a goal that’s really important to you?

Research by Gallup shows that 48 percent of American workers would be willing to switch to a new job if offered better skills training opportunities. If you’re looking to retain your best employees, help them progress in their careers and figure out how your company can help.

Team Check-In Questions

1. Are there any tools or resources out there that could help us do better? 

The answer to this question is going to be different across every team and type of responsibility. But it’s important to know if anyone feels they're missing a particular software, tool, learning course, resource or program that would speed up their workflows (and save them some stress).

2. How can these meetings be more helpful? (Every three to four meetings)

Meetings are only as helpful as the information that comes out of them. Checking in with the entire team about how the meetings are structured and run should come up at least once every three or four meetings. This gives everyone involved the chance to share their opinions and thoughts on what would work well for the whole group.

3. What’s an exciting thing coming up for you this week?

Before you wrap up a team meeting, end the session on a positive note. This is one of the best team-building questions that you can ask, as you’ll gain some insight into what’s important in the lives of each of your employees—which will help you all build deeper bonds with each other.

4. Is there anything we mentioned in today’s meeting that we should discuss more at the next one?

Sometimes meetings can run over and people start to mentally check out. Shelving a discussion point for the top of the next meeting’s agenda can keep employees engaged and prevent meetings from becoming a drag. 

Remote Employee Questions

1. Is there anything we can do to make you more comfortable working at home?

Whether it’s a comfier office chair, access to development resources, or organizing a virtual happy hour with remote co-workers, there’s always something that your company can do to improve the experience of your remote team

2. What’s the biggest challenge or benefit you’ve experienced working remotely this week?

Feelings about working remotely can change over time, so it’s smart to ask a question like this one frequently in your check-ins. It’ll help you get a sense of whether your employee is loving their work arrangement or is dealing with some drawbacks that you can help resolve.

3. Is there anything you feel I missed this week?

Remote work offers a lot of conveniences, but that reduced face-to-face time with managers can also be concerning. Asking this type of question gives your employee a chance to shine a spotlight on anything they want you to be aware of—whether it’s a project they finished, a piece of positive customer feedback they received or something else.

General & Icebreaker Questions

1. What are you reading or watching at the moment?

This question might seem unnecessary, but downtime is a vital part of work-life balance, Questions like this emphasize the company’s support of employee well-being. They recognize that workers have a life outside of working hours and that you’re invested in them as a whole person—which can help boost their engagement, loyalty, and morale

2. Where do you want to go on your next trip?

This is another fun and light-hearted question and it has the added benefit of reinforcing that you value their work-life balance and their time outside of the office. It might even give you some ideas on how you can reward them for a job well done. Do they dream of eating at a five-star restaurant in a different city? Maybe you could get them a gift card when their next project wraps.

3. How do you usually unwind after work? 

Just like asking about travel dreams, this question is another good way to gain some insight into what your employees like to do outside of work and can help you bond over shared interests and even plan for some special treats.

Why Do You Need to Ask Check-In Questions?

Before you toss out a few of these questions in your next meeting (whether it's in a one-on-one or in one of your larger team meetings), you might be wondering why you should bother asking these at all. Let's look at a few reasons why individual and team check-ins are important:

Get a Sense of What Work is Being Done–and When

Starting with the more obvious benefits, regular check-ins are a great opportunity for team leaders to understand the status of current projects, how everything is moving along, and where the team might need additional support. 


Typically, check-in questions focused on the team's current workload will be front and center on the meeting agenda.

Fix Problems

Particularly in one-on-one or follow up meetings, managers can use this time to get a sense of their employee’s overall well-being


This has become even more crucial since the start of the COVID-19 pandemic, with research from Deloitte showing that nearly 80 percent of businesses consider the well-being of their team members to be an important factor in their company’s success. 


For instance, if somebody keeps missing deadlines, check-in questions can identify the problem. Perhaps there’s a work-life balance issue that your employee is struggling to deal with and it’s impacting their workday. Showing your employees empathy and compassion in those moments, along with offering practical guidance for managing their workload, is a great way to build trust. 

Improve Teamwork

When your team spends the majority of their day actually doing the work you’re paying them for, there’s usually little opportunity for interaction outside of project discussions. And since many businesses shifted to remote work in 2020, creating meaningful connections between employees has become even more challenging. 


Gallup reports that only 36 percent of U.S. employees feel engaged at work, so how can businesses reignite their employees' passion and commitment? 


Starting a meeting with a fun ice breaker question can be a good way for people to get to know their co-workers better. That camaraderie lays the groundwork for way more effective teams.

When Should You Ask Questions in Check-Ins?

Some check-in questions are lighthearted and casual while others dig deeper into an employee's experience. So, when there's such a range of questions to ask, how can you know when to touch base with your employees? 


A lot of it will rely on gut feel. Easy and fun questions could be asked in passing around the coffee pot or at the start of a meeting. Ones that are more in-depth should likely be saved for team meetings or one-on-one conversations.


Here's a little more information to help guide the timing of your check-in questions, so you don't catch your employees off guard. 

During Scheduled Meetings

Putting a general check-in question or two at the top of the meeting agenda can help your employees prepare ahead of time and is a good way to align everyone’s focus before you dig into the more important topics. 


You could even sprinkle a few in throughout different points of the meeting, such as when you’re wrapping up one section of the agenda. That way, you can make sure the whole team is engaged during the whole conversation. 

During Recurring Check-Ins

For some teams, a recurring stand-up meeting is the best place for check-ins. These types of meetings are brief, typically around 10 to 15 minutes, and review the high-level updates that everyone needs to know. 


A daily stand-up works especially well for project management teams who may need to share information on a more frequent basis than other groups in the company. Setting a daily stand-up for first thing in the morning is a good way to begin the day and get people on the same page before they get to work.


Your team members may not work on the same schedule, particularly if they’re remote. A standing meeting may not be best in this situation, but there are other ways that you can check in regularly. 


If your team uses a communication tool like Slack, you could set up a dedicated channel for responses to check-in questions. The whole team can see their responses when they log in and they post their own replies. 

Don't Guess How Employees Are Feeling

Try your best to avoid making assumptions about how your employees are doing—and ask them if you can.


It’s easy to forget about the personal or fun questions when you’re more focused on the nitty-gritty work details. You’ve only got a limited amount of time to get through everything, so why bother with the casual small talk? 


Remember, though, that the key to building more effective and engaged teams is all about making people feel supported, and asking all kinds of check-in questions is one big way to do that.

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