30+ check-in questions to create connection with your team

Too often, managers have a hard time just being with their team members. They want to fill dead air with chatter but don’t always know what to say or how to make a connection. Meanwhile, employees often have their own struggles. Like how to craft a well-articulated question? Or, how can I make my boss feel comfortable talking with me? Luckily, there are some powerful communication tools like check-in questions that managers can use to authentically connect with their team without crossing the line of formality.

These tools help us notice what’s going on in the moment and ask the kinds of questions that draw out valuable information. And, because they’re so simple, you’ll find plenty of opportunities to use them.

In this article, we’ll run through some simple communication techniques and formats, then share 21 straightforward yet powerful themed check-in questions that will create a strong connection between you and your team members.

Setting off on the right foot: How to keep things positive

Using casual and friendly language can help lower defenses and create an environment where your team or colleagues feel comfortable sharing their thoughts and feelings. Keeping the questions focused on them also helps take any focus off you, so they’re not feeling like they’re being judged or evaluated by their manager.

Generally speaking, conversations can skew positive, neutral, or negative — and as the manager, it’s your job to guide this.

• Positive: “How’s that article coming along? Is there any additional support you need?”
• Neutral: “Have you finished that article?”
• Negative: “That article was due yesterday. Where is it?”

As you can see, all three check-in questions say a similar thing, but the tone they create for the rest of the conversation is very different. The last question has an accusatory tone, and it’s not helpful to anyone involved. Steer clear of this approach at all costs.

How to ask check-in questions that get good answers

When you’re asking questions, there are a few simple things you can keep in mind to get the best results.

Cadence

This refers to the rhythm of your check-in questions.

• If asking multiple questions in one sitting, e.g., in a job interview, you should ask questions in a steady stream so that the other person doesn’t feel like they’re waiting too long to answer one before asking another.
• If you’re asking questions to colleagues over the long-term — e.g., enquiring about project updates — make sure you don’t ask too regularly. By asking the same question when the answer is unlikely to change, your team may feel like you’re micromanaging, which is never a good look.
• On the flip-side, if you don’t ask often enough — say, only holding an employee review once a year — you could be missing out on valuable feedback that could be used to improve your management style or company culture.

There’s no right or wrong way. The secret sauce is to just listen, pay attention, and think carefully about the kind of results you want. Remember: Questioning should always be about moving things forward or providing support — not to serve your own interests.

Context

Making sure your questions align with the subject is important and the key to getting relevant, thoughtful answers. It’s also worth considering the communication channel you use to ask these questions. Quick, friendly check-ins can be sent over your team’s messaging app — whereas weightier topics are best kept for face-to-face catch-ups.

Before asking any check-in questions, ask yourself these things:

• Has it been asked too soon?
• Has it been asked often enough?
• Is it relevant to the context and recipient?
• Is it for the benefit of the recipient?

How to pick the right format for your check-in questions

Part of getting good answers is asking the right questions in a format that helps the recipient respond in a helpful way.

Answers can be broken down into two types: qualitative and quantitative.

Quantitative answers provide numerical evidence, such as numbers and statistics — and qualitative answers can be used to provide the evidence for those numbers. They’re more open-ended and encourage the recipient to elaborate as much as they feel necessary.

When you’re just starting to ask questions, stick to qualitative feedback. It’s better to get your team members accustomed to having these conversations than to overwhelm them with too much information at once. As your check-ins become more routine, you can start adding more quantitative questions — but don’t force it! It will still be valuable even if there aren’t any figures attached.

Here are some more question types to guide you:

Open questions — these allow team members to answer without much direction from you.

Probing questions — these are meant to help you understand the respondent’s thoughts and feelings. They don’t have a set answer — generally, they encourage the respondent to elaborate on their response before moving on to another topic. Providing time for your employees to finish answering can be helpful if they need more clarification or feel unacknowledged.

For example, asking, “What actually motivates you?” can be followed up with, “What makes you want to excel at this job?”, “Is there anything we should change about our rewards and incentives program?”, etc. It’s an open-ended question with several parts.

Closed questions — these provide a limited number of answers that the respondent must choose between. Closed questions take a little more thought but can help elicit the exact information you need.

These include Yes/No (“Are you having fun at work?”), as well as Multiple Choice and Ranking (“What is your favorite aspect of our new team building activities? Least favorite? Rank them in order”). You can combine these into open-ended closed questions (“What is the single most helpful thing I could do for your happiness at work?” or “How often do you find yourself thinking about how much happier you’d be working somewhere else?”).

If you want a focused answer, then a closed question is your best bet. A good example of a quantitative check-in question would be, “On a scale of one to five, how happy are you working as part of this team?” If, however, you want a more detailed response that can be used to plan change, then a good qualitative question might be, “What’s the one thing that would improve your current team?”

Following up on questions

Asking for clarification is good and shows you’re trying to understand the situation, but remember to keep the tone positive.

Positive: “I think I understand, but can you give me an example?”

Neutral: “So you’re ready to start. If we make these changes, do you think they’ll be in line with what you want?”

Negative: “You didn’t answer my question. Are you able to complete this task or not?”

This last question is very different from the other two because it doesn’t allow the person receiving the question to elaborate on their thoughts. They have no choice but to give a dramatic ‘yes’ or ‘no.’ If they say yes, then great! But if they say no, then the tone gets even more negative.

Now, let’s take a look at some question examples.

Icebreaker questions

Icebreakers are a great way to get the conversation rolling. One of our favorite approaches is using these questions as part of a monthly all-hands company meeting. Start with one big question that everyone can answer, then break into smaller groups for more targeted conversations. Here are some examples:

What are you most proud of this month?

What’s the one thing you want to learn next month?

What do you wish more people at the company knew about your job?

What’s a cool project someone else is working on that we should all know about?

What is the best bit of advice you’ve ever received?

What’s the biggest barrier in your way right now?

What do you wish people would stop doing in meetings?

What are three words to describe what makes our team unique?

If you were company/team/division president for a day, what would you do?

If money were no object, what would you be doing right now? (This is a fun question.)

Where are you from? — Asking about your hometown is a great way for people who didn’t grow up in the same place to connect over shared experiences.

What kind of pets do you have? — This can be better than asking what animals they like because it helps us appreciate how our friends and colleagues view the world beyond their professional selves.

General wellbeing questions

Employee wellbeing has a big effect on the entire company. Checking in regularly gives managers an opportunity to keep their finger on the pulse of the business and spot opportunities for improvement. Here are some questions to ask:

How are you doing?

On a scale of one to five, how would you rate your work-life balance?

Do you feel you have all the support you need to complete this project?

What challenges have you faced this week?

How well do you feel your current project aligns with organizational goals?

What’s going especially well for you this week?

In meetings:

Before: “What’s your main goal for this meeting?”

During: “What are three things that would make this a productive meeting for you?”

After: “Is there anything else we need to discuss?” “On a scale of one to 10, how useful did you find this meeting?” “What topics should we cover in more depth during the next meeting?”

Remote employee check-in questions

Remote employees miss a lot of interaction that keeps others updated and aware of their activities. They also miss the support and encouragement that normally comes from non-verbal cues like a smile or nod, especially in non-video meetings.

For this reason, it’s important to connect with remote employees continuously through frequent check-ins. A simple way to do that is by using instant messaging for quick check-in questions, like “What are you working on?” “How can I help?”

If you’re looking for more variety, consider asking these six questions every couple of weeks:

1) What are your biggest priorities right now?

2) What’s your biggest takeaway from our last discussion/meeting/work update?

3) Were there any resources I could have used better?

4) How productive have you been this week?

5) What was the most challenging part of your week, and how could I have made that better?

6) How is your current project going?

As well as project-related questions, it’s important to look after your remote workers’ well-being with more general questions about WFH life.

• How connected do you feel with your teammates?
• On a scale of one to 10, how would you rate your working setup?
• What could we provide to make your job easier?
• How productive do you feel working from home?
• Which team socializing activity would you feel most interested in? (multiple choice)

Questioning tips

• Keep them short — Five minutes is about as long as any one conversation should take before moving on to someone else. If it goes on longer, that person might start feeling exhausted or vaguely attacked by all of these questions. You want the recipient to feel comfortable and invited to open up, not wary and dreading another question.
• Questions should be non-judgemental — While you’re trying to help your colleague feel supported, don’t ask anything that implies judgment or blame (“What did you do wrong?” “When did you screw up?”). The more specific the question is, the less it will sound like a lecture on what they’ve been doing wrong lately.
• Try starting with an icebreaker or commonality — Find something you can start talking about before getting into any heavy questions. Maybe it’s about how long they’ve worked for your company, maybe it’s about their kids (or grandkids!), maybe it’s where they went for vacation last summer. Keep things light and casual.
• Get the pacing right — When you’re pausing and giving people time to give an answer, do it at the right moments. For example, you could pause after asking a question but before repeating it back if someone needs clarification on something. That way, they can clarify without feeling rushed. If you make the pacing natural and add pauses only when necessary, your team won’t get frustrated or nervous about not getting all of their answers out quickly enough.
• Don’t interrupt — If you want to get good results from check-ins with your team members, start by avoiding this habit during regular conversations outside of check-ins. Let them speak without interjecting your thoughts, opinions, or judgments on what they say. When you interrupt people’s responses to you, it can cause them to feel rushed or that their ideas aren’t important. This makes it harder for them to share all of the information you’re asking about.
• Be open — You should ask questions in a way that encourages team members to give honest answers and express themselves in an open manner. Avoid phrasing questions in ways that make it difficult for someone to answer (like with very broad topics or many possible answers).
• Make time — You should ask questions as frequently as necessary, both out loud and visibly. Designate time for them in each all-staff meeting (e.g., “We’ll start with a 3-minute check-in). Use an auto-text field on your company chat platform that lets everyone fill it out during meetings and post daily/weekly/monthly metrics around the office — if people can see, they are more likely to participate.

Final thoughts

Studies show that employees who feel their voice is valued and heard are more engaged, which can result in improved morale and productivity. Plus, research shows that employees with positive feelings about their work reported experiencing less conflict with managers. So there’s really no downside!

To foster a culture of open communication, invest in tools that make it easier to connect with employees wherever they are in the world. Chat apps, cloud-based project management platforms, and videoconferencing — these are all options the modern workplace needs if it wants to stay collaborative and connected.