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check-in questions

21 Simple, Yet Powerful Check in Questions Your Team Wishes You'd Ask

Learn how to establish a practice of simple check-in questions that empower your colleagues and foster a stronger, more engaging employee experience.

HR and People Ops

Never underestimate the power of a simple check-in.

It might seem like a small gesture, but check-ins are an essential element of strong communication. While regular check-ins can be valuable in all sorts of relationships, we’re going to focus on working relationships in this guide.

Healthy communication themes

Communication themes, especially between between leaders and direct reports, can have a material impact on a range of outputs from efficiency to engagement and retention. These themes generally skew positive, neutral, or negative.

  • Positive: “How’s that report on widget theory coming along—any support I can provide?”
  • Neutral: “Do you have that report on widget theory finished?”
  • Negative: “I asked for that widget theory report yesterday. Where is it?”

You can ask a similar question multiple ways. While each of these questions is driving toward the same topic (widget theory and deadlines), the outcomes of those three question styles will differ dramatically.

In other words, good check-in outcomes rely on good check-in questions.

Check-ins vs. micromanagement

While a check-in can be helpful and motivating, micromanagement is often de-motivating and hinders progress. Without thoughtful framing, a well-meaning check-in question could be perceived as micromanagement.

So, how do we get the most from check-ins while steering clear of micromanagement?

Cadence, context, and cause

There are three key elements of a good check-in: cadence (the rhythm your check-ins follow), context (how well the check-in fits the situation), and cause (what is your goal for checking in?). By understanding these elements and why they matter, you can deliver check in questions that uplift and empower the recipient.

Cadence matters because it helps define the value of both the question and answer.

If the answer isn’t likely to change since the last check-in, the cadence is too short. Anyone who has been on a long car ride with kids (or as a kid) is probably familiar with the question “Are we there yet?” Sure, that can be a useful question to ask, but it gets less valuable if it’s asked at a rapid cadence.

On the other side of the coin, a cadence that spans too long between check ins can miss a lot of important information. If you ask a direct report how happy they are with their job once a year, there’s a good chance you’ve missed multiple opportunities to provide support and guidance.

There’s no perfect cadence for all check-ins or all recipients. The secret to getting cadence right is simply to pay attention. Start with a cadence that aligns with your mutual goals and adjust as necessary.

Context matters because it aligns your check-in to the subject at hand, setting your recipient up to give the most relevant and useful response. If you make a phone call to ask someone in the midst of a time crunch how connected they feel to their remote peers, that’s an example of poor context.

If you send a group message in Microsoft Teams or Slack to check in on everyone’s blockers at the beginning of the week, that’s an example of good context, and you’ll probably get some useful information as well as build goodwill among your teammates.

Cause matters because it defines the level of discretionary effort and cooperation you’re likely to experience.

If you’re checking in because you want to provide support during a difficult time or on a challenging pursuit, there’s a greater chance you’ll get candid and helpful responses. However, if your check-in exists purely to serve your own interests, it’s less likely to inspire the same discretionary effort.

Balance

A successful check in strategy hinges on the balance of individual and mutual benefit. As a quick check before asking a question, use this simple litmus test.

Is this check-in:

  • asked often enough?
  • asked too often?

Is this check-in:

  • contextual to the situation or the work it relates to?
  • relevant to the recipient?

Is this check-in:

  • for my benefit?
  • for the benefit of my counterpart?
  • for our mutual benefit?

Getting useful answers

OK, so you’re ready to start asking good check-in questions, but how do you ensure you get good, helpful answers? Part of a successful check in strategy is formatting the questions in a way that helps your audience give good answers.

Data types

There are two fundamental types of data you'd hope to capture:

  • Quantitative Data - data that can easily be quantified, codified, and viewed in aggregate. Quantitative answers are usually much faster and take less mental bandwidth to give.
  • Qualitative Data - data that cannot easily be quantified, codified, and viewed in aggregate. Qualitative answers usually require more time and thought to give.

To determine what type of data you need, check in with yourself as you’re forming or choosing check-in questions and ask:

  • “What do I need to learn from this exchange?”
  • “Why do I need to learn that?”
  • “What will I do with the knowledge?”

Both types of data are helpful to capture, depending on what you need to learn, and just like above, the key is balance.

Check-in question formats

The number of formats you can ask a question in are almost unlimited, but to standardize the answers, most common question formats for check-ins are:

  • Open-ended What do you think of this check-in guide?
  • Multiple choice What is your favorite section of this guide?
    • a) Healthy communication themes
    • b) Getting better answers
    • c) Example check-in questions
    • d) All of the above
  • Multi-select What are you most excited to learn about? (Choose at least one)
    • ☑ Question formats
    • ☑ Delivery methods
    • ☑ Question phrasing
  • Numeric range On a scale of 1-10 with 1 being terrible, and 10 being amazing, how would you rate this guide?
    • 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10
  • Descriptive range I’m finding this guide to be:
    • very helpful
    • moderately helpful
    • somewhat helpful
    • unhelpful
  • Illustrative/emoji range reading this guide makes me feel:
    • 😃🙂😐😕☹️😫

If you’re looking for a laser-focused quantitative answer, then it’s only logical to ask it in a quantitative format. A good example of a quantitative check-in question would be “On a scale of 1-10 with 1 being completely dissatisfied and 10 being extremely satisfied, how satisfied are you with your remote work setup?” That’s a great start, but the answer you receive can only tell you if there’s a problem.

If your cause is improving the remote work experience, a good qualitative follow-up to the quantitative check-in question above would be “What is one thing that would improve your remote work setup?”

Using question formats to get more (and better) answers

The trick to getting a useful answer without burdening your audience is to narrow the response range. Once again, it’s all about balance. You want to narrow the range enough that it makes the question quick and easy to answer, but not so much that you’re not getting the depth you need to move forward.

Doctors and other medical practitioners often use a similar strategy when trying to gauge a patient’s pain levels. Instead of asking patients to describe their pain level in a subjective, open-ended format, they utilize the pain scale: an illustrated, color-coded numeric range to help contextualize the question.

If you ask a series of open-ended check in questions, you may find that your audience struggles to answer them in good time (or at all). You can fix this by finding a balance between the type and fidelity of info you need, and the burden it requires. The formats we discussed above are one of your most powerful means of finding that balance.

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25 crucial check-in questions by theme

Now that you know how to ask good questions and get good answers, it’s time to dive into a list of example check-in questions for inspiration. They’re separated into categories to make finding the right questions easier, but you may find some to be dual-purpose.

These questions are a good starting point, but as a certified check-in question expert, you can (and should) adapt these questions to perfectly fit your needs.

General wellbeing check-ins

Employee wellbeing has reverberating effects across an entire organization. Checking in on wellbeing makes it easier to pinpoint opportunities to provide the support employees need to do the best work of their career.

Most of these questions are simple, but because situations range so significantly, it’s often helpful to start with tools like ranges to get an initial datapoint.

How are you doing?

😃🙂😐😕☹️😫

Care to elaborate?

This is an exceptionally broad and qualitative question, but it’s actually one of the most important check-in questions you can ask because it can lead to some much deeper learnings. Because it’s so broad, it can be helpful to help recipients by using a relative range with the option to share extended qualitative answers.

Do you feel supported by your team and leadership?

Always | Usually | Sometimes | Infrequently | Never

Leadership support is one of the most important things an organization can provide employees. If employees aren't feeling supported, it’s crucial to find out why, and develop a plan to provide that support. Doing so can provide better work outcomes and address retention issues before they evolve into turnover. The first step toward making progress is to gauge overall sentiment.

I have a good work-life balance.

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10

It’s not just about the number of hours you spend. There are a dizzying number of factors that play into work-life balance. That’s why a numeric range can be a great starting point to begin understanding the relative levels of balance across your team, and for individuals.

Tactical check-ins

Tactical questions are usually quick, focused, and to the point. That usually makes them comparatively easy to answer, even if they’re open-ended. You might be asking about the status of a particular body of work, or where you can clear blockers for your team.

Do you feel like you have enough time to complete your list of tasks?

Yes | No

Capacity planning is a key aspect of effective management and leadership. If your team doesn’t have the time they need to complete their work, it’s an opportunity to either consider how the work is delegated, or how you can support them in efficiency.

Do you feel like you have enough information to complete your work?

Yes | No

Without the requisite information, the challenge of a task compounds. Some work is ambiguous in nature, but the more information and guidance you can share, the better.

What are some things that went well with your projects this week?

(Open-ended)

This is an opportunity to learn from the perspective of your teammates closest to the work. Their triumphs are your triumphs, and learning what they find exciting or engaging about their work can help guide them toward the roles and responsibilities that fit best.

What are some challenges you faced this month with your work?

(Open-ended)

This is a good question to help uncover hidden obstacles your team faces. In some cases, it’s an easy thing for you to fix, but not for them. This question should address more overarching issues at a longer cadence, while a more specifically targeted question like below can handle day-to-day blockers.

Are you blocked on anything this week?

Yes | No

If so, where are you blocked?

(Optional, open-ended)

Blockers decrease your team’s velocity, and they’re not always apparent until the project is in motion. This check-in should be asked somewhat frequently to avoid a blocker slowing down progress.

What is your #1 priority this week, and why is it important?

(Open-ended)

It’s valuable to ask this question so that you can better understand the alignment between what individual members of your team find important in comparison with your own views. Asking this question also encourages reflection, breaking the tendency to work on autopilot.

Strategic check-ins

Strategic check-ins cover broad themes and concepts. These questions should usually come at a less frequent cadence because the answers aren’t likely to change often.

How often do you feel like your work aligns with organizational goals?

always | most of the time | sometimes | not very often

Goal alignment isn’t just a key element of employee engagement; it’s also an essential part of realizing a strategic vision. If the strategic vision and the work being done to achieve it don’t align, it’s critical to know that.

How clear do you feel your role is within the team?

very clear | mostly clear | somewhat clear | unclear

Roles naturally shift over time, but if an employee is frequently randomized or feels unsure about where their contributions fit in, that’s an important datapoint.

What do you see as an untapped opportunity for our team?

(Open-ended)

The people closest to the work often have unique insights about it. Checking in with your colleagues on this topic can help reveal those insights, potentially revealing some key opportunities that would have been missed otherwise. For that reason, using an open-ended format is often best.

Meeting check-in questions

The time and bandwidth your colleagues share during meetings is a gift. Meeting check-in questions make it easy to honor that gift by delivering an engaging, illuminating, and valuable experience for everyone involved.

Pre-meeting check-in: Which topic from the agenda do you want to focus on most?

  • a) topic 1
  • b) topic 2
  • c) topic 3

Taking a moment to gauge the audience’s interest in advance of a presentation or meeting can help you to align the content to their expectations. Focusing in on the things they care about most helps ensure they’ll be engaged throughout.

Mid-meeting check-in: engagement and Checking for Understanding (CFU): How much do you think our traffic grew over the past quarter?

  • a) 30%
  • b) 50%
  • c) 200%

A quick, engaging check-in partway through your meeting or presentation can help keep everyone focused and offer them an opportunity to feel involved. Additionally, it’s a great way to ensure everyone is absorbing the material at the same rate, and whether certain topics might need more time.

Post-meeting check-in: how useful did you find this meeting?

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10

One of the best ways to improve is to measure your performance. Ideally, any meeting or presentation is providing the audience a value greater than that of another use of their time. To confirm that, simply check in after the meeting.

Post-meeting check-in: what topics should we cover in more depth for the next meeting?

  • ☑ widget sales
  • ☑ widget R&D
  • ☑ widget usage

While it’s important to know in general how valuable a meeting was, it’s also great to learn what would make it more valuable. In the example above, we’re addressing topics, but you could also check in on meeting length, the scope of the audience, or any number of other avenues for improvement. Even if attendees scored the experience well, there’s always an opportunity to improve next time.

Remote employee check-ins

Remote work changed the way many of us communicate with our colleagues. It provides less impromptu interactions where you might build connections. Remote work also brings new questions to the table, from ergonomics to relationship-building. Proactively checking in can help address these issues early on, before they become problems.

How satisfied are you with your remote work setup?

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10

After a sudden shift to remote work, many people still lack an appropriate productive space to get things done. While it may not be possible to address all of these issues, some might be easier than expected. The first step toward identifying them is to gauge overall sentiment.

How productive do you feel working from home?

More than usual | Less than usual

Some people feel significantly more productive working remotely, while others find it extremely difficult to stay focused. There are myriad reasons for this, from a person’s living situation to their innate personality and preferences. Asking this question and reviewing it in aggregate can help gauge changes in sentiment about the work environment and guide future decisions around workspaces.

What could we provide to make it easier to do your job remotely?

(Open-ended)

Working remotely can be a big shift for people used to a co-located office. There are several comforts a co-located work environment normally provides that would make a big difference in the remote work experience. It could be something as small as a new mouse, an external monitor, fun snacks, or a quick session with IT on improving internet connectivity, but you’ll never know if you don’t ask.

How would you rate the connection you feel with your teammates?

Excellent | Good | Okay | Poor

Social connection can still be strong among remote teams, but it requires a different kind of effort. The first step toward building that connection is knowing where you stand. Because the answer to this question can change over time, given the abundance or lack of effort in building connection, it can be helpful to ask it periodically to gauge the effectiveness of remote team-building efforts.

Which remote team activity would you be most interested in?

  • ☑ Zoom happy hours
  • ☑ Talent show
  • ☑ Group yoga

It’s not easy to guess what sort of activities will appeal to your team, but it’s easy to ask. Some remote team activities sound like a good idea in theory, but are hard to get going in practice.

Before putting the effort into developing a program, consider checking in on which activities have the most interest among the group, so it’s easier to focus on those with the greatest potentials to succeed.

How are you checking in?

These check-in questions are a starting point, but you now have the knowledge you need to frame a thoughtful set of questions that fit your team. Let us know @polly_ai which check-in questions you've found most valuable and feel free to share some of your own that aren't on this list!

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