For managersOther meetings

Questions to Ask Employees in Check-In Meetings (Examples)

Updated October 27, 2026KAKEAI, Inc.

Short answer

In meetings with a direct report, we recommend asking about one piece of work they're handling now before any big questions like a 6-month summary or long-term plans. For example, ask, "Which of your current work is taking the most effort?" In KAKEAI's survey of 10,000 employees in Japan, 25.6% of people who meet with their manager every 6 months chose "nothing in particular" when asked what they want from their manager. After you hear their answer, share your own view, and end by deciding together what to work on before the next meeting.

By the numbers

In KAKEAI's survey of 10,000 employees in Japan, among people who meet with their manager every 6 months, both the share who discuss performance evaluation and the share who want nothing in particular from their manager were higher than among respondents overall. Meanwhile, even among people who meet every 6 months to once a year, those who talk about specific work were more likely to feel their meetings contribute to results. The farther apart your meetings, the more it helps to narrow your question to one piece of work instead of asking broadly, "Is there anything?"

25.6%: 10,000-person survey; Share who chose "nothing in particular" when asked what they want from their manager, among people who meet every 6 months; Among all respondents, it was 15.6%. In semiannual meetings, the share who want nothing in particular from their manager is higher than among respondents overall.
69.8%: 10,000-person survey; Share who discuss performance evaluation in meetings, among people who meet with their manager every 6 months; Among all respondents, it is 43.4%. People who meet every 6 months are more likely than respondents overall to discuss performance evaluation in their meetings.
21.6%: 10,000-person survey; Share who feel their meetings contribute to results, among people who meet every 6 months to once a year and talk about "specific work"; At the same frequency, it was 15.8% among people who don't talk about specific work. Even when meetings are far apart, people who talk about work are more likely to feel results.

The 25.6% and 69.8% figures are for people who meet every 6 months, while 21.6% is for people who meet every 6 months to once a year, so the groups differ slightly.

Source: KAKEAI, Inc. “1-on-1 Survey” (N=10,000, May 2026, online survey of employees in Japan)

The survey asked 10,000 employees in Japan who meet their manager regularly how those meetings feel from their side.

Source: KAKEAI, Inc. “Kakeai AI 1on1 usage data” (records of 300,000 1-on-1 sessions extracted from sessions held between October 12, 2025 and October 3, 2026, aggregated so that no company or individual can be identified)

What to ask in an employee meeting depends on how often you meet

We recommend adjusting what you ask in a meeting with a direct report (an individual meeting, a regular check-in, a 1-on-1, and so on) to how often you meet. The less often you meet, as with semiannual or quarterly meetings, the more you should narrow your questions to one piece of work they're handling now.

When meetings are far apart, it's tempting to ask broad questions like "How have the past 6 months been?" or "Is anything bothering you?" But when someone tries to sum up 6 months in a sentence, the small details drop out, and you tend to get "Things have mostly gone fine" or "Nothing in particular."

In KAKEAI's survey of 10,000 employees in Japan, 69.8% of people who meet with their manager once every 6 months discussed performance evaluation in those meetings, compared with 43.4% of all respondents. When asked what they want from their manager, 25.6% of the every-6-months group chose "nothing in particular," compared with 15.6% of all respondents. So people who meet every 6 months are more likely than respondents overall both to talk about evaluation and to want nothing in particular from their manager. Meanwhile, only 20.3% of the every-6-months group felt their meetings were contributing to results, below the 31.9% of all respondents.

In the same survey, among people who meet every 6 months to once a year, 21.6% of those who talk about "specific work" felt their meetings were contributing to results, compared with 15.8% of those who don't. Among people who meet every 2 to 3 months, it was 28.4% for those who talk about work and 24.0% for those who don't. Even when meetings are far apart, people who talk about their work are more likely to feel results.

How often you meet	Scope of questions	Example opening question
Every 6 months	One piece of work from the past 6 months	In the 6 months since April, which piece of work took the most effort?
Quarterly	One piece of work from the past 3 months	In the past 3 months, did any work take longer than planned?
Monthly or more	Follow-up on what you decided last time	How is the invoice-checking procedure we decided on last time working out?

Four things to ask in an employee meeting, with example questions

There are four main things to ask about: work that's become hard to move forward, the work they put the most into this period, what they want to take on next period, and how they're working plus any requests they have for you. In a 30-minute meeting, it's usually enough to cover two of these in depth. For reference, in KAKEAI's survey, the most common length for a meeting with one's manager was 30 minutes, at 41.7%.

Before you ask any question, decide what you'll do once you've heard the answer. If the next meeting is 6 months away, anything that ends with just listening stays untouched for 6 months. In the same survey, among people who named "My manager doesn't apply what we discussed in daily work or doesn't keep promises" as a problem, 23.2% felt their meetings were contributing to results, below the 31.9% of all respondents.

Change the order and number of questions to fit the person and the timing. The examples below assume a semiannual meeting with someone on the accounting team.

1. Work that's become hard to move forward

Instead of asking broadly, "Is everything going smoothly?", narrow it down to specific work.

Of the work you're handling now, which takes the most effort?
In the month-end close, which task takes especially long every month?
For expense reports that get sent back, which department do most of them come from?
On that, is there anything I should raise with that department's head myself?

Once you've heard the answer, ask what they're hoping you'll do. If they want your opinion, first ask what they think, then share your view concretely. If they want to think it through together, start by understanding what they're struggling with and what they want to do.

What you just said, is it closest to wanting me to listen first, wanting us to think it through together, or wanting my opinion?
Where would you like to start?
I think it's best to start with the most common reason reports get sent back.

2. The work they put the most into this period

You ask about the work they put the most into so you can learn about work you weren't aware of.

In the 6 months since April, which work did you put the most into?
Did you change anything about that work compared with the previous 6 months?
If you did it again, is there any work you'd approach differently?
If there's work I haven't been aware of, please tell me.

Once you've heard the answer, tell them specifically what you had noticed. You can't decide the evaluation result alone, but you can tell them what you'll write in your evaluation comments.

I noticed that invoices have been going out 2 days earlier since July. I'll include that in my evaluation comments too.

3. Work they want to take on next period, and skills they want to build

A question like "Where do you want to be in 5 years?" is hard to answer on the spot. It's easier to answer when you limit it to the time before the next meeting.

If you had to name one thing you'd like to be able to do over the next 6 months, what would it be?
In your current role, is there any work you'd like to do more of, or any that feels like a burden?
For the switch to the new expense system in October, how much of it would you like to handle?
Is there anything I can set up on my side to help with that?

Once you've heard what they'd like, consider telling them what work you'd like to ask of them and why. That said, what people want from their manager differs by person and by session, so it's fine if some sessions end with just listening.

I'd like to ask you to put together the procedure manual for the switch, because you know the month-end close process best. What do you think?

4. How they're working, their health, and requests for you

Ask about how they're working and their health only as far as it relates to work. Requests for you are easier to answer if you ask for just one.

Is your current workload closer to too much, about right, or still room for more?
In the past 3 months, when were you leaving especially late?
Is there anything about how I ask you to do things that makes it harder? Could you tell me one thing?
Has my slow reply ever caused you problems?

When health or personal life comes up, we recommend not jumping to advice and listening first. In 300,000 1-on-1 sessions extracted from the records of Kakeai, KAKEAI's 1-on-1 service (Kakeai AI 1on1), for the topic "personal life," direct reports picked "I want you to listen" as what they wanted from the manager 21.8% of the time. It was 17.4% for "physical and mental well-being" and 7.5% for "work progress and how to approach the work." For "personal life" and "physical and mental well-being," "I want you to listen" was chosen more often than for "work progress and how to approach the work."

If a physical or mental health issue comes up, don't make a judgment on your own in the meeting. For leave or adjustments to how they work, check your company's employment policies and talk with HR. For the health issue itself, encourage them to talk with occupational health services or a medical professional.

Thank you for telling me. I'll check with HR about how you can take time off, and I'll tell you what I find out by Friday.

Once you've heard their request for you, promise one thing you'll change, right then.

That's really helpful. I'll reply to approval requests on the same day I receive them.

One question to ask at the end of the meeting

Use the last 5 minutes to decide together what each of you will work on before the next meeting. If the next meeting is 6 months away, also set a date in between to check progress together.

Before our next meeting, what should we start with?
Our next meeting is 6 months away, so how about we check in on progress once for about 15 minutes after the November close?

Example questions you can use as is, by situation

Here are example opening lines for 5 situations.

When you send questions 3 days before the meeting

When meetings are far apart, it often helps to send two things you'd like to ask ahead of time. In Kakeai's records, a topic had been entered at the time a 1-on-1 was scheduled in about 1 in 4 cases.

At next week's meeting, there are two things I'd like to ask about: the work that's taking you the most effort right now, and the work you put the most into in the 6 months since April.
If there's anything you'd like to talk about or anything you want from me, let me know that too. There's no need to write anything up and submit it.

When they answer "Nothing in particular"

Then could I ask you about one thing? When last month's close ran a day late, which task took the time?
It doesn't have to be a problem. Could you tell me which work is taking up most of your time right now?
Today, there's also something I'd like to get your input on.

In a meeting during review season

I read your self-assessment. Which item did you go back and forth on the most?
For that item, is there anything that happened that I might not be aware of?

At month-end, when you only have 20 minutes

I'm sorry I only have 20 minutes today. Could we focus on just two things: the work that's hard to move forward right now, and what you'll work on before our next meeting?

When you can't get a meeting room and people are nearby

There are people around today, so shall we keep it to work topics? Let's talk about health or evaluation another day when we can get a meeting room.

What to avoid when asking employees questions

Here are four things to avoid. Based on its experience supporting more than 3 million 1-on-1s and its survey of 10,000 employees in Japan, KAKEAI believes that the questions you ask in meetings with direct reports are there to move their work and growth forward. Getting them to talk for a long time is not the goal in itself.

Asking every item on the meeting form in order, top to bottom. When it's one question and one answer after another, the meeting turns into a spoken survey. The more you ask, the more you'll need to follow up on, so keep it to a number you can act on before the next meeting.
Deciding not to talk about work in meetings. Some advice says, "A meeting isn't the place to check on work progress," but KAKEAI doesn't recommend avoiding work topics in meetings. When you ask about progress, talk all the way through to what comes next.
Only asking questions and never giving your own view. Some advice says, "The manager should only ask questions and wait for the employee to find the answer," but KAKEAI doesn't recommend locking in that approach. In KAKEAI's survey, 59.8% of people chose at least one of "I want concrete advice," "I want your opinion," or "I want us to think it through together" as what they want from their manager (up to 5 answers). On the other hand, you'll also want to avoid starting to talk before your team member has finished answering.
Asking questions when you've already decided the answer. "Don't you think you could have come to me sooner?" is criticism disguised as a question. If you want them to change something, don't frame it as a question. Say it directly, with the reason.

About last month, if you'd told me on the day you realized it would be late, I think I could have helped you deal with it. From now on, could you give me a heads-up that same day?

You can tell whether your questions worked by what happens after the meeting

Whether your questions worked isn't measured by how much your team member talked during the meeting. Look back at what happened after it. Here are three points to review together.

At the end of the meeting, was what they'll work on before the next meeting put in their own words?
Did you carry out one thing you took on within a week, and let them know the result?
On the check-in date in between, were you able to pick up where you left off, with something like "How's the expense system switch going?"

In KAKEAI's survey, even among people who meet with their manager less often than once every 2 months, 52.8% of those whose meetings lead to action felt their meetings were contributing to results. Among people who meet at least once a week but whose meetings don't lead to action, it was 12.7%. Even when meetings are infrequent, people whose meetings lead to action are more likely to feel results.

Even with a semiannual meeting, it often helps to end with you and your team member each deciding on one thing to work on next.

What Kakeai AI 1on1 can do in this situation

When you're unsure what to ask in a meeting with a direct report, or want to carry what you decided into the next meeting, Kakeai AI 1on1 lets you do the following.

Before the 1-on-1

Choosing a topic and the response you'd like
Before a 1-on-1, the team member can choose the topic they want to discuss and how they would like their manager to respond (the expected response). Depending on your settings, managers can choose topics too. The selections appear on both of your screens.
Sharing notes in advance
Before a 1-on-1, you can write what you want to talk about in the "Notes for This 1-on-1" section. What you write also appears on the other person's screen.
Conversation history digest by topic
On the "Overview" screen for each person you meet with, you can look back at a written digest of the past six months of 1-on-1s prepared by Kakeai AI, along with what you have discussed under each topic. You both see the same content.

Day to day

Summaries and next steps in one place
The summary of each 1-on-1 is collected on the "Schedule & History" screen, and the next steps you decided are collected on the "MOVE" screen, organized by each person you meet with. You can look back at them anytime.

Kakeai AI 1on1 is currently available in Japanese. If you would like to use it in English, let us know.

Used by 600+ companies / 3,000,000+ 1-on-1s supported

Frequently asked questions

How many questions should I prepare for an individual meeting with an employee?

Four questions is plenty: two you want to explore in depth, and two more to ask if there's time. For each question, it takes about 10 minutes to hear the answer and agree together on what to work on next. In a 30-minute meeting, it's realistic to expect to go deep on two at most.

In a semiannual meeting, what should I ask my employee first?

A good first question asks them to pick one piece of work, like "In the 6 months since April, which piece of work took the most effort?" If you ask broadly, "How have the past 6 months been?", you tend to get a short answer that sums up the whole period. When you narrow it to one piece of work, what was hard and how you can help are more likely to come up.

Should I send my questions to the employee ahead of time? Do they need to write and submit answers?

We recommend sending about two questions at least 3 days before the meeting. Also ask what they'd like to talk about and what they want from you. They don't need to write and submit answers. In KAKEAI's survey of 10,000 employees in Japan, 12.6% of people named "the burden of preparation, such as filling in a required form or format in advance" as a problem with their meetings.

Is it OK to ask an employee about their health or personal life in a meeting?

If you ask about health or personal life, keep it to what relates to their workload and how they work, and say first, "You don't have to answer anything you'd rather not." If a health issue comes up, it's important not to make a judgment on your own. For leave or adjustments, check your company's employment policies and talk with HR. For the health issue itself, encourage them to talk with occupational health services or a medical professional.

What questions work well when asking an employee about their career or future?

When you ask about their career, it works well to limit the question to the time before your next meeting. "If you had to name one thing you'd like to be able to do over the next 6 months, what would it be?" is easier to answer on the spot than "Where do you want to be in 5 years?" After you hear what they'd like, also tell them what work you'd like to ask of them and why. It's fine if some sessions end with just listening.

Sources and how to cite these figures