Characteristics of Effective Check-in Questions

The most essential characteristics of check-in questions include that they:

Check-in questions send compatible implicit messages

My colleague Aruna is a web developer. She specializes in what’s called SEO or “search engine optimization.” Because appearing near the top of Google’s search results increases website traffic and can make or break a business, Aruna and her peers apply all sorts of strategies to help their clients achieve that coveted position.

One approach they use is to embed key words, or “meta tags,” in the code of sites they build. Meta tags are unseen by visitors like you or me, but these hidden messages influence how the website performs.

Likewise, check-in questions also carry a kind of meta tag. They send implicit messages to the people to whom we ask them—messages about our interests, expectations and goals. And they influence how people perform.

The fundamental tacit message that accompanies almost all questions is: “I’m interested in you.” Whether I ask what you want for lunch, or what you think about the new product line, if the question is genuine, it communicates that I am curious about you, and perhaps even that I care.

In a check-in, your question’s unspoken message can be as vivid as the question itself. To get a sense of this, consider the following check-in questions, along with the potential “meta-messages” they might communicate to participants:

  • “What’s a recent success you’ve had at work?” (Possible message: The things that motivate and inspire me are relevant to this group.)
  • “What’s something that needs to be improved in the new manufacturing process?” (Possible message: my experience and insights are valued here.)
  • “What was a highlight of your holiday break?” (Possible message: I can bring more of myself to this endeavor than just my work persona.)
  • “If you could give one piece of advice to our CEO, what would it be?” (Possible message: It might be possible to broach real issues here that I don’t usually discuss.)
  • “What is something you enjoy watching on TV?” (Possible message: there will be room in this group to “let my hair down” and have some fun. (NOTE: I know at least a few of you are thinking…”that question is not fun, it’s stupid and a waste of my valuable time!” But trust me: in the context of an effective check-in, such a question has the power to even win you over!)
  • “Share an example of when you have personally fallen short of our goal?” (Possible message: it might be safe to admit mistakes and be more transparent than usual in this group.)
  • Share a challenge from your childhood that shaped how you show up as a leader? (Possible message: I might have to take some risks in this group.)

Check-in questions can send counterproductive messages as well. Lonnie’s team at a large insurance company hadn’t been doing the paperwork he expected of them. The check-in question he chose to ask the group was: “How come you aren’t keeping track of data?”

This closed-ended and accusatory question unwittingly sent the message “It’s not safe here; if we speak honestly we might regret it.”

It’s no surprise that Lonnie reported that instead of answering the question directly, team members became defensive and withdrawn, and the group felt less cohesive after the check-in than before. (Lonnie used the check-in process to awkwardly raise his concern rather than to openly inquire of the group. It would have been more consistent with Lonnie’s intentions, and may have inspired trust rather than reduced it, if he had directly shared his concerns about paperwork later in the meeting instead of as a check-in. “I’m worried that people aren’t handing in their data sets. Can we put our heads together to figure out why that’s happening? Perhaps there’s something I’m missing.” In this way he might have been able to engage the group in a discussion that would address his concern.)

When you ask a question, it’s as if a sign floats above the gathering on which messages like these are written:

  • “your opinion matters”
  • “we are going to get to know each other well”
  • “our work will benefit from an unusual level of frankness” or
  • “run for the hills!” (as in Lonnie’s example)

The reason you select a specific question doesn’t have to be a secret: the group’s stated mission, the agenda, even the way you introduce the question can telegraph it. As leader, your job is to ensure that the questions you select both explicitly and implicitly urge people in the direction the group needs to travel.

You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.


Check-in questions are open

Openness refers to a number of essential and closely related aspects of questions.

Most importantly, openness refers to that fact that, with few exceptions, check-in questions should not have a “right” answer.

The Foundation for Critical Thinking distinguishes three categories of question:

  1. Those with one right answer. (How many sides does a square have?)
  2. Those with better or worse answers. (How can we best address the challenge of a lack of diversity at the highest levels of our organization?)
  3. Those with as many answers as there are different human preferences. (What do you think is our team’s greatest asset and why? or What’s the best way to spend a summer day?)

Check-in questions should almost always fall into category 3, and only occasionally in category 2. Group members should feel that any legitimate reply to a question is welcome; they don’t have to “perform” by offering the “right” answer. (Otherwise they’ll have an experience similar to those on Lonnie’s team.)

Openness also refers to the breadth of a question: the width or narrowness of its range of concern. Consider the following sets of potential check-in questions, each set moving from wide to narrow:

Please share with us:

  • Something you’ve thought about since our last meeting
  • Something you’ve thought about since our last meeting that has inspired you
  • One insight from our last meeting that you can commit to applying in the next two weeks

Please share with us:

  • One of your proudest accomplishments
  • One of your proudest accomplishments at work
  • One of your proudest accomplishments on this team

Please tell us:

  • Something about you that we might not know
  • Something about your family that we might not know
  • Something about your childhood that was challenging

Be mindful of the range you want your question to delimit. It’s often better to ask questions with a broader range, particularly when groups are new. This puts power in group members’ hands, enabling them to “show up” as they would like. When questions are too narrow too soon, it can force people to “do the assignment” rather than take the opportunity, each in their own fashion, to reveal more of who they are (and in so doing, make the group safer and stronger).

Check-in questions are compelling

The best check-in questions grab people’s attention and inspire them to respond. Participants literally lean forward during effective check-ins; they want to be part of the conversation.

To create compelling questions, be mindful of two factors: relevance and variety.

Relevant questions connect to a group’s interests, enabling participants to learn something new about a topic they care about. A group of managers might share a success from the past month. A team serving gang-affiliated youth might share a challenge they remember from their own adolescence, or describe a young person who inspires them. Veteran miners learning about new safety procedures might describe one thing that they don’t miss about the old days. Marketers might share a commercial that had a big impact upon them as a child. A group of lawyers could each describe one of their most challenging recent cases.

Remember that questions don’t have to link to the substantive focus of a group to make them relevant. Almost everybody shares an interest in: 1. getting to know one another, and 2. enjoying themselves.

For this reason, powerful questions that help people connect personally, whether about formative experiences, career paths, favorite music or personal passions, also tend to be compelling. They enable people to speak about what is meaningful to them. And they are fun.

Sometimes relevance comes through connecting to contextual factors like the time and place of your meeting. If the meeting is being held at the end of the year, ask people to describe one accomplishment from the year, or one hope they have for the upcoming one. If the Academy Awards were broadcast that week, ask groups members to share a favorite movie and why. If the first snow has just blanketed the ground, consider asking people to share one winter memory.

I was leading a meeting in Paris not long ago, and I asked the international group “What’s something that you like to eat when you are in Paris?” Croissants, steak frites, macarons, frogs legs, good wine, chocolate, cheese… Their responses were delightfully diverse and stimulating.

The better you know your group, the easier it is to determine relevancy. “What’s your favorite color?” might be a compelling question for a group of interior designers, but not so for most other adults. When you select questions that don’t matter to people, it distances them and generates anxiety that your time together might be unfulfilling.

The second factor that keeps questions compelling is variety. When working with the same group over time, strive to come up with questions that differ from one another in terms of focus, depth, whether they are fun or serious, etc. If you’ve asked a number of relationship-building, “connecting” questions in a row, switch to a question that is about work, or vice versa.

You can even build variety into a single check-in by asking a set of questions, one about work, and the other about something outside of work.

A question has to catch people where they are, to meet them where there is the most energy and relevance for them, and then use that energy to go deeper.


Check-in questions have the appropriate level of risk

Leaders from a multinational investment bank were meeting in a sleek conference room high above New York City. Because they were based across the globe, many had never met.

After mingling tentatively, their leader gathered the group together, formally welcomed them, and explained the goals for the day. Then, for a check-in, he asked each leader to “share one of the biggest mistakes you have made as a leader.”

Participants looked warily around the room, gulped, and I assume thought to themselves “what in the world have I gotten myself into?!”

Check-ins enable group members to bring more of their insight and passion to their work. But to create the psychological safety necessary for that to happen, you must choose questions that have the appropriate level of risk.

When a group is new, it’s usually best to start with low-risk, “easy” questions. In fact, one of the most fundamental rules for check-ins is: New group, easy questions.

When groups meet for the very first time, always begin with the basics: Name, role, position, location, etc. Humans have a deep, animal need to know this information about strangers—ideally presented in the person’s own voice—before they can feel comfortable. Given that it can be challenging for many people to speak at all in front of a new group, simple and easy is better.

In addition to the basics, consider adding a light, relationship-building question when a group is first forming. One personal favorite is to ask participants to finish the sentence “I like…” The many benefits of this question include that it’s open, it’s easy, responses are very quick, it brings more of each person into the room, and it elicits diverse answers (food, fishing, kids, reading, politics). It also usually results in shared laughter, which is almost always salubrious.

As people come to know one another over time, increase the level of risk. Whether the questions you select are focused personally or professionally, it’s fine to provoke a bit of anxiety in participants; that indicates the question is meaningful. Choose questions that intentionally stretch groups into ever greater levels of transparency, learning and connection.

Mature groups can handle questions that carry even higher risk. The question that was too intense for the relative strangers at the investment firm—“share one of the biggest mistakes you have made as a leader”—might be useful (and not even that challenging) for a group that had more trust. And there are endless others:

  • “What’s something that we tend to not talk about that you feel we should?”
  • “If you were to give yourself one piece of challenging advice, what would it be?”
  • “What’s one way that you personally contribute to the challenge we are facing?”

The best questions are not always the most intense or intimate ones, however. Sometimes a fun, simple question can open new doors even for a mature group. As described above, keep your questions varied and balanced.

One approach to choosing questions that have the right level of risk is to put control in participants’ hands and select questions that provide what I call “depth choice.”

When we dare to reveal our vulnerability, it is both an act of courage and an act of generosity.


Questions with depth choice are open not only to content, but also to depth. They enable each participant to decide for themselves how revealing they are going to be: Whether they answer more superficially, or with great personal revelation, both answers are correct.

As an example, consider the following question: “Please share something that’s been on your mind lately?” A participant could choose to discuss her excitement about a craft project she is working on, or the more intimate concern of how she is going to help her mother after her father’s recent death. It’s up to her to decide which answer to give, and both are completely appropriate.

As explored elsewhere, one of the most wonderful aspects of check-ins is that each individual’s risk establishes a new “acceptable” depth for those who follow. And given the right circumstances, follow they will, setting ever deeper levels with time.

Eventually a degree of safety can be achieved that enables each person to choose whether to show up in the deep or the shallow end of the pool on any given day. A safety created by participants themselves, one by one, in response to your respectful invitation.

Check-in questions elicit responses of the desired length

The length of time you can devote to the check-in is a final important consideration when selecting your questions. You don’t want your check-in to prevent your group from devoting the necessary time to its most crucial work.

First, determine how much time you have for the check-in. This is primarily a function of the duration of your gathering. For an hour long, one-off meeting, you might want the check-in to take less than 5 minutes. In a three-day retreat of a group that will be working closely for months, a 60 minute check-in could be a wise investment of time.

Then, as you consider potential questions that fulfill your purpose, estimate how much time it will take for a typical group member to respond. This can vary considerably. As an example, consider these three questions and estimated response times:

  • Where were you born? (10 seconds per person)
  • Please share one thing that is top of mind for you personally, and one thing that is top of mind professionally. (60-90 seconds per person)
  • What is a crossroads that you find yourself in now? (2-3 minutes per person)

By multiplying the estimated response time by the number of participants in your group, you can roughly calculate the overall time that using a particular question would require. Then you can select from among the questions whose response time will meet your needs.

The marvelous thing about a good question is that it shapes our identity as much by the asking as it does by the answering.


Additional suggestions for selecting effective check-in questions:

Ask questions that invite unspoken concerns

Making it safe for group members to reveal private concerns leads them to feel connected and hopeful. Effective questions therefore enable people to express what they might be thinking but not saying.

A few examples of such prompts include:

  • “one thing that you find difficult about working here”
  • “please share one thought about maintaining our momentum now that Anya (former leader) has moved on.
  • “please share a reflection on how we should manage the widely publicized product failure (or CEO indictment, funding reduction, political crises, research findings, celebrity misstep, etc).”

Indirect can be more effective than direct

Imagine that you are beginning a leadership-development program for a group of managers who don’t know one another well. Some questions—such as “What’s something you’d like to get better at as a leader?”—might be too risky for the group. But a less direct question might uncover the same aspirations and be easier for the managers to answer. Try instead: “What’s something you admire in another leader?”

It can also be easier for group members to explore concerns if they raise them themselves rather than in response to your direct questions.

Let’s say that a recent round of layoffs has dampened a team’s spirits and threatens to impact their health and performance. Rather than potentially shutting people down by bluntly asking “Let’s check in and hear people’s thoughts about the recent layoffs,” it can be more effective to ease into the subject.

You might instead ask: “Let’s hear any thoughts/concerns you have about what’s been happening here and its effect upon the team,” or even more obliquely, “Please share an insight or concern about the next phase of our work together.” Group members can then raise their concerns gradually, person by person, at a pace that suits them.

There is absolutely nothing wrong with directness. But sometimes approaching issues indirectly is the most direct route.

Concrete is generally preferable to abstract

Because abstract questions lose people’s interest quickly, strive to ask questions that enable people to respond from their own experience and feelings. Such questions energize speakers and engage listeners.

Add “why” to elicit richer responses

When you ask group members to share their personal hero, most rewarding client relationship, biggest concern or best vacation, consider adding “and why” to the question. It’s a great lever that can lead to more interesting and revealing responses. (One caveat: In certain contexts, asking “why” can make people feel defensive.  A question like, “Why haven’t we solved this problem already?” would tend to shut people down rather than open them up.)

Good questions work on us, we don’t work on them. They are not a project to be completed but a doorway opening onto greater depth of understanding, action that will take us into being more fully alive.


Enable group members to pick their own check-in questions

After groups become comfortable with check-ins, they often enjoy selecting their own questions. Not only does this generate questions you might not have considered, it can increase members’ investment in the process. Always reserve the right to select questions, however, because sometimes you’ll need a specific prompt to move the group forward.

Use questions in combination

It is quite common to use multiple questions in combination instead of a single question. Name, position and tenure with the organization—aka, “the basics”—are three questions right there (which, incidentally, take only about 15 seconds to answer!). A few examples of multiple question check-ins include:

  • One thing that’s going on for you in your personal life, and one concern or thought that you have about the next stage of our work
  • Share someone who is a hero to you, and an example of when you embodied one of the qualities that you admire in that person
  • Share a highlight of your summer break, and one goal you have for today’s meeting
  • Share something most people here don’t know about you, one hope for our meeting, and if there is anything going on in your life that might affect your participation and focus today.

Be sure to be mindful of the total amount of time you can devote to your check-in. I’ve seen leaders ask too many questions, and then pay for it with a check-in that eats up too much valuable meeting time.

When asking multiple questions it can help group members to display them on a flip chart, whiteboard, or slide.