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The Power of the Check In Question

Updated: Oct 12, 2022

As a conscious leader, I start every meeting with a check-in.


In short, it builds healthy teams and unlocks information flow that is critical to running a clear, coherent, and resilient team.

What is a check in?

In my own definition, it is a practice that is done at the start of any meeting to promote presence, awareness, and transparency, at the individual, team, and organizational levels.

On the surface, it looks like asking a question that others answer. In a 1:1, that might look like asking a team member a specific question that you both take turns answering. Within a small team meeting, it often looks like going around the room and each person answering the same question. In a large virtual meeting, it can look like dropping a question in the chat that everyone present answers in the chat. Regardless of format, the whole process shouldn't take more than the first 5-10 minutes of the meeting. The ROI on this practice is the reason I don't skip it (yep, leadership practices have ROI).

The real magic of the check in comes from:

  1. the leader's ability hold space and listen

  2. the quality of the question itself, and its "stacked functionality" (meaning it's serving multiple functions at once)

Stacked function is a term frequently used in permaculture, a practice for growing food (and community) sustainably. One thing about nature is that she loves energy efficiency, and designs all of her systems to be as energy efficient as possible. A species or process rarely serves only one purpose.

The practice of checking in has "stacked function" because it serves on both a human level and strategy level. Let's look at each category for a moment.

On a human level, this practice:

  • Allows meeting participants to fully arrive, settle in, and become more present

  • Invites participants to check in with themselves and build their own self-awareness

  • Generates human connection across team members while increasing empathy and deep listening skills

  • Makes the invisible visible, so that a team can self-organize itself around whatever is present in the field

  • Promotes clear communication and "asks for help" across team members

  • Gets everyone's voice in the room at the start of a meeting, communicating that each person's voice matters, is welcome here, and matters.

All the of the conditions above are necessary conditions for tapping into collective intelligence and flow state. It allows a team to "drop in" and attune to what is here now, which changes from moment to moment. This creates a more sentient team that is contextually aware. Conscious leaders know how to hold space and create the conditions necessary for their conscious team to flourish.

On a strategic level, the check in (if done well) can:

  • Build psychological safety, which we know improves retention of talent

  • Redirect resource flow to the "weakest link," strengthening the resilience of the whole system

  • Help a team get out ahead of risk by making roadblocks or friction points more visible

  • Unlock information flow and shorten feedback loops across people and departments

  • Warm up the voices of the introverts in the room, who often have such incredible insights and observations but may not always share (as an introvert myself I can attest to this)

What makes for a great check in question?

I often say that questions are portals. A well-played question can change everything. It can lead to breakthrough innovation or illuminate something monumental that had previously been missed. The best questions pull the answer from the depths of our subconscious and make it conscious. Sitting in the energy of a great question opens us to new possibilities.

Great check in questions are:

  • Invitational. People are invited to participate but not mandated. Anyone can opt out of answering without giving a reason.

  • Genuinely curious. If you don't genuinely want to know the answer, it's not the right question. People will feel it if you're not.

  • Open. They can be answered with more than a yes / no answer, and cause the mind and body to feel open, rather than closed and restricted.

  • Human. They invite the person to show up in the response, and share their unique experience or circumstance relative to what you're asking about. The person can choose to answer in whatever way that is true for them, whether their answer comes from their work context or personal life.

  • Illuminating. They help shine a light on something that hasn't previously been seen or considered.

  • Self-reflective. Perhaps this is a question that people haven't had time to ask themselves yet.

  • Simple and direct. The question can be understood instantly. If the question is too complicated or wordy, people will expend mental energy trying to understand the question itself, and this takes them out of their connection to their body's wisdom / creative potential.

  • (Sometimes) Vulnerable. In the right context, among a team that already has safety and trust, a more vulnerable question can strengthen the closeness that a team feels. Vulnerable questions require more space to be held, for the answers or emotions that could arise (aka don't ask it if you can't hold the space for whatever may come up)

Choosing the right question

I've worked with thousands of entrepreneurs and executives from around the world, and have had the opportunity to hold space for some incredible check in questions, and what they can unlock. I've also seen plenty of questions flop!

Here are some of my favorite questions of all time. I'm going to share these questions in their simplest possible form first, and then we will look at how to adapt them to specific contexts below.

  • What do you feel challenged by?

  • What are you proud of?

  • Where could you use more support?

  • What are you learning?

  • What are you celebrating?

  • What are you surprised by?

  • What are you growing into?

  • Where do you feel stuck?

  • What do you need?

Do any of these seem really interesting to you? Then they may be questions to ask yourself or bring to your team first!

Adapting questions for context

Any of these questions can be adapted to the meeting context or timeline that you are existing within.

Let's look at an example:

Base Question:

What are you learning?

Adding focused simplicity (great for time constraints):

What is one thing you are learning?

Adding time-related specificity:

What is one thing you learned today?

What is one thing you learned this week?

Inviting the human into work:

What is one thing you learned about yourself during this project?

Do you see how this last question connects the human experience to the shared context of work? Do you feel your body and mind open as you read this?

As a conscious leader, do you see how asking a question like this helps you BOTH read the temperature of your team and where each member is at AND cultivates self-aware learning out-loud? The benefits of this are so enriching.

Additional Tips

What if you're short on time?

  • Ask each person to set a 1-minute timer on their phone, at the start of their response.

  • Specify the length of the answer you're looking for. For example "in 1-2 sentences..." or "in 1-2 out-breaths"

  • Opt for a one-word check-in. For example, "in one word, how are you feeling today?"

Promoting playfulness

All animals play! Sometimes we just need to lighten the mood and connect with our inner child. If you're at a team retreat or leading a creative session, you can ask a check-in question that promotes playfulness.

Here are some examples:

  • If you were a superhero, what would your superpower be?

  • If you were an animal, what animal would you be?

Promoting the mind-body-soul connection

Self-awareness is a prerequisite for self-managing, autonomous team members, who have clarity about their goals and needs, and operate from of place of integrity and shared values. Here's one question I love that helps promote self-awareness across mind, body, and soul. I recommend keeping this question anchored in the present moment.

  • On a scale of 1-10, how is your mind, heart, body right now?

People can either answer with just the number, or briefly elaborate on each if they wish.

Adding a one-word check OUT question

Gathering as a team and having a group conversation can shift the energy of a person and their entire day. Asking a check OUT question can be a helpful way to get a read on how a meeting went, and where people are at as they depart from a meeting. Having a meeting-length feedback loop as a leader can save you a ton of time and guesswork. As leaders we want to reduce or eliminate assumptions within our team dynamics, to prevent drama and wasted time and resources.

Here are two examples of check-out questions, to place at the end of your meetings.

  • On a scale of 1-10, how would you rate this meeting?

  • What's one-word to describe how you feel?

As a team gets used to this practice, it can become part of team culture and how others within your team run their meetings. This is especially helpful for new managers and project leads. It's important to have enough psychological safety for people to give honest answers, and you as a leader should be prepared to support your managers if they receive low marks, so that together you can quickly turn it into a positive learning experience. Make it clear that honest low marks do not mean failure, they just mean we are learning something new.

For more practices and tips like this one, be sure to subscribe to my newsletter, The Regenerative Leader.

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