Top Good Check-In Questions to Boost Team Engagement

In the fast-paced modern workplace, the simple act of checking in can become a routine, hollow gesture. We ask, "How are you?" and expect a reflexive, "Fine, thanks," in return, missing a critical opportunity to foster genuine connection, uncover hidden roadblocks, and gauge the true pulse of our team. The difference between a surface-level interaction and a transformative conversation lies in the quality of the questions we ask.

Truly good check in questions are more than just pleasantries; they are precision tools designed to build psychological safety, enhance self-awareness, and unlock a deeper level of engagement and performance. They signal to your team that you care not just about what they do, but how they are. By moving beyond the superficial, leaders can create a space for meaningful dialogue that addresses well-being, workload, and alignment.

This guide provides a curated list of powerful, actionable questions that can fundamentally change the dynamic of your one-on-ones and team meetings, turning them into catalysts for growth, support, and collective success. We will explore specific examples and offer practical tips for implementation, empowering you to foster a more connected and effective team.

1. How are you feeling right now?

Moving beyond the surface-level “How are you?” this question cuts directly to the emotional core of an individual's experience. It’s a foundational query that prioritizes emotional state over task lists, creating an environment of psychological safety. By asking about feelings, you acknowledge that team members are human beings whose emotional landscape directly influences their focus, creativity, and collaboration. This is one of the most effective and good check-in questions because it builds a bridge between personal well-being and professional performance.

This approach is championed by experts like Brené Brown, whose research on vulnerability underscores the power of open emotional expression in building trust. It’s a simple yet profound way to gauge the team's collective mood and identify underlying issues before they escalate.

When and Why to Use This Question

Use this question to kick off one-on-ones or team meetings. It sets a human-centric tone, signaling that you care about the person, not just their output. It is particularly powerful in high-stress periods, during significant organizational change, or in remote settings where emotional cues are easily missed.

The goal is to foster an environment where sharing feelings is normalized. This practice can lead to stronger interpersonal connections, reduced burnout, and a more resilient team culture. It allows you to address emotional needs proactively, offering support where it's most impactful.

Actionable Implementation Tips

• Model Vulnerability: As a leader, answer first. Sharing that you’re feeling “a bit stressed but optimistic” or “energized after a good weekend” gives others permission to be honest.
• Provide Tools: For team members who find it hard to articulate feelings, use an emotion wheel or a simple 1-10 scale. You can ask, “On a scale of 1 to 10, how are you feeling today?”
• Set Clear Boundaries: Frame the check-in with a time limit (e.g., “Let’s take 5 minutes for everyone to share one word about how they’re feeling”). This keeps the meeting on track while ensuring everyone gets a chance to speak.
• Follow Up Privately: If someone shares something concerning, like feeling overwhelmed or anxious, make a note to connect with them privately after the meeting. This shows you are listening and care about their well-being beyond the public forum.

2. What's one thing going well for you this week?

This question deliberately shifts the focus from problems to progress. By asking about a "win," you invite team members to share positive experiences, no matter how small. This strengths-based approach, rooted in positive psychology, helps build momentum, boosts confidence, and cultivates a solution-oriented mindset. It's one of the most powerful good check in questions because it actively celebrates progress and reinforces a culture of appreciation and forward movement.

This method aligns with frameworks like Appreciative Inquiry and the principles popularized by Martin Seligman, which emphasize building on what works rather than solely fixing what's broken. It's a simple way to inject positive energy into a conversation and acknowledge the ongoing efforts that lead to larger successes.

When and Why to Use This Question

Use this question to start team meetings, especially at the beginning of the week, to set a positive and motivated tone. It is also highly effective during one-on-ones to gauge individual progress and morale. This question is particularly useful for teams that may be experiencing fatigue or facing long-term projects, as it reminds them of their capabilities and recent accomplishments.

The goal is to create a regular habit of recognizing success, which can improve team cohesion and individual motivation. By consistently highlighting wins, you help build a shared narrative of competence and resilience, which is a key driver of employee engagement.

Actionable Implementation Tips

• Celebrate Small Wins: Emphasize that a "win" doesn't have to be a monumental achievement. It could be fixing a stubborn bug, receiving positive feedback from a client, or even having a productive, focused morning.
• Model the Behavior: Start by sharing your own win. This could be professional, like "I finally organized my project plan," or personal, like "I had a great weekend with my family." This encourages others to share more openly.
• Prompt, Don't Pressure: If a team member struggles to think of something, offer gentle prompts. You could ask, "What was a moment last week where you felt proud of your work?" or "Did you learn anything new that felt like a breakthrough?"
• Avoid Toxic Positivity: Acknowledge that focusing on wins doesn't mean ignoring challenges. Frame it as one part of the check-in, ensuring there is also space to discuss roadblocks or difficulties later in the conversation.

3. What's your energy level today, and what do you need to be successful?

This two-part question is a powerful tool for proactive management, moving from a reactive to a strategic support model. It first assesses an individual's current capacity without judgment and then immediately pivots to empowerment by asking what they need. This approach acknowledges that energy is a finite resource that fluctuates daily, a concept central to energy management theories from experts like Tony Schwartz. It's one of the most practical and good check in questions because it connects an individual's state directly to their required resources, enabling realistic planning and effective support.

This method also resonates with the principles of "spoon theory," popularized by Christine Miserandino, which explains how people with chronic illness manage their energy. Its application in the workplace helps create a more inclusive and sustainable performance culture. By asking this, you are not just checking in; you are actively collaborating on creating the conditions for success, recognizing that needs change day by day.

When and Why to Use This Question

This question is ideal for the start of a work week, a project kick-off, or during one-on-ones. It’s particularly effective in fast-paced or demanding environments, such as healthcare teams adjusting patient loads or creative agencies assigning tasks. Using it helps prevent burnout by aligning workloads with actual capacity rather than assumed availability.

The goal is to foster a culture where team members feel comfortable being honest about their limits and confident in asking for help. This practice leads to smarter delegation, improved well-being, and higher-quality outcomes. It allows leaders to allocate resources dynamically, providing support like uninterrupted focus time, collaborative help, or a shift in priorities where it's needed most.

Actionable Implementation Tips

• Use a Simple Scale: To make the energy assessment concrete, ask team members to rate their energy on a 1-10 scale. This provides a quick, quantifiable snapshot of the team's overall capacity.
• Provide Support Options: Help team members articulate their needs by offering examples. You might ask, "To be successful, do you need more focus time, collaboration with a teammate, clearer instructions, or a less urgent deadline?"
• Follow Through and Act: The question loses its power if you don't act on the responses. If someone needs help, make a tangible plan to provide it. This builds trust and demonstrates that their input matters.
• Track Patterns Over Time: Encourage individuals to notice their own energy patterns. This self-awareness can help them structure their weeks more effectively, aligning high-energy days with demanding tasks and protecting low-energy days for recovery and planning.

4. What's on your mind that you haven't had a chance to share?

This question serves as a powerful, open-ended invitation to uncover what lies beneath the surface of day-to-day work. It acknowledges that important thoughts, brilliant ideas, or pressing concerns often don't fit neatly into standard agenda items. By creating a dedicated space for these unspoken topics, you signal that every voice and observation is valued. This is one of the most insightful good check in questions because it can unearth hidden roadblocks, spark innovation, or reveal personal challenges impacting an employee's engagement.

This approach is rooted in coaching methodologies and therapeutic practices, like Carl Rogers' person-centered therapy, which emphasize the importance of giving individuals the floor without a prescriptive agenda. It is a cornerstone of building deep trust and fostering high emotional intelligence within your team. It shows you are genuinely interested in their complete experience, not just their progress on assigned tasks.

When and Why to Use This Question

Use this question toward the end of a one-on-one meeting after you've covered formal business. This placement allows it to act as a "catch-all" for anything that wasn't addressed. It is also highly effective in team retrospectives to uncover subtle group dynamics or process improvements that might otherwise go unmentioned.

The primary goal is to surface latent information that could be critical for team health, project success, or individual well-being. By regularly asking this, you create a reliable outlet for communication, preventing small issues from festering into major problems and ensuring great ideas are never lost for lack of an opportunity to share them.

Actionable Implementation Tips

• Embrace the Silence: After asking, resist the urge to fill the silence. Give the person ample time to gather their thoughts. The pause itself communicates that you are genuinely waiting and listening.
• Listen to Understand, Not to Solve: Your initial role is to be a sounding board. Focus on active listening and asking clarifying questions rather than immediately jumping to solutions. The goal is to first understand their perspective fully.
• Take Visible Notes: Jotting down key points as they speak shows that you are taking their input seriously and value what they are sharing. This simple act validates their contribution.
• Create a Follow-Up Loop: If a significant point is raised, make sure to address it. Whether it's a private follow-up or an agenda item for the next meeting, closing the loop demonstrates accountability and reinforces trust.

5. On a scale of 1-10, how supported do you feel right now?

This question transforms the abstract concept of "support" into a measurable metric. By asking for a numerical rating, you provide team members with a simple way to quantify a complex feeling, making it easier to track changes over time. It shifts the conversation from a vague "Are you okay?" to a specific, data-driven starting point that can reveal hidden challenges or needs for resources. This is one of the most practical good check in questions because it creates a clear baseline for addressing team and individual well-being.

The approach mirrors the principles used in Net Promoter Score (NPS) and Gallup's engagement research, applying a quantitative lens to internal team dynamics. It effectively turns a subjective feeling into a tangible data point, allowing leaders to identify trends, pinpoint issues with specific projects or roles, and measure the impact of their support initiatives. This method is particularly useful for remote teams, where feelings of isolation or lack of resources can be difficult to spot.

When and Why to Use This Question

Use this question in monthly one-on-ones or quarterly team health checks. It is exceptionally valuable for tracking sentiment during periods of high workload, organizational restructuring, or when new processes are being introduced. It provides a consistent benchmark to see if your efforts to improve team support are actually working.

The goal is to move beyond guesswork and start a targeted conversation. A low score (e.g., a 4 or 5) is not a failure but an invitation to dig deeper. It signals that a team member may need more resources, clearer guidance, or simply a listening ear, allowing you to intervene proactively before frustration leads to disengagement or burnout.

Actionable Implementation Tips

• Define 'Support': Before asking, clarify what "support" means in your context. It could mean having the right tools, access to information, help from colleagues, or managerial guidance.
• Follow Up on the Number: The number is just the beginning. Always follow up with an open-ended question like, “What would it take to move that number closer to a 10?” or "Can you tell me more about what's contributing to that score?"
• Track Trends, Not Scores: Focus on the pattern over time rather than a single number. A consistent drop in the team's average support score is a red flag that requires immediate attention.
• Encourage Honesty: Reassure your team that there are no "wrong" answers and that their honest feedback is crucial for making improvements. Model this by being transparent about challenges from your own perspective.

6. What's one thing that would make your day/week better?

This question shifts the conversation from passive reflection to active problem-solving. It empowers individuals by inviting them to identify a specific, actionable improvement to their immediate situation, fostering a sense of agency and control. Instead of dwelling on what's wrong, it focuses on what could be made right, often revealing simple yet powerful interventions that can significantly boost morale and productivity. This is one of the most proactive and good check in questions because it turns a check-in into a collaborative improvement session.

This solution-oriented approach is rooted in methodologies like Kaizen, which champions continuous improvement, and human-centered design thinking. It frames challenges not as dead ends but as opportunities for innovation. By asking this, you are communicating that you are an ally in making their work life better, which is a cornerstone of employee happiness. For additional strategies on this topic, you can explore tips for how to keep employees happy.

When and Why to Use This Question

Use this question in regular one-on-ones or team retrospectives. It is especially effective when a team seems stuck in a rut, is experiencing low-grade frustration, or when you want to cultivate a culture of proactive improvement rather than reactive complaint. It’s a constructive way to address minor annoyances before they become major roadblocks.

The goal is to empower your team to co-create their work environment. It shows you value their perspective and are willing to invest in solutions, no matter how small. This practice can uncover critical workflow inefficiencies, resource gaps, or environmental factors impacting focus and well-being.

Actionable Implementation Tips

• Focus on What’s Controllable: Guide the conversation toward small changes that are within the team’s or individual’s power to influence. This could be anything from a quieter workspace to a clearer process for feedback.
• Brainstorm Solutions Together: If someone struggles to identify an improvement, help them. Ask follow-up questions like, “What is the most tedious part of your week?” to pinpoint areas ripe for a fix.
• Commit and Follow Through: The power of this question lies in the action that follows. If a reasonable suggestion is made, commit to implementing it. Track these small wins to build momentum and trust.
• Celebrate the Wins: When a suggested improvement is successfully implemented and makes a positive difference, acknowledge it publicly. This reinforces the value of the feedback and encourages continued participation.

7. How connected do you feel to the team/purpose right now?

This question probes two of the most critical drivers of employee engagement: a sense of belonging and a connection to a meaningful purpose. It moves beyond daily tasks to evaluate an individual's psychological attachment to both their colleagues and the organization's broader mission. By asking this, you gain insight into potential isolation or a drift from the company’s "why," which are often precursors to decreased motivation and higher turnover. This is one of the most insightful and good check in questions because it uncovers the foundational elements that fuel long-term commitment.

This approach aligns with the extensive research on engagement from organizations like Gallup, as well as the work of Simon Sinek, who emphasizes the power of starting with "why." It acknowledges that employees are most fulfilled and productive when they feel they are part of a supportive community working toward a shared, significant goal.

When and Why to Use This Question

Use this question during quarterly reviews, one-on-ones, or after major project milestones. It is especially valuable for remote or hybrid teams where social bonds can weaken and for organizations undergoing change where the connection to purpose may become diluted. It helps you diagnose the health of your team's social fabric and its alignment with strategic objectives.

The goal is to identify and address feelings of disconnection before they impact morale and performance. A strong sense of connection fosters resilience, collaboration, and a culture of mutual support. Regularly checking in on this creates the psychological safety needed for team members to thrive. Learn more about creating a safe team environment.

Actionable Implementation Tips

• Separate the Concepts: If needed, ask two distinct questions: "On a scale of 1-10, how connected do you feel to the team?" and "How connected do you feel to our company's mission right now?" This provides more specific feedback.
• Share Impact Stories: Regularly share stories and testimonials from customers or stakeholders that highlight the real-world impact of the team's work. This powerfully reinforces the "why" behind their efforts.
• Create Connection Opportunities: If social connection is low, organize intentional team-building activities, whether virtual coffee chats or in-person offsites. If purpose is low, hold workshops to reconnect the team's daily tasks to the company vision.
• Follow Up with Individuals: If a team member reports a low level of connection, schedule a private conversation to explore their feelings. Ask what would help them feel more integrated or more aligned with the mission, and co-create a solution.

7 Key Check-In Questions Comparison

Integrating Powerful Questions into Your Leadership Rhythm

We’ve explored a powerful collection of good check in questions designed to move beyond surface-level updates and foster genuine connection. From gauging immediate emotional states with "How are you feeling right now?" to understanding support needs with a simple 1-10 scale, each question serves as a specific tool for building a more transparent and empathetic team culture. The journey from knowing these questions to truly leveraging them lies in consistent, intentional application.

Adopting this practice is not about rigidly following a script; it’s about fundamentally shifting your leadership approach towards one rooted in curiosity and active listening. The goal is to make these insightful conversations a natural and anticipated part of your operational rhythm, transforming routine meetings into opportunities for meaningful human connection. This consistency is what builds the foundation of psychological safety, allowing team members to share openly and honestly over time.

Putting Your Knowledge into Action

To begin integrating these techniques, avoid overwhelming yourself or your team. Instead, follow a structured, incremental approach:

• Start Small and Experiment: Choose one or two questions from this article that resonate most with your team’s current dynamics or challenges. Try one in your next team huddle and another in your one-on-one meetings. Observe the responses and the quality of the conversation that follows.
• Vary Your Channels: Don't limit these check-ins to formal meetings. A well-timed question in a team chat channel or an asynchronous survey can be just as effective. For example, asking "What's one thing that would make your week better?" in a Monday morning Slack message can set a supportive tone for the days ahead.
• Listen, Validate, and Act: Asking a great question is only half the battle. The true impact comes from how you receive the answer. Listen actively without interrupting, validate their feelings by saying things like "That makes sense" or "I appreciate you sharing that," and most importantly, take action when a clear need is identified. Following up demonstrates that their feedback is valued and that you are a reliable source of support.

The Strategic Value of Consistent Check-Ins

Mastering the art of the check-in elevates your role from a manager who directs tasks to a leader who develops people. When you consistently ask good check in questions, you unlock a wealth of real-time data about your team’s well-being, engagement levels, and potential roadblocks. This isn’t just about making people feel good; it’s a strategic imperative.

A team that feels heard and supported is more resilient, innovative, and committed. These regular touchpoints are your early warning system for burnout, disengagement, and interpersonal friction, allowing you to intervene proactively rather than reactively.

Ultimately, the power of these questions lies in their ability to build bridges of trust and understanding. By making space for vulnerability and honest dialogue, you cultivate a workplace where people feel safe to bring their whole selves to work. This human-centered approach is the bedrock of high-performing teams that can navigate uncertainty and thrive together. You are not just checking in; you are investing in the human capital that drives your organization forward.

Ready to move from manual check-ins to a strategic, data-driven approach? Happily.ai integrates these powerful principles into an intelligent platform, helping you automate meaningful connection and gain real-time insights into team health. Discover how our AI-powered tools can help you scale empathy and build a more engaged workforce at Happily.ai.