In a remote-first world, the casual conversations that once built team cohesion have vanished. Meaningful connection now requires deliberate effort. Generic check-ins like "How are you?" often fall flat, met with a simple 'I'm fine.' To truly understand your team's pulse-their challenges, triumphs, and energy levels-you need a better toolkit. This is where good check in questions become essential.

This guide provides a curated list of specific questions designed to foster psychological safety, uncover hidden roadblocks, and build a more resilient, connected, and productive remote team. We'll explore questions that move beyond the surface, offering a framework for when and how to use them to create genuine dialogue and support. Just as it's crucial to ask intentional questions during check-ins, it's also important to consider how you can gain more insights by asking better questions of your data to drive productivity.

Ultimately, these aren't just questions; they are tools for building a culture where every team member feels seen, heard, and valued. By replacing routine queries with more intentional prompts, you can transform simple meetings into powerful moments of connection and alignment.

1. How are you feeling today?

This is one of the most simple yet profoundly effective check-in questions you can ask. It moves beyond the automatic "How are you?" to invite a genuine, present-moment reflection on someone's emotional state. By asking how a person is feeling, you acknowledge them as a whole person, not just a colleague or a contributor.

This question is a powerful tool for building team cohesion and trust. It lays the groundwork for a culture where vulnerability is accepted, which is a core component of team performance. By consistently making space for emotional check-ins, you can cultivate a more supportive and connected environment.

When to Use This Question

Use this question to kick off meetings where human connection is as important as the agenda. It sets a people-first tone and helps everyone arrive more fully.

• Daily Stand-ups: A quick "feeling check" can surface hidden blockers or low morale before they impact a sprint.
• 1-on-1 Meetings: It's an essential starting point for a meaningful conversation beyond project updates.
• Team Retrospectives: Understanding the team's emotional journey through a project provides crucial context for feedback.

How to Implement It Effectively

• Model Vulnerability: As the leader, answer first. Share your own feelings honestly, whether you're feeling "energized," "a bit scattered," or "optimistic."
• Listen Actively: Don't just wait for your turn to speak. Pay attention to what's said and what isn't. Your goal is to understand, not to fix.
• Accept All Answers: Someone might just say "good," and that's okay. The key is to create the space; forcing a deep share can backfire.

By integrating this question, you signal that you care about your team's well-being, which directly contributes to building a secure and open atmosphere. This practice is fundamental to establishing the kind of environment where people feel safe to contribute their best work. To go deeper on this topic, you can learn more about psychological safety at work.

2. What's one thing you accomplished this week?

This is a strengths-based check-in question that immediately shifts the focus toward progress, wins, and positive momentum. Instead of dwelling on problems or to-do lists, it invites team members to reflect on what they’ve successfully completed, fostering a sense of agency and building motivation.

This question is a powerful tool for morale-building and performance management. Regularly highlighting accomplishments, no matter how small, reinforces a culture of recognition and helps individuals see their direct contribution to team goals. It counteracts the natural tendency to only focus on what's left to be done.

When to Use This Question

Use this question to inject positivity and a sense of progress into your regular team touchpoints. It’s excellent for reminding everyone of their capabilities and collective forward movement.

• Weekly Team Meetings: Kicking off a weekly sync by sharing wins sets an upbeat and productive tone for the entire meeting.
• 1-on-1 Meetings: It's a great way to start a performance or development conversation on a positive note.
• Agile Sprint Retrospectives: This helps the team recognize what went well and builds confidence for the next sprint.
• End-of-Week Wrap-ups: It allows the team to leave for the weekend feeling a sense of closure and achievement.

How to Implement It Effectively

• Define 'Accomplishment' Broadly: Make it clear that an accomplishment can be anything from shipping a feature to learning a new skill or helping a teammate.
• Celebrate Publicly: Acknowledge and genuinely celebrate the shared wins. This reinforces the value of each person's contribution.
• Document Achievements: Keep a running list of these accomplishments. They are invaluable for performance reviews and tracking progress over time.
• Balance with Challenges: For a complete picture, you can pair this question with one about challenges, but always start with the positive.

By making this one of your good check in questions, you build a rhythm of positive reinforcement. This practice is especially effective in the context of regular performance conversations. To learn more about structuring these conversations, see these tips for a better one-on-one meeting.

3. What's one challenge you're facing?

This is one of the most proactive and supportive check-in questions you can ask. It directly invites team members to share obstacles, demonstrating that the environment is safe for discussing difficulties. This question shifts the focus from just status updates to genuine problem-solving and support.

By asking about challenges, you normalize the reality that work isn't always smooth. It’s a powerful way to build trust and uncover hidden issues before they escalate. This approach fosters a culture of mutual assistance, where team members feel comfortable asking for and offering help.

When to Use This Question

This question is ideal for settings where the goal is to unblock progress and offer targeted support. It’s particularly effective in focused, goal-oriented meetings.

• Weekly 1-on-1s: It opens the door to discuss personal or professional hurdles beyond the scope of project tasks.
• Agile Retrospectives: This question helps identify specific impediments that affected a sprint's outcome.
• Mentorship Sessions: It allows a mentor to provide direct, relevant guidance on a mentee’s current struggles.

How to Implement It Effectively

• Ask with Curiosity: Your tone should be supportive and non-judgmental. The goal is to understand and help, not to assign blame for a problem.
• Don't Impose Solutions: Listen first, then ask if they’d like to brainstorm solutions together. Empower them to find their own path with your support.
• Follow Up: In future check-ins, refer back to a previously shared challenge. Asking "How did that situation with X go?" shows you were listening and that you care.

Integrating this question turns check-ins into an opportunity for growth and connection. It’s a foundational practice for creating a resilient team that tackles problems together. To further develop this skill, you can learn more about collaborative problem-solving steps.

4. What do you need support with?

This is a direct, action-oriented question that moves past simply identifying problems and focuses on finding solutions. Instead of asking about challenges, which can sometimes feel like a complaint session, this question empowers team members to articulate their specific needs. It shifts the dynamic from passive problem-stating to proactive help-seeking.

This question is a powerful tool for building a culture of mutual support and resourcefulness. It signals that asking for help is not a sign of weakness but a strategic step towards achieving goals. By explicitly inviting requests for assistance, you foster an environment where team members feel seen, heard, and backed by their colleagues and leadership.

When to Use This Question

This question is ideal for contexts where progress and unblocking team members are the primary goals. It is one of the most practical and good check in questions for tangible outcomes.

• 1-on-1 Meetings: It's a perfect way to move from project updates to identifying specific ways you can help your direct report succeed.
• Project Kick-offs or Mid-point Reviews: Use it to ensure everyone has the resources they need before a potential issue escalates.
• Peer Support Sessions: Encourages team members to lean on each other's strengths and offer assistance directly.

How to Implement It Effectively

• Model Asking for Help: Start by sharing something you need support with. This normalizes the act and makes it safer for others to do the same.
• Follow Through Consistently: If someone asks for support, make sure you follow up. Failing to do so will quickly erode trust and render the question useless.
• Create Multiple Channels: Not everyone is comfortable asking for help in a group setting. Offer private or anonymous ways for people to make requests. For more on this, you can explore options for your team to ask anonymous questions.

By integrating this question, you transform check-ins from a simple status report into a powerful mechanism for collaboration and problem-solving. This builds a resilient team that knows how to leverage its collective strength to overcome any obstacle.

5. How are your energy levels?

This wellness-focused check-in shifts the conversation from emotions to capacity. Instead of asking how someone feels, it gauges their physical and mental energy, acknowledging that burnout and fatigue are critical factors in both wellbeing and productivity. This is one of the most practical and good check in questions for high-stress or remote environments where the lines between work and life often blur.

Tracking energy levels helps identify patterns of overwork or disengagement before they become chronic issues. It gives leaders tangible data to discuss workload adjustments, scheduling changes, or the need for rest. Normalizing conversations about low energy makes it acceptable for team members to be human, fostering an environment where people feel supported in managing their capacity.

When to Use This Question

This question is ideal for contexts where performance and sustainability are closely linked. It moves the focus from short-term feelings to long-term operational health.

• Beginning of the Week Check-ins: Gauge the team's collective starting capacity for the week ahead.
• Project Kick-offs: Understand if the team has the energy required to take on a demanding new initiative.
• 1-on-1s with High-Performers: Proactively monitor for signs of burnout in your most dedicated team members.

How to Implement It Effectively

• Use a Simple Scale: Ask team members to rate their energy on a 1-10 scale. This makes it easy to track trends over time.
• Ask Follow-up Questions: If someone reports low energy, ask, "What's draining you?" or "What could help you recharge?"
• Connect to Action: Use the answers to make concrete changes, such as adjusting deadlines, encouraging breaks, or re-prioritizing tasks.
• Normalize Low Energy: Reassure the team that it's okay not to be at 100% all the time. The goal is awareness, not constant high performance.

By making energy a regular topic of conversation, you empower your team to manage their own sustainability. To take this further, you can explore concrete strategies to beat burnout and stay creative.

6. What are you learning or working on developing?

This growth-oriented question shifts the focus from daily tasks to long-term personal and professional development. It encourages a growth mindset by framing work as a continuous opportunity to learn and improve, which is essential for employee engagement and retention. It shows that you value team members for their potential, not just their current output.

This question is a cornerstone of a strong learning culture, common in innovative companies that thrive on skill development. By asking it, you signal that the organization invests in its people's futures. It opens the door to conversations about career goals, mentorship opportunities, and aligning individual aspirations with organizational needs.

When to Use This Question

Use this question in settings dedicated to growth and long-term planning. It moves beyond immediate project deadlines to focus on career trajectory and skill acquisition.

• 1-on-1 Meetings: It's a perfect way to transition from performance review to professional development planning.
• Quarterly Reviews: Frame conversations around skills gained in the last quarter and goals for the next.
• Mentorship Check-ins: This is a core question for tracking progress and identifying new learning opportunities.

How to Implement It Effectively

• Connect Learning to Goals: Help your team member see the link between what they are learning and where they want to go in their career.
• Offer Resources: Be prepared to suggest courses, mentors, or internal projects that can support their development goals.
• Celebrate the Process: Acknowledge the effort of learning, not just the outcome. Make it safe to discuss challenges and failures along the way.

By regularly including this among your good check in questions, you foster an environment where continuous improvement is the norm. It demonstrates a commitment to your team's growth, making them feel valued and motivated to contribute their developing skills back to the team.

7. How connected do you feel to your team/purpose?

This question moves beyond daily tasks to tap into the deeper human needs for belonging and meaning. It probes two critical dimensions of engagement: social connection with colleagues and personal alignment with the organization's mission. In remote or hybrid settings, where organic team bonding is less frequent, explicitly asking about connection is vital for retention and morale.

Asking this question signals that you value not just what employees do, but also how they feel about their role and their place within the team. The answer can be a powerful leading indicator of engagement, burnout, or potential turnover, giving you a chance to address systemic issues before they escalate.

When to Use This Question

This question is ideal for deeper, more strategic conversations where you want to gauge long-term alignment and satisfaction. It's less for a quick daily stand-up and more for moments of reflection.

• Quarterly Reviews: Use it to understand an individual's sense of belonging beyond their performance metrics.
• 1-on-1 Meetings: It's a perfect way to check in on overall job satisfaction and career alignment every few months.
• Team Offsites or Planning Sessions: Assess the group's collective connection to the mission before setting future goals.

How to Implement It Effectively

• Reinforce Purpose: Regularly connect day-to-day tasks back to the company's larger mission. Show how individual contributions make an impact.
• Follow Up Thoughtfully: If someone feels disconnected, ask, "What's one thing that could help you feel more connected?" This shifts the focus toward a collaborative solution.
• Facilitate Connection: Don't leave connection to chance. Create structured opportunities for team bonding, both virtual and in-person, that go beyond project work.

By making this one of your good check in questions, you actively monitor and nurture the sense of purpose and belonging that keeps teams motivated, resilient, and aligned.

8. What's one thing you're grateful for or appreciating?

This question shifts the focus from tasks and challenges to positivity and recognition. Grounded in positive psychology, asking about gratitude encourages a mindset of appreciation, which can significantly improve team morale and individual well-being. It's a simple yet powerful way to build resilience and strengthen interpersonal connections.

Introducing a gratitude practice helps counterbalance the natural tendency to focus on problems. When teams regularly acknowledge the good, whether it's a helpful colleague or a successful project milestone, they build a more supportive and optimistic culture. This question is one of the most effective good check in questions for fostering a positive atmosphere.

When to Use This Question

Use this question to intentionally inject positivity into a meeting, especially when the team might be feeling stressed or focused on difficulties.

• Weekly Team Meetings: Start the week on a high note by sharing appreciations.
• Project Kick-offs: Build positive momentum and camaraderie from the beginning.
• Retrospectives: Use it in the "what went well" section to specifically highlight appreciation for team members' contributions.

How to Implement It Effectively

• Model Specificity: As the leader, share your own specific gratitude first. Instead of "I'm grateful for the team," try "I'm grateful for Sarah's detailed feedback on the proposal yesterday; it was a huge help."
• Encourage Peer-to-Peer Appreciation: Frame the question to include gratitude for colleagues' actions, fostering stronger team bonds.
• Allow for Silence: Give everyone a moment to genuinely reflect. Not everyone will have an answer immediately, and that's perfectly fine.

By consistently making space for gratitude, you cultivate an environment of recognition and mutual respect. This practice helps team members feel seen and valued, which is fundamental to creating a culture where people are motivated and engaged.

9. What would make this better for you?

This question shifts the focus from problems to potential solutions, empowering individuals to contribute to their own work environment. It's a constructive and forward-looking check-in that hands agency to your team members, positioning them as experts on their own experience and inviting them to co-create improvements.

This is one of the most effective good check in questions for uncovering actionable feedback. Instead of just identifying dissatisfaction, it prompts people to think critically about what specific changes would have a positive impact. It’s a direct invitation to improve processes, tools, or team dynamics, fostering a culture of continuous improvement and shared ownership.

When to Use This Question

This question is ideal for situations where you want to move beyond venting and into collaborative problem-solving. It's particularly useful for refining systems and processes.

• Project Retrospectives: After discussing challenges, ask this to generate ideas for the next project cycle.
• 1-on-1 Meetings: Use it to explore how you can better support a direct report's performance and well-being.
• Following Feedback: After a team member shares a frustration, this question opens the door to a productive conversation.

How to Implement It Effectively

• Ask for Specifics: Encourage concrete, actionable suggestions. Instead of "more support," guide them toward "a weekly check-in on this specific task."
• Follow Up Visibly: When a suggestion is implemented, announce it. This shows you're listening and that feedback leads to real change.
• Explain the "Why Not": If a suggestion can't be implemented, transparently explain the reasons. This builds trust and respect.
• Prioritize Together: Work with the person to identify which of their suggestions would make the biggest difference.

10. How are you doing with work-life integration/balance?

This question directly addresses the well-being and sustainability of your team members, acknowledging that their lives extend far beyond their job descriptions. It moves past project status to explore how work fits into their broader life, which is crucial for preventing burnout and fostering long-term engagement, especially in remote or hybrid settings.

This check-in is one of the most proactive and supportive questions a leader can ask. It shows you care about your team as individuals and recognize that a healthy work-life balance is a prerequisite for high performance. Companies like Microsoft and Salesforce champion this approach, understanding that employee well-being is directly tied to business success.

When to Use This Question

This is a perfect question for more private, in-depth conversations where you can genuinely explore the topic without an audience. It requires a high degree of trust.

• 1-on-1 Meetings: It's the ideal setting to discuss boundaries, workload, and personal well-being confidentially.
• Performance Reviews: Use it to frame conversations around sustainable career growth and support.
• After a High-Intensity Project: Check in to ensure team members are decompressing and re-establishing a healthy rhythm.

How to Implement It Effectively

• Model Healthy Boundaries: Share how you are managing your own work-life integration. Mention taking breaks, logging off at a reasonable time, or prioritizing family events.
• Be Prepared to Offer Solutions: This question may uncover real challenges. Be ready to discuss flexible scheduling, adjusting workloads, or connecting the person with wellness resources.
• Listen Without Judgment: The goal is to understand their reality, not to evaluate their time management skills. Create a safe space for an honest conversation about their challenges.

By consistently asking this question, you build a culture that values sustainable effort over constant availability. This practice helps retain top talent by showing your organization is invested in their holistic well-being, making it a powerful addition to your list of good check-in questions.

10 Check-In Questions Comparison

Check-in prompt	🔄 Complexity	⚡ Resources	⭐ Expected outcomes	📊 Ideal use cases	💡 Quick tips
How are you feeling today?	🔄 Low — simple, open-ended	⚡ Low — minutes, minimal tools	⭐ Builds emotional awareness; varies by trust	📊 Standups, therapy, quick team check-ins	💡 Model vulnerability; follow up
What's one thing you accomplished this week?	🔄 Low — structured prompt	⚡ Low — tracking helpful (notes)	⭐ Boosts recognition and motivation	📊 All-hands, 1:1s, retrospectives	💡 Define accomplishment broadly; celebrate
What's one challenge you're facing?	🔄 Moderate — needs safety & time	⚡ Moderate — discussion + support resources	⭐ Surfaces issues early; enables problem-solving	📊 1:1s, retros, supervision	💡 Ask curiously; co-create solutions
What do you need support with?	🔄 Moderate — requires actionable process	⚡ Moderate‑High — resources & coordination	⭐ Clarifies needs; enables targeted support	📊 Manager check-ins, coaching, peer programs	💡 Be specific about available support; follow through
How are your energy levels?	🔄 Low — often a simple scale	⚡ Low — use 1–10 scale, tracking tools	⭐ Early burnout indicator; informs adjustments	📊 Wellness programs, standups, healthcare checks	💡 Use consistent scale; ask causes and remedies
What are you learning or working on developing?	🔄 Moderate — ongoing focus	⚡ Moderate — training, mentors, time	⭐ Promotes growth; identifies skill gaps	📊 Mentorship, dev check-ins, PD programs	💡 Link learning to goals; provide resources
How connected do you feel to your team/purpose?	🔄 Moderate — may need deeper follow-up	⚡ Moderate — surveys, bonded activities	⭐ Reveals engagement & retention risks	📊 Remote teams, engagement surveys, mission-driven orgs	💡 Ask "what would help?"; reinforce purpose regularly
What's one thing you're grateful for or appreciating?	🔄 Low — positivity-focused	⚡ Low — minimal time	⭐ Improves morale and resilience when genuine	📊 Team appreciations, wellness rituals	💡 Be specific and sincere; model gratitude
What would make this better for you?	🔄 Moderate — invites actionable feedback	⚡ Moderate — time to prioritize & implement	⭐ Generates improvement ideas; increases buy-in	📊 Feedback systems, design workshops, advisory boards	💡 Request actionable suggestions; close the feedback loop
How are you doing with work-life integration/balance?	🔄 Moderate‑High — sensitive topic	⚡ Moderate‑High — may need policy changes	⭐ Identifies boundary issues; supports retention	📊 Flexible work programs, coaching, wellness initiatives	💡 Ask specifics; offer flexible options and resources

Transforming Conversations into Connections

The journey from a simple "How are you?" to a truly insightful team dialogue is paved with intentionality. The list of good check in questions you've just explored isn't a magic script, but rather a toolkit designed to unlock deeper, more meaningful conversations within your remote or hybrid team. Moving beyond surface-level updates transforms routine meetings into powerful opportunities for connection, support, and genuine collaboration.

The real value of these questions lies not just in asking them, but in the environment you create for the answers. A question like, "What do you need support with?" only works when team members feel psychologically safe enough to be vulnerable. Similarly, asking "How are your energy levels?" becomes a powerful tool for preventing burnout, but only if the response is met with empathy and a willingness to adjust workloads or offer resources.

Your Actionable Path Forward

Integrating these practices doesn't require a massive overhaul of your current processes. The key is to start small and build momentum. Here are your next steps:

1. Select and Start: Choose just one or two questions from this list that resonate most with your team's current needs. Perhaps you want to focus on well-being ("How are you doing with work-life integration?") or on professional growth ("What are you learning or working on developing?").
2. Integrate Intentionally: Decide where these questions will live. Will they kick off your weekly team sync? Will they be the foundation of your one-on-one meetings? Consistency is crucial for building a habit of open communication.
3. Listen and Act: The most critical step is to actively listen to the answers and, where appropriate, take action. If someone shares a challenge, follow up. If a need for support is identified, help facilitate it. This follow-through builds trust and proves that these check-ins are more than just a formality.

Ultimately, mastering the art of the check-in is about shifting from a management mindset focused on output to a leadership mindset focused on people. When you show a genuine interest in your team's holistic well-being, their challenges, and their aspirations, you cultivate a culture of trust and mutual respect. This foundation is what enables teams to not only navigate the complexities of remote work but to thrive, innovate, and produce their best work together. These good check in questions are your starting point for building a more connected, resilient, and effective team.

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