60 Thoughtful & Open Check-In Questions For Meetings

For a lot of managers, it’s easy to get caught up in the day-to-day grind of work without stopping for a second to catch-up with team members and see how they are getting along. For organisations who don’t have dedicated HR support, it can be difficult to escape the world of KPIs and find the time to sit down and have a genuine conversation with staff. But, what topics should you be covering to connect with your team? How should you make sure they are happy at work?

Whether you're meeting face-to-face or virtually, this guide from the team at Make Venues is here to help you conduct check-in meetings effectively. By using this article as a resource, you can make sure you are asking all the right questions to keep your team engaged and feeling passionate about their work.

What Are “Check-ins”?

Check-ins, or check-in meetings, are regular catch ups held between line managers and their direct reports. They are an opportunity for managers to talk to their team members one-to-one about how things are going at work, what they are currently working on, and discuss any challenges they are facing. 

Check-in meetings typically have a more relaxed atmosphere compared to more formal appraisal meetings. These check-ins involve a casual sit-down between an employee and their manager to discuss the progress of work and the employee's current feelings or well-being.

Why Should You Hold Check-in Meetings?

As a manager, it’s vital to hold regular check-in meetings with your team, both to look after their well-being at work, and to keep projects on-track. They serve as a useful communication channel for teams to have open discussions about anything that’s on their mind at work, sometimes even out of work. Check-ins help to create a positive work culture where employees feel valued and know their voices are being heard.

With that in mind, let’s explore our selection of the most useful check-in questions that managers can use during these informal catch ups with team members.

General Ice-Breaker Check-In Questions

To kickstart your catch-up, here are some simple and effective questions you can ask to help your colleague feel at ease and settle into the conversation. You can use their answers as a basis for steering the discussion later in the meeting.

• How are you feeling today, both personally and professionally?

• Is there anything on your mind that you'd like to share with the team?

• Are there any personal or professional accomplishments you're particularly proud of lately?

• What's one thing you're looking forward to this month?

• How do you prefer to receive feedback and support from your colleagues and managers?

• Are there any recent wins or successes you'd like to celebrate with the team?

• How would you rate your overall satisfaction with your work environment and team collaboration?

• Is there anything outside of work that's impacting your focus or energy that you'd like to discuss?

• What strategies do you use to stay motivated and focused during challenging times?

• How can we, as a team, better support each other in achieving our goals and maintaining a positive work environment?

Progress-Related Check-In Questions

Tracking progress and addressing challenges in a timely manner are essential for making sure that your team members are on track to meet their objectives. These progress-related check-in questions are designed to help you assess the current status of your team’s ongoing projects and tasks while also providing support where needed.

• What progress have you made since our last check-in, and what challenges have you encountered?

• Are there any tasks or projects that you're struggling to make progress on, and how can we help?

• What steps have you taken to overcome any obstacles you've encountered recently?

• Are there any specific accomplishments or milestones you'd like to highlight since our last meeting?

• How do you feel about the pace of your work and your ability to meet deadlines?

• Are there any areas where you feel you could be more efficient or productive?

• What support or resources do you need to continue making progress on your current tasks or projects?

• Are there any lessons learned from recent experiences that you'd like to share with the team?

• How can we adjust our priorities or strategies to better support your progress and success?

• What are your top priorities for the upcoming week, and how can we align as a team to support them?

Goal-Oriented Check-In Questions

The following questions are great to ask when you are checking in with an employee to discuss their progress towards achieving a specific goal or reaching a certain milestone in their work. They are designed to help team members remain focussed and on-track towards their own personal objectives, while also ensuring that broader team projects are progressing smoothly.

• Are your current tasks aligning with your broader professional goals, and if not, how can we adjust?

• What progress have you made towards your short-term and long-term goals since our last discussion?

• Are there any goals or objectives that you feel unsure about or need clarification on?

• How confident are you feeling about achieving your current goals, and what factors contribute to that confidence level?

• Are there any new goals or aspirations you'd like to discuss with the team?

• What steps can you take to ensure your daily actions are aligned with your wider goals?

• Are there any skills or experiences you'd like to develop further to support your career goals?

• How do you measure success in relation to your goals, and how can we support you in tracking your progress?

• Are there any potential roadblocks or challenges on the horizon that we should address to keep you on track with your goals?

• How can we, as a team, collaborate more effectively to achieve our collective goals and objectives?

Check-In Questions For Remote Workers

Due to the nature of working remotely, regular check-ins with remote workers are crucial to gauge their progress and overall well-being. Working remotely can often lead to feelings of isolation, lacking the interaction an employee would typically have in a hybrid or office-based setting.

These check-in questions are written specifically for remote workers, aiming to address their unique challenges and needs while also helping them to feel valued, supported and engaged as members of your team:

• How are you managing your workload and staying productive in a remote setting?

• Are there any tools or resources you find particularly helpful for remote collaboration?

• What strategies do you use to maintain a healthy work-life balance while working remotely?

• How do you stay connected with your colleagues and maintain team camaraderie while working remotely?

• Are there any specific challenges you've encountered while working remotely that you'd like to discuss?

• How can we ensure that remote team members feel included and supported in team discussions and decision-making processes?

• What adjustments can we make to our remote work policies or practices to better support your productivity and well-being?

• Are there any training or development opportunities you'd like to explore to enhance your remote work skills?

• How can we improve our communication and collaboration processes to better accommodate remote work arrangements?

• What support or resources do you need to feel more connected and engaged with the team while working remotely?

Feedback and Development Check-In Questions

The most successful teams always tend to embrace a culture of continuous self-improvement and professional growth. As a manager, it’s important for you to do as much as you can to encourage your team members to reflect on their previous work, and give them the confidence to challenge themselves to take on development opportunities. Here are some questions you can use in your next check-in to do just that:

• What feedback do you have for your colleagues or the team as a whole based on recent experiences?

• Is there any specific feedback you've received recently that you found particularly valuable or actionable?

• How do you prefer to receive feedback, and is there anything we can do to ensure it's delivered effectively?

• Are there any areas where you'd like to receive additional training or support to further develop your skills?

• What opportunities for growth or development do you see within your current role or projects?

• How can we, as a team, create a culture of continuous feedback and learning?

• Are there any mentors or role models within the organisation whom you admire and would like to learn from?

• What steps can you take to actively seek feedback and incorporate it into your professional development?

• How do you measure your progress and growth over time, and what milestones do you hope to achieve?

• How can we better recognise and celebrate individual and team achievements to foster a culture of appreciation and growth?

Well-Being Check-In Questions

To conclude our list of check-in questions for managers, we thought we’d address how you can make sure your team is feeling happy at work and their mental health is prioritised. Stress and burnout significantly impacts mental health and work-related performance - it’s vital to check-in with your team members frequently to look after their well-being and offer support wherever possible. Here are some questions you can use to gauge the mental well-being of your team and help them to manage their work-life balance:

• How are you managing your work-life balance, and are there any areas where you're struggling with?

• Are there any habits or routines you've adopted to support your physical and mental well-being?

• How do you recharge and unwind after a particularly challenging day or week?

• Are there any stressors or sources of anxiety in your work or personal life that you'd like to talk about?

• What support do you need from your manager or colleagues to maintain your well-being while juggling work responsibilities?

• Are there any company policies or practices that you find particularly supportive of employee well-being?

• How can we foster a culture of well-being within our team and organisation as a whole?

• Are there any resources or initiatives you'd like to see implemented to support employee wellness?

• What role do hobbies or outside interests play in your overall well-being, and how do you make time for them?

• How can we better accommodate your individual needs and preferences to promote a healthy work environment for everyone?

Premium and Modern Meeting Rooms for your Team

Are you looking for a new, fresh environment to hold meetings with your team? At Make Venues, we have 3 modern corporate event venues at central locations in London, Bristol, and Leamington Spa. We offer award-winning service at each of our purpose built venues, with meeting rooms fit for small or large numbers of delegates. With fully-fitted video conferencing technology, a range of catering options, and expansive communal areas, there’s no better place to hold your next team meeting.

Get in touch with us for more information about Woodland Grange, Broadway House, and Engineer’s House and book a meeting space today!