Management

Best Check-In Questions For Productive Meetings

Max 11 min read

Best Check-In Questions For Productive Meetings

Best Check-In Questions For Productive Meetings

Check-in meetings, if done well, can prove to be a valuable way of conducting effective communication in the workplace. This enables employees to get more done in less time, developing an open and balanced line of communication between everyone on the team and improving collaboration overall.

The relationship between a manager and their direct report is a significant one, having the ability to affect all aspects of the employee experience. Everything from engagement, retention, performance, and motivation are all directly impacted by the health of these particular interactions. Check-in meetings can help facilitate the conversations that reveal insightful information about the employee’s mindset and can lead to quicker decision-making based on the feedback presented, so it’s important that the check in-questions used during these meetings be structured and strategic, avoiding simple “Yes” or “No” answers. To get the best results that drive productivity, let’s take a look at the best check-in questions for meetings and why they’re important.

What are Check-In Questions

What are Check-In Questions?

Check-in questions are a series of pointed questions that elicit feedback from the employees about project updates, workload, efficiencies (or inefficiencies) in any current business processes, conflict-resolution, performance, and employee well-being and mindset. In short, you can use these questions in a variety of meetings and for different purposes.

The best check-in questions can also keep the team up to date on the status of any group assignments, boost engagement, and sustain a positive and inviting atmosphere, bolstering the sense of community. When kept as specific and focused as possible, good check-in questions can give you a valuable understanding of where everyone stands, which guides how you move forward and complete essential objectives.

Why Is It Important To Have Good Check-In Meetings?

As with all meetings, it’s important to remember that effective meetings should have a clear structure, be respectful of the team’s time, and be guided by a purposeful agenda. So having focused questions that not only guide the discussion but encourage the employees to speak openly about their assessments is vital.

Having good check-in questions does a few key things in the workplace:

  • Gives an opportunity to touch base – This is especially crucial in regards to remote (or hybrid) teams where communication is essential to the success of the group as a whole. In some cases, employees might not have opportunities to ask questions of their managers or vice versa depending on the day’s schedule and respective workloads. This can result in miscommunication, leading to generally poorer outcomes when expectations are not met as a result. Scheduled check-in meetings designate a time dedicated to updating one another, posing their questions, and giving a platform to provide any necessary feedback to keep the momentum and energy flowing.
  • Fills in the blind spots – It can be common for managers, especially ones just entering into leadership roles, to rely on a consistent stream of feedback so they can best improve processes and communication moving forward, ensuring that everyone collaborates successfully and has all the resources they need to do their job efficiently. Without check-in meetings, managers may not be aware of how the team is performing, where their mindset is, and what gaps exist in the current operations until serious issues arise. To stay ahead of these types of problems that can be detrimental to motivation and morale, managers should use these check-in meetings to their advantage, filling in potential blind spots so they have the most current information on their team and associated projects.

    Provides real-time health of the team

  • Provides real-time health of the team – Another important aspect of check-in meetings is the ability to gauge how the team is doing from a mindset and moral perspective. Are they feeling demotivated, overwhelmed, stressed, or unsupported? When a team is struggling, these may not be the most comfortable of meetings, often with many individuals hesitating to speak up. Understandably, this is an awkward and difficult situation that has the potential to grow into deeper issues if not resolved appropriately. The best practice is to stay engaged with the team, be proactive about issues, keep the meetings structured and focused, and encourage collaboration. If the team is feeling overwhelmed, a plan of action can be constructed to help alleviate some of the pressures and redistribute any relevant workloads as necessary.
  • Increases engagement – Real-time problem-solving can actually lead to increased engagement from the entire team. Check-in meetings that focus specifically on a certain situation can involve all the relevant decision-makers so outcomes can be reached faster and more efficiently. Being given this opportunity to debrief and communicate about proposed actions and solutions ultimately shepherds the team to quicker success, allowing them a platform to exchange ideas and be creative with the process.
  • Gathers proactive insights – Regularly scheduled check-in meetings are another way of receiving valuable insights into various areas of the work process. Managers can get a better understanding of what is working well, what needs to be improved, and what (if any) can be done to accomplish objectives faster and more accurately. Check-in meetings are a great way to stay ahead, anticipate any potential problems before it becomes unmanageable, and include the team in important decisions that affect the company. Employees who have an opportunity to be heard and have the opportunity to have their insights included in important decisions tend to feel more motivated and focused.
  • Creates a two-way street – While it’s easy to use a check-in meeting as a means of gathering information from a direct report, if used effectively, it can actually be a beneficial way of creating communication that goes both ways. The employee has the opportunity to update their manager, ask questions, and provide feedback. Simultaneously, the manager can use this time to give their direct report on major (or upcoming) updates, give feedback of their own, and ask relevant questions that can help guide the conversation in a meaningful way. Having this two-way street improves communication all around, ensuring that everyone is on the same page and reducing the chance of important topics slipping through the cracks.

Check-in meetings with specific questions and a strategic structure can provide a ton of benefits that the entire team can appreciate. Now that we understand the importance of check-in meetings, let’s talk about the most effective questions managers and leadership can ask in order to gain the best insights.

Daily Check-in Questions

Daily Check-in Questions

Daily meetings, often called daily huddles, scrums, or daily standup meetings, are used more commonly in technological or software-related fields and are typically brief, averaging 15-30 minutes at most; however, these types of regular and frequent meetings are a good way to stay updated on the progress of major projects and keeps the team aligned. It’s a useful way to track workflow and identify problems quickly to avoid any interruptions to the process. Daily meetings also encourage high team participation and engagement, get the team behind a shared vision for the company, improve interpersonal communication, and help coordinate efforts for maximum efficiency.

To make the most out of these daily meetings, these are the types of questions that can keep the momentum moving positively forward and gather the most important data so that the team can do their own parts successfully:

  1. What did you accomplish yesterday?
  2. What did you find about yesterday’s work that was successful, or not successful?
  3. What are you looking forward to completing today?
  4. What are your priorities for the day?
  5. What resources do you need today?
  6. What can I do, as your leader, to support you today?
  7. Is there anything that you need from the team that will support you today?
  8. Do you anticipate any challenges for your progress?
  9. How close are you to achieving your goal for today?
  10. Are you comfortable with your workload for today? If not, what can we do as a team to help you?

As daily meetings are intended to be short, ask the questions you feel would be more relevant to the day’s tasks according to any project demands and deadlines. However, these questions will help you gain an understanding of your employee’s workload, their confidence and ability to get their work done, and the support needed in order to successfully meet their goals for the day.

Weekly Check-In Questions

Weekly Check-In Questions

Weekly check-in meetings are a way for a manager and their direct report to reflect on the past week, plan for the week ahead, and provide ample opportunity to ask clarifying questions that will help them prepare for the coming days. Weekly 1:1 meetings are typically longer than daily meetings with the average duration being one hour to give enough time for thoughtful discussion.

A weekly check-in meeting has many valuable benefits including building effective communication skills as you reflect on the past week of performance, improving problem-solving skills as both employee and manager need to be proactive about particular issues, zoning in on key tasks, creating an essential culture of accountability, and raising motivation.

Here are some of the most important questions to ask during a weekly check-in meeting to ensure that time is being used wisely, fueling productivity:

  1. How are you feeling about this past week?
  2. What are you looking forward to completing this coming week? How do you feel about that?
  3. What are the current challenges that you’re facing this week?
  4. What do you need from me in order to make this week more productive for you?
  5. What would you like to accomplish this week?
  6. What wins did you have this past week?
  7. Where do you need support?
  8. Do you need any clarification on any of our current processes?
  9. Do you have any important updates for me?
  10. What questions do you have for me this week?
  11. What is the best way to communicate with you this week?
  12. Are there any scheduling conflicts that I need to know about?
  13. How is your workload?

These questions will help guide the conversation during the weekly check-in meeting, targeting workload capacity, any support needed to successfully make it through the end of the week until the next check-in, and sets expectations for both manager and employee, which gives them clarity for the days ahead.

Monthly Check-in Questions

Monthly Check-in Questions

Hosting monthly check-in meetings can be one way of staying positive about the future, reflecting back on past achievements, and identifying the best ways to improve on future processes and performance. These monthly meetings can last up to one hour depending on the circumstances and project needs. Just like daily and weekly check-in meetings, even though a few weeks have come and gone, it’s a good way to check in with your employees and get a sense of their well-being. Specific business processes are analyzed by the whole team, creating a sense of cohesion amongst the relevant parties.

These are the top questions to ask during monthly check-in meetings to ensure you’re getting the most out of this designated hour:

  1. What do you consider to be your core responsibilities?
  2. What do you consider to be your strengths?
  3. What areas are you looking to improve?
  4. What do you consider one of your biggest accomplishments in these past 30 days?
  5. In what areas would you like to receive additional training or development?
  6. What can I do to make it easier for you on the team?
  7. What part of your role are you most passionate about?
  8. What would you consider to be your biggest challenge right now?
  9. What resources do you need to find success in the next 30 days?
  10. What can I do to support you for the next month?
  11. Have you been inspired by anyone or anything at work recently?
  12. Do you have any final thoughts or comments that we should go over before our next meeting?

Using these targeted questions about their overall experience within the last month, focusing on achievements and problem-solving areas in need of improvement, help the employee feel much safer and more confident in their abilities to complete their tasks in a timely and efficient manner.

Culture Check-in Questions

Culture Check-in Questions

In order to foster a positive work environment that prioritizes the employee’s well-being and loyalty to the company, meetings dedicated to the topic of improving employee engagement and culture can be useful for this purpose. You can also integrate these types of questions into the daily, weekly, or monthly 1:1 check-in meetings to make sure that you’re keeping a temperature read on the employee’s thoughts on the company’s direction.

Asking questions specifically tailored towards workplace culture can provide sensitive information that can improve the company as a whole and help make the team feel more included. Here are the main questions you can ask about culture:

  1. How would you describe the current workplace environment?
  2. Why are you proud to work at this company?
  3. Do you feel that the company supports you with your professional development?
  4. Is there anything that you would change about the company? If so, what would it be?
  5. When and how do you like to receive feedback?
  6. Do you feel that the company celebrates our successes?
  7. Do you feel that the processes here are clear?
  8. Are you comfortable giving and receiving feedback?
  9. How supported do you feel by your team? With your manager?
  10. Do you think the company approaches and solves conflicts in an effective matter? If not, what do you think we can do to improve?

Workplace culture is imperative to an employee’s happiness and longevity at the company. Performing regular check-ins with the team can improve retention and keep communication consistent between managers and employees. If done well, this can also create a culture of safety, in which the employee feels that they can freely provide feedback without fear of repercussion or embarrassment from their team or managers. Creating psychological safety in the workplace is another facet of building an environment that people want to be part of.

Team Check-in Questions

Team check-in meetings are another good way to align perspectives on a project, provide important updates for everyone to hear, and share progress and initiatives relevant to the team and their tasks. As with individual meetings, these can range anywhere between 30 minutes to an hour depending on the topic at hand.

To avoid going over the allotted time and keep the energy high and focused for those in attendance, these are the type of team check-in questions you can ask:

  1. What is your focus for this week?
  2. Do you have any shoutouts you want to give?
  3. What does your workload look like?
  4. What do you need help with?
  5. What tasks are taking longer than expected? Are they creating bottlenecks that we need to address?
  6. What areas in our workflow do we need to identify, discuss, and resolve in order to do our tasks more efficiently?
  7. Do you have any important updates for the team?
  8. Are there any changes to your schedule that the team needs to know about?
  9. Does anyone else have action items that we need to discuss?
  10. Does anyone have any concerns we need to address as a group before our next check-in?

Ice Breaker Check-In Questions

Ice Breaker Check-In Questions

Starting off a meeting with a solid ice breaker is normally an efficient way to warm up the group, reduce any tension, and increase participation from everyone in attendance. Light and fun ice breaker questions have the ability to create a positive, inviting atmosphere, allowing employees to feel more comfortable sharing with their colleagues. Here are some ice breaker questions you can ask at the start of a check-in meeting.

  1. What is your positive focus for the week or months ahead?
  2. What is your goal for the year?
  3. If you won the lottery, what’s the first thing you would buy?
  4. If you could read one book for the rest of your life, what would it be?
  5. You now have all the free time in the world. What do you spend it doing?
  6. What is your favorite holiday and why?
  7. If you could choose one superpower to help you do your job, what would it be?
  8. What would you like to see yourself doing 5 years from now?
  9. Is there something that happened to you recently that brings you gratitude?
  10. Is there an app that you can recommend that helps you out every day?

In Conclusion

The best check-in meeting questions can help create situations where the team is focused and moving forward in constructive ways. To have the best results in which everyone has had an opportunity to engage in meaningful discussion is through purposeful meetings that have the right questions in place.

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