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Five Check-in Questions for Team Meetings

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According to a recent report by Cisco, 37% of U.S.-based employees spent between 4 – 12 hours in meetings each week. In the hyper-connected, fast-paced world of modern-day employment, that’s a lot of time spent away from projects, deep work and striving towards our long-term career goals.

As a leader, project manager or professional yourself, you might be looking to explore better ways to conduct team meetings so as to not waste anyone’s time or become a drain on productivity. 

Especially for remote teams.

Chances are that you know better than anyone that effective leadership involves more than just delegating tasks and making decisions. Perhaps even more critical, is the role you play in fostering a collaborative environment where the members of your team feel valued, engaged, and supported. 

Nowhere is this more important than in remote, global workplaces where much of your day-to-day operations and communication occurs asynchronously; meaning the face-to-face, real-time minutes you have with your employees is often limited and you will have to work doubly hard to make those minutes count

That makes the time you do spend catching up and connecting online, whether through the phone or a video conferencing platform or an in-person meeting (say, at an annual retreat in one predetermined location) all the more crucial.

So, what is a check-in and why are they so essential in keeping business operations running smoothly?

What is a Check-in Meeting?

This meeting is set at a predetermined date and time for both employers and employees. Check-ins are sometimes one-on-one, and other times with the whole team or a specific group – to have open and honest conversations regarding updates, a project's continued success and other happenings across the company. 

From project meetings to one-on-one meetings, these discussions can be casual or formal, which you choose will depend on the workplace and expectations from team leaders. 

Sometimes team building activities, like impromptu games or fun icebreaker questions, will be incorporated as a way to boost morale and build connections - which can be especially for those who are involved in remote work.

How often should you have a Meeting to check-in?

The frequency of your check-in meetings will depend on your organization, your team, and your individual leadership style. Some leaders are more hands off and don’t require weekly meetings, others like to keep their finger on the pulse a little more closely and therefore bi-weekly or monthly meetings will fall short. 

It's also important to consider the current work life balance of your team. Some teams may require fewer meetings to help ensure an ideal balance between work life and home life, while other teams find these check-ins to be beneficial to maintaining the perfect balance.

These are three of the most common meeting types for check-ins:

Daily Check-In

In a remote working environment email, phone or video chat are three common ways you can conduct daily check-ins with your teams. It’s a quick way you can connect with your employees, holding them accountable and keeping projects on track.

Weekly Check-In

A weekly check-in is a more in-depth update than daily check-ins. Think of it like a progress report from your teams on how things are going and any issues or questions they may need to address. A weekly check-in can also allow you to help your team's goal set for the week upcoming, setting clear expectations of what needs to be accomplished.

Bi-Weekly Check-In

This kind of check-in will be the most thorough and time-consuming since more time will pass by before you get an update. As a leader, you can decide to increase or decrease the frequency of your check-ins depending on the projects at hand and the level of managing and oversight you feel you need to conduct over your employees.

Now that you’ve decided on a frequency, how can you create a check-in that accomplishes your goals for the meeting, fosters connection and allows you to glean the insights on projects and plans you need.

Components of a Successful Check-in Meeting

Performance Reviews

Performance reviews are ideal for one-on-one check-ins since a check-in is a standing meeting, typically booked out for months. 

Going over a performance review with your colleague during an already scheduled meeting time is ideal because you don’t have to find time in your schedule or your employees’, maximizing time and efficiency.

Brainstorm Sessions

Team check-ins are the ideal backdrop for a meaningful, collaborative brainstorming session. You already have your employee(s) time blocked in their calendar and can simply redirect your typical one-on-one meetings to a brainstorm session instead. 

The more creative ideas and unique perspectives you have in the room, the better insights and big picture thinking you will get by the end of the scheduled time.

Icebreaker Games

Incorporating ice breaker games or fun virtual events and activities is a way to connect with your employees on a more personal level. After all, work should be enjoyable!

Open-ended Discussions

Perhaps your check-in meetings are more of a dedicated time for you and your employees to connect and talk about work more generally. 

If you don’t have anything specific topics planned, like brainstorm sessions or icebreaker games, it is wise to come equipped with check-in questions that can help you foster better collaboration. 

Learning how to guide conversations with your employees will ensure you are maximizing everyone’s time together. As an employer, you will be able to better glean any ongoing issues your team may be having, talk through any project plans or updates and also foster meaningful connections with individuals you don’t have the opportunity to see all the time. 

For employees, these face-to-face conversations can be a way to discuss any issues they may be having, report back on any personal or team successes and work through any other issues they may be experiencing. But what should you ask to maximize time and ensure everyone in the meeting is getting the most out of their time?

We’ve compiled five essential check-in questions that you can use to promote open communication, teamwork, and overall team success.

Five Essential Team Check n Questions to Ask Your Remote, Global Employees

1. How has everyone been feeling with work life balance this week?

Starting a meeting with a question about emotions is a great way to build a supportive professional atmosphere that invites people to be honest about their feelings - both good and bad. 

By creating a safe space for employees to open up and promoting emotional honesty, leaders like you have the opportunity to address concerns that might impact productivity and team morale. 

This can help to create employees that feel supported, practice self care and are more receptive to constructive feedback when the time comes. 

Not only that, but it helps to establish an expectation for work life balance, create boundaries and help to ensure that all members of your team are on the right track. With the right approach, you can create a positive company culture dedicated to the well being of your team!

2. What progress have you made since our last meeting?

To build a high-performing team you need to create an environment where colleagues are accountable. 

Regularly asking about ongoing achievements and updates creates a sense of responsibility and enforces the idea that employees should come to meetings prepared and with meaningful updates to share. 

This question not only keeps everyone informed about ongoing projects but also highlights the collective progress towards shared goals.

3. Any issues or challenges you're currently facing?

Recognizing and addressing obstacles promptly is critical for project success. This question prompts team members to openly discuss any challenges they're encountering and provides you an opportunity to weigh in and offer guidance or support.

4. Is there something new or exciting you'd like to share with the team?

Effective leadership extends beyond work-related matters. Building personal connections among your team contributes to a positive work environment. 

By inviting individuals to share personal achievements, hobbies, or positive news, leaders foster a sense of camaraderie and demonstrate genuine interest in their team members as individuals.

5. What resources or support do you need to succeed?

A leader's role is to empower their team. This question emphasizes that leadership is committed to providing the necessary tools and support for success. 

By giving employees and remote workers alike a platform to voice their needs, leaders ensure that everyone has the resources required to excel in their roles.

With your check-in questions in tow, how can you organize your next meeting? Try these six steps.

Six Steps to Organize your Next Check-In

1. Establish goals

Each meeting should have an overarching goal. Are you meeting with employees to get regular status updates for projects? Perhaps you’re using them as a dedicated thirty minutes to connect and exchange creative ideas. 

Goals may also be as simple as improving communication, increasing efficiency, or eliminating misunderstandings between departments. 

With goals in tow, your check-in meetings will feel like a valuable use of company time and motivate employees to attend and actively participate. 

2. Choose a frequency

Decide on a frequency of meetings that are going to be the most beneficial for the team, depending on which projects are being completed currently. Holding a poll or survey may be a useful way to understand how often your team thinks a meeting is going to be helpful. 

Management can always adjust the frequency at a later date if your team feels like they need more or fewer opportunities for communication.

3. Decide on a convenient time

It's important to choose times for check-ins that aren't going to conflict with any team member's schedules because valuable check-ins require every member of your team to be present to contribute. 

The occasional absence is understandable, but it's best for most meetings to occur at accessible times to ensure full attendance. Ensure you choose a time that works for everyone’s schedule, and put a recurring hold in everyone’s calendar so they get the reminders each week. 

4. Take notes

Note-taking is an important task in meetings to maintain dated documents of discussions, ideas, and potential changes to projects. 

Creating a rotating schedule for the individual responsible for note-taking on any given meeting day so the load is divided equally between all team members. 

If a member of your team cannot attend a meeting, or an individual wants to refer to a talking point from a past meeting, it's crucial to have notes serving as a record of what was discussed. 

As more check-ins occur over time, individuals can analyze notes for growth or patterns, seeing the development of their projects as a result of discussions, feedback, and teamwork.

5. Encourage participation from each team member

The presence of a manager to mediate meetings can provide structure and ensure the focus stays on topic. It is your job to foster an environment where each team member actively contributes and feels confident and comfortable doing so. 

Of course, everyone is different and some may be more willing to speak than others, so try to employ some gentle encouragement and ask fun check-in questions to help ensure equal participation. 

6. Ask for feedback

Regularly receiving and incorporating feedback will help improve the quality of your check-in meetings. Feedback and ideas may include things like: prompts for icebreakers, different locations for future meetings, or ways to improve participation during brainstorming. 

An individual who not only encourages feedback but also applies it's more likely to empower team members so always be open and receptive to these ideas when employees come to you. 

The Best Communication Tools for Collaborating Remotely

Now that you have your check-in questions, frequency and structure planned, it’s time to consider how you will conduct this meeting. For remote, globally distributes teams the tools and technologies you leverage will be critical for your check-in meeting’s success. 

Below is a round up of tools that can help engage and manage your remote-first, distributed workforce in a way that improves productivity and reduces the risks of miscommunication during check-in meetings that are meant to provide clarity and boost connectedness.

Microsoft Teams

Microsoft Teams is another platform where users can chat, make video calls and share files while integrating natively with all other Microsoft products. 

This tool makes collaboration simple by allowing users to easily find, share, and edit files together in real time with apps like Word, PowerPoint, and Excel.

Slack

Slack is a messaging app for businesses that helps connect teams to the information they need. With Slack, your team can navigate a user-friendly interface that lets them chat with their colleagues, share files, collaborate and more. 

The tool also can integrate with other commonly used business products like G Suite, Adobe Creative Cloud, DropBox and many more.

Slack is an effective tool not only for work-related queries, but also for the members of your team to connect with one another. This can be especially beneficial for the well-being and overall work experience for remote employees, who may otherwise connect with colleagues at the coffee station!

Zoom

Zoom is a communications platform that allows users to connect via video, audio, phone, and chat. It’s become a popular choice among remote-first employers who want to collaborate and host meetings from a distance. 

With Zoom, you can have breakout rooms, and use emoji reaction functions and filter features. There are free and paid-for subscriptions depending on your organization’s specific needs.

Skype

Skype is a videoconferencing platform similar to zoom that allows voice calls, along with instant messaging, file transfer, debit-based call features.

Google Meet

Ideal for companies that already use the Google Workspace Suite, Google Meet is a versatile platform that can be used for a range of meetings, including leadership 1:1s, team check-ins, and top-down meetings like company town halls or all-hands. 

It also offers multiple dial-in options, so you can call in from your mobile device too.

Effective Team Leadership: Check-In Questions, Team-Building Activities and Valuing Team Dynamics

Effective leadership involves more than just managing tasks. It's about nurturing a culture of collaboration, open communication, and mutual support. 

All of this is made possible by the kinds of platforms you use to conduct meetings, the frequency and the structure of the check-in. 

Asking specific check-in questions, such as the five essential questions we outlined earlier in this blog, will help you get the most of your meetings.

By incorporating these five check-in questions into team meetings, leaders can create an environment where your team feels valued, engaged, and motivated. 

Remember, adapt these team check-in questions to fit your team dynamics, and watch as the power of meaningful conversations transforms your team's performance and cohesion.

Interested in more insights from Borderless with tips on how to manage your remote, global teams? 

Check out our blog with useful articles like Managing and Tracking PTO, The Key Questions to ask in a Remote Interview, Advantages of Asynchronous Work and so many more!

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