Weekly Check-In Questions to Ask Your Team

9 Best Check-in Questions To Ask Your Team Every Week

Posted by Luke Thomas
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If you’ve got 99 problems, make sure an unhappy team isn’t one.

All great managers and leaders will tell you that communication is key to building a team that works well together – it’s a key piece of the continuous improvement process.

One of the easiest things you can do to create a well-oiled team machine is to have regular check-ins (also known as retros) with a great set of team-building questions to improve your employee engagement.

We’ve rounded up a list of our favorite weekly questions to ask your team including the tactics behind each one and why they’re a great way to end every workweek.

P.S. - Friday makes it easy to automate weekly check-ins. You can try it for free and get up and running in less than five minutes.

What is a Weekly Check-In?

A weekly check-in and team update is a meeting cadence to gauge the progress for the week and identify any successes, problems, and blockers. It is meant to be tactical and actionable, similar to one-on-one meetings.

The weekly check-in is one of many meeting templates available in Friday as an asynchronous meeting. This feature is geared towards team leaders (typically with five or more direct reports) and is meant to provide tactical insights about an individual’s work experience for that week. If you are familiar with agile methodology, it is similar to a sprint retrospective. We wrote more here about why weekly check-ins are important for your team.

You can see exactly how this works in the video below. I use this cadence to save at least two hours a week in meetings that didn't need to happen:

Weekly Check-In Question #1: What can we improve on with how we are launching project XYZ?

Original question: What can we improve on?

Tip: Good questions avoid sweepingly broad statements. They are specific.

Although it’s great to offer up broad statements that encourage employees to give candid feedback, it’s much easier for them to respond to specifics. If you’re hoping to find out what you can do better as a manager or within the company as a whole, rephrase those questions so that an employee can use it in real-time scenarios.

Plus, specific feedback is more actionable. If you want to use an employee’s candor as a way to initiate change and react to in real-time, responding to current issues will be much easier.

Keep more general questions to be circulated during your quarterly reviews, weekly check-ins are for the tactics.

Weekly Check-In Question #2: What do I do as a manager that's currently a roadblock?

Original Question: What can I do better as a manager?

Tip: Don't force criticisms.

Some questions are punts. And asking for an employee to critique their manager? That’s not going to get you anywhere near the end zone.

As a manager, you need to probe for an insight you can use. Give them the opportunity to suggest room for improvement instead and build trust with what you do with that information. Employees will value being able to say, "I'd love faster turn around on edits to get blog posts published more quickly" rather than saying, "You could be quicker about responding to emails."

Give them the opportunity to suggest room for improvement instead. Employees will value being able to say, “I’d love faster turn around on edits to get blog posts published more quickly” rather than saying, “You could be quicker about responding to emails.”

Think about it. Saying “You suck” to someone is way harsher than saying “You suck at responding to emails.”

Specificity wins out and also helps people know exactly where they can improve. 

Weekly Check-In Question #3: What Did You Think About The Latest Episode Of...?

Original Question: What are you doing this weekend?

Tip: Don't make it all about work.

Try and make one of the weekly questions to ask your team be something fun you can all weigh in on as an icebreaker question that has nothing to do with work.

For example, if you all love a particular podcast, shoot out a weekly question about the latest episode. Or start an office book club that invites everyone to check in with their thoughts on the latest chapter.

It’s always good to throw in a personal, just-for-fun question when you’re checking in. You want to maintain a friendly rapport and casual questions are a great way to do just that. By elevating it with something you’re all interested in rather than zeroing in on general weekend plans creates an inter-office camaraderie that will eventually feel more natural than rehearsed. 

Weekly Check-In Question #4: If You Were Me, What Would You Improve About the Company?

Original Question: What can the company be doing better?

Tip: Periodically throw a curveball reflection question.

Weekly check-ins aren't just about building relationships and constructive feedback, but about keeping tabs on how well the company is doing too.

Offer employees opportunities to really think outside-the-box when it comes to how the company performs. Throw them for a loop and ask a question about a specific project that just wrapped up. Or have them answer a fill-in-the-blank question about your managing style that requires more than just a run of the mill response.

Weekly Check-In Question #5: What Are You Looking Forward to Working on Next?

Original Question: What did you feel good about today?

Tip: Ask questions that allow your team members to think about projects that have finished, projects that are ongoing, and projects that are in the pipeline.

Ask questions that allow your team members to think about projects that have finished, projects that are ongoing and projects that are in the pipeline.

Happy employees are more productive, which is why it’s important to look at how they’re feeling about their entire work journey, not just the day-to-day. Making sure a recently completed project gives them a feeling of satisfaction is as important as checking in to see that they have something to look forward to. Good experiences all around are key to keeping them blissed out at their desk.

At a higher level, it’s also good for an employee to take a step back and look at their strengths. Asking them to look back and forward is a great way to help them self-assess and bring their greatest potential to the table.

But they don’t need to be looking towards the future or towards the past every week. Just make sure it’s something you keep in mind when looking at employee happiness on a holistic level. 

Weekly Check-In Question #6: What was the best part of this week?

Original Question: What could you have done better this week?

Tip: Celebrate the wins.

It's important for employees to acknowledge their successes at the end of the week. A failure is easier to spot since as a manager, it's easy to see when things fall through the cracks. But small wins in the present moment are often overlooked.

Employees need to be encouraged to share when they’ve gone out of their way in a project or successfully fixed an issue on their own. By asking them for the best part of the week, you’ll not only be able to see some of these triumphs, but you’ll be able to acknowledge them too.

Phrasing the question this way also gives them the opportunity to share a win outside of work. If their intramural dodgeball team made the playoffs, let them flex their bragging rights.

Weekly Check-In Question #7: Who would you like to thank?

Tip: Celebrate each other

Building gratitude and thankfulness among the team is a great way to connect especially for remote teams. It also provides a tip to managers about who the team thinks is valuable and is doing great work.

You say thanks for a job well done right inside Friday. If someone receives a kudo in Friday, they receive an email. Kudos can be sent privately or publicly to the whole team.

This feature is powerful as it’s a great source of motivation, and it also encourages more people to check-in.

Weekly Check-In Question #8: Anything else you would like to share?

Tip: Allow for space to openly share

Not everyone will answer this question, but it can help with culture. You may want to give examples here, but often it's about problems, new initiatives, or future goals. It could also be something innocuous like a fun outing or project.

The point is that your team members should be able to feel free to share what is happening, especially in regards to their work, but your team culture will depend on that. You may also uncover something that you were trying to get at in an earlier question--this provides another avenue for that discovery process.

Weekly Check-In Question #9: Icebreaker Questions

Tip: Find ways to connect

Icebreaker questions are a great way to get to know each other and your whole team better. You may not want to set this up in a one-on-one meeting environment, but in a team weekly check-in, it can be a powerful get-to-know-you tool. And you can set them up right inside Friday. You can load icebreaker questions, add them to your weekly check-in routine, and then team members can answer a different one each week.

Not sure what to ask? We put together a list of more than 80+ icebreaker questions that you can add to Friday.

Conclusion: Weekly Check-Ins Are a Powerful Way to Gain Insights

Regular check-ins are a powerful way to understand what's going on at work. Feel free to try out our free weekly check-in workflow to start asking your team these questions on a regular basis. P.S - You can apply the same principles of weekly check-ins on a personal basis with work journaling.

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