When most of the teams went fully remote a 5 years ago, we all were a bit lost on how to keep everyone connected without turning into that boss who’s always pinging.

I’d catch myself wondering: Are they okay? Are projects on track? Should I send a quick “Hey, what’s up?” or just chill?

If you’re managing a remote team, you’ve probably had the same thoughts. Figuring out how often to check in with your remote employees is like finding the perfect coffee brew - too weak, and it’s flat; too strong, and it’s overwhelming.

Here’s what we’ve learned about striking that balance, with practical tips to keep your team thriving, no matter where they’re logging in from.

1️⃣ Start with a rhythm, not a rule

Based on the work experience of your team, set up a check-in schedule. For junior members, try connecting with them once every 2-3 days to get a pulse check on their progress, to stay focused . For senior members, these frequent check-ins might be a overkill so you can schedule a call once a week and talk through the status updates and next plan.

A good starting point?

Try a weekly team all-hands meet to sync on goals and a monthly one-on-one for deeper discussions. Adjust based on what your team needs.

Tools like TimeDive.io can help here - it's task tracking lets you see progress at a glance, so you’re not bugging folks unnecessarily but still know when to check in.

2️⃣ Read the Room (or the Zoom)

Remote work is a bit tricky and hides a lot of cues you’d catch in an office as you are working in-person - like someone looking stressed or a project quietly stalling.

Do watch out for these digital signals. If someone’s updates get vague or they’re missing deadlines, that’s your cue to reach out personally.

Once, I noticed a teammate’s Slack replies went from chatty to one-word answers.

A quick call revealed they were swamped, and we sorted it out with a lighter workload. Check in more often when someone’s new joined your team or if they are working on a big project - maybe a quick daily chat or a shared tool for updates.

Trust your gut and lean on tools to spot when someone needs your help.

3️⃣ Make check-ins meaningful, not mechanical (or boring!)

If your daily standups and check-ins like a status report with a bullet points or areway more detailed that stretches beyond 20 mins, you need to change that.

People started dreading them, and it surely won't build trust.

Kick off with something human, like asking about their weekend or that new hobby they've picked recently. It’s amazing how a little warmth opens up real talk about work challenges or wins.

Use check-ins to listen, not just track tasks. Ask about roadblocks or any new ideas - they’ll feel valued, and you’ll catch issues early.

4️⃣ Avoid the micro-management trap

Are you're checking in way too often, thinking it shows that you cared. Nope - it will make your team feel like you didn’t trust them to do their job.

Constant pings kill morale and make folks feel micromanaged.

Instead, set up systems that reduce the need for check-ins. Your team can TimeDive.io to log task updates, so you can see what’s moving without asking. If you’re checking in more than a couple of times a week outside scheduled chats, take a step back. Empower your team to take ownership of their work - you’ll both feel better and can focus on your own to-do list.

5️⃣ Celebrate and connect, even from afar

Try to add celebration while your team check-ins.

When someone nails a project, call it out - maybe a shout-out in our team chat or a virtual high-five during a call.

Last month, I sent a teammate a coffee gift card for smashing a deadline.

Tiny gestures go far. Check-ins are also a chance to keep the team vibe alive. Share a quick story about any new/interesting thing that happened or ask about their home office setup. It’s not just about work - it’s about showing you see them as people.

Monthly “no-agenda” team calls help too, where you join for a virtual coffee sessions, laugh and swap random life updates.

Why getting this right matters?

Checking in with your remote employees isn’t just about keeping tabs on work - it’s about building a team that feels supported and connected, no matter the miles and oceans between you.

I’ve seen how the right cadence can turn a group of solo workers into a crew that’s got each other’s backs and the dream team harmony every leaders wish for.

Tools like TimeDive.io make it easier, letting you track progress and chat seamlessly so check-ins feel like collaboration, not a boring chore.

So, experiment with what works for your team. You’re not just managing them - you’re creating a culture where everyone can shine.

Give it a try, stay open to feedback, and watch your team grow stronger, one check-in at a time.