Gallup's latest numbers tell a pretty stark story: employee engagement in the U.S. fell to a ten-year low in 2024. Only 31% of workers say they feel engaged anymore. And it gets worse—the basics are slipping, too. Just 46% of employees say they actually know what's expected of them (that's down from 56% in 2020), and only 30% feel like someone at work is actively encouraging their development. When people lose clarity and coaching, they check out.
Here's the thing, though: it's not that employees suddenly stopped caring. The real issue is that manager-team communication broke down somewhere along the way. And the fix? It doesn't require some massive culture overhaul. Most of the time, it starts with something much simpler—asking better questions consistently and actually meaning what you ask.
That's where regular check-ins come in. They're not just performance updates or box-checking exercises. They're your chance to actually listen, clear up confusion, and build real trust. These conversations create space for honesty and help you spot issues while they're still small—before they calcify into burnout or someone's two-week notice.
This guide will help you understand the what, when, how, and why of asking employee check-in questions to strengthen your relationships with your team.
Table of contents
- When to Ask Check-In Questions
- Check-in Questions for Meetings
- Best Practices for Impactful Employee Check-In Questions
- Final Thoughts
When to Ask Check-In Questions
Frequency matters more than you might think. Weekly one-on-ones tend to pack the biggest punch because they keep feedback and priorities current. According to Gallup, employees who got meaningful feedback in the past week were far more likely to be fully engaged. There's a reason for that—when time stretches between conversations, context gets lost and small problems compound.
Now, if weekly isn't realistic for your situation, don't let perfect be the enemy of good. Every two weeks or even monthly is still valuable. Research shows that employees who connect with their managers at least biweekly are 157% more likely to believe their leader actually understands what their day-to-day work looks like.
What really makes the difference, though, is consistency. That's what transforms a meeting on the calendar into a reliable rhythm people can count on. When your team knows there's protected time to talk—really talk—they show up prepared. They bring updates, concerns, questions, and ideas. What started as just another meeting becomes an ongoing cycle of alignment and trust.
That said, one size doesn't fit everyone. Someone in the middle of launching a critical initiative might need to check in more often. A highly autonomous team member who's crushing it might do better with monthly conversations. The key is starting with a standard baseline, then adjusting to what each person actually needs. For more ideas on building this kind of adaptive team structure, see How to Build a Future-Ready Team.
Check-in Questions for Meetings
Consistency is the name of the game. Set a consistent meeting agenda, written or otherwise, with thoughtful questions.
Your questions determine the quality of insight you'll get back—it's really that simple. A vague "How's it going?" rarely surfaces anything you can act on. More intentional, specific questions encourage real reflection, uncover actual challenges, and show that you're genuinely listening, not just going through the motions.
Below are examples organized into four areas: well-being, status, strategic alignment, and feedback. Think of these as a starting point you can adapt, not a script to follow verbatim.
General Wellbeing Questions
A strong check-in starts with the person, not the project. That might feel counterintuitive when you've got deadlines breathing down your neck, but here's why it matters: Gallup reports 58% of employees globally are struggling at work right now, and that disengagement is costing the world economy $438 billion in lost productivity. Asking about well-being helps you catch stressors before they metastasize into turnover.
How are you doing? This open-ended starter lets employees guide the conversation toward what's most pressing for them. Pay attention not just to what they say, but how they say it and what they’re not saying. A shift in tone, a hesitation, unusual flatness—these can signal something's off that's worth digging into.
How are you feeling about your current workload? Workload paralysis happens when people feel so buried they can't even figure out what to prioritize anymore, and it absolutely tanks performance. Asking this directly opens the door to talk about capacity before it becomes a crisis.
What is the most frustrating part of your job right now? Unchecked frustration is a fast track to disengagement—or worse, to someone quietly job hunting. You won't be able to fix everything on the spot, but just acknowledging pain points builds trust significantly.
How supported do you feel by your team? Is there anything more we can do to help you? Here's a sobering stat: only 39% of employees strongly agree someone at work cares about them as a person, down from 47% in 2020. That's a real problem. Asking this question—and then actually doing something with the answer—shows you're paying attention and that they matter.
What's energizing you at work lately? Not every question needs to be problem-focused. In fact, they shouldn't be. When you understand what lights people up, you can help them spend more time in that zone.
Status Questions
Now we shift to the tactical, in-the-trenches stuff. These are your right-now questions that keep priorities aligned and help you clear roadblocks before small hiccups snowball into major setbacks.
What is your #1 priority this week? This confirms you're both on the same page about focus and outcomes. If their answer surprises you, that's actually valuable information—it means there's a disconnect somewhere that needs fixing.
What are your current blockers? It's way easier to clear a small obstacle in week one than to try rescuing a deadline that's already slipping in week four. This question invites early, practical problem-solving while you both can still do something about it.
What current project are you most excited about? Excitement and engagement go hand in hand—they're basically two sides of the same coin. When you know what energizes someone, you can lean into their strengths and set up more wins, which benefits everybody.
Are there any deadlines approaching that you don't expect to meet? Why? Asking this early gives people permission to raise red flags without worrying they'll get blamed for it. But here's the catch: you have to respond consistently and without blame, or your team will stop being honest with you. The safety you create around this question determines how useful it actually becomes.
Are there any tools or resources you need that you don't currently have? Missing tools create endless workarounds and frustration that quietly eats up hours every week. If this keeps coming up, it might be time for a time audit to see where gaps are actually slowing the team down.
Strategic Questions
These questions zoom out from daily tasks to connect the dots with bigger organizational goals. When people understand how their work ladders up to what the company is trying to achieve, both their motivation and their decision-making get sharper. You'll also discover disconnects where strategy isn't actually translating into clear action on the ground.
Do you have a clear understanding of project and task ownership on your team? Ambiguity about who owns what breeds dropped balls, duplicated effort, and friction between team members. If one person is unclear on ownership, others almost certainly are too—it's rarely an isolated thing.
Do you feel like [specific project/task] is clearly aligned with our KPIs? Employees often catch misalignment that leadership completely misses because they're closer to the actual work. If the connection to KPIs isn't clear, it means one of two things: either context is missing and you need to communicate better, or the work itself needs a rethink. Both scenarios deserve your attention.
How does your current work contribute to our team's goals? If someone struggles to answer this, it's a clear signal that either priorities aren't clear or communication has fallen short somewhere. Strong performers should be able to draw that line from their daily tasks to team objectives without having to think too hard about it.
Feedback Questions
Feedback should flow both ways—that's non-negotiable if you want a healthy team culture. Sure, employees who receive useful feedback are five times more likely to be engaged. But they also need to know they can safely give feedback to you. Creating that two-way street is what these meeting questions are for.
Do you have any feedback for me? You probably won't get brutal honesty the first time you ask this question—people need to test whether it's actually safe to share their thoughts unfiltered. But consistency builds that trust over time. When you do finally hear something tough, your response matters: resist every urge to defend yourself, thank them for the feedback, and then actually reflect on it later.
Do you have any concerns about our strategic direction or the work in progress? People who are closest to the work spot problems early, often before leadership sees them coming. This question gives explicit permission to voice doubts so you can course-correct before small issues escalate into big failures.
Are there any specific areas or projects where you'd like more feedback or guidance from me? Everyone learns differently. Some people want constant coaching; others prefer autonomy with occasional check-ins. Use this question to tailor your approach to where it'll have the most impact. Developing strong leadership skills includes figuring out how to adapt your style to what different team members actually need from you.
What's one thing I could do differently to support you better? Asking for one specific, concrete change makes the question way less overwhelming to answer and way easier for you to act on. Both of those things build trust in ways that vague "how am I doing?" questions never will.
Best Practices for Impactful Employee Check-In Questions
Great check-in questions are only half the equation. The timing, tone, and follow-through determine whether these conversations actually build engagement—or just fill calendar space.
Time Your Questions
Not every question belongs in every setting and mixing them up can actually backfire. Sensitive topics—workload stress, personal challenges, career goals—need the safety of one-on-ones. Team meetings work better for status updates, cross-functional handoffs, and alignment that affects everyone. Anonymous surveys can surface candid views on organization-wide issues, though you're trading conversation for candor when you go that route.
Think about it this way: the forum you choose signals how you'll use the information. Ask about personal frustrations in a team meeting, and you're forcing people to choose between honesty and self-preservation. Ask about team dynamics anonymously, and you miss the chance for real dialogue that could actually solve something. Match your questions to the setting that'll produce the most useful, honest responses.
For distributed teams, consider these remote team communication strategies.
Encourage Self-Reflection
Open-ended questions take time to answer well—that's the whole point of asking them. Share key prompts in advance so people can actually think them through. If someone isn't ready to answer in the moment, give them space to process and circle back next time. You'll get more thoughtful answers that way, and more accurate ones too. Rushed answers are almost never the most useful answers.
Make Your Questions Specific
Generic questions invite generic replies—there's just no way around that. Push yourself toward the concrete: instead of "How's the project going?" try "What's been most challenging about implementing the new database schema?" Swap "Any feedback?" for "What's one thing about our code review process that isn't working?"
Specificity shows you're paying attention to individual circumstances. It also makes it easier for employees to give actionable input. The more precisely you can frame questions around their actual work, current projects, or stated goals, the richer the resulting conversation will be.
Make it a Routine
Consistency builds safety, period. When check-ins happen regularly and reliably, they stop feeling like performance reviews or emergency interventions and simply become normal conversations about work.
So protect that time. Even 15 minutes, held reliably week after week, is more effective than a full hour that keeps getting bumped or rescheduled. Your team notices when you cancel, and they draw conclusions about what actually matters to you.
Use What You Learn
Nothing erodes trust faster than asking for input and then doing absolutely nothing with it. You don't have to fix everything immediately—that's not realistic. But you do need to acknowledge what you heard and close the loop. Share what will happen next or explain why a change isn't possible right now. That follow-through is what separates organizations that build a culture of continuous improvement from one where problems just get quietly buried until people leave.
The most powerful outcome of regular check-ins isn't actually the notes you capture or the action items you track. It's the relationships you strengthen over time.
Final Thoughts
Check-ins aren't about mechanically plowing through a script of questions you found online. They're about building a steady habit of real communication. When employees know their manager actually listens—not just hears, but really listens—they raise issues sooner, work together better, and stay more engaged over the long haul.
The payoff isn't just higher morale, though you'll get that too. It's a stronger, more connected team that can handle whatever comes at it. And it happens one honest conversation at a time.