5 Check-in Questions Every Manager Should Ask in Team One-on-One Meetings

No one likes the proverbial my-way-or-the-highway boss, the control freak, or the micromanager. So how do you avoid being a bad leader to employees?

It’s all about asking the right check-in questions in one-on-one meetings with your team. These aren’t stuffy performance review questions—but real questions that can dramatically boost an employee’s morale, output, and quality of work.

Let’s take a closer look at some questions every manager should regularly ask their team to improve performance and strengthen trust. 

One-on-one questions to ask in team check-in meetings

Asking team members the right questions is perhaps the only way to be a truly effective manager. Here are 5 great questions to ask your team during monthly or weekly employee check-ins or 1:1s.

1. What’s your biggest accomplishment this week/month?

Everyone likes talking about their wins, so why not start with that? Here are a few ways you might phrase this 1:1 question:

• What have you been working on recently?
• Is there any work you’re proud of?
• What are some highlights of your recent work?
• Any good success stories?

Why this check-in question is effective

• This question provides a sense of forward motion and progress. A worker needs to know things are moving along and getting better.
• Relaying positive information gives your team member a sense of personal accomplishment. By communicating positive information, they’re setting an upbeat context for any further discussion.
• The answer can give you both oversight power and improvement potential. You have a measurable way to track your employee’s work and to see if they’re contributing in the ways you need them to.

2. What’s your biggest challenge right now?

Challenges are good things because they make us better. While this question may not have the same psychological uptick as the first one, it’s important to ask in one-on-one meetings nonetheless.

Why this check-in question is effective

• First, you get to understand where your team member is struggling. You may have no idea the software is malfunctioning or a coworker is slacking. As a manager, you’ve got to be aware of any pinch points in an employee’s process, work, or even the company culture.
• This one-on-one question also puts your conversation into problem-solving mode. And a problem-solving conversation is a productive one. You’ve gone beyond small talk and office chit-chat and are actually working on things that have ROI.
• You get to improve processes, eliminate barriers, and enhance team productivity. When you know about a problem, you can fix it. Thankfully, most challenges have a solution.

3. What should we do differently?

Every team member has a different perspective on the company. Your job as a manager is to synthesize all this information and improve the company.

Everyone can add value—and not just the value that comes from performing a strictly defined job title. Your team can provide value by sharing their own managerial insights.

One question my CEO asks me is: What processes can we improve? Every week. Same question. I don’t always have any improvements to suggest, but at least the opportunity is there.

Why this check-in question is effective

• It shows your team things can be done differently. A good company is dynamic—adapting to staff needs, adjusting to the shifting market, and accommodating industry trends. Introducing “do different” terminology into your discussions opens up the possibility of change and improvement. That’s invaluable for both employee satisfaction and company growth.
• Team members recognize the value they can provide beyond their job description. As mentioned above, everyone has a larger role to play in the company. You’ve got to harness this contribution. Your workers need to understand their role in improving the company as a whole.
• You gain insight that enables you to introduce changes that make the company better. Sure, you may not always act on every suggestion. But now and then, you’re going to discover some things that truly need to change.

4. What resources would be helpful to you right now?

Using the word resources leaves the door open to a wide variety of things—whether it’s a virtual assistant, a larger desk, a better computer, more meetings, fewer hours, or even a vacation. Just be sure there’s a mutual understanding that you can’t deliver everything they want every time.

Why this check-in question is effective

• This question gives you concrete, actionable information you can use to help a team member grow and improve. It also lets them know you’re prepared to do anything you can to help.
• You may be surprised by the answers you get. Sometimes, what you think your employees need is different from what they actually do. You may be prepared to throw more people or money at a project when the real need is a small, inexpensive tweak. You won’t know unless you ask.

5. Is there anything I can help you with?

Finally, provide a connection that lets your employee know you’re not just a manager—you’re a human. This is the broadest check-in question of all and can transcend the office, work, and business.

Feel free to spin the question in a more specific way based on things you know are going on in your team member’s life:

• Perhaps your employee had water damage in their basement. “You guys had some damage from the flooding? Is there anything I can help you with?”
• Maybe she’s participating in a community volunteer project. “You’re heading up the Main Street Cleanup this week. Anything you might need help with?"

Why this check-in question is effective

• This question reaches beyond strictly professional needs, allowing you to understand any personal factors that may influence an employee’s work.
• Communicating your interest in a team member’s life and growth helps build trust and strengthens your working relationship.
• Asking this question in a 1:1 meeting truly demonstrates your concern for staff success and well-being. You’re more than just a company-minded manager. You’re available to improve their work-life balance.

How to make employee check-in meetings more effective

Just as important as asking the right questions is asking them in the right way. Otherwise, these questions will be useless.

Here are 3 tips for a productive and engaging conversation in one-on-one meetings with employees.

Ask sincerely.

Ask these 1:1 questions with authenticity so your team member will trust you really want to know the answers. You’re not reading a form—you’re engaging with a person.

Ask humbly.

You ask questions to get answers. In other words, you ask to learn. Be prepared to hear answers you may not like.

This isn’t a time to protest answers with a no-can-do attitude. It’s a time to listen—openly and honestly. Be patient, and hear your team member out.

Ask frequently.

Totally transparent answers may not be forthcoming the first time you try. But every time you ask employees these questions, the gears begin to turn, and the thoughts begin to flow. 

Make these check-in questions a regular part of your weekly or monthly one-on-one meeting to establish a positive rapport over time.

Use employee check-in questions to build trust as a leader

Being an effective manager is about understanding. You won’t understand unless you ask the right questions and listen to learn.

Questions are one of the manager’s most powerful tools. Knowing how to wield them with precision in one-on-one meetings with your staff is your key to becoming a better leader.

Want to boost your team’s productivity and morale?

TeamGantt makes it easy to lead your team to success. Set clear deadlines and direction, collaborate on projects, and quickly spot and resolve bottlenecks.

And with TeamGantt’s team availability and workload management features, late nights and job burnout can finally be a thing of the past. You’ll have your whole team cheering across the finish line! 🙌

Watch the video below to see how TeamGantt works, and give our online project management software a free try today!

‍