5 Check-in Questions Every Manager Should Ask in Team One-on-One Meetings
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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?
Itâs all about asking the right check-in questions in one-on-one meetings with your team. These arenât stuffy performance review questionsâbut real questions that can dramatically boost an employeeâs morale, output, and quality of work.
Letâs take a closer look at some questions every manager should regularly ask their team to improve performance and strengthen trust.Â
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. Whatâs 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 youâre 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, theyâre 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 employeeâs work and to see if theyâre contributing in the ways you need them to.
2. Whatâs 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, itâs 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, youâve got to be aware of any pinch points in an employeeâs 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. Youâve 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 valueâand 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 donât 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 dynamicâadapting to staff needs, adjusting to the shifting market, and accommodating industry trends. Introducing âdo differentâ terminology into your discussions opens up the possibility of change and improvement. Thatâs 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. Youâve 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, youâre 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 thingsâwhether itâs a virtual assistant, a larger desk, a better computer, more meetings, fewer hours, or even a vacation. Just be sure thereâs a mutual understanding that you canât 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 youâre 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 wonât know unless you ask.
5. Is there anything I can help you with?
Finally, provide a connection that lets your employee know youâre not just a managerâyouâre 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 memberâs life:
- Perhaps your employee had water damage in their basement. âYou guys had some damage from the flooding? Is there anything I can help you with?â
- Maybe sheâs participating in a community volunteer project. âYouâre 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 employeeâs work.
- Communicating your interest in a team memberâs 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. Youâre more than just a company-minded manager. Youâre 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. Youâre not reading a formâyouâre 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 isnât a time to protest answers with a no-can-do attitude. Itâs a time to listenâopenly 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.Â
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 wonât understand unless you ask the right questions and listen to learn.
Questions are one of the managerâs 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.
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