Leadership Check-In Questions to Improve Employee Engagement and Workplace Culture

Apr 28, 2026

A Smorgasbord of Check-In Conversation Questions

The following questions are taken from my latest book, “Small Moments, Big Outcomes: How Leaders Create Cultures That Fuel Extraordinary Results.” But before I get to the check in questions, I want to remind you why check-in conversations are so valuable.

An Ernst and Young study found 40% of employees (the number one response) felt the greatest sense of belonging at work happens simply when someone checks in with them. A study reported in Forbes magazine found that when employees have one-on-one, bi-weekly check-in conversations with their boss, employee engagement scores increase by 230% and employee burnout is reduced by 84%.

Now, if you have teenagers at home, you know there’s a difference between checking in with someone and checking up on someone. Checking up on employees can be perceived as micromanaging and lead to feelings of a lack of autonomy – a major source of workplace unhappiness and stress. In fact, micromanaging leaders consistently show up as one of the number one reasons employees say they leave their jobs.

Conversely, checking in with employees on a regular basis ensures that employees don’t feel abandoned, and, when done right, regular check-in conversations with leaders have an enormous impact on retention rates. A workplace survey by the American Psychological Association found that employees who felt supported by their managers were more than twice as satisfied in their jobs. And a study reported in Forbes magazine found the regular one-on-one conversations with managers resulted in:

A 432% increase in the odds that an employee has a strong sense of leadership;
A 226% increase in terms of how employees rate their overall work experience; and
A 430% increase in the odds that an employee will be highly engaged.

Project Oxygen was launched by Google to assess what made the best leaders the best leaders. One of the key findings was that higher-scoring managers are more likely than lower-scoring managers to have frequent one-on-one meetings with their team members.

How frequent?

The frequency will vary depending on the nature of different jobs and how many direct reports you have, so it might be weekly, every two weeks, or once a month. The key is to commit to these conversations (and think of them as a conversation and not a meeting) and conduct them consistently.

Ideally, hold the conversations in neutral territory. You can mix things up by going for a walk or holding it over breakfast, lunch, or coffee. Explain to your employees why you are doing this and why you view these conversations as a priority, so they feel supported and valued, not “checked up” on. On that note, it’s a small thing, but call them check-ins, not check ups!

Set an agreed-upon agenda for the conversation, recognizing that as things arise your employee should be able to add things to the agenda. Although administrative-type stuff will certainly rise around topics like vacations or expense reports, try to focus on topics that are better dealt with face-to-face.

A Menu of Check-in Questions

Here are some great check-in questions that can guide a rich conversation. You don’t need to, nor should you, ask all these questions, but choosing a few as a template to work from can be helpful. For example, asking what’s working well, what’s not working well, and what can you do to support them is a simple, three-question framework that works great.

What’s working well for you right now?

This starts you off on a positive tone and gives employees an opportunity to share what they might be excited about or proud of.

What’s not working well?

This allows employees space to bring up any concerns. Follow-up questions such as, “Why do you think this isn’t working well?” or “Do you have any recommendations on how we could improve this?” will help clarify the issue and offers them the opportunity to give input. Asking how “we” could solve this matter sets up a partnership mindset, so the employee doesn’t feel like the onus is 100% on them (or you) to fix it.

What are you seeing that perhaps I’m not seeing?

Based on their background, role, personality, and position in your organization, everyone sees things differently. You can’t be everywhere as a leader, and this question acknowledges that reality while giving employees an opportunity to share their unique perspective.

What can I do to support you?

“Support” is the key word here. Your job as a leader is to support your employees, but not necessarily help them fix all their challenges. Making this offer lets them know you have their back.

What does support look like for you?

This is a critical question to ask because support looks different to different employees. Some employees need more hand-holding, especially if they’re in a new position or have taken on a demanding new project. Other employees thrive best when you give them full autonomy to do their job. So, support varies in terms of degree, but also in the nature of your support, so it can also be helpful to frame follow-up offers of support this way, “Would it be helpful to you if I __________?”

Is there anything I should stop doing or anything I should start doing that would make your life easier?

This is a simple question to solicit feedback from employees. Using the “stop or start” model helps them think of just one specific thing you need to stop doing that’s getting in the way of their progress or one thing that would support their progress.

Do you have any feedback for me?

As we’ll get to shortly, creating a culture of open and honest feedback is critically important, and as a leader you need to model a willingness to accept feedback. Asking this question instead of the “stop or start” question creates space for them to think in broader terms about feedback they may want to share with you.

Is there something else you’d like me to know?

Asking this question at the end of your check-in often solicits surprising insights. The word “something” is key here. A study found that when doctors ask their patients, “Is there something else they should know?” instead of, “Is there anything else?” there was a substantial increase in the percentage of patients who offered information that was valuable to the doctor.

Finally, when you end a check-in conversation, don’t miss out on the opportunity to pass along some positive praise. This is a great chance to show appreciation for their efforts. The more specific you can be the better, so think of one thing you want to highlight, and whenever possible, tie the praise back to your cultural values and praise them with a growth mindset in mind – so praise their effort, not their natural ability.

For more on the power of conversations at work and mastering workplace conversations, you may want to check out my recording of the webinar: Mastering Workplace Conversations.

What do you think? Do you hold check-in conversations? What check-in questions have you found to be the most effective? Please leave a comment or question below!

Known as “The Workplace Energizer!” Michael Kerr is a Canadian Hall of Fame keynote speaker on workplace culture, workplace culture leadership, and humor in the workplace. Michael Kerr is the author of nine books, including Small Moments, Big Outcomes: How Leaders Create Cultures That Fuel Extraordinary Results. Michael is known as one of the most entertaining, humorous, and insightful keynote speakers on workplace culture and leadership in Canada.