How To Check In With Checked Out Employees

137 Meaningful Conversation Starters To Close The Leader-Employee Perception Gap

SUMMARY: A disturbing disconnect is developing between thriving business leaders and their struggling employees, particularly Gen Z, women, and frontline workers. However, with consistent and meaningful check-ins, leaders can rapidly course-correct and co-create a thriving workplace.

Disassociation Inc.

Business leaders have lost the plot.

In a recent survey of 30,000 people across 31 countries, a striking 61% of business leaders (likely to be male, information workers, and farther along in their careers) reported that they were “thriving”—a stark 23 percentage points higher than those without decision-making authority.

Disturbingly, the most disempowered of their employees—those who reported “surviving” or “flat-out struggling”—were Gen Z, women (including single mothers), frontline workers, and new employees (especially employees of color).

Up to?75% of people?experience a dissociative episode at some point in their lives. However, disassociation is likely a daily occurrence in a broken workplace helmed by leaders who are out of touch with employees.

A Little More Conversation, Please

The fallout from the disconnect is clear: according to Gallup, 77% of the global workforce is checked out. They show up, do the bare minimum, and are uninspired by their work.

The?bad news?is that employer trust is rapidly declining, perpetuating cultures that tolerate or neglect disengagement. But here’s the good news: this trend can be reversed. With regular, intentional conversations, leaders can quickly close the gap and rebuild team trust.

In “Culture Shock,” Gallup’s Chief Scientist, Dr. Jim Harter, says the most important habit of a great leader is “One meaningful conversation per week with each team member.”

“Lousy conversations are holes in your boat. Meaningful conversations propel you forward.” - Dr. Jim Harter

In a recent?article, researchers at Workhuman revealed that workers who check in with their manager weekly are twice as likely to trust and respect their manager, twice as likely to believe they can grow in their organization, and five times less likely to be disengaged.

Frequent and intentional check-ins are the closest thing business leaders have to a culture cure-all.

137 Meaningful Conversation Starters

In the same article, Workhuman’s researchers shared several open-ended questions to use in the different types of check-ins:

General Check-Ins

• What do you want to accomplish today?
• What is your greatest challenge at the moment?
• What work are you most proud of?
• If you were to receive some constructive feedback right now, what would you expect it to be?
• What tools could we provide you to better your job flow?

Dailey Check-Ins

• What tasks do you want to achieve today?
• Are you currently facing any obstacles?
• What are you most looking forward to doing?
• What is your main priority for today?
• Do you need any help in executing a task?

Project Check-Ins

• How do you plan to execute this project?
• Do you predict any incoming issues you may face during the project?
• How will you measure your project’s overall success?
• What are your short-term and long-term goals for this project?
• What is a part of the project you’re most looking forward to completing?
• What do you require from me to successfully execute this project?
• What current hurdles are you facing in the project?
• What should we stop or keep doing in the project?
• Are there any off-course actions in the project that you wish to share?
• If so, how have they impacted your workload?

One-On-One Check-Ins

• How do you feel about your teammates?
• How has your day been so far?
• What is your workload like?
• Do you feel confident in your team’s performance?
• Is there any way we can assist you?

Project Wrap-Up Check-Ins

• What are you most proud of in this project?
• How has the project aligned with the company’s objective?
• What would you have done differently?
• Were you able to follow the project’s initial plan?
• If not, what went differently and why?

Team Check-Ins

• What do you think is a missed opportunity in terms of collaboration?
• Which tasks are facing delays?
• Do you think we’re collaborating remotely well?
• Are you able to easily approach anyone on the team?
• What is a discussion topic you would like to address with the rest of the team?
• How can we improve our line of communication?
• What is everyone’s current workload like?

Team-Building Check-Ins

• Who is your biggest role model?
• What do you think are the most important qualities in a colleague?
• If you could swap roles with anyone in the company, who would it be?
• What are your pet peeves?
• What are your goals in your career?
• What would you say is your best attribute?

Remote Team Check-Ins

• How do you schedule your work routine?
• Would you feel more productive while working in an office?
• What is a struggle you continuously face while working from home?
• How often do you take breaks?
• How would you rate your work-life balance?
• Is there anything we can provide to help you complete your remote work?

Feedback Check-Ins

• Which task or project are you most confident in and why?
• How would colleagues and clients address your work?
• What are some hurdles you’ve experienced since our last check-in?
• How would you describe your work quality?
• What can we do to better improve your performance?

Coaching Check-Ins

• What actions are you implementing that seem to be working?
• What are the actions that don’t?
• What steps are you taking to improve your work quality?
• How effective have these steps been so far?
• What tools would you need from me to assist your action plan?

Goals Check-Ins

• Which goals were you able to accomplish since our last check-in?
• How have we helped you achieve these goals?
• What better way can you achieve your goals?
• What are your long-term goals in this career?
• How were you able to contribute your work to achieve the company’s goals?

Growth And Development Check-Ins

• Do you see yourself growing better in another department?
• What is the most challenging part of your growth?
• What are the necessary tools needed to improve your development?
• How have you advanced in your role since the past check-in?
• How have your colleagues assisted you on this path to growth and development?

Mindset Check-Ins

• What is your current mindset towards work?
• What are your thoughts on the company’s organizational culture?
• What tasks are you able to fulfill out of your comfort zone?
• Do you feel hesitant about any aspect of work?
• Do you face any distractions from work?

Office Environment Check-Ins

• How close do you feel to your coworkers?
• Do you feel supported by your managers?
• What are your thoughts on your team?
• What’s your favorite part about the company culture?
• What would you like to see changed in your office environment?

Wellness And Mental Health Check-Ins

• Are you happy?
• How often do you feel anxious?
• What excites you about work?
• What frustrates you at work?
• What aspect of work inspires you the most?

Work-Life Balance Check-Ins

• Are you taking good care of yourself?
• Are you satisfied with your current work hours?
• Have you ever missed a personal event due to work?
• Do you often work overtime?
• How could we improve your work-life balance?

New Employee Check-Ins

• How has the company met your expectations so far?
• Do you feel welcomed by the team?
• What’s your favorite part about your position?
• What’s your least favorite part about your position?
• How would you describe the company’s culture so far?

Random Check-Ins

• If you had to work full-time in the last place you went on vacation, would you do it?
• If we had a team-building trip, where would you want to go?
• What is an interesting fact you recently learned?
• What kind of music do you listen to while you work?
• If you could find out one of the world’s mysteries, which one would it be?
• What’s your favorite pastime?
• What’s one thing we don’t know about you?
• What was your favorite subject as a student?
• What’s the weirdest email you’ve ever received?
• What was your first job?
• What was your dream job as a child?
• What’s your favorite TV show/movie?
• If you could time travel, which period would you choose to visit first?
• Would you characterize yourself as an introvert or extrovert?

Close The Gap

A recent Gallup and Bentley University survey involving 5,458 people examined the growing perception gap between employees and business leaders in finer detail. They found that while 81% of workers believe offering fair wages to all workers is crucial, only 30% think their employers are excelling in this area. Similarly, 82% of employees feel reducing the pay gap between CEOs and workers is essential, but a mere 13% are satisfied with their company's efforts. Moreover, 41% of workers favor employers taking a stance on political issues. However, 61% of workers of color and 53% of workers ages 18 to 29 are likelier to want their employers to take a stance.

Left unchecked—and to the irreperable detriment of the entire organization—such perception gaps can only widen. But by committing to regular, meaningful conversations and addressing systemic issues, leaders can bridge the growing leader-employee perception gap and build a resilient, engaged, and empowered workforce.

As leaders, it’s well within our power to ensure that thriving happens together. And it can start as early as your next one-on-one meeting.