6 Employee Check-In Questions to Find Out How They Are Really Doing

In Harvard Business Review’s article “6 Questions to Find Out How Your Employees Are Really Doing,” author Rebecca Knight argues that managers need to move beyond surface-level check-ins like “How are you?” and ask better employee check-in questions in focused one-on-one conversations. Published December 17, 2024, the article emphasizes that leaders cannot truly support engagement, performance, growth, and well-being unless they understand how employees feel about their roles, work, relationships, ambitions, and futures.

For business leaders, the article is a practical reminder that employee well-being and engagement are not abstract HR concerns. HBR notes that employee well-being is under strain, citing Gallup data that roughly 60% of workers say they are struggling with engagement and one in five report feeling lonely. Managers who do not create trust-based conversations may miss warning signs until employees disengage, underperform, or leave.

Executive summary for business leaders

Overarching theme: Great managers practice continuous learning about their people. Knight’s article positions one-on-ones not as status updates, but as leadership tools for discovering what energizes employees, what drains them, what they want next, how connected they feel, and what would make their work more meaningful. The central message is that employees need to be seen as people with ambitions, dreams, concerns, and ideas — not simply as resources assigned to tasks.

The article’s value for executives is its simplicity. Leaders do not always need a new engagement platform or another annual survey to learn how employees are really doing. They need managers who ask thoughtful questions, listen without defensiveness, follow up on what they hear, and treat employee insight as a source of organizational intelligence. HBR’s related tips adapted from the article highlight questions about what drains employees, their career goals, and what would make the job or organization more compelling over the long run.

Major takeaways – employee check-in questions

1. “How are you?” is usually not enough

The article’s premise is that surface-level interactions rarely reveal how employees truly feel about their work, role, relationships, or future. Many employees will answer “fine” even when they are overwhelmed, lonely, bored, underused, or quietly planning to leave.

Business implication: Managers need better questions and safer conversations if they want honest insight rather than polite answers.

2. Employee well-being affects business performance

HBR frames employee well-being as a serious performance issue, not only a personal concern. Employees who are not thriving are less productive, less committed, and more likely to negatively affect company performance.

Business implication: Leaders should treat manager check-ins as part of performance management, retention, and risk sensing.

3. Managers need to ask about what drains people

One of the HBR-adapted questions asks what makes employees feel depleted or drained at work and what the manager can do to support them. This moves the conversation from vague stress talk to specific obstacles, energy drains, and support needs.

Business implication: Leaders should identify patterns: repeated administrative burden, unclear priorities, meeting overload, toxic interactions, under-resourcing, or unnecessary friction.

4. Career goals deserve direct conversation

The article encourages managers to ask about employees’ career goals and dreams, and how they can help move toward them. This matters because employees often disengage when they cannot see a future inside the organization.

Business implication: Career conversations should not be limited to annual reviews. Managers should regularly connect today’s work to tomorrow’s growth.

5. Long-term commitment depends on what employees find compelling

HBR’s related tip highlights the question: “What could make this job or organization more compelling for you in the long run?” That question helps leaders understand what would deepen commitment before employees decide to leave.

Business implication: Retention improves when leaders understand the real reasons people stay — growth, flexibility, purpose, compensation, autonomy, belonging, challenge, or leadership trust.

6. Employees often have useful ideas for the organization

A Wake Forest summary of Knight’s HBR piece emphasizes that managers should learn what ideas employees have for the organization. Employees closest to the work often see broken processes, customer pain points, culture gaps, and innovation opportunities before executives do.

Business implication: Listening to employees is not only about morale; it is also a source of operational improvement and strategic insight.

7. Meaning matters

The same Wake Forest summary highlights the importance of asking how work could feel more meaningful. This is a critical question for leaders because meaning affects motivation, effort, retention, and resilience.

Business implication: Managers should help employees connect their work to customers, colleagues, learning, contribution, and the larger mission.

8. Trust determines whether employees answer honestly

The article’s core logic depends on trust. Employees will not share real concerns if they believe their manager will dismiss them, punish honesty, or fail to act. HBR’s summary stresses focused one-on-one settings as the place to move beyond surface-level interaction.

Business implication: Leaders need to train managers not only to ask better questions, but to receive answers well.

9. One-on-ones should address practical and personal needs

HBR’s related article on one-on-ones notes that good meetings between managers and direct reports address employees’ practical and personal needs, supporting performance, growth, well-being, team success, and organizational outcomes.

Business implication: A strong one-on-one is not just a project update. It should include priorities, blockers, feedback, growth, energy, and connection.

10. Connection is now a leadership responsibility

HBR’s broader coverage of loneliness at work warns that loneliness can weaken trust and team cohesion, both of which affect performance, innovation, and resilience.

Business implication: Leaders should view connection, belonging, and honest dialogue as part of the management system, not as optional culture work.

Leadership talking points regarding employee check-in questions

Managers should not assume silence means employees are fine.

Better questions create better insight, but only if managers listen without defensiveness.

Employee well-being is a business issue because it affects commitment, productivity, retention, and culture.

One-on-ones should reveal energy drains, career aspirations, meaning, connection, ideas, and long-term commitment risks.

Asking questions is not enough. Leaders must follow up, remove barriers, and show employees that candor leads to action.

The more leaders understand employees as whole people, the better they can lead performance sustainably.

Reflection questions

Do our managers know how employees are really doing, or only whether tasks are on track?

Are our one-on-ones mostly status updates, or do they uncover motivation, stress, growth, and connection?

What is draining our employees that leaders may not see?

Do employees believe it is safe to be honest with their managers?

Are we asking people about their career goals before they start looking elsewhere?

What would make our organization more compelling for high-performing employees over the next two years?

How do we capture employee ideas and turn them into visible improvements?

Do managers have the time, training, and emotional skill to hold meaningful check-ins?

Potential action items

Create a manager guide for deeper one-on-ones, including questions about workload, energy, growth, meaning, connection, and support.

Train managers to ask open-ended questions and listen without immediately defending, fixing, or minimizing.

Add a quarterly “stay conversation” focused on what would make employees more likely to remain and grow with the organization.

Ask managers to identify common energy drains across their teams and escalate systemic issues.

Build career-development conversations into regular management rhythms, not just annual reviews.

Create a simple mechanism for employees to share ideas for improving team processes, customer experience, or workplace culture.

Review whether remote, hybrid, and in-office employees have equal access to connection, feedback, and informal support.

Measure whether one-on-ones are happening regularly and whether employees find them useful.

Recommended similar articles related to employee check-in questions

“28 Questions to Ask Your Boss in Your One-on-Ones” — A useful HBR companion article on making one-on-ones more productive by addressing practical and personal employee needs.

“Why Your Team Members Need Daily Check-Ins” — A helpful HBR article on how brief, frequent check-ins can help employees get what they need to do their work well without micromanagement.

“Make the Most of Your One-on-Ones with Your Employees” — A practical HBR tip on avoiding common one-on-one mistakes, especially managers doing most of the talking.

“Loneliness Is Reshaping Your Workplace” — A strong related read on why loneliness undermines trust, cohesion, performance, innovation, and resilience.

“6 Science-Backed Ways to Improve Your Well-Being at Work” — A useful companion article that frames employee well-being as an organizational issue shaped by workload, flexibility, management, and team culture.

“How Companies Can Improve Employee Engagement Right Now” — A broader HBR piece on why managers need to take proactive steps to improve engagement and reduce burnout and turnover risk.