The difference between a 1:1 that builds trust and one that feels like a checkbox is almost always the questions being asked. Good questions open doors. Bad questions close them. Most managers have never thought critically about which questions they are using and why.
Here is a practical breakdown.
Questions to Ask Every Time
These are the questions that consistently surface useful information and signal to your direct report that you are paying attention.
"What is on your mind?" This is the best opening question in management. It is open-ended, non-threatening, and puts the employee in control. It works whether someone is having a great week or a terrible one. Let them set the direction.
"What is blocking you right now?" Specific enough to be actionable, broad enough to cover anything from a technical problem to a relationship issue. When you ask this consistently, people learn that you are someone who removes obstacles instead of adding them.
"How are you feeling about [specific project or responsibility]?" Asking about feelings, not just status, gives you a window into engagement and confidence. Someone might be on track with deliverables but feeling overwhelmed by the pace. You will not know unless you ask.
"Is there anything I should be doing differently as your manager?" This is uncomfortable the first few times. That is the point. Asking for upward feedback normalizes the idea that feedback goes in every direction. You will not get honest answers immediately. Keep asking. The signal it sends matters even before the answers improve.
"What is one thing you want to learn or get better at?" This keeps development in the conversation without requiring a formal career planning session every week.
Questions to Ask Regularly (Not Every Meeting)
"Do you feel recognized for your contributions?" Ask this once a month. The answer tells you whether your feedback habits are working or whether good work is going unnoticed.
"How is your workload right now? Manageable, heavy, or light?" Simple and direct. People often will not tell you they are drowning unless you give them an easy way to say it.
"Where do you see yourself in a year?" Ask this quarterly. It helps you align their current work with their longer-term goals and shows that you are thinking about their career, not just their tasks.
Questions to Stop Asking
"How is everything going?" This sounds friendly but produces nothing useful. It is too vague. The answer is almost always "fine" or "good." Replace it with something specific.
"Do you have any updates for me?" This turns the 1:1 into a status meeting. If you need project updates, get them through standups, project tools, or async check-ins. The 1:1 is for topics that require trust and nuance.
"Why did you do it that way?" This framing sounds like an accusation, even if you do not mean it that way. It puts people on the defensive. Try "Walk me through your thinking on that" instead. Same information, completely different tone.
"Is there anything else?" As a closing question, this rarely produces anything meaningful. People default to "Nope, I think we are good." Instead, try "What is the most important thing we did not get to today?" It is a small change, but it gives people permission to raise one more thing.
"Are you happy here?" Too direct, too loaded. People will not answer this honestly in a 1:1, especially if the answer is no. You will get better data from pulse surveys and by watching for behavioral signals over time.
Why the Questions Matter
Your direct reports learn what you value by the questions you ask. If you only ask about status and deadlines, they learn that output is all you care about. If you ask about their growth, their blockers, and their experience, they learn that you are invested in them as a person.
The questions in this article are not magic. They work because they signal curiosity, create safety, and surface the information that actually matters. Pick three or four that feel natural, use them consistently, and watch the quality of your 1:1s change.