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Beyond “I’m Fine”: Open the Door to Better One-on-Ones
12 one-on-one questions better than “How are you?”
Skip the predictable “I’m fine” and start conversations that matter.
How are you?
I’m fine.
Which part of your workload is taking more time than expected?
… a real answer
“How are you?” isn’t a bad question. It just rarely gets a real answer.
One-on-ones are where managers can learn how employees are doing beyond daily tasks: workload, career goals, workplace challenges and feedback that never come up in team meetings. Questions that invite people to share experiences and concerns open that door.
Here are 12 practical questions in four areas: workload, growth, trust and feedback.
Short on time? Get three for your next 1:1
One random question from three different areas.
Area 1Workload: priorities and challenges
These conversations show whether people have enough time, resources and support, and can surface problems that project updates and performance reports miss.
Which part of your workload is taking more time than expected?
Reveals tasks that are more complicated than planned, and where extra resources, guidance or process fixes might help.
Are there any priorities that feel unclear or difficult to manage right now?
People often get requests from different managers and juggle several projects. This surfaces competing priorities so you can clarify what comes first.
What is one thing we could change to make your work more manageable?
Instead of guessing what people need, invite practical suggestions: deadlines, communication or less unnecessary admin.
Area 2Growth: career goals and development
One-on-ones shouldn’t be only about current tasks. They’re a chance to learn about ambitions and how people want to develop.
What skill would you like to develop over the next few months?
Gets people thinking about development and helps you spot relevant training, mentoring or learning opportunities.
Is there a project or responsibility you’d like to take on?
Some employees want new responsibilities but don’t know how to say so. Asking directly can open up opportunities.
What kind of support would help you move towards your career goals?
Goals alone aren’t enough. People may need guidance, practical experience, training or regular feedback, and this shows which.
Area 3Trust: open, supportive relationships
People share concerns when they believe their manager will listen without immediately judging or dismissing them. That takes time, consistency and genuine attention.
Do you feel comfortable raising concerns when something isn’t working?
Shows whether employees feel safe discussing problems. If they hesitate, explore what would make communication easier.
Is there anything about our team’s working environment that makes your job harder?
Not every challenge is about individual performance. Communication gaps, unclear processes, team dynamics and limited resources all play a part.
What could I do differently to help you feel more supported?
Invites feedback on your approach and shows you’re willing to reflect and improve.
Area 4Feedback: honest conversations
Feedback shouldn’t wait for annual reviews. Regular conversations show what’s working, where to improve and that people’s opinions matter.
What is one thing our team is doing well that we should continue?
Recognising what works matters as much as spotting problems. Employees may point out habits, communication methods or processes worth keeping.
Is there anything about my management approach that you think I could improve?
Encourages upward feedback about how your decisions affect their work. Listen openly rather than getting defensive.
What feedback or suggestion have you wanted to share but haven’t had the opportunity to?
Ideas and concerns don’t always fit everyday conversation. An open invitation can uncover useful suggestions and unresolved issues.
Making the meeting count
Good questions are only the beginning.
Create room. Give people enough time to explain without feeling rushed or judged.
Don’t ask all 12. Pick a few based on the employee’s current priorities and let the conversation develop naturally.
Follow up gently. Follow-up questions clarify concerns, but avoid turning the meeting into an interrogation.
Act on what you hear. If someone raises a workload concern or asks for development support, discuss what’s realistic and follow up next time.
Why action matters. Asking questions without responding to concerns can gradually weaken trust.
Final thoughts
Meaningful one-on-ones aren’t about a long list of questions. They’re about understanding people, recognising their challenges and creating room for honest communication. Ask about workload, growth, trust and feedback, and you’ll get a clearer picture of what employees need to succeed. The best conversations happen when people feel heard and see their input lead to thoughtful action.
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