What questions should you ask in a one-on-one?
Dongyoung Kim, CPO
Pick one or two one-on-one questions from five topics: wellbeing, work, growth, feedback, and team. Rather than asking everything at once, start with the topic the team member most wants to discuss, and after hearing the answer add a question that leads to a next step, such as "What support would help?" The questions below are examples compiled by Orblit.
Four principles for choosing one-on-one questions
Before the question lists, here are principles that apply whichever questions you choose. The same question can sound like a check-up or like genuine interest, depending on how you ask it.
- Ask only one or two at a time. With too many questions, the team member feels audited rather than heard.
- Use open questions. A question that can be answered with yes or no tends to end the conversation right there.
- Rephrase questions that start with "why" as "what" or "how." "Why did this take so long?" sounds like assigning blame, while "Which part took the most time?" sounds like an invitation to look at the situation together.
- Ask a follow-up after the answer. "Tell me a little more" is often enough to deepen the conversation.
These principles follow from what a one-on-one is for. A one-on-one is a place to align on expectations and build trust, and within it to give and receive feedback and work through roadblocks together (HBR, 2024). Questions should aim at understanding, not evaluation.
If picking a topic is hard, split the one-on-one into two questions: is the work running well, and is the person doing it okay? Here is what to look at under each.
| What to look at | What to find out |
|---|---|
| Work: progress against goals | Where the most important work stands compared with the plan |
| Work: what is stuck | What they can solve alone and what needs someone else's help |
| Work: the weight of the work | Whether time goes to what matters, and whether work is piling up on one person |
| Person: energy | How draining the work feels lately, and what wears them down or lifts them up |
| Person: the people they work with | Whether anything is difficult in working with colleagues, other teams, or the leader |
| Person: what they want to learn | What they are learning in their current work and what they want to try next |
The example questions below turn this frame into five topics: wellbeing, work, growth, feedback, and team. You do not need all five every time; pick one or two from the topic that fits the team member's situation. This frame is a suggestion based on materials from Upstream that Orblit referred to and on field experience.
Wellbeing
How are you feeling about your workload lately?
Work
Where are you blocked, if anywhere?
Growth
What would you like to be doing a year from now?
Feedback
What could I do to make your work easier?
Team
Is there something you did not get to say in the team meeting?
One-on-one questions about wellbeing
Wellbeing questions open the conversation. Checking how the team member is doing before going straight to work makes it easier to decide what to cover first.
- How are you feeling about your workload lately?
- What took the most energy from you this week?
- When did work feel easiest lately, and when did it feel hardest?
- Is there anything weighing on you right now?
- If you rated how you are doing from 1 to 5, what would it be and why?
One-on-one questions to check in on work
Work questions are not for collecting status reports; they are for finding what is stuck and deciding where the leader can help. If you already know the progress, focus on blockers and priorities.
- What is the most important thing you are working on right now?
- Where are you blocked, if anywhere?
- What decision or support from me would help move things along?
- Is there anything where the priority is unclear?
- How far along is what we agreed on last time?
One-on-one questions about growth and career
According to Gallup, 51% of employees who left voluntarily said that in the three months before they left, neither their manager nor any other leader spoke with them about their job satisfaction or their future with the organization (Gallup, 2019). Even when the work seems to run smoothly, missing conversations about growth and career can leave people preparing to leave. That is why growth and career questions are worth asking regularly.
- What are you learning, or want to learn, these days?
- What would you like to be doing a year from now?
- Which skill in your current work do you most want to build?
- How much does your current work help you grow?
- Is there a role or project you would like to try?
These questions take time to think through. Rather than asking them every time, set aside time about once a quarter to ask calmly whether their current work connects to the direction they want, what field interests them lately, and whether there is a project they would like to take on.
One-on-one questions for giving and receiving feedback
Talking about growth naturally leads to feedback. Many leaders hesitate to give corrective feedback, but when Zenger Folkman surveyed about 2,500 employees, 57% preferred corrective feedback and 43% preferred praise and recognition(CBIA, 2014). Feedback questions start by drawing out the feedback the team member wants.
- What could I do to make your work easier?
- Of the feedback I gave recently, what helped and what did not?
- What are you proudest of this past month?
- Is there something I do not know but should?
- Is there anything you would like from me?
One-on-one questions about team and collaboration
It is hard to talk about colleagues or other teams in a team meeting. Hearing about friction in collaboration early, in a one-on-one, lets you sort it out before it grows into conflict.
- How is working with the people around you?
- Is there anything about the team you would like to improve?
- Was there anything uncomfortable about working with another team?
- Is there something you did not get to say in the team meeting?
- What should our team start or stop doing to do better?
Getting past "I'm fine"
If the conversation still ends with a quick reassurance after you pick your questions, the questions may be too broad or have an obvious answer. Small changes to common questions draw out specific answers.
| Instead of asking | Try asking |
|---|---|
| How are things? | What was on your mind most this week? |
| Nothing difficult, right? | Is there anything I could help with right now? |
| Why isn't this done yet? | Where did you get stuck as you worked on it? |
| Does that make sense? | How did you understand what I explained? |
The questions on the left invite "yes, fine," while those on the right tend to draw a specific answer. This table is Orblit's suggestion.
To make a question sharper, put the person's situation into it. A question you could ask anyone gets a generic answer. Instead of "Anything hard lately?", try "Last week's release slipped a day. Which part was the tightest?" Putting their current work and what the leader noticed into the question brings back a specific answer.
One-on-one questions to avoid
On the other hand, some questions put team members on the defensive even when the intent is good. Avoid questions like these.
- Questions that imply comparison: "The others do it this way."
- Questions that look for someone to blame: "Who dropped the ball on this?"
- Several questions asked at once
- Leading questions: "This is the right way, isn't it?"
If it is hard to choose where to start, begin from the topics the team member wrote in advance and the commitments from the last conversation. A form for keeping topics and commitments is in the one-on-one doc. Orblit suggests tailored questions based on the team member's prep notes and previous one-on-one history; learn more at Orblit 1on1.
Frequently Asked Questions
- Q.How many one-on-one questions are enough?
- One or two at a time. Too many can feel like an audit, so spend your time listening and following up.
- Q.What should I ask in a first one-on-one?
- Ask about working preferences, past experience, and expectations. For example, "How do you like to receive feedback?" or "What worked well on your previous team?" See how to run a one-on-one for the steps.
- Q.What if the team member does not answer?
- Wait a few seconds before rephrasing. If it is still hard, narrow the question or start with an easy factual one such as "What kept you busiest last week?"
- Q.Can I put one-on-one questions into a template?
- Yes. Have the team member list topics in the prep form, and note the questions you chose in the meeting record. The one-on-one doc has ready-to-use formats.
Sources
- 5 Signs Your One-on-Ones Aren't Working · Harvard Business Review (Jen Dary) · 2024-06-03
- This Fixable Problem Costs U.S. Businesses $1 Trillion · Gallup (Shane McFeely, Ben Wigert) · 2019-03-13
- What Feedback Employees Really Want · CBIA (Zenger Folkman survey) · 2014-03-08