You will be able to ask questions that bring out concerns a person would not raise unprompted.
Wei Ling asks Arjun how things are going. He says "all good, quite busy". She asks if there's anything he needs from her. He says "no, I'm fine, thanks". The meeting is over in twelve minutes. Three weeks later, he tells a colleague he is fed up with how escalations are being handled, and Wei Ling hears it second-hand.
Arjun wasn't hiding anything. "How are things?" is a greeting, and greetings get greeting-sized answers. If you want the real answer, you have to ask a question that makes the real answer easy to give.
Broad questions get broad answers. "How are things?" "Any issues?" "Anything on your mind?" They let the other person stay polite without saying anything at all, and most people, especially with a new manager, will take that option.
Specific questions work better because they point at something real. Try these in place of the general ones.
"What was the most frustrating part of your week?" assumes something was frustrating, which in most jobs it was, and it gives the person permission to name it.
"If you could change one thing about how we handle escalations, what would it be?" points at a real process and asks for an opinion, not a complaint.
"What's taking more of your time than it should?" often surfaces the broken handover or the tool nobody likes.
"Which of your client accounts worries you most right now?" goes straight to the work they are carrying.
Notice that none of these can be answered with "fine".
The question that tells you most about your own management is a version of "what could I do differently?" Asked plainly, it often gets a polite non-answer, because criticising your boss feels risky. In many Singapore workplaces, where respect for hierarchy runs deep and people work hard to avoid making a senior person lose face, it can feel riskier still. Communicate at work covers this in lesson 8.2, Hierarchy, face and hearing an indirect no.
Two things help. First, make the question small and specific. "Is there one thing I could do to make your week easier?" is easier to answer than "how am I doing as a manager?" Second, react well to whatever comes back. If someone says "maybe reply to the group chat a bit faster", thank them, and then actually do it. The size of the answer doesn't matter much. What they are testing is whether it was safe to say.
Amy Edmondson of Harvard Business School calls the shared belief that a team is safe for interpersonal risk-taking psychological safety. It is built in small moments like this. A person who sees that a small criticism was welcomed and acted on is far more likely to bring you the big one later.
If every one-on-one is about this week, you will know a lot about the work and very little about where the person is heading. Every few weeks, swap in a question about growth or the longer term.
"What would you like to be doing more of a year from now?" "Is there a skill you'd like to build that this job isn't giving you?" "What did you enjoy most in your last role?" These are slower questions, and people often need a week to think about them. It's fine to ask one, take whatever answer comes, and say you'll come back to it. Module 6 builds these answers into a growth plan.
This is the hardest habit for most new managers. You ask a good question, there is a pause, and you jump in to fill it, often by answering for them or by softening the question until it means nothing.
Wait instead. Count slowly to five in your head if you have to. The first answer is often the polite one, and the real answer tends to arrive after a pause, once the person has decided it is safe to say. On a video call the silence feels even longer, so you may need to wait longer than feels comfortable.
When Wei Ling tried this with Arjun, she asked what was taking more of his time than it should. He said "nothing much, really". She waited. After a few seconds he added, "Well, the escalations. I'm getting the angry calls but I can't approve anything, so I just pass them on and get shouted at twice." That was the conversation she needed to have, and it took about six seconds of silence to reach it.
Good questions are hard to invent on the spot, especially at the end of a long day. Most managers who run strong one-on-ones keep a short list to draw from, grouped by what they are for, so they can pick two or three before each meeting rather than falling back on "how's it going?"
You are going to write that bank now. Draw on the examples above, but write each question in your own voice, the way you would actually say it to the people on your team.
Write a bank of twelve one-on-one questions in three groups: this week, working together and growth.
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