You will be able to ask questions that bring out concerns a person would keep to themselves unless asked.
Wei Ling manages a small team, and Arjun handles the escalation calls from clients. In their one-on-one she asks him how things are going, and he says all good, quite busy. She asks if he needs anything from her, and he says no, he's fine, thanks. The meeting ends after twelve minutes (Wei Ling, Arjun and the timings here are invented examples).
Three weeks later Arjun 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?" works as a greeting, greetings get greeting-sized answers, and he gave her one. To get the real answer, you need to ask a question that makes the real answer easy to give.
Broad questions such as "How are things?", "Any issues?" and "Anything on your mind?" get broad answers. They let the other person stay polite without saying anything at all, and most people take that option, especially with a new manager.
Specific questions work better because they point at something real. Ask what the most frustrating part of the person's week was. It assumes something was frustrating, which is true in most jobs, and gives them permission to name it. Ask what one thing they would change about how the team handles escalations. This points at a real process and asks for their opinion rather than a complaint. Ask what is taking more of their time than it should, which often brings up a broken handover or a tool nobody likes. Ask which client account worries them most right now, which goes straight to the work they are carrying. None of these can be answered with "fine".
The question that tells you most about your own management is some 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 it can feel riskier still, because respect for hierarchy runs deep and people work hard to avoid making a senior person lose face. Communicate at work, lesson 8.2, "Hierarchy, face and hearing an indirect no", goes further into why.
Two things help. First, make the question small and specific. Ask if there is one thing you could do to make their week easier, rather than asking how you are doing as a manager. Second, react well to whatever answer comes back, which means thanking the person and then actually acting on it. If someone suggests you reply to the group chat a bit faster, thank them and do it. The size of the answer matters little, because the person is testing whether it was safe to say.
Amy Edmondson of Harvard Business School uses the term psychological safety for the shared belief that a team is safe for interpersonal risk-taking. It is built in small moments like this one. A person who sees a small criticism 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 learn 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. You might ask what they would like to be doing more of a year from now, whether there is a skill they want to build that this job is not giving them, or what they enjoyed most in their last role.
These questions are slower, and people often need a week to think about them. It is fine to ask one, accept whatever answer comes, and say you will come back to it. Module 6 builds those answers into a growth plan.
Letting silence work is the hardest habit for most new managers. The common mistake is that you ask a good question, there is a pause, and you fill it, often by answering for the person or by softening the question until it means nothing. Instead, wait, and count slowly to five in your head if you need to. The first answer is often the polite one, and the real answer tends to come after a pause, once the person has decided it is safe to say. On a video call silence feels even longer, so you may need to wait longer than feels comfortable.
When Wei Ling tried this, she asked Arjun what was taking more of his time than it should. He said nothing much, really. She waited, and after a few seconds he added that the problem was escalations: he gets the angry calls but cannot approve anything, so he passes them on and ends up getting shouted at twice. That was the conversation she needed, 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 of questions grouped by purpose, and pick two or three before each meeting instead of falling back on "how's it going?" Your groups can follow the habits above:
specific questions about the work small questions asking for feedback on your management growth and longer-term questions
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 twelve one-on-one questions and sort them into three groups: this week, working together and growth.
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