How do parents know when to push their children's limits, and when to dial back the pressure?
For Education Minister Chan Chun Sing, the answer can be found in understanding each child's strengths and weaknesses.
Calling on parents to take time to build this bond of intimacy, Mr Chan also stressed the importance of offering a listening ear rather than jumping into "solution-seeking mode" whenever their children go to them with problems.
"We need to really spend time to have a deep understanding of our own children - to know what they are comfortable with, and where they might be reaching their limit, beyond which it's not healthy for us to keep pushing them," he said at a dialogue on Friday.
The warning signs? One example is when a child does a task when asked to, but clearly does not enjoy it, Mr Chan said.
"Then we'll work on something else that really affirms them on their areas of strength, and we find some other time to come back to areas where we think they might want to work on," he said.
The session on youth mental well-being was organised by The Straits Times, and saw the minister joined by eight students from various secondary schools and junior colleges.
All the participants agreed that parents play a critical part in supporting their children's aspirations and helping to moderate their stress levels - even if their role is as simple as listening without offering advice or judgment.
As Secondary 3 student Sophia Lai from Queensway Secondary School put it: "Sometimes we just want to vent our feelings... and sometimes when we confide in our parents, if they're able to just hear what we have to say and encourage us, then it's good."
Others spoke of the impact that parents' expectations can have.
Year 4 Integrated Programme student Andrea Gracia Andradi from Singapore Chinese Girls' School said: "One thing that's really important for parents to do is to shift the focus.
"Instead of expecting their children to meet their own expectations, I think it's very important to emphasise that what's most important is that they do their best and they put in their best efforts."
Mr Chan, who has three children - a girl and two boys - also spoke of the importance of assuring children that their parents' love is not conditional on their achievement.
"They're just my kids, and I love them regardless. Full stop," he said. "It seems quite trivial, but it's important for our children to know that, so that they know that we are not constantly trying to judge them, constantly trying to measure them - especially measure them against someone else."