The Second Question
Go one layer past the answer everyone else accepts.
Most conversations run on first answers. Someone says work is busy, you say mine too, and nothing has been said by either person.
First answers are rehearsed and nearly content-free. The second question is where the actual information is, because nobody has a prepared answer to it. It also signals that you were listening rather than waiting for your turn, which is rarer than it should be and very noticeable.
Take the last specific thing they said
Not the general topic. The specific noun. They mentioned a project, a place, a person. That is the hook.
Ask about that, not about them
Which part is taking the time. What made it complicated. Specific beats personal and is easier to answer.
Leave a beat before filling the silence
The pause is where the real answer forms. Filling it hands the conversation back to small talk.
Do not immediately match it with your own
The instinct to say the same happened to me ends their answer. Let it run first.
Go deeper
What the paid version adds to this one.
The four question shapes that reliably open a conversation up
How to do this in a group, where the dynamics work differently
When the second question is intrusive rather than interested
Recorded conversations with the second questions marked