You finish and feel like nothing happened. The fix isn't a new topic — it's how you engage with whatever topic you already have.
Turn the fact into the feeling.
They said they work in tech. Don't ask more facts — ask 'do you actually love it or is it just a job?' Feelings are depth.
Add your own perspective.
Don't just ask questions — share your actual view. 'I find that people who do X often think Y — is that true for you?' Perspective invites perspective.
Be willing to be a little controversial.
Bland agreement keeps things shallow. A thoughtful disagreement or unexpected opinion opens the conversation up.
Go first.
Depth requires someone to go first. Most people are waiting for permission. Give it to them by going there yourself.