How Do You Get Better at Connecting With People?

Interested beats interesting

Most people walk into a conversation quietly auditioning. They are deciding what to say, how to sound, what story to tell. That effort is aimed at the wrong target. The person who leaves the strongest impression is usually the one who asked the best questions, not the one who told the best story.

Five exercises you can run this week

1. The two-question rule: before you talk about yourself, ask two questions about them. Second one has to build on their answer.
2. The pause: count two seconds after someone stops talking. Most people will keep going, and the second thing they say is usually the real thing.
3. The detail log: after any meaningful conversation, write down one non-work detail about that person. Review the list before you see them again.
4. The 48-hour follow-up: contact anyone new within two days with something specific from the conversation.
5. The no-agenda check-in: reach out to one dormant relationship a week with nothing to ask for.

What to do when conversation feels awkward

• Ask about what they are working on, not what they do.
• Ask about how something happened, not just what happened.
• Say the obvious thing out loud: "I'd rather talk about something real than the weather — what's been taking up your week?"
• If you go blank, repeat the last thing they said and ask why it mattered.

If you are more introverted

You likely do not need more conversations. You need fewer, deeper ones. Set a target of two real conversations at an event instead of twenty short ones, and leave when you have them.

How this ties into Connection Reps