LESSON 27 · HOW TO APPROACH SOMEONE

The Question That Starts Any Chat

Thirty easy ways to use the question that starts any chat, so conversation begins without effort.

One good question starts it. Curiosity opens doors.

30 tipsEasy things to say7-day plan

30 tips that really help

These ideas come from How to Win Friends and Influence People (Dale Carnegie), The Like Switch (Jack Schafer), The Charisma Myth (Olivia Fox Cabane), and everyday practice. Pick one tip and try it today.

Photo for the tip: Why a question works
TIP 1

Why a question works

People love talking about themselves. A friendly question hands them the floor and takes pressure off you.

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Ask one.
Photo for the tip: Ask about the place
TIP 2

Ask about the place

What brings you here today? It fits almost any setting.

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Use it.
Photo for the tip: Ask about their day
TIP 3

Ask about their day

How is your day going so far? Simple and kind.

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Use it.
Photo for the tip: Ask how they know the host
TIP 4

Ask how they know the host

How do you know Sam? Great at parties.

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Use it.
Photo for the tip: Ask about interests
TIP 5

Ask about interests

What do you enjoy doing outside work? Easy and open.

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Use it.
Photo for the tip: Use open questions
TIP 6

Use open questions

Start with what, how or tell me about. Open questions get longer answers.

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Go open.
Photo for the tip: Avoid yes or no questions
TIP 7

Avoid yes or no questions

They end chats fast. Add a what or how.

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Open them up.
Photo for the tip: Use a friendly tone
TIP 8

Use a friendly tone

Warm voice and soft eyes. The tone sets the mood.

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Warm up.
Photo for the tip: Wait for the answer
TIP 9

Wait for the answer

Count to three silently. Give them time.

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Wait.
Photo for the tip: Listen for a hook
TIP 10

Listen for a hook

Pick one word you can follow up on. Hooks keep chats going.

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Find a hook.
Photo for the tip: Follow with tell me more
TIP 11

Follow with tell me more

Three easy words that deepen talk. Use often.

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Use it.
Photo for the tip: Share a little back
TIP 12

Share a little back

Answer your own question briefly after they reply, because sharing a little keeps the chat balanced.

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Share back.
Photo for the tip: Script: place
TIP 13

Script: place

What brings you here today? Say it with a smile.

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Use it.
Photo for the tip: Script: day
TIP 14

Script: day

How is your day going so far? Say it warmly.

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Use it.
Photo for the tip: Script: host
TIP 15

Script: host

How do you know the host? Say it lightly.

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Use it.
Photo for the tip: Script: follow-up
TIP 16

Script: follow-up

That sounds interesting, tell me more. Say it with interest.

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Use it.
Photo for the tip: Script: closing
TIP 17

Script: closing

That was interesting, thanks for sharing. Say it gladly.

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Use it.
Photo for the tip: Mistake: firing too many questions
TIP 18

Mistake: firing too many questions

It feels like an interview, so mix comments.

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Mix it.
Photo for the tip: Mistake: asking only closed questions
TIP 19

Mistake: asking only closed questions

Closed questions with yes or no answers stall a chat, so use open ones that start with what or how.

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Open them.
Photo for the tip: Mistake: not listening to the answer
TIP 20

Mistake: not listening to the answer

If you ignore the answer it shows, so listen fully and let their words guide your next question.

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Listen.
Photo for the tip: Mistake: asking personal questions too early
TIP 21

Mistake: asking personal questions too early

Keep it light first, so start simple.

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Start simple.
Photo for the tip: Mistake: checking your phone while they answer
TIP 22

Mistake: checking your phone while they answer

It kills warmth, so keep eye contact.

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Look at them.
Photo for the tip: Troubleshoot: when they give a short answer
TIP 23

Troubleshoot: when they give a short answer

Ask a gentle follow-up or share a story. Warm up.

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Follow up.
Photo for the tip: Troubleshoot: when they ask nothing back
TIP 24

Troubleshoot: when they ask nothing back

If they ask nothing back, offer something about yourself, because a small share invites balance.

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Share a bit.
Photo for the tip: Troubleshoot: when you run out of questions
TIP 25

Troubleshoot: when you run out of questions

Comment on the setting or food. Easy topics.

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Comment.
Photo for the tip: Troubleshoot: when it feels like an interview
TIP 26

Troubleshoot: when it feels like an interview

If it feels like an interview, add a comment between questions, because a relaxed mix feels warmer.

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Add comments.
Photo for the tip: Troubleshoot: when they seem uneasy
TIP 27

Troubleshoot: when they seem uneasy

Ease off, smile and offer space. Respect.

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Ease off.
Photo for the tip: Drill: collect five questions
TIP 28

Drill: collect five questions

Write five open questions and keep them. Use one today.

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Write them.
Photo for the tip: Drill: ask three people
TIP 29

Drill: ask three people

Ask three people one question each. Practise.

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Try it.
Photo for the tip: Drill: follow up twice
TIP 30

Drill: follow up twice

Follow up twice in your next chat. Notice depth.

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Practise.

Easy things to say

When you are stuck, pick one of these. They work in many everyday friendships.

PLACE

“What brings you here today?”

DAY

“How is your day going?”

LINK

“How do you know the host?”

INTEREST

“What do you enjoy doing?”

FOLLOW

“Tell me more about that.”

CLOSE

“That was interesting.”

Your first week

One small action a day. Each day is only a little bigger than the last.

DAY 1
Pick a question
DAY 2
Say it warmly
DAY 3
Wait
DAY 4
Listen
DAY 5
Follow up
DAY 6
Share a little
DAY 7
Ask another

Further reading

  • How to Win Friends and Influence People (Dale Carnegie)
  • The Like Switch (Jack Schafer)
  • The Charisma Myth (Olivia Fox Cabane)

The tips above are written in our own words and are general guidance. The books are suggestions for further reading.

More lessons in “How to Approach Someone”

Keep going. Small steps every day make a big change.

← Previous: Introduce Yourself SimplyNext: Use Humour Lightly →

  1. What You Are Really Afraid Of
  2. Most People Are Glad You Spoke First
  3. The Spotlight Effect at Parties
  4. A Rejection Is Rarely What You Imagine
  5. Why Waiting Makes It Harder
  6. Reframe Approaching as Being Kind
  7. The Worst Realistic Outcome Is Small
  8. Spot Open and Closed Signals
  9. The Right Moment to Say Hello
  10. Approach Alone, Pairs and Groups Differently
  11. What to Do When They Look Busy
  12. Wait for the Natural Pause
  13. Notice Who Is Standing Alone
  14. Be Respectful if It Is Not the Time
  15. Smile Before You Speak
  16. Walk Over at an Angle, Not Straight On
  17. Keep Open and Relaxed Posture
  18. The Friendly Introduction Handshake
  19. Eye Contact That Feels Warm
  20. Say Your Name With a Smile
  21. Do Not Hover: Commit to Hello
  22. Comment on the Shared Situation
  23. Ask for a Small Opinion
  24. Give a Genuine Compliment
  25. Ask for a Small Favour
  26. Introduce Yourself Simply
  27. The Question That Starts Any Chat
  28. Use Humour Lightly
  29. Approach at a Party
  30. Approach at Work
  31. Approach in Class
  32. Approach at the Gym
  33. Approach Online First
  34. Approach a Neighbour
  35. Keep the Chat Going for One More Minute
  36. Exit Gracefully if It Is Not Clicking
  37. Suggest Meeting Again Casually
  38. Handle a Cool Reception Without Hurt
  39. Reflect and Learn After Each Approach
  40. Practise Approaching Every Week
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