LESSON 07 · HOW TO START A CONVERSATION

Start With a Compliment on Choice, Not Looks

Thirty-two easy ways to start with a compliment on choice, not looks, so your kindness feels warm and safe.

Praise choices, not bodies. It always lands well.

28 tipsEasy things to say7-day plan

28 tips that really help

These ideas come from The Fine Art of Small Talk (Debra Fine), How to Talk to Anyone (Leil Lowndes), We Need to Talk (Celeste Headlee), and everyday practice. Pick one tip and try it today.

Photo for the tip: Why choices are safe
TIP 1

Why choices are safe

Praising what people chose, like a book, a hat or a plan, feels friendly. Praising bodies or looks can feel personal or awkward.

TRY THIS
Choose wisely.
Photo for the tip: Notice a choice
TIP 2

Notice a choice

Look at bags, books, pins, scarves, drinks or ideas they shared. Choices tell stories.

TRY THIS
Notice one.
Photo for the tip: Be specific
TIP 3

Be specific

Say, I love your choice of bag, the colour is great. Specific beats general.

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Be specific.
Photo for the tip: Be sincere
TIP 4

Be sincere

Only say what you mean. Insincere praise feels hollow.

TRY THIS
Be real.
Photo for the tip: Add a question
TIP 5

Add a question

Ask, where did you find it? People love to share stories.

TRY THIS
Ask.
Photo for the tip: Praise skills and efforts
TIP 6

Praise skills and efforts

Say, you explained that really well. Effort praise lifts people.

TRY THIS
Notice effort.
Photo for the tip: Praise taste
TIP 7

Praise taste

Say, great taste in music. Taste praise is personal but safe.

TRY THIS
Notice taste.
Photo for the tip: Praise ideas
TIP 8

Praise ideas

Say, that is a clever idea. People love being heard.

TRY THIS
Praise ideas.
Photo for the tip: Praise kindness
TIP 9

Praise kindness

Say, that was a kind thing you did. Kindness praise warms.

TRY THIS
Notice kindness.
Photo for the tip: Keep it short
TIP 10

Keep it short

One sentence is enough. Do not overdo.

TRY THIS
Be brief.
Photo for the tip: Receive their thanks
TIP 11

Receive their thanks

Smile and say, my pleasure. Do not argue.

TRY THIS
Smile.
Photo for the tip: Move on naturally
TIP 12

Move on naturally

After a compliment and a question, follow their answer. The chat opens.

TRY THIS
Follow.
Photo for the tip: Script: bag
TIP 13

Script: bag

I love your choice of bag, the colour is great. Say it warmly.

TRY THIS
Use it.
Photo for the tip: Script: question
TIP 14

Script: question

Where did you find it? Say it with interest.

TRY THIS
Use it.
Photo for the tip: Script: idea
TIP 15

Script: idea

That is a really clever idea, thank you for sharing it. Say it sincerely.

TRY THIS
Use it.
Photo for the tip: Script: kindness
TIP 16

Script: kindness

That was such a kind thing you did. Say it gently.

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

Script: closing

It suits you well, enjoy your day. Say it kindly.

TRY THIS
Use it.
Photo for the tip: Mistake: over-complimenting
TIP 18

Mistake: over-complimenting

Too much feels fake, so keep one.

TRY THIS
Be balanced.
Photo for the tip: Mistake: compliments that sound like flirting
TIP 19

Mistake: compliments that sound like flirting

Keep them neutral, so be clear and respectful.

TRY THIS
Be careful.
Photo for the tip: Mistake: comparing people
TIP 20

Mistake: comparing people

Comparisons can hurt, so praise on their own.

TRY THIS
Stay personal.
Photo for the tip: Troubleshoot: when they brush it off
TIP 21

Troubleshoot: when they brush it off

Smile and say, it is true. They may be shy.

TRY THIS
Be kind.
Photo for the tip: Troubleshoot: when it feels awkward
TIP 22

Troubleshoot: when it feels awkward

Keep it short and move to a question. Awkwardness fades.

TRY THIS
Move on.
Photo for the tip: Troubleshoot: when culture differs
TIP 23

Troubleshoot: when culture differs

Some cultures prefer less personal praise. Choose objects and effort.

TRY THIS
Adapt.
Photo for the tip: Troubleshoot: when you feel shy
TIP 24

Troubleshoot: when you feel shy

Practise with a friend first. Say it aloud.

TRY THIS
Rehearse.
Photo for the tip: Troubleshoot: when you are not sure it is welcome
TIP 25

Troubleshoot: when you are not sure it is welcome

Praise the choice, not the person. It is rarely unwelcome.

TRY THIS
Stay safe.
Photo for the tip: Drill: give three compliments
TIP 26

Drill: give three compliments

Give three specific choice-based compliments this week. Note smiles.

TRY THIS
Do it.
Photo for the tip: Drill: write five compliment lines
TIP 27

Drill: write five compliment lines

Write five choice-based compliments you could use. Save them.

TRY THIS
Write.
Photo for the tip: Drill: pair with a question
TIP 28

Drill: pair with a question

For each compliment write a question to follow. Practise.

TRY THIS
Pair.

Easy things to say

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

COMPLIMENT

“I love your choice of bag.”

ASK

“Where did you find it?”

SHARE

“I have been looking for something like that.”

WONDER

“Is there a story behind it?”

THANK

“Thanks for sharing.”

CLOSE

“It suits you well.”

Your first week

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

DAY 1
Notice a choice
DAY 2
Pick something specific
DAY 3
Say it warmly
DAY 4
Add a question
DAY 5
Listen
DAY 6
Share a thought
DAY 7
Move on kindly

Further reading

  • The Fine Art of Small Talk (Debra Fine)
  • How to Talk to Anyone (Leil Lowndes)
  • We Need to Talk (Celeste Headlee)

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 Start a Conversation”

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

← Previous: Share a Small ObservationNext: Open Questions vs Closed Questions →

  1. Ten Easy Openers for Any Situation
  2. The Weather, the Venue, the Day
  3. Ask What Brought Them Here
  4. The Question That Beats How Are You
  5. Use Your Surroundings
  6. Share a Small Observation
  7. Start With a Compliment on Choice, Not Looks
  8. Open Questions vs Closed Questions
  9. The Follow-Up Question Habit
  10. Ask About Their Story, Not Their Job Title
  11. Ask About Their Weekend Plans
  12. Ask Their Opinion on Something Light
  13. Ask About Passions and Hobbies
  14. Questions to Avoid on a First Chat
  15. The Ping-Pong Rule of Conversation
  16. Give Back as Much as You Ask
  17. Find Common Ground Fast
  18. Use Their Last Words to Continue
  19. Share Opinions and Stories Gently
  20. Move From Small Talk to Meaningful Talk
  21. Add a Little Humour
  22. Listen With the Goal of Understanding
  23. Put the Phone Away Completely
  24. Nod, Smile and Say Mm-Hm
  25. Reflect Back What You Heard
  26. Do Not Plan Your Reply Early
  27. Let Silence Breathe
  28. Remember Details and Bring Them Back
  29. What to Do When the Chat Dies
  30. When Your Mind Goes Blank
  31. When You Disagree
  32. When They Are Shy Too
  33. When Someone Talks Too Much
  34. Recover From a Silly Comment
  35. Join a Group Conversation Smoothly
  36. Start a Chat With a Colleague
  37. Start a Chat With a Neighbour
  38. Exit Lines That Never Offend
  39. Say Goodbye and Plan to Meet Again
  40. Your Daily Conversation Practice
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