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Sales Skills / Hear What They Really Mean / Lesson 12
LESSON 12 · HEAR WHAT THEY REALLY MEAN

Say "How Am I Supposed to Do That?"

Practical ways to use “How am I supposed to do that?” as a polite way to say no and invite creative solutions.

A question can say no kindly. Let them solve the problem with you.

11 tipsEasy things to say7-day plan
Start with tip 1
Jump to the 7-day plan

11 tips that really help

These ideas come from Never Split the Difference (Chris Voss), You’re Not Listening (Kate Murphy), The Lost Art of Listening (Michael Nichols), and everyday practice. The first six help the most. Pick one and try it today.

Photo for the tip: A polite question can say no
TIP 1

A polite question can say no

How am I supposed to do that? asks the other person to solve the problem without causing offence.

TRY THIS
Learn the phrase.
Photo for the tip: Say it with a warm tone
TIP 2

Say it with a warm tone

The question should sound curious, not sarcastic.

TRY THIS
Practise softly.
Photo for the tip: Pause and listen
TIP 3

Pause and listen

After asking, give them time to think and respond honestly.

TRY THIS
Count to five.
Photo for the tip: Use it for unreasonable requests
TIP 4

Use it for unreasonable requests

When a demand cannot work, this question shows the limit kindly.

TRY THIS
Pick suitable moments.
Photo for the tip: Repeat gently if needed
TIP 5

Repeat gently if needed

A second asking in the same tone keeps pressure on the problem not the person.

TRY THIS
Stay calm.
Photo for the tip: Follow with a suggestion
TIP 6

Follow with a suggestion

After listening, you can offer an alternative that fits.

TRY THIS
Prepare options.
Photo for the tip: Avoid using it too often
TIP 7

Avoid using it too often

Overuse can feel like stalling, so save it for key moments.

TRY THIS
Use it sparingly.
Photo for the tip: Combine with empathy
TIP 8

Combine with empathy

Start with I want to help, then ask the question.

TRY THIS
Blend both.
Photo for the tip: Use in writing carefully
TIP 9

Use in writing carefully

In email, soften with a friendly line to avoid sounding sharp.

TRY THIS
Read it aloud.
Photo for the tip: Know your limits first
TIP 10

Know your limits first

Decide what you can and cannot do so the question comes from clarity.

TRY THIS
Write your boundaries.
Photo for the tip: Practise with a friend
TIP 11

Practise with a friend

Role-play to get the tone right.

TRY THIS
Try three times.

Easy things to say

When you are stuck, pick one of these. They work in many sales conversations.

ASK

“How am I supposed to do that?”

SOFT

“I would love to help. What would you suggest?”

GENTLE

“Help me understand how that could work.”

PAUSE

“(Wait for their reply.)”

CHECK

“Is there another way?”

THANKS

“Thank you for working with me.”

Your first week

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

DAY 1
Practise the question aloud
DAY 2
Use a kind tone
DAY 3
Pause after asking
DAY 4
Listen to their answer
DAY 5
Offer an alternative
DAY 6
Avoid sarcasm
DAY 7
Review the outcome

Further reading

  • Never Split the Difference (Chris Voss)
  • You’re Not Listening (Kate Murphy)
  • The Lost Art of Listening (Michael Nichols)

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

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These lessons share general learning and everyday ideas. They are not medical or mental health advice. If you feel very anxious, low or unwell, please talk to a doctor or a qualified professional.

More lessons in “Hear What They Really Mean”

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

← Previous: Use a Calm, Slow VoiceNext: Get to "That Is Right" →

  1. Why Listening Sells More Than Talking
  2. Give Full Attention, Every Time
  3. Put Your Phone Away
  4. Stop Planning Your Reply
  5. Let Them Finish
  6. Listen for the Feeling Underneath
  7. Make Silence Work for You
  8. Label the Emotion: "It Sounds Like..."
  9. Mirror Their Last Words
  10. Say "That Seems Hard" and Mean It
  11. Use a Calm, Slow Voice
  12. Say "How Am I Supposed to Do That?"
  13. Get to "That Is Right"
  14. Why Empathy Is Not Weakness
  15. Tone Tells More Than Words
  16. Watch for Hesitation
  17. What a Long Pause Means
  18. Spot Buying Signals
  19. Spot Warning Signs Early
  20. Ask the Question Behind the Question
  21. Notice What They Keep Repeating
  22. Summarise in Your Own Words
  23. Ask "Did I Get That Right?"
  24. Write Down Their Exact Phrases
  25. Use Their Words in Your Proposal
  26. Clear Up Confusion Kindly
  27. Confirm Priorities Before Moving On
  28. Ask "What Else?" One More Time
  29. Let an Angry Customer Vent
  30. Stay Calm When They Attack
  31. Acknowledge Before You Answer
  32. Handle Interruptions Gracefully
  33. Listen to a Rambler Without Getting Lost
  34. When the Customer Is Quiet
  35. Practise With Friends and Family
  36. Record and Review a Call
  37. Count Your Talk Time
  38. The One-Question-Per-Topic Rule
  39. Take Better Notes
  40. Become the Best Listener in the Room
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