👽 Why you want to ask “weird” questions

“What did it smell like?”, I asked.

He looked at me like I was an alien. Then he grimaced. Then he smiled widely.

I saw the transformation in real time, one I am familiar with. I knew it landed.

This is a real interaction I had with my Spanish teacher, Gonzalo, last week.

Gonzalo had just returned from a trip to Paris. We were chatting about it in Spanish but the conversation was a little stiff. Standard questions, standard answers. Forced.

So, I did something I like to do both in my personal life and in my coaching sessions - I asked a highly specific “weird” question.

At first, Gonzalo asked if I’d got the words wrong (as I asked in Spanish!), but when I confirmed that I said what I meant I saw him go through the transformation - a look of confusion, then reminiscence, then joy.

I’d got him to relive the experience.

When we ask generic questions, people just react. Generic questions elicit generic responses. We often don’t even think about them - “How are you?”, “Fine thanks, you?”. Automatic. We never become present in the interaction.

Asking weird questions has a few major advantages:

1. You get better answers. People answering “weird” questions become proactive in their responses, giving you snippets of insider information.

   
   

   1. E.g. if you ask someone about a sound that makes them feel peaceful, you learn a lot about them based on how they respond - their partner’s voice, the sea, specific music, etc.

      
      

2. It makes you seem more interesting. You aren’t like other people, weird questions help you seem to be more interested and more interesting.

   
   

3. It’s more fun. The person you ask gets to relive a situation - in many cases their brain transports them back to the moment they’re remembering, it is visceral. You get to think of and ask odd things, and enjoy bonding over the response. Your conversations will improve dramatically.

   
   

Asking weird questions is useful in your daily life with friends and family, but also in your work if you run a service business.

Some of my favourite weird questions:

• What was an unexpected (or interesting) smell/sound/touch/texture/taste/feeling you experienced during x?

• What is something that surprised you recently?

• What was the trigger that made you want to do x?

• If you only had one (time period) to do (goal), what would you do? E.g. if you only had one week to sign 3 paying clients, what would you do?

• If you were the main character in a movie, what would the audience be screaming at you to do right now?

• When do you feel most like yourself?

• If a camera crew followed you for a week, what would they be confused by?

• What sound/theme music would go with this situation? What genre of story are you in right now (comedy, thriller, coming-of-age, etc.)?

• What would take this from a 4/10 to a 10/10? Forget 5-star, what would a 10-star experience of this look like?

• What do you wish people would ask you about more often?

• What would your 80 year old self say to you about this decision? What would your 8 year old self say?

  
  

What are your favourite “weird” questions? I’d genuinely love to hear them. You can reply to this email, or add a comment below on Substack.

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💡 Quote I'm pondering

“Don't chase strangers, remind allies” - Jamie Brindle

As I’ve shared before, people need to be reminded more than they need to be told.

Keep reminding people you exist; when done right they will reward your reminders by buying or referring people to you.

Rookie entrepreneurs chase new leads. Experienced entrepreneurs follow up with old ones.

I shared this in my Work Smart Wednesday newsletter. Want the full set of related insights? You can read them here: https://worksmartwednesday.substack.com/p/work-smart-wednesday-july-16-2025

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