How to ask questions you can’t rush through.

A couple of years ago, I was putting together an event to help strangers connect through conversation prompts.

I wanted to check if my questions would guide people towards introspective answers, so I asked my partner if he’d mind answering a few of the questions I had written down.

To my dismay, his answers were nothing like I had imagined.

He was supposed to pause, cheek in palm, say “great question Jess, you’ve got me thinking” and detail a thoughtful and introspective story, reflect on what it meant to him, and go through three thought-provoking notes about what that story taught him.

It’s tempting to say “uh, actually, your introspection isn’t the one I had wanted… Could you try again?” But saying that during a real-life conversation would be.. insane.

So I reread the question I had actually asked him.

I realised that my question was the problem. It was vague and there were a million different ways it could be answered.

My goal was cultivating a space where people could reflect on the areas of their life that they wanted to be more intentional about. Only, with the questions I had written down, I wasn’t really guiding people anywhere at all.

For example, I wrote: “In what ways do you need to work on your communication skills?”

Without thinking, someone could easily respond: “I could listen more to others, what about you?”

It’s generic, easy to intellectualise and only promotes self-critique. It was too easy to do a quick throw-away self-assessment and move onto another question.

Now, over two years since I asked him those questions in our living room, I've just finalised my prompts for my first deck of conversation cards.

The question has evolved from: “In what ways do you need to work on your communication skills?”

To: “Consider the signals that indicate someone is really present with you. How could you lead with more patience, attention, and curiosity in your daily conversations?” 

And this is why: 

• It prompts visualisation and encourages someone to remember a felt experience: “Consider the signals…” 

• It guides someone towards specific value-based behaviour "patience, attention and curiosity” 

• It invites personal ownership and focuses on daily actions.

With that, here are some of my personal tricks for creating more introspective prompts: 

1. Use Imagination & Visualisation
Encourages someone to create vivid scenarios and feel more real.
“Imagine you’re at an event…”

2. Contextual Framing
Anchors the reflection in a real experience, encouraging the response to feel more grounded.
“Think of a person...”

3. Open-Ended with Depth
Think who, what, how - these prompts guide someone to a specific insight.
“How could you redesign your environment…”

4. Personal Connection
Helps someone to reflect on their lived experience in comparison to the prompt.
“Why does it resonate…”

5. Invitation to Agency and Action
Moves the conversation towards growth and self-autonomy.
“What skills could you develop…”

6. Develop Specific Constraints & Specifics
Encourages a specific thought and makes insights more actionable.
“What are three examples...”

7. Prompt a Story
Anchors insights in emotion and invites connection.
“Describe a situation…”