Wednesday, November 4, 2026

What’s Working

For readers looking for what’s still working in the world

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My Greatest Generation grandad had one rule to never run out of things to say in conversation

The story of the author's grandfather offers a refreshing perspective on the art of conversation, emphasizing the power of curiosity over charisma. With a simple rule, "Always ask the last question," he imparted wisdom that transcends generational divides. This approach not only keeps conversations lively but also fosters genuine connections by showing interest in others. In a world increasingly focused on personality as a pathway to success, this grandfather's method underscores the enduring value of character and etiquette.

Research supports this approach, highlighting that people who ask more questions are better liked, a testament to the grandfather's intuitive grasp of human interaction. His legacy suggests that the true essence of being engaging lies in listening and asking questions, a practice that can counteract the modern tendency to prioritize self-promotion over meaningful dialogue. This story invites us to reconsider our conversational habits and prioritize making others feel heard.

Constructive analysis

The constructive-journalism lens: not just what happened, but what works.

The problem
The challenge of maintaining meaningful conversations in an era focused on self-promotion and charisma.
The actions
The grandfather consistently asked questions to engage others and deepen conversations.
Evidence of progress
Research from Harvard Business School shows that people who ask more questions are better liked by their conversation partners.
What we can learn
Others can learn to prioritize curiosity and interest in others over trying to be the most entertaining or charismatic person in the room.
PERMA profile of this story

How this story scores across the PERMA dimensions.

Positive Emotion
7
Engagement
8
Relationships
9
Meaning
6
Accomplishment
5
PERMA

Character strengths in play

Top VIA strengths this story embodies.

  • Curiosity

    His advice to us grandkids about being a great conversationalist was always the same: 'Always ask the last question.'

  • Love

    He made an unforgettable impression on everyone who knew him.

  • Kindness

    That emphasis on making other people feel comfortable and heard in social settings, instead of advancing your own status and standing, would be a welcome return.

Try this today

Next time you find yourself in a conversation, try asking three follow-up questions to show genuine interest in the other person's responses. Notice how this changes the dynamic and depth of the interaction.