The Art of Conversation with Charlotte Jackson

What this episode covers

In this episode, you will learn from Charlotte Jackson, Co-founder of the Candid card deck, Substack writer, and transitions coach, about transforming conversations through better questions. Charlotte explains why "What's the dream?" works better than "What do you do?" You will learn her “pebble vs. boulder" approach to asking specific, disarming questions that invite genuine responses rather than rehearsed answers. You will also learn about finding conversational "trailheads" and how intentional questions can deepen relationships and self-understanding. Excited for you to build and grow your Portfolio Career!

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Frequently Asked Questions

How long is this episode of Portfolio Career Podcast?

This episode is 41 minutes long.

When was this Portfolio Career Podcast episode published?

This episode was published on September 11, 2025.

What is this episode about?

In this episode, you will learn from Charlotte Jackson, Co-founder of the Candid card deck, Substack writer, and transitions coach, about transforming conversations through better questions. Charlotte explains why "What's the dream?" works better...

Can I download this Portfolio Career Podcast episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.