Rethink with Rachel

Rethink with Rachel

Share this post

Rethink with Rachel
Rethink with Rachel
How to have difficult conversations
Rethink Newsletter

How to have difficult conversations

Some books you can read to before approaching a difficult conversation

Rachel Botsman's avatar
Rachel Botsman
Mar 27, 2023
∙ Paid
4

Share this post

Rethink with Rachel
Rethink with Rachel
How to have difficult conversations
Share

Dear Rethinkers,

Having a hard conversation with a friend or colleague feels to me like getting into cold water. I hate standing on the side. I prevaricate about getting in (lots of toe dipping and “ooh it’s cold”). But once I do, it’s totally fine.

Jumping in is the hard part about all kinds of difficult conversations:

  • Asking for something when we’re not …

Keep reading with a 7-day free trial

Subscribe to Rethink with Rachel to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Rachel Botsman
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share