Leaders have difficult, crucial conversations with their people more frequently as they represent the company to their team and become the first point of contact for things that their folks don’t feel comfortable sharing in a larger setting. Listening with compassion when someone shares a deeply personal problem can feel awkward or even taboo. It’s rarely obvious when you should keep lending an ear versus when the other person is oversharing or making a request you simply aren’t equipped to handle.
The resources below will help you navigate these conversations with confidence and care.
The two most recommended books on this topic are Difficult Conversations and Crucial Conversations - the summaries below capture their key insights.
Recommended Resources
Managers - What do you do when your teammate shares their grief: Lara Hogan offers a brief, helpful primer on difficult conversations. I love how she’s not just covering potential situations, but also shares specific phrases you can draw from in case you ever find yourself in a heartbreaking moment. Don’t be ashamed to use her “I’m actually not equipped to help with XYZ” line as that’s true for most mental health struggles you will hear about as a leader. (7 min read)
Summary of "Difficult Conversations: How to Discuss What Matters Most”: The Conflict Research Consortium Staff published a helpful, brief Difficult Conversations book summary. Listening to the other person is essential but may be challenging when emotions run high. Personally, I most commonly fall into the trap of being surprised or frustrated why someone is still hurt after I explain my intentions. What is your most frequent mistake in difficult conversations? (9 min read)
Frameworks to Facilitate Crucial Conversations: Norbert Hires provides a personal Crucial Conversations book summary. A lot of the book’s tools focus on de-escalating and listening. Your mindset and opening play an enormous role in putting every participant into a collaborative over a combative conversation. How will you invite others to contribute during your next crucial conversation? (11 min read)