How to have difficult conversations - Rethink Recommendations

Some books you can read to before approaching a difficult conversation

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 sure how the other person will respond - such as a raise or bonus.

• Addressing something that happened that has damaged your trust.

• Talking through an issue where the other person believes something entirely different.

• Or just being really annoyed about something someone said or did.

Most of us run as fast as we can from any kind of confrontation. We find even the idea ‘stressful’. Too often we avoid these difficult conversations, especially in the workplace. The tension builds up like heat. Perhaps we talk about the conversation with others but not with the person we need to be talking to!

Part of the problem is we are never taught to have a difficult conversation let alone productively disagree. And disagreement in the workplace has become a conflicting issue in itself:

• What are we allowed to disagree about? 

• What happens if the other person is offended by what I say?

• Are there consequences for challenging other people openly?

An idea that has helped me shift my association with difficult conversations is to see “conflict as information” (as psychology professor Nickola Overall puts it). It’s an opportunity not to share what you think but to learn about others. 

Difficult conversations around a problem or idea are a sign that someone cares. It’s a powerful signal of trust. 

Here are three super books I’d recommend on this topic:

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1. Conflicted by

Ian Leslie

(also author of the excellent newsletter

The Ruffian

) is a fascinating deep dive into the immense benefits that come from ‘productive disagreement.’ 

The book will make you rethink why being “disagreeable” has come to mean something or someone we don’t like. Leslie writes:

“I think curiosity is the antidote to polarization, judgmentalism, and defensiveness, whether it’s between two people or a whole country.”

My big takeaway was around why disagreeing well requires both sides to feel like they are working with - not against - each other. That requires putting aside the ‘righting reflex’ and trusting there is a shared intention.

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2. The Art of Disagreeing Well by Bo Seo (or listen to the fantastic podcast episode on

Adam Grant

podcast WorkLife). My copy of the book is full of notes and scribbles!

A valuable framework Bo provides is an argument structure centred around the four W’s:

·      What is the point?

·      Why is it true?

·      When has it happened before?

·      Who Cares?

The book made me think differently about how often we avoid conflict because we’ve jumped to a negative story of how the conversation will go before it’s even happened. Bo writes:

“Conflict aversion seemed to be premised on a much darker set of assumptions. It held that disagreements were bound to be ineffectual, if not divisive and outright destructive…that we could not be trusted to do right by one another.”

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3. The Thin Book of Trust by Charles Feltman. I’m frequently asked for recommendations to help people with situations where trust has broken down. How do they repair the damage?

Feltman’s book is a practical gem. It’s full of exercises and actionable tools to prepare for difficult conversations. Feltman writes:

“The disaster of distrust in the workplace is that the strategies people use to protect themselves inevitably get in the way of their ability to effectively work with others.”

Alternatively - or additionally - listen to the podcast episode with Charles Feltman Brene Brown on restoring trust.

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Is there a difficult conversation you need to have at work? What’s really holding you back? I hope these recommendations help.

Warmly,

MORE FROM RETHINK WITH RACHEL.

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Here are some links to further reading recommendations from the Rethink archive:

• Rethink Recommendations on Beliefs: After reading and researching a lot on the complicated and thorny topic of beliefs, here are my top recommendations on where you can start to dig deeper yourself.

• Rethink Book Club: How to change your relationship with regret

• Rethink Book Club: How to act with empathy