Difficult Conversations

Preparation frameworks, delivery techniques, and follow-up and repair tools for navigating high-stakes conversations with confidence.

What's inside

This collection walks clients through the full arc of a difficult conversation — from understanding why they're hard, through preparation and delivery, to follow-up and repair. It covers 13 topics across four stages. Each topic includes a micro lesson, blind spots, journal prompts, and a habit builder.

The four stages:

Understanding What Makes It Difficult — The emotional and psychological dynamics: the three layers underneath every difficult conversation, the stories we tell ourselves before we start talking, and your default conflict style.

Preparing for the Conversation — Getting clear before you speak: clarifying your real purpose, separating impact from intent, and planning an opening that invites dialogue rather than triggers defence.

Navigating the Conversation — Staying effective when things get tense: leading with curiosity, managing emotional flooding, saying the hard thing clearly and kindly, and finding shared ground.

After the Conversation — Following up and following through on commitments, repairing when it went badly, and extracting learning through structured reflection.

How to use this collection

As a structured programme, work through sequentially over four to six weeks, covering two to three topics per week. This works well for clients who want to fundamentally shift how they handle conflict.

For targeted coaching, jump to the most relevant stage. A client preparing for an upcoming conversation can work through just the Preparing stage. Someone whose conversation went badly can start with the Repair section.

As pre-work for a specific conversation, use the Understanding and Preparing stages before the conversation, then the After stage for structured debriefing.

Available to registered Coaching Workspace members. You'll be asked to sign in if you're not already.