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Webinar 01/17/2026 586 views 322 likes

Difficult Conversations with Family Members: A Practical Guide

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Difficult Conversations with Family Members: A Practical Guide
About this webinar

What this session covers

Declan had been putting off a conversation with his brother for almost two years. It was about money, but it was also about something older and harder to name. Every time he rehearsed it in his head, it ended badly. So he kept not having it. That delay cost him more than the original problem would have. The relationship cooled. The resentment compounded. By the time he finally spoke, there was more to repair than just the original issue.

Family conversations carry weight that other conversations do not. The history is longer, the stakes feel higher, and the patterns are older. A comment that would be unremarkable from a colleague can land completely differently from a parent or sibling. This is not irrational. It reflects the fact that family relationships involve a kind of identity investment that other relationships typically do not.

This webinar is for people who need to have a specific conversation they have been avoiding, or who have tried and watched it go wrong. We look at what makes family conversations structurally different from other difficult discussions, and what preparation actually helps versus what just creates more anxiety.

The session covers how to enter the conversation, how to stay in it when it gets uncomfortable, and how to end it in a way that leaves room for the relationship to continue. Facilitator Gwen Alcott has worked with families in mediation contexts for over a decade and brings that practical experience into the session.

Session outline

Programme details

Program Overview

  1. Why family conversations feel different

    An honest look at the psychological dynamics that make family communication harder. We examine role patterns, historical grievances, and the way family members often speak to a version of each other that no longer exists.

  2. Preparing without over-scripting

    How to clarify your own position before entering the conversation. We cover a simple preparation method that takes about 20 minutes and significantly reduces the chance of derailment.

  3. Opening the conversation

    The first 60 seconds matter more than most people realise. We look at specific ways to open a difficult topic that reduce the chance of immediate defensiveness.

  4. Staying in the conversation

    What to do when the other person escalates, deflects, or goes quiet. Practical techniques for maintaining your own steadiness without shutting down the exchange.

  5. Endings and follow-through

    How to close a conversation that did not fully resolve, and what to do in the days that follow to prevent things from reverting to the previous pattern.

  6. Participant questions

    Live Q and A with the facilitator. Participants can submit questions in advance or ask in real time.

Accessibility and recording

Session runs for two hours. Captions provided. All participants receive a recording and a short written summary of the key frameworks covered.