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Holding Environment — Creating Containers For Difficult Conversations

Every organization has conversations it's avoiding: the merger that's not working, the executive everyone complains about, but no one confronts, the value conflict no one wants to name. 

You can't force those conversations. But you can create the conditions where they become possible — even productive. 

A holding environment is the relational and structural container that allows people to stay in the heat of difficult work without fragmenting, blaming, or checking out. It's built from: 

  • Shared purpose (why this matters enough to endure discomfort) 

  • Psychological safety (we won't punish honesty) 

  • Bounded challenge (we're working this specific tension, not everything at once) 

  • Skillful facilitation (someone who can regulate the temperature and protect dissent) 

In this session, we'll explore: 

  • What Is a Holding Environment? The architecture of trust and productive conflict 

  • Designing the Container: How to set boundaries, clarify purpose, and build safety 

  • Facilitating Inside the Heat: Tactics for managing polarization, silence, and blame 

  • Real Case Example: How one organization created a cross-functional forum to work persistent tensions (rather than delegate them downward) 

  • When the Container Breaks: What to do when safety fractures or people disengage 

You'll leave with: 

  • A design template for creating a holding environment in your context 

  • Facilitation tactics for navigating resistance, silence, and intensity 

  • Confidence to convene the conversation your system is avoiding 

This session is for you if: 

  • Your team avoids conflict (or escalates too quickly) 

  • You've tried "dialogue sessions" that felt performative, not productive 

  • You want to create the container where real work — not just venting — can happen 


The workshop fee is $119. You will receive an email with payment link after registration. If you have a discount code, please enter it in the registration form.

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June 2

Leadership Circle Profile (LCP) — Upgrade Your Internal Operating System