Estimated Read Time: 8.5 minutes

Hi Reader,

"I think I need to have one of those clearing conversations you told me about."

My family member's voice was quiet when they called. They'd been carrying tension with their cousin for years - someone they'd grown up with, someone who'd been part of their life for over 50 years.

Family gatherings had become awkward. Shared history felt contaminated by unspoken resentment. Other family relationships were being affected by the strain.

They were ready to give up. But they also knew they'd regret not trying one more time. They wanted to have a clear conscience about making the effort, even if it didn't work out.

"I just don't know how to even start that conversation," they said. "What if I make it worse?"

This is the question I hear most often when I talk about clearing conversations - not whether they're needed, but how to actually do them. The fear of making things worse often keeps people stuck in relationships that are slowly dying from what's never said.
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So today, I'm walking you through the complete process.

If you missed my first email about why we need clearing conversations and how to know when you need one, you can read it here: The cost of avoiding hard conversations​

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​Readers responded:

Phase 1: Making the Request (The Most Intimidating Part)

How you invite someone into a clearing conversation matters. The invitation itself begins the repair process.

Here's the template I gave my family member (and that I've used myself):
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My family member was terrified to make this request. They were certain their cousin would say no, or worse - agree but show up defensive and hostile.

Instead? Their cousin said yes almost immediately. "I've been wanting to talk about this too, but I didn't know how to bring it up."

That response is more common than you'd think. Often, both people are feeling the strain, but neither knows how to initiate repair.

If they're hesitant:

• Acknowledge their hesitation as valid
• Offer to send them information about the process in advance
• Ask what would help them feel safe enough to try
• Offer the option of a neutral third-party facilitator
• Emphasize that they can pause or stop at any time

If they decline:

• Respect their choice
• Ask if there's anything specific preventing them from engaging
• Offer to revisit the conversation later
• Consider whether you need to accept this as the relationship's natural endpoint

Phase 2: Setting Up the Conversation

Logistics matter more than you'd think:​
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Time: 60-90 minutes minimum, uninterrupted

• This isn't a "quick chat" - give it the space it needs
• Schedule it when neither person is rushed or depleted

Space: Neutral, comfortable, private

• Not across a desk if possible (power dynamics!)
• Consider side-by-side rather than face-to-face if that reduces intensity
• Natural light, comfortable temperature
• Perhaps water or tea is available

Environment: Create a sense of intentionality

• Simple touches like candles or flowers can help create a feeling of care and respect
• These small elements signal that this conversation matters

Facilitator: Consider bringing in support if...

• Significant power imbalance exists (boss/employee, client/vendor)
• Previous attempts at direct conversation have failed
• The stakes are very high (key client, critical team member)
• Either party has experienced trauma related to conflict

Phase 3: Opening the Container

Start by reading this structure out loud (yes, reading is fine - it keeps things clear and reduces pressure):
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Key Point: Get their agreement to the structure. This creates co-ownership of the process.

Phase 4: The Exchange

Part A: First Person Shares

Read your letter following the structure from Email 1:

1. Data & Facts

• "Here's what happened from my perspective..."
• Be specific: dates, times, exact words when possible
• Avoid generalizations ("you always..." "you never...")
• Allow space for them to correct factual misunderstandings

2. Your Emotions

• "When that happened, I felt [sad/mad/scared/bad/glad] because..."
• Connect emotion to unmet need: "I felt scared because I need reliability in our communication."
• Avoid blame disguised as feelings: "I felt like you were dismissing me" (that's a thought, not a feeling)

3. Your Story/Judgments

• "The story I made up about this is..."
• "I found myself assuming that you..."

Key: Own these as YOUR interpretations, not facts

4. Your Responsibility

• "What I regret is..."
• "My part in this was..."
• "I realize I contributed by..."

5. Your Request

• "Going forward, what would help me is..."
• "I'm asking if you would be willing to..."

Part B: Second Person Mirrors & Clarifies

"What I heard you say is... [summarize]. Did I get that right?"​
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This mirroring is crucial. It ensures the first person feels truly heard before you move forward.

Capture Action Items: Note any agreements or requests that are emerging.
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Part C: Second Person Shares

Now the second person has the same opportunity to share their perspective, emotions, stories, responsibility, and requests.
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Part D: First Person Mirrors & Clarifies

Repeat the mirroring process to ensure understanding.
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Part E: Joint Action Planning

Review all action items together:

• What are we each committing to?
• How will we know if this is working?
• When will we check in?
• What happens if tension arises again?

Phase 5: Closing

Express Gratitude:

• Thank each other for showing up
• Acknowledge the courage it took
• Name any shifts you already feel
• Appreciate the commitment to the relationship

Optional Closing Ritual:

• Shake hands or hug (if comfortable)
• Share one word for how you're feeling now

Phase 6: After the Clearing

Immediate Follow-Up (24-48 hours)

Send a brief message:

• Reaffirm appreciation for their willingness to engage
• Confirm your commitments in writing
• Note any action items with timelines

The Repair Period (First 30 Days)

• Keep your commitments - this is where trust is rebuilt
• Notice your patterns - are you falling back into old stories?
• Be patient with yourself and them - behaviour change takes time
• Check in at agreed intervals

When Tension Resurfaces

It's normal for old patterns to emerge. When they do:

• Name it early: "I'm noticing some of that old tension coming up for me."
• Reference the clearing: "Remember our conversation about X? I think this relates."
• Request a mini-clearing if needed - you have the tools now

What Happened With My Family Member

The clearing conversation opened up lines of communication that had been closed for years.

The most powerful moment? When they each realized the stories they'd been telling themselves about the other person were wrong. Assumptions built on assumptions, neither person checking if they were true.

They didn't resolve everything in one conversation. But they established new boundaries around how and what they communicate about. They found a way to be in relationship that honoured both people's needs.

Today, they're still in relationship. And my family member has more confidence about approaching similar situations in the future.

The framework gave them something they didn't have before: a structure that created enough safety to risk being vulnerable.

Common Pitfalls to Avoid

Pitfall 1: Waiting Too Long

• The longer tension sits, the more stories accumulate
• Action: If you've thought about it three times, it's time to address it

Pitfall 2: Skipping Personal Preparation

• Going in emotionally unregulated derails the conversation
• Action: Do your internal work first, always

Pitfall 3: Making It About Being Right

• This kills curiosity and prevents repair
• Action: Get clear on your intention before you begin

Pitfall 4: Not Following Through on Commitments

• Trust is rebuilt through consistent action, not just conversation
• Action: Treat your commitments as sacred

Pitfall 5: Using the Process as a Weapon

• "Well in a CLEARING you're supposed to..." becomes about control
• Action: Stay flexible and human within the structure

Pitfall 6: Ignoring Power Dynamics

• The process assumes equal emotional safety
• Action: Acknowledge power differences and adjust accordingly (facilitator, different format, etc.)

Signs the Clearing Worked

• You can think about the person without immediate emotional charge
• Communication feels more direct and honest
• You're not making up stories about their intentions
• The relationship has space for imperfection
• You both reference the clearing as a positive turning point

Navigating these nuanced interpersonal dynamics - knowing when repair is possible, how to facilitate it, and when it's time to let a relationship go - is exactly the kind of strategic, human-centred work I do as a Fractional Chief of Staff.

Through managing teams of 8+ freelancers during my VA agency days, coaching clients through their relationships with EAs and VAs, and mediating conflict in my role as Director of People and Development, I've developed both the frameworks and the experiential knowledge to help leaders navigate these moments effectively.

This is the kind of expertise you might not realize a Chief of Staff can bring to the table - but it's often what makes the biggest difference in a leader's effectiveness and peace of mind.

If you're currently facing:

• An important relationship that feels broken
• Tension with a team member you're not sure how to address
• A pattern of avoiding difficult conversations
• Uncertainty about whether repair is possible

I'd love to talk with you.​
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Reply to this email and let me know what's happening. We can explore whether a clearing conversation is the right approach, whether you need support facilitating one, or whether there's a different path forward that would serve you better.
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Sometimes the most strategic thing you can do is repair the relationships that power your work.
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Talk soon,

Moriah

P.S. The clearing conversation framework is something I share freely because I believe these skills should be accessible to everyone. If this email series has been valuable to you, I'd love to know. Hit reply and tell me - did you try it? What happened? What questions do you still have?

P.P.S. Know someone who's been avoiding a conversation that could repair an important relationship? Feel free to share this series with them. Sometimes, just knowing that structured repair is possible changes everything. New readers can subscribe here.

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